How I Invest with David Weisburd

David sits down with Bryon Hargis, co-founder of Castelion, to unpack why rebuilding America’s defense manufacturing capacity has become a national security imperative. Bryon explains why decades of consolidation and outsourcing weakened the defense industrial base, why America could struggle against an adversary with significantly greater manufacturing capacity, and why Castelion is betting that deterrence ultimately requires weapons that can be produced affordably by the thousands. Highlights:

• Why America’s defense problem is increasingly a manufacturing problem.
• How the defense industry’s “Last Supper” reshaped the industrial base.
• What Bryon learned about speed and iteration at SpaceX.
• Why “the best part is no part” is more than an Elon Musk catchphrase.
• Why Castelion combines product and sales instead of separating them.
• How mission-driven hiring helps protect culture as a startup scales.
• Why Bryon left SpaceX even when defense hardware was considered nearly uninvestable.
• How Castelion survived almost 100 VC rejections.
• Why one major investor can completely change a startup’s access to capital.
• Inside Castelion’s plan to manufacture hypersonic weapons at massive scale.

Guest Bio:

Bryon Hargis is the co-founder of Castelion, a defense technology company focused on developing and manufacturing advanced hypersonic weapon systems in the United States. Before founding Castelion, Bryon worked at SpaceX, including on the Starshield program and in government satellite sales. His work focused on applying SpaceX capabilities to national security problems, an experience that helped shape Castelion’s hardware-first and customer-driven approach.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Bryon Hargis:

LinkedIn:https://www.linkedin.com/in/hargsb/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why America Needs Hypersonic Missiles (3:00) How Defense Manufacturing Lost Its Edge (5:30) What SpaceX Taught Bryon About Building Hardware (10:00) Why Product and Sales Should Be the Same Team (15:30) The Traits Bryon Looks for When Hiring (20:00) SpaceX’s Responsible Engineer Culture (25:00) Why Aerospace Became Too Risk-Averse (30:00) The Danger of Too Much Process (37:00) Nearly 100 VC Rejections to $1B (44:00) Building Hypersonic Missiles at Massive Scale

Why do so many GPs misunderstand what institutional LPs actually care about? David sits down with John-Austin Saviano, an Backing & Building Challenger Investment Firms and Former Endowment CIO, argues that one of the biggest mistakes GPs make is overemphasizing track record. Great LPs care less about the headline returns than how those returns were generated. They want to understand the investment process, whether it is repeatable, and whether the people and market conditions that produced past performance still exist today. Highlights:

• Why track record is less predictive than most GPs believe.
• What LPs actually want to understand about an investment firm.
• How great allocators separate good decisions from good outcomes.
• Why being different is necessary to generate differentiated returns.
• What investors misunderstood about David Swensen’s endowment model.
• Why Fund I may actually be more knowable than Fund XIV.
• How challenger firms become the R&D of an institutional portfolio.
• The hunt, farm, and fish framework for raising institutional capital.

Guest Bio:

John-Austin Saviano is Backing & Building Challenger Investment Firms and Former Endowment CIO. Over more than 20 years as an institutional allocator, he helped launch two ten-figure endowments, served as the founding CIO of UC Berkeley’s endowment, was part of the founding investment team at the Gordon & Betty Moore Foundation, and worked on the private capital team at Cambridge Associates. Today, he draws on his experience backing dozens of challenger firms and reviewing billions of dollars of fund commitments to help investment firm founders navigate fundraising, firm building, and the transition from talented investor to enduring investment organization.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with John-Austin Saviano:

LinkedIn: https://www.linkedin.com/in/john-austin-saviano/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Track Record Is Overrated (8:20) Why Private Markets Got So Much Harder (18:22) What the Best Fund Managers Have in Common (25:08) The Danger of a Great Track Record (29:51) What Everyone Got Wrong About the Yale Model (36:34) Why First-Time Funds May Be Less Risky (43:18) How a Former CIO Would Build an Endowment Today (47:50) The Mistake That Kills Most GP Pitches (56:27) The Fundraising Strategy Most GPs Ignore

What if the biggest edge in private equity isn’t finding better deals, but designing better incentives? In this episode, I sit down with Jack Purcell, Managing Partner at Ridgemont Equity Partners, to unpack how alignment helped turn a Bank of America spinout with fewer than 15 people into a private equity firm managing more than $11 billion. Jack explains why Ridgemont invests significant GP capital alongside its LPs, why more than two-thirds of the team participates economically in its funds, and how a nine-person unanimous investment committee uses a proprietary 40-point scorecard to evaluate deals. Highlights:

• Why traditional GP economics can create the wrong incentives.
• How Ridgemont grew from fewer than 15 people to nearly 70.
• Why more than two-thirds of the team invests in the funds and participates in carry.
• The nine-person investment committee where every member has a veto.
• Why Ridgemont spends an average of three years with companies before investing.
• How one founder relationship took 10.5 years before becoming an investment.
• Why Ridgemont generated more than $2 of DPI for every $1 generated by the industry in recent years.
• How a $4 billion Fund V stays focused on three core sectors instead of chasing novelty.
• Why Jack personally visits every institutional investor partner each year.
• The lesson Jack learned from being too conservative after the Global Financial Crisis.

Guest Bio:

Jack Purcell is Managing Partner at Ridgemont Equity Partners, where he helps lead the firm and focuses on investments across business and technology services and industrial growth. Ridgemont traces its history to 1993 and has managed third-party institutional capital since its 2010 spinout from Bank of America.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Jack Purcell:

Website: https://www.ridgemontep.com/team/jack-purcell/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Incentives Matter More Than Great Investments (3:25) How Ridgemont Built an $11B Private Equity Firm (7:57) Why Most Firms Get Succession Wrong (12:29) The Incentive Model Most PE Firms Won’t Copy (17:50) Why Ridgemont Waits Years Before Investing (24:22) The Hidden Advantage That Wins Competitive Deals (30:58) The Communication Mistake GPs Make in a Crisis (34:21) Why Chasing the Hottest Sector Usually Backfires (38:48) Inside a Nine-Person Investment Committee With Veto Power (45:43) The Investing Mistake Jack Would Fix From 2010

What if the biggest AI investment opportunity isn’t AI companies, but the infrastructure required to make AI possible? David sits down with Stuart Waugh, Managing Partner of Northleaf Capital Partners, to explore why the AI boom is creating massive demand for power, data centers, communications networks, and other essential infrastructure. Stuart explains why Northleaf estimates roughly $40 trillion of infrastructure investment will be needed across its addressable markets over the next decade, and why governments increasingly need private capital to help fund it. Highlights:

• Why AI’s biggest bottleneck may be infrastructure, not computing.
• The investment opportunity behind AI’s enormous demand for power.
• Why Northleaf sees roughly $40 trillion of addressable infrastructure investment.
• How infrastructure can provide long-term cash flows, inflation protection, and lower correlation.
• Why the middle market becomes more attractive as mega-funds get bigger.
• How secondaries became a mainstream portfolio management tool.
• Why relationships and proprietary information still create an edge in secondaries.
• How institutional investors are approaching today’s private credit uncertainty.
• Why Stuart believes “boring” can be an investing advantage.
• The lessons behind scaling Northleaf from five people to more than 300.

Guest Bio:

Stuart Waugh is the Managing Partner of Northleaf Capital Partners and a member of the firm’s Executive Committee. He oversees the direction and development of Northleaf’s private markets investment strategies and fund management capabilities and chairs its Investment Committees. Stuart joined Northleaf’s predecessor, TD Capital, in 2002. Earlier in his career, he worked at McKinsey & Company, BPI Financial Corporation, and McCarthy Tétrault. He holds a B.A. from Trinity College at the University of Toronto and an LL.B. from the University of Toronto Faculty of Law.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Stuart Waugh:

Website:https://www.northleafcapital.com/person/stuart-waugh

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why AI’s Biggest Opportunity Isn’t AI (8:56) The $40 Trillion Infrastructure Opportunity (15:36) Why Deglobalization Could Make Infrastructure More Valuable (23:18) Why the Traditional 60/40 Portfolio Is Disappearing (27:54) The Private Markets Liquidity Engine Most Investors Miss (33:14) The Hidden Advantage in Buying Secondaries (42:47) Is the Private Credit Fear Creating a Buying Opportunity? (50:08) What Most GPs Get Wrong About Their LPs (56:14) Why “Boring” May Be the Best Investment Strategy

Venture capital was designed around a relatively simple model: invest in a startup, help it grow, and eventually exit through an acquisition or IPO. David sits down with Benjamin Black Powerlaw Corp. (Nasdaq: PWRL), Akkadian Ventures, Ben invests in growth-stage technology companies while providing alternative liquidity to founders, employees, angel investors, and venture funds. In this episode, Ben and David unpack the evolution of the venture secondary market, why great companies staying private longer creates an entirely different opportunity set, how sophisticated investors price illiquid private-company shares, and why liquidity itself is becoming a critical piece of venture capital infrastructure. The result is a different way to think about private markets: the investment opportunity doesn't end after the primary financing round. Highlights:

• Why venture secondaries have become a major private-market opportunity
• What happens when great companies stay private for much longer
• How Akkadian approaches growth-stage technology investing
• Why founders and employees increasingly need pre-IPO liquidity
• How investors price private-company secondary transactions
• The difference between primary and secondary venture investing
• Why venture funds themselves can become secondary sellers
• How liquidity can strengthen rather than weaken a cap table

Guest Bio:

Benjamin Black Powerlaw Corp. (Nasdaq: PWRL), Akkadian Ventures, an investment firm focused on growth-stage technology companies and private-company secondary transactions.

Akkadian provides alternative liquidity solutions for entrepreneurs, employees, angel investors, and venture capital funds, giving Ben a distinctive perspective at the intersection of venture capital, growth investing, and the rapidly evolving private secondary market.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Ben Black:

LinkedIn:https://www.linkedin.com/in/benblack/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Venture Capital Is Finally Going Public (7:51) Why the 10-Year VC Fund Model Is Broken (11:41) Why Late-Stage Secondaries Are Getting Overcrowded (14:47) The Information Advantage in Private Markets (17:01) Why Ben Black Built a Public Venture Fund (22:38) What He Learned After Taking Venture Capital Public (26:52) Who Is Actually Investing in Public Venture Funds? (31:49) Why Startups Are Warming Up to Public VC Funds (38:17) How to Get Access to the Hottest Private Companies

Most venture firms think AI is another productivity tool. David sits down with John Melas-Kyriazi co-founder and CEO of Standard Metrics—the AI-native portfolio management platform used by leading venture capital and private equity firms—to discuss how AI is transforming every stage of investing, from sourcing and diligence to portfolio management, follow-on decisions, and firm operations. John explains why the best venture firms are becoming AI-native organizations, how investors are using large language models today, why every investment memo should be "red teamed" by AI, the rise of MCPs, when firms should build software versus buy it, what Standard Metrics is seeing across more than 12,000 portfolio companies, and why human judgment will become even more valuable as AI automates everything else. Highlights:

• How AI is changing every stage of venture investing.
• The AI workflows top VC firms already use every day.
• Why every investment memo should be "red teamed."
• MCPs explained and why they'll reshape enterprise software.
• Build vs. buy: what VC firms should develop internally.
• The surprising data behind today's fastest-growing AI companies.
• Why judgment—not research—becomes the scarce resource.
• How Standard Metrics analyzes thousands of private companies.
• Hiring lessons from building an AI-native company.
• Why culture matters more than tools in the AI era.

Guest Bio:

John Melas-Kyriazi is the co-founder and CEO of Standard Metrics, an AI-powered portfolio management platform trusted by many of the world's leading venture capital and private equity firms. Before founding Standard Metrics, he was an investor at Spark Capital and previously worked as a research scientist at Stanford University. Today, he works with thousands of investors and portfolio companies, giving him a unique perspective on how AI is transforming the future of venture capital.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with John Melas-Kyriazi:

LinkedIn:https://www.linkedin.com/in/johnmk/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why AI Will Transform Venture Capital (8:04) The AI Workflows Top VC Firms Use Today (18:31) Build vs. Buy: Where AI Should Replace Software (30:15) What Actually Creates Alpha in the AI Era (43:11) Why the Best Investors Double Down on Winners (53:02) The Future of AI-Native Services Businesses

Most investors spend their careers trying to eliminate risk. David sits down with Alec Litowitz the founder of Qstar Capital, founder and former CEO of Magnetar Capital, and one of Citadel's earliest partners to explore the difference between risk and uncertainty, why adaptability is becoming the world's most valuable skill, how elite investors make decisions when there is no model to follow, and the cultural principles behind building one of the world's leading hedge funds. Alec also shares lessons from building Magnetar, working alongside Ken Griffin during Citadel's early years, hiring exceptional talent, creating organizations that continuously learn, why ego destroys great investing, and the core ideas behind his upcoming book The Adaptability Quotient. Highlights:

• Why uncertainty creates bigger opportunities than risk.
• The investing framework that built Magnetar Capital.
• Lessons from working with Ken Griffin during Citadel's early years.
• Why adaptability matters more than IQ in the AI era.
• How elite investors update their beliefs without ego.
• Building organizations that learn faster than competitors.
• Why the best decision-makers embrace feedback loops.
• How to identify uncertainty that can actually be resolved.
• The hidden cost of certainty in investing and business.
• Why great investors think in systems, not predictions.

Guest Bio:

Alec Litowitz is the founder of Qstar Capital and founder and former CEO of Magnetar Capital, one of the world's leading alternative asset managers. Previously, he was one of the four original partners at Citadel Investment Group, where he led Global Equities. He is the author of the forthcoming book The Adaptability Quotient, which argues that adaptability—not IQ or EQ—will become the defining competitive advantage in an increasingly uncertain world. He also founded Magnetar Academy, serves on multiple educational initiatives, and holds degrees from MIT and the University of Chicago.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Alec Litowitz:

LinkedIn:https://www.linkedin.com/in/aleclitowitz/ Book: https://www.theaqbook.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Most Investors Misunderstand Risk (6:58) How to Profit From Uncertainty Before Everyone Else (15:04) The Adaptability Mindset That Built Magnetar (24:36) Why Great Investors Change Their Minds Faster (34:02) Building a Culture of Excellence Without Ego (44:21) The Hiring Traits That Matter More Than IQ (54:47) Can You Teach Drive or Is It Innate?

Why do the largest investment firms keep getting bigger? David sits down with Joel Holsinger, Co-Head of Ares Alternative Credit, to discuss why scale has become one of the biggest competitive advantages in investing, how Ares evaluates multi-billion-dollar opportunities, why data centers and AI infrastructure are reshaping private credit, and how great investors think about downside protection. Joel also shares the leadership principles behind building world-class investment teams, why reputation compounds like capital, the power of Kaizen, and how Ares' Pathfinder funds have connected institutional investing with large-scale philanthropy through Promote Giving. Highlights:

• Why scale has become the biggest moat in private markets.
• How Ares thinks about AI infrastructure and data centers.
• The hidden advantage of having a trusted reputation.
• Why great investors obsess over downside protection.
• Joel's "Kaizen" framework for building elite investment teams.
• How Ares combines investing with large-scale philanthropy.
• Why visualization improves investment decisions.
• The biggest career mistake young investors make.
• Why intellectual property matters more than salary.
• The timeless investing advice Joel would give his younger self.

Guest Bio:

Joel Holsinger is Co-Head of Ares Alternative Credit and a member of the Ares Operating Committee. He oversees one of the world's leading asset-based finance platforms and serves as Portfolio Manager for the Pathfinder fund family, which pioneered a model of donating a portion of carried interest to global health and education initiatives through Promote Giving. Before joining Ares, Joel was a Partner at Fortress Investment Group and previously a Founding Partner of Atalaya Capital Management. He also serves on several nonprofit and educational boards, including PATH Global Health and the Ares Charitable Foundation.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Joel Holsinger:

LinkedIn:https://www.linkedin.com/in/joel-holsinger-0739a74/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why the Biggest Investment Firms Keep Winning (4:56) The Moat That Most Investors Overlook (10:41) Why Reputation Beats Price in Finance (16:35) The Hidden Art of Great Dealmaking (22:08) How Elite Investors Build Trust (28:44) The Leadership Secret Behind Ares (34:51) Why Winning Teams Think Long Term (40:18) The Framework That Builds Better Investors (46:09) Build Your Intellectual Property, Not Your Salary (50:07) The Career Advice Every Young Investor Needs

For years, defense investing was considered off limits for most venture capital firms. Today, billions of dollars are flowing into defense startups as AI, drones, autonomy, advanced manufacturing, and national security become some of the biggest investment themes of the decade. David sits down with Jake Chapman, Managing Director at Marque Ventures, to discuss why defense became mainstream, how government procurement is changing, why Anduril and SpaceX transformed venture investing, where the biggest opportunities still exist, and why the next generation of iconic venture-backed companies may be built around national security rather than consumer software. Highlights:

• Why Silicon Valley suddenly embraced defense investing.
• The Anduril playbook that changed venture capital.
• How SpaceX created an entirely new venture category.
• Why AI is accelerating defense innovation.
• The hidden challenges of selling to the U.S. government.
• Why manufacturing may be the biggest overlooked investment.
• How defense startups compete against Lockheed and Raytheon.
• The future of autonomous warfare.
• Why venture firms are changing their view on defense.
• Jake's optimistic vision for technology, humanity, and the future.

Guest Bio:

Jake Chapman is the Managing Director of Marque Ventures, an early-stage venture capital firm focused on national security and defense technology. He invests across AI, robotics, aerospace, autonomy, quantum computing, semiconductors, manufacturing, biotech, defense, and energy, backing founders building technologies that strengthen American national security. Jake believes technological innovation is the path toward a future of abundance, exploration, and human progress, inspired by Gene Roddenberry's vision of humanity's future while recognizing the importance of maintaining American strength during a period of global geopolitical change.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Jake Chapman:

LinkedIn: https://www.linkedin.com/in/jakechapman/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Defense Tech Became Silicon Valley's Hottest Bet (5:28) The $2 Trillion Market Most Investors Miss (11:14) How SpaceX and Anduril Changed Venture Capital (17:02) Why Selling to the Pentagon Is So Difficult (23:46) The Story Behind Defense's "Last Supper" (30:11) How the Best Defense Startups Break Into the Market (37:55) Where the Biggest Defense Opportunities Still Exist (46:20) The Ethical Case for Investing in Defense (54:08) What the Best Defense Founders Do Differently

For decades, fundraising was driven by relationships. Today, it increasingly starts with AI. David sits down with Lex Suvanto, Global CEO of Edelman Smithfield, to discuss how artificial intelligence is changing fundraising, why reputation is becoming one of the most valuable assets for investment firms, how GPs can differentiate themselves in an increasingly crowded market, and why authentic thought leadership may become the biggest competitive advantage in private markets. Highlights:

• Why AI is becoming every GP's first impression.
• The surprising reason reputation now matters more than returns.
• How the best investment firms differentiate themselves.
• Why thought leadership compounds into fundraising success.
• The role of media in building institutional trust.
• How AI rewards firms with authentic expertise.
• Why every GP needs a clear point of view.
• The biggest communication mistake investment managers make.
• How private markets are adapting to the wealth channel.
• Why trust will become venture capital's most valuable asset.

Guest Bio:

Lex Suvanto is the Global CEO of Edelman Smithfield, where he advises boards, CEOs, and senior executives of leading public and private companies on strategic communications during transformative events, fundraising, shareholder activism, governance, and investor engagement. Over his career, he has advised on hundreds of domestic and cross-border transactions while helping investment firms strengthen their reputation, communicate with investors, and navigate complex situations. Before joining Edelman Smithfield, Lex was a Managing Director at Abernathy MacGregor and previously held strategy and client service leadership roles at Havas across New York, Paris, and London. He earned his MBA from Harvard Business School.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Lex Suvanto:

LinkedIn:https://www.linkedin.com/in/lex-aleksi-suvanto-40b599/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why AI Became Every LP's First Impression (5:46) The Branding Mistake Most GPs Still Make (12:00) Why Most Investment Firms Sound the Same (18:34) The Secret to Building Trust Before Performance (24:52) How Smaller GPs Can Beat the Biggest Firms (31:42) The CEO Matters More Than Your Returns (38:10) How Great Firms Find Their Competitive Edge (46:18) Why Every Audience Needs a Different Message (56:07) The Hidden Cost of Playing It Safe (1:03:48) The Skill That Compounds for Decades

Most venture firms are experimenting with AI. Footwork rebuilt the entire firm around it. David sits down with Nikhil Trivedi, Co-Founder & General Partner at Footwork, to explore what an AI-native venture capital firm actually looks like, how autonomous agents are changing sourcing, diligence, portfolio management, and investment decisions, and why judgment and relationships may be the last true competitive advantages in venture capital. Highlights:

• What an AI-native venture capital firm actually looks like.
• Why Footwork replaced manual CRM work with AI agents.
• The AI systems helping investors make better decisions.
• Why learning speed is becoming the most valuable founder trait.
• How venture firms should approach AI adoption internally.
• Why relationships and judgment will remain the last human advantages.
• How writing a newsletter compounds into better investing.
• Why exceptional startups deserve exceptional investment decisions.
• The fundraising strategy that attracted elite university endowments.
• How AI could fundamentally reshape venture capital over the next decade.

Guest Bio:

Nikhil Trivedi is the Co-Founder and General Partner of Footwork, an early-stage venture capital firm based in San Francisco. He has invested early in companies including Canva, ClassDojo, Frame.io, Athelas, GPTZero, Watershed, Lattice, The Farmer's Dog, and Brigit, among many others. Nikhil was named to the Forbes Midas Seed List in both 2025 and 2026 and is widely recognized for pioneering the concept of an AI-native venture capital firm. He also writes the popular newsletter Next Big Thing, where he shares insights on venture capital, startups, and emerging technologies.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Nikhil Basu Trivedi:

LinkedIn:https://www.linkedin.com/in/nikhilbt/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) What an AI-Native VC Actually Looks Like (3:29) Inside Footwork's AI Operating System (10:28) How to Build an AI-First Organization (16:52) Why Every VC Firm Needs an AI Operator (20:13) Can AI Become an Investment Partner? (23:40) The Future of Venture Capital in an AI World (28:21) Why Writing Compounds as a VC (32:33) How to Build an AI-Native Venture Firm From Scratch (37:19) The Two Things That Compound Most in Venture (47:48) The Biggest Lessons From Footwork's First Two Funds

AI isn't just changing technology—it is reshaping how investment firms create value, evaluate managers, and generate alpha. David sits down with Thomas Scriven, Managing Director University of Pennsylvania Office of Investments, institutional investor with experience across private equity, endowment management, and investment banking, to discuss why AI-native investment firms may outperform traditional firms, how great LPs evaluate GPs, why concentrated portfolios often outperform diversification, and the investing frameworks that separate elite allocators from everyone else. Highlights:

• Why AI-native private equity firms have a structural advantage.
• The framework Thomas uses to evaluate every GP.
• Why concentrated portfolios often outperform diversification.
• The hidden importance of incentives between LPs and GPs.
• How AI is changing operational value creation.
• Why thinking time is one of an investor's biggest competitive advantages.
• The mistake allocators make by overprotecting the downside.
• Why the best venture firms continue attracting elite founders.
• How secondaries have transformed institutional portfolio construction.
• The advice Thomas would give himself starting over today.

Guest Bio:

Thomas Scriven Managing Director University of Pennsylvania Office of Investments, institutional investor with more than 15 years of experience spanning private equity, endowment management, investment banking, mergers and acquisitions, portfolio construction, and special situations investing. During his career, he has helped build one of the world's leading university endowment private equity programs while partnering with top-performing venture and buyout firms globally. His investment philosophy emphasizes concentrated conviction, strong GP relationships, operational value creation, and long-term alignment between investors and managers.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Thomas Scriven:

LinkedIn:https://www.linkedin.com/in/thomas-scriven-435281/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why AI Will Reshape Every Investment Firm (4:12) The AI Playbook That Wins Private Equity Deals (11:48) Why Most Investment Firms Don't Have Enough Thinking Time (18:02) The Hidden Incentives That Drive Every LP and GP (25:06) Frameworks Beat Rules in Investing (33:10) Why Concentrated Portfolios Win (41:02) What Actually Makes a Top Venture Firm (49:17) The Psychology Behind Elite Investors (56:28) AI Will Separate the Winners From Everyone Else (1:04:48) The Investing Lesson Thomas Learned Too Late

Most venture firms are using AI to save time. Earlybird is using it to generate alpha. David sits down with Andre Retterath, General Partner at Earlybird, to discuss how his firm built an AI-native venture platform, why proprietary data is becoming venture capital's biggest competitive advantage, how machine learning improves investment decisions, and why the future of venture belongs to investors who combine technology with exceptional judgment. Highlights:

• Why AI should automate venture capital—not replace investors.
• The hidden cost of missing great startups.
• How Earlybird built an AI-native investment platform.
• Why founder branding has become a competitive advantage.
• The surprising traits shared by successful AI founders.
• How machine learning improves venture capital decision-making.
• Why the best investors optimize for judgment, not activity.
• The framework Andre uses to evaluate every AI startup.
• How proprietary data creates lasting venture alpha.
• Why exceptional investors spend less time screening and more time thinking.

Guest Bio:

Andre Retterath is a General Partner at Earlybird, where he leads the firm's AI and infrastructure investment practice, focusing on frontier AI models, databases, developer tools, automation platforms, and AI infrastructure. He has led investments in companies including Aleph Alpha, Black Forest Labs, DeepCode, EthonAI, and Energy Robotics, while helping build one of Europe's leading AI-focused venture franchises. Before joining venture capital, Andre worked as a process automation engineer at ThyssenKrupp and as a management consultant at GE. He also earned a Ph.D. from the Technical University of Munich researching machine learning and the value of data in venture capital, research that continues to shape Earlybird's AI-native approach to investing.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Andre Retterath:

LinkedIn:https://www.linkedin.com/in/andreretterath/ Website: https://earlybird.com/ Newsletter: https://datadrivenvc.io/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Venture Capital Became Groupthink (3:34) The Portfolio Rule That Cost Them a 50x Winner (7:15) Why Great Fundraisers Keep Winning (10:09) The Founder Traits That Actually Matter (18:26) The Startup Patterns That Never Change (23:15) Why Founder Branding Became a Competitive Advantage (27:44) Inside EarlyBird's AI-Native Venture Platform (34:48) The Hardest Part of Bringing AI Into Venture Capital (1:01:10) Where Alpha Comes From in the AI Era (1:15:59) The Career Advice Andre Wishes He Learned Earlier

Consumer startups may grab the headlines, but some of the most valuable companies are built by solving mission-critical problems for businesses. David sits down with Rick Heitzmann, Managing Director at FirstMark Capital, to discuss how he identifies high-growth technology-enabled business services, why sectors like data infrastructure, compliance, marketing technology, and information services continue to generate outsized opportunities, and what separates enduring enterprise businesses from short-lived trends. Highlights:

• Why B2B investing remains one of venture's biggest opportunities.
• The characteristics of exceptional enterprise software companies.
• How data has become a competitive advantage.
• Why compliance is creating entirely new categories of startups.
• The evolution of marketing and advertising technology.
• What makes technology-enabled business services highly scalable.
• How recurring revenue creates durable businesses.
• Where Rick sees the next wave of venture-backed winners.
• The investment frameworks FirstMark uses when evaluating founders.
• Why solving critical business problems creates lasting enterprise value.

Guest Bio:

Rick Heitzmann is a Managing Director at FirstMark Capital, where he invests in high-growth emerging media and technology-enabled business services. His investment focus includes data and information management, compliance and risk mitigation, marketing and advertising technology, and business process outsourcing. Rick has built his career identifying scalable enterprise businesses that become critical infrastructure for their customers and benefit from long-term technology adoption.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Rick Heitzmann:

LinkedIn:https://www.linkedin.com/in/rickheitzmann/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) The Venture Capital Advantage Nobody Can Copy (1:51) Why Relationships Compound Faster Than Capital (8:06) The Hidden Framework Behind Every Great VC Investment (13:07) Why Most Relationships Never Compound (21:23) The AI Trend Almost Everyone Is Missing (25:13) Why the Best Venture Bets Always Look Wrong (35:01) The Founder Test That Predicts Billion-Dollar Companies (47:29) How FirstMark Survived the 2008 Fundraising Crisis (56:06) The Fundraising Lesson That Changed Everything (1:07:48) The One Piece of Advice Every Investor Needs

Most investors chase what's exciting. Jason Koenig built a $6.5 billion firm by investing where almost nobody was looking. In this conversation, Jason explains why overlooked industrial assets can produce exceptional long-term returns, how ITE grew from $60 million to $6.5 billion in assets under management, why culture compounds just like capital, and the leadership lessons he learned while scaling an investment firm from startup to institutional platform. Highlights:

• Why the best investments are often hiding in overlooked industries.
• How Jason spotted a billion-dollar opportunity by watching trains.
• The founder mindset required to build conviction before everyone else.
• Why culture becomes a firm's biggest competitive advantage as it scales.
• The leadership framework behind hiring years before you actually need people.
• Why compensation should reward teamwork, not individual empires.
• The psychology every great investor must understand.
• Lessons from negotiating against Carl Icahn.
• Why entrepreneurs need both conviction and humility.
• The career advice Jason wishes he had followed much earlier.

Guest Bio:

Jason Koenig is the Founder, Managing Partner at ITE Management, an investment firm specializing in transportation infrastructure and industrial real assets. Since founding the firm in 2013, he has grown ITE from a startup into a platform managing $6.5 billion in assets, with approximately $13.5 billion of assets owned and managed. Before launching ITE, Jason held investing and legal roles at Avenue Capital, Hale Capital Management, Kirkland & Ellis, Latham & Watkins, and Cooley. He earned an MBA from the Wharton School and graduate degrees from the University of Michigan.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Jason Koenig:

LinkedIn:https://www.linkedin.com/in/jason-koenig-goblue/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Everyone Ignored a $6.5B Opportunity (2:46) From $60M to $6.5 Billion AUM (8:34) The Entrepreneur's V-Shaped Ego (15:17) Why Great Leaders Need Humility (25:13) The Hardest Part of Scaling a Firm (31:09) Hire 3 Years Before You Need Them (35:02) The Best Career Pattern for Leaders (43:37) How Great Cultures Police Themselves (46:19) Why Investing Is Really Psychology (57:02) The Career Advice Everyone Gets Wrong

Venture capital isn't about avoiding losses. It's about owning the handful of companies that change everything. Scott explains why HarbourVest has built its venture strategy around power laws, why secondaries have become essential to modern venture investing, and how institutions evaluate managers, partners, and companies across thousands of investment opportunities. Highlights:

• Why accepting losses is the price of capturing venture's biggest winners.
• The data behind why 10% of companies generate 90% of industry returns.
• How secondaries allow LPs and GPs to stay invested in generational companies.
• Why some of the best venture funds intentionally extend beyond their original 10-year life.
• Why great venture investments almost always look "too expensive" at the time.
• How HarbourVest evaluates individual partners instead of just venture firms.
• The subtle signals Scott looks for when conducting GP references.
• Why diversification across vintages matters more than trying to time venture cycles.
• How HarbourVest believes venture investing will evolve over the next decade.

Guest Bio:

Scott Voss is a Partner at HarbourVest, a $160B multi-manager private equity firm, where he leads venture and co-investment strategies. With 27 years at the firm, he has helped scale HarbourVest from $150M to $160B AUM, pioneering the firm’s secondary, direct, and continuation vehicle strategies. Scott specializes in portfolio construction, private market diversification, and building long-term strategic GP relationships to generate repeatable alpha.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Scott C. Voss:

LinkedIn: https://www.linkedin.com/in/scott-voss-b91b94/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

HarbourVest Partners, LLC is a registered investment adviser under the Investment Advisers Act of 1940. This material is solely for informational purposes and should not be viewed as a current or past recommendation or an offer to sell or the solicitation to buy securities or adopt any investment strategy. The opinions expressed herein represent the current, good faith views of the author(s) at the time of publication, are not definitive investment advice, and should not be relied upon as such. This material has been developed internally and/or obtained from sources believed to be reliable; however, HarbourVest does not guarantee the accuracy, adequacy or completeness of such information. There is no assurance that any events or projections will occur, and outcomes may be significantly different than the opinions shown here. This information, including any projections concerning financial market performance, is based on current market conditions, which will fluctuate and may be superseded by subsequent market events or for other reasons. The information contained herein must be kept strictly confidential and may not be reproduced or redistributed in any format without the express written approval of HarbourVest.

Nothing herein should be construed as a solicitation, offer, recommendation, representation of suitability, legal advice, tax advice, or endorsement of any security or investment and should not be relied upon by you in evaluating the merits of investing in HarbourVest funds or in any other investment decision.

(0:00) Why Venture Capital Is a Power Law Business (2:08) The Liquidity Decision That Can Make or Break a Fund (5:33) Why Great Investors Keep Underestimating Their Biggest Winners (8:54) The Hardest Truth Every Venture Investor Must Accept (12:49) Why Consensus Investing Rarely Creates Outlier Returns (15:20) The Secret Behind HarbourVest’s Three-Pronged Venture Strategy (21:04) Why HarbourVest Tracks Individual Partners Instead of Just Firms (29:54) How Elite Venture Firms Quietly Lose Their Edge (33:49) What to Do If You Can’t Access Top-Tier Venture Funds (36:20) What Venture Capital Will Look Like in 10 Years

Venture capital has never been more competitive. Aram Verdian argues it has also never been more concentrated. Drawing on Accolade Partners' research across more than 3,000 U.S. venture firms, Aram explains why fewer than 20 firms have consistently produced 3x net returns, what separates the firms that keep winning, and why venture is increasingly becoming a winner-take-all business. From portfolio construction and manager selection to AI, late-stage investing, and fund sizing, he shares the framework his team uses to identify the next generation of exceptional venture firms. Highlights:

• Why fewer than 1% of venture firms consistently outperform public markets.
• The data behind venture capital's winner-take-all dynamics.
• Why seed investing has become more competitive than ever before.
• The "right to win" framework Aram uses to evaluate emerging managers.
• Why many successful seed firms struggle after raising larger funds.
• How LPs should think about concentration versus diversification.
• Why AI has fundamentally changed venture fundraising and company building.
• How private markets continue to delay IPOs and reshape venture returns.
• Why great LPs become long-term strategic partners instead of capital providers.
• The importance of relationships and culture in building enduring investment firms.

Guest Bio:

Aram Verdian is a Partner at Accolade Partners, where he focuses on venture capital fund investments, growth equity, and digital assets. Previously, he invested at Andreessen Horowitz and earlier spent several years at Accolade before returning as Partner. Today, he helps oversee more than $3 billion in assets under management while leading the firm's blockchain initiatives and identifying emerging venture managers capable of generating long-term, top-decile returns.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Aram Verdiyan:

LinkedIn:https://www.linkedin.com/in/aram-verdiyan-8099186/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Only 20 Venture Firms Consistently Win (3:42) The 3X Rule Every LP Should Know (9:07) Why Seed Investing Has Never Been Harder (16:20) The VC Math Behind Billion-Dollar Returns (23:05) Why Great Investments Are So Rare (33:16) Why Consistency Beats One Lucky Fund (38:23) The Secret Behind a VC's "Right to Win" (50:18) Why AI Broke Venture Capital (1:02:09) The Biggest Mistake Investors Make in AI (1:16:25) The Career Advice That Changed Everything

Most companies use AI to make employees slightly more productive. Sushanth Raman believes AI should do the work instead. As the CEO of Pallet, Sushanth is building an AI workforce for the $12 trillion logistics industry, helping carriers, brokers, freight forwarders, and shippers automate mission-critical operations inside the systems they already use. He explains why reasoning-driven AI represents the next wave of enterprise software, why logistics is uniquely positioned for AI transformation, and how businesses can move from copilots to fully autonomous workflows. Highlights:

• Why AI should execute workflows instead of simply assisting employees.
• The biggest inefficiencies still holding back the logistics industry.
• How reasoning models differ from traditional AI automation.
• Why enterprise AI adoption depends on integrating with existing software.
• Lessons from building an AI company in a $12 trillion industry.
• How logistics companies can deploy AI without replacing their core systems.
• Why domain expertise matters as much as technical expertise in AI startups.
• The future role of human operators in an AI-native logistics ecosystem.
• What investors often misunderstand about enterprise AI adoption.
• Why logistics could become one of AI's largest commercial opportunities.

Guest Bio:

Sushanth Raman is the CEO of Pallet, an AI company building a reasoning-driven workforce for the logistics industry. He founded Pallet in 2021 after seeing how one of the world's largest industries still relied on manual, error-prone workflows. Since launch, the company has raised $50 million from investors including Bain Capital Ventures, General Catalyst, Bessemer Venture Partners, and Activant. Today, Sushanth combines deep technical expertise with his family's roots in shipping to help carriers, brokers, freight forwarders, and shippers automate mission-critical operations with AI.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Sushanth Raman :

LinkedIn:https://www.linkedin.com/in/sushanth-raman/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why AI Won’t Transform Most Companies Anytime Soon (2:33) The #1 Trait of Companies That Actually Deploy AI (6:01) Why Employees Resist AI Even When They Believe in It (10:11) How Wall Street Could Force AI Adoption Overnight (17:27) Why the SaaS Apocalypse Is Being Misunderstood (20:23) The Future of Enterprise Software Is Hyper-Personalized (27:16) Why Supply Chain Is the Biggest AI Opportunity Nobody Sees (37:13) The Tiny Decisions That Compound Into Great Companies (44:13) Founder Mode vs Micromanagement Explained (55:50) The Advice Every Young Founder Needs to Hear

The best venture investors don't just identify great markets. They recognize exceptional founders before everyone else does. Michael Gilroy shares lessons from investing at Coatue, Microsoft's M12, Battery Ventures, Insight Partners, and now Marathon Management Partners. He explains what separates extraordinary founders from everyone else, how venture investors evaluate conviction versus consensus, why AI is changing the investment landscape, and how decades of experience shaped his founder-first investing philosophy. Highlights:

• Why the best venture investments begin with founders instead of markets.
• The founder characteristics Michael consistently looks for before investing.
• Lessons from investing across Coatue, M12, Battery Ventures, and Insight Partners.
• Why consensus thinking often produces average venture returns.
• How AI is reshaping the next generation of technology companies.
• The difference between backing great businesses versus great founders.
• Why founder obsession matters more than polished presentations.
• How exceptional venture investors develop long-term conviction.
• The lessons Michael carried into launching Marathon Management Partners.
• Why founder-first investing continues to outperform market-first investing.

Guest Bio:

Michael Gilroy is the Founding Partner of Marathon Management Partners, where he invests in exceptional technology companies across venture and growth stages. Before launching Marathon, he was a General Partner at Coatue, investing across both private and public technology markets. Earlier in his career, he held investing roles at M12 (Microsoft's Venture Fund), Battery Ventures, and Insight Partners, developing deep expertise in enterprise software, AI, and technology investing. Today, Michael brings a founder-first perspective shaped by decades of experience backing category-defining companies alongside many of the industry's leading investors.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Micheal Gilroy:

LinkedIn: https://www.linkedin.com/in/michaelbgilroy/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why the Best Venture Firms Think in Decades (2:17) The Biggest Mistake Founders Make When Building Boards (5:46) Why Great Board Meetings Aren't About the Past (9:12) The Simple Change That Makes Every Board More Valuable (13:41) How Incentives Quietly Shape Venture Capital (18:25) Why the Best Investors Measure People, Not Just Companies (23:08) The Hidden Cost of Growing Too Fast in Venture (28:16) The Framework Behind High-Performing Startup Boards (30:37) The Truth About Second-Generation Investors (36:45) The Leadership Trait That Separates Elite Investors

Most investors obsess over pre-tax returns. Scott Abookire argues they're measuring the wrong thing. As Chief Investment Officer of Pincus Capital, Scott oversees globally diversified public and private portfolios for multi-generational families. In this conversation, he explains why after-tax returns are the metric that truly matters, why he abandoned the traditional endowment model, and how sophisticated family offices think about risk, liquidity, and long-term compounding. Scott also shares the portfolio framework Pincus uses to manage drawdowns, why governance matters more than forecasts, and how the best investors stay disciplined when markets become emotional. Highlights:

• Why after-tax returns matter more than headline investment performance.
• The hidden cost taxes have on long-term wealth compounding.
• Why Pincus Capital moved away from the traditional endowment model.
• A better framework for portfolio construction based on liabilities instead of arbitrary asset allocation targets.
• How elite family offices manage risk without sacrificing long-term returns.
• The biggest mistakes investors make with private equity commitments.
• Why drawdown management is more important than volatility statistics.
• How long-term relationships create investment edge.

Guest Bio:

Scott Abookire is the Chief Investment Officer at Pincus Capital, a New York-based multi-family office that provides investment management and strategic advice to a select group of families with significant multi-generational wealth. Before joining Pincus Capital, he was a member of the investment team at the Metropolitan Museum of Art and previously worked at Cambridge Associates. Scott is a CFA Charterholder and earned his BS from Indiana University's Kelley School of Business.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Scott Abookire:

LinkedIn: https://www.linkedin.com/in/scottabookire/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Most Investors Measure Returns Incorrectly (2:58) The Problem With Pre-Tax Performance (5:37) How Pincus Capital Calculates After-Tax Returns (9:54) Why Taxes Change Portfolio Construction (11:41) Why Scott Left the Traditional Endowment Model (17:54) The Drawdown Framework Every Family Office Should Know (31:52) The Hidden Risk of Private Equity Capital Calls (37:40) Why Great Portfolios Fail During Market Stress (42:43) Lessons From the 2022 Private Markets Reset (47:45) Why Venture Capital Is All About Pacing

Most investors believe raising more capital is always a sign of success. Stephen Ketchum has spent nearly two decades proving the opposite. As Founder, CEO, and CIO of Sound Point Capital, Stephen built a $46 billion credit platform by resisting one temptation that destroys investment firms: deploying capital simply because it's available. Instead of maximizing assets under management, Sound Point limits fund sizes, turns away capital when opportunities aren't compelling, and prioritizes long-term trust over short-term fees. Stephen explains why excess capital weakens discipline, why incentives shape every organization, and why culture compounds just as powerfully as investment returns.

This material does not constitute an offer to sell or a solicitation of an offer to buy any securities. It is being provided solely for informational and reference purposes only and is not intended to be, and must not be, the basis for any investment decision. Statements represent the subjective views of Sound Point as of the date of the recording and cannot be independently verified and are subject to change. All investing involves risks, including the risk of a total loss. Source for other lender software exposure: J.P. Morgan Global Alternative Investment Solutions, Goldman Sachs, J.P. Morgan Investment Bank Credit Research. February 2026. Past performance is not necessarily indicative of future results.

Highlights:

• Why having more capital than ideas is one of investing's biggest risks.
• How Sound Point intentionally limits fund sizes instead of maximizing AUM.
• Why saying "no" to investors can strengthen long-term LP relationships.
• Why founder-led firms have an advantage in building trust with LPs.
• The hiring framework Stephen uses to avoid costly culture mistakes.
• Why incentives alone don't create great organizations.
• Why relationships, not money, have compounded the most over

Guest Bio:

Stephen Ketchum is the Founder, Managing Partner, CEO, and CIO of Sound Point Capital Management, a $46 billion alternative asset manager specializing in credit strategies. With more than 35 years in the credit markets, he previously led Media & Telecom Investment and Corporate Banking at Banc of America Securities and held senior investment banking roles at UBS and Donaldson, Lufkin & Jenrette.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Stephen Ketchum:

LinkedIn:https://www.linkedin.com/in/stephen-ketchum-7174366/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why More Capital Can Hurt Investment Returns (1:44) Knowing When a Hot Market Has Peaked (6:19) How Sound Point Manages $46B Without Losing Discipline (10:25) Why Being "Long-Term Greedy" Wins (15:42) Warren Buffett's Lesson Beyond Financial Compounding (19:51) The Founder Advantage in Asset Management (27:30) The Culture Code Every Firm Should Learn (31:58) Scaling Culture From 5 to 210 Employees (39:27) What a Founder Actually Does All Day (47:31) Making Time to Build the Next Five Years (52:48) How AI Can Increase Alpha

Everyone is asking which AI company will win. Lucas Swisher thinks investors are asking the wrong question. The biggest opportunities won't necessarily come from picking a single model or application. They'll come from understanding where durable advantages are created across the AI stack. Drawing on Coatue's investments in companies like OpenAI, Anthropic, Databricks, and SpaceX, Lucas explains why talent compounds, why data infrastructure may outlast today's application boom, why companies become harder—not easier—to disrupt as they scale, and how AI is reshaping the economics of software, semiconductors, and enterprise technology. Highlights:

• Why the AI application layer is far more resilient than many investors believe.
• The two AI infrastructure layers Lucas believes will generate the most enduring returns.
• Why companies above $10B may actually produce better venture outcomes than earlier-stage startups.
• How OpenAI and Anthropic continue extending their lead despite rapid industry innovation.
• Why talent has become the ultimate competitive moat in AI.
• How Coatue thinks about NVIDIA, custom silicon, and the next generation of chip companies.
• Why AI is making high-performing organizations more productive instead of replacing them.
• The biggest mistakes investors are making during today's AI investment cycle.

Guest Bio:

Lucas Swisher is a Co-Head of Growth Investing at Coatue Management, where he co-leads growth investing and software investing with a focus on AI, enterprise software, and cybersecurity. He has helped oversee Coatue's investments in OpenAI, Anthropic, SpaceX, and Databricks. Previously, he worked at Kleiner Perkins, Insight Partners, and Delivery Hero, and graduated from Harvard University.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Lucas Swisher:

LinkedIn:https://www.linkedin.com/in/lucasswisher/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Who Captures the Value Created by AI? (0:38) Will Foundation Models Crush AI Applications? (2:01) How to Identify Durable AI Companies (5:29) Why Frontier Models Keep Pulling Ahead (11:13) Is the Mag Seven Already Dead? (16:40) The Two AI Layers Coatue Is Most Bullish On (19:24) Why OpenAI and Anthropic Are Growing So Fast (26:13) Will AI Replace Jobs or Create More? (35:17) The Surprising Data Behind 10x Companies (37:43) Why Talent Beats Technology (44:52) The Biggest Bottleneck Holding AI Back (48:00) Can Anyone Challenge NVIDIA? (53:44) The Biggest Mistakes AI Founders Are Making (57:26) Where AI Investors Are Most Likely to Lose Money (59:39) What Lucas Changed His Mind About in AI (1:01:05) Why Coatue's Public + Private Strategy Matters (1:02:36) The Career Advice Lucas Wishes He Learned Earlier

After more than 400 conversations with investors, founders, CIOs, and capital allocators managing over $10 trillion, the tables finally turn. In this special episode, Curtis Pierce, Co-Founder of Weisburd Pierce and the How I Invest podcast, interviews host David Weisburd about the biggest ideas that have permanently changed his thinking. David argues that the greatest compounding force isn't capital. It's relationships, reputation, access to information, and the ability to surround yourself with excellence early in your career. From venture capital and family offices to LP-GP relationships and organizational culture, he shares the principles shaping how Weisburd Pierce invests and builds enduring partnerships. Highlights:

• Why relationships compound faster than money
• The hidden advantage of brand and access
• How elite investors think about long-term partnerships
• Why the best opportunities rarely reach everyone
• Lessons from interviewing 400+ world-class investors
• Why culture becomes the only lasting competitive advantage
• How to build conviction instead of chasing consensus
• The investing philosophy behind Weisburd Pierce

About David Weisburd:

David Weisburd is a Co-Founder of Weisburd Pierce and host of the How I Invest podcast. Previously, he served as Partner and Head of Venture Capital at 10X Capital, leading investments in companies including Robinhood, HoneyBook, Palantir, Circle, and DraftKings. Earlier in his career, he helped build venture-backed startups iSocket and RoomHunt, both of which were acquired. He has served on the boards of three public companies and holds degrees from Dartmouth's Tuck School of Business and Harvard University.

About Curtis Pierce:

Curtis Pierce is a Co-Founder of Weisburd Pierce and the How I Invest podcast. Previously, he served as Senior Vice President at 10X Capital, where he led venture investing and capital markets initiatives, including the firm's investment in Cerebras Systems. He began his career at Wells Fargo Securities and serves as President of the New York City Chapter of the University of Utah Alumni Association.

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Curtis Pierce:

LinkedIn: https://www.linkedin.com/in/curtisapierce/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Einstein Was Wrong About Compounding (0:52) The Biggest Lesson From 400 Interviews (5:48) Why Excellence Changes Everything (10:27) Social Friction vs Intelligence (12:25) Why Relationships Compound (20:30) Building Long-Term Partnership Advantage (28:54) Culture Is the Ultimate Competitive Moat (40:00) Why Great LP-GP Relationships Matter (47:48) How David Thinks About Venture Investing (57:34) The One Lesson Every Investor Should Remember

Most investors spend their lives searching for more ideas. Anthony Pompliano thinks the real money comes from finding the rare idea and refusing to let go. Across public markets, private markets, Bitcoin, startups, and careers, Anthony argues that value follows power laws: a tiny number of companies, people, and decisions drive almost everything. The hard part is not effort. It is recognizing durable asymmetry early, pressing your winners harder, and resisting the temptation to sell simply because liquidity is available. The deeper lesson is scarcity. Great companies are scarce. Great investors are scarce. Great people are scarce. And when you find one, the job is not to constantly rotate into something new. The job is to understand what you own, build conviction, and let compounding do the work. The Numbers Behind This Episode

• 46 companies have created 50% of the $90T of stock market value since 1925.
• The NASDAQ has historically been viewed as a 13% return vehicle, while venture funds average around 17% to 18%.
• Antonio Gracias reportedly invested in SpaceX 30 times.
• Anthony describes one company with 11 employees serving $50B in assets on its software platform.

Highlights:

• Why 5% of ideas can drive 95% of outcomes
• How durability, asymmetry, and volatility create exceptional investments
• Why selling may be harder than buying
• Why liquidity can become a behavioral disadvantage
• How SpaceX became the ultimate example of pressing a winner
• Why concentration is often a sign of conviction
• Why “luck” may be more psychological than real
• How winning cultures are built through standards, exposure, and mission

Guest Bio:

Anthony Pompliano is an entrepreneur, investor, and one of the most widely followed voices at the intersection of business, finance, and technology. He is the founder and CEO of Professional Capital Management, author of the daily Pomp Letter newsletter, and host of The Pomp Podcast, where he interviews many of the world's leading investors, entrepreneurs, and executives.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Anthony Pompliano:

LinkedIn:https://www.linkedin.com/in/anthonypompliano/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Power Laws Rule Investing (1:15) Durability, Asymmetry, and Volatility (2:33) Building Portfolios Around Best Ideas (5:18) Buffett, Compounding, and Starting Early (7:25) Why Selling Is the Hardest Decision (10:04) Is Liquidity Actually a Problem? (14:06) Finding Non-Consensus Asymmetric Bets (18:02) Physical AI, Robotics, and the Next Big Theme (20:18) The SpaceX Conviction Test (21:33) Why 46 Companies Created Half the Wealth (26:05) Discipline in Venture Fund Construction (28:22) Why Luck Is Not Real (32:31) Attracting Success Instead of Chasing It (37:21) Turning Losers Into Winners (40:43) Building a Winning Culture (46:02) What Great Organizations Have in Common (50:50) Why Mission Creates Intensity (1:00:00) Scaling Culture With Small Teams (1:04:27) Go Bigger and Take Bigger Risks (1:05:59) Scarcity Is Value

Most investors assume that once a venture firm reaches $43 billion in assets under management, the real opportunities shift toward writing larger checks. Yuri Sagilov believes the opposite. General Catalyst continues to push deeper into seed because that's where investment themes are born, founder relationships are formed, and category-defining companies are first recognized. Rather than optimizing for larger deployments, the firm optimizes for ownership, conviction, and seeing the future before everyone else. It's also why General Catalyst intentionally removed signaling risk from its seed strategy, giving founders confidence that early backing won't become a disadvantage later. Throughout our conversation, Yuri explains why AI-native founders think differently, why the best venture firms remain generalists, and why the next decade of venture may look very different from the last. Highlights:

• Why General Catalyst believes seed delivers some of venture's best returns.
• How the firm eliminated signaling risk without sacrificing ownership.
• Why Anduril changed the way investors think about defense startups.
• Why today's AI-native founders are building from a completely different starting point.
• The case for staying a generalist instead of launching sector-specific funds.
• Why ownership matters more than the size of the initial investment.
• How private markets could keep the best companies private much longer.
• The relationship philosophy Yuri says has compounded the most throughout his career.

Guest Bio:

Yuri Sagilov is a Partner at General Catalyst, where he focuses on seed investing across the firm's global platform. Previously, he founded Wayfinder Ventures, a first-check seed fund whose portfolio companies have created more than $23 billion in value.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Yuri Sagalov:

LinkedIn: https://www.linkedin.com/in/yurisagalov/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why a $43B Firm Still Bets on Seed (2:39) Finding Categories Before They Exist (4:00) Learning From Founders Living in the Future (5:47) Why Great Seed Investors Stay Generalists (8:51) Eliminating Signaling Risk (12:08) Building General Catalyst's New Seed Strategy (13:27) Inside a 200-Company Seed Portfolio (14:40) Does Every Investment Need to Return the Fund? (16:05) Recognizing Power Law Companies Early (18:04) Why the Best Companies May Stay Private Longer (24:50) The Highest Compounding Asset in Venture (26:33) Why Yuri Became More Bullish on AI

What separates the venture investors who consistently outperform from those who simply get lucky? In this episode, I sit down with Miguel Luina, Co-Head of Global Venture Capital at Hamilton Lane, to discuss how one of the world's largest private markets investors evaluates venture managers, constructs portfolios, and thinks about the future of innovation investing. Miguel explains why venture and growth have become an essential allocation for institutional investors, how LPs distinguish skill from luck, and why conviction investing, secondaries, and portfolio construction may be the biggest drivers of long-term returns. Highlights:

• Why venture capital is entering a new liquidity cycle driven by AI and IPOs
• How Hamilton Lane distinguishes skill from luck when selecting venture managers
• Why sourcing, selection, and access are the three pillars of venture investing
• The importance of conviction investing—and doubling down on exceptional companies
• Why venture secondaries represent one of the most undercapitalized opportunities in private markets
• How continuation vehicles are reshaping venture liquidity
• Why institutional investors can no longer ignore venture and growth allocations
• The evolution of portfolio construction across funds, co-investments, and secondaries
• How the best venture managers compound relationships over decades
• Miguel's timeless advice on investing in people and letting relationships compound

Guest Bio:

Miguel Luina is Co-Head of Global Venture Capital at Hamilton Lane, where he oversees the firm's global venture, growth equity, and technology investment strategy. He leads investment sourcing, due diligence, and portfolio management across venture capital funds, co-investments, secondaries, and growth equity opportunities while serving as a member of the firm's investment committee. Hamilton Lane manages and supervises more than $1 trillion in assets across private markets, making it one of the world's largest private markets investment firms.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Miguel Luina:

LinkedIn: https://www.linkedin.com/in/miguel-luina/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Venture Capital Is Entering a New Golden Age (1:06) How SpaceX, OpenAI, and Anthropic Could Reshape Venture (3:13) The Secret to Separating Skill From Luck in Venture Capital (6:05) Has Venture Capital Become a Consensus Trade? (11:41) Why Ignoring Venture Is Now a Massive Allocation Bet (16:10) The Portfolio Strategy Most Venture LPs Get Wrong (20:03) Why Continuation Vehicles Are Exploding in Venture (28:17) The Structural Alpha Hidden Inside Venture Secondaries (35:58) The Portfolio Construction Mistake That Kills Returns (40:56) Why the Best Investors Keep Doubling Down on Winners

What if the greatest edge in venture capital isn't having the biggest fund—but building the strongest relationships? In this episode, I sit down with Elizabeth Weil, Founder and Managing Partner of Scribble Ventures, to discuss how emerging venture firms can outperform by staying focused, collaborative, and relentlessly founder-centric. Elizabeth shares how she built Scribble into a $280 million venture platform by backing exceptional founders at the earliest stages, why venture is fundamentally a network effects business, and why staying authentic has become one of her greatest competitive advantages. Highlights:

• Why venture capital is ultimately a network effects business
• How Scribble Ventures raised an oversubscribed fund in one of the toughest fundraising environments
• Why relationships compound more than almost anything else in investing
• Elizabeth's framework for identifying exceptional founders before consensus forms
• The importance of staying authentic with founders, LPs, and partners
• Why smaller venture funds can outperform larger platforms
• How Scribble approaches ownership, fund sizing, and portfolio construction differently
• The value of saying no—to both founders and LPs—when the fit isn't right
• Why breakout investing extends beyond simply finding companies at seed
• Lessons from Twitter's hypergrowth years and Andreessen Horowitz's rise
• The role of curiosity, consistency, and daily habits in long-term investing success
• Why every career ultimately compounds through relationships

Guest Bio:

Elizabeth Weil is the Founder and Managing Partner of Scribble Ventures, an early-stage venture capital firm managing approximately $280 million in assets focused on partnering with exceptional founders at the pre-seed, seed, and breakout stages. Over more than two decades in venture capital and technology, she has invested in more than 60 technology companies including SpaceX, Slack, Coinbase, Whatnot, Gusto, Grab, Calm, Envoy, Hipcamp, and Daily.co.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Elizabeth Weil:

LinkedIn: https://www.linkedin.com/in/elizabethweil/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) How Elizabeth Raised an Oversubscribed Venture Fund in 2026 (1:47) The Network Effect That Separates Great Venture Firms (6:14) The Fastest Way to Build Judgment as an Investor (8:34) The Founder Traits That Matter More Than the Idea (12:34) The LP Fundraising Lesson Most Emerging Managers Miss (19:12) Why She Turned Down LP Capital on Purpose (22:25) What Elizabeth Looks for Before Writing a $3 Million Check (28:25) The Venture Capital Myth That Most LPs Still Believe (33:04) When Venture Firms Stop Being Investors and Become Asset Managers (38:47) The Career Advice That Compounds for Decades

What if AI's most valuable commodity isn't software—but the computing power that makes intelligence possible? In this episode, I sit down with Kush Bavaria, Co-Founder and CEO of Ornn, to discuss why AI compute is becoming the next global commodity and how financial markets are evolving to support it. Kush explains why GPU capacity should trade like oil or electricity, how derivatives and futures markets could reshape AI infrastructure, and why access to compute may become one of the defining competitive advantages of the next decade. We also explore data centers, energy constraints, AI capital markets, and what it takes to build a venture-backed company at just 22 years old. Highlights:

• Why AI compute could become the world's next strategic commodity
• How Ornn is building a financial exchange for GPU capacity
• Why data centers need futures markets and price indices
• The growing importance of compute in the AI arms race
• Why energy, not capital, may become the biggest bottleneck for AI
• The investment opportunity behind data centers and AI infrastructure
• How America can maintain its competitive advantage in AI
• Building one of the fastest-growing AI infrastructure startups at age 22
• Why customer obsession has become Ornn's biggest competitive advantage
• Kush's biggest lesson about hiring and scaling a startup

Guest Bio:

Kush Bavaria is the Co-Founder and CEO of Ornn, an AI infrastructure company building the financial markets for compute. Backed by Andreessen Horowitz, Ornn creates standardized price indices, exchanges, and derivatives that allow GPU capacity to be bought, sold, and hedged like traditional commodities. The company helps data centers monetize future compute capacity while enabling AI companies, developers, hedge funds, and enterprises to access computing power more efficiently.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Kush Bavaria:

LinkedIn:https://www.linkedin.com/in/kush-bavaria/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Compute Could Become the World’s Most Important Commodity (0:47) The $7 Trillion Market Most Investors Still Don’t Understand (2:03) Why AI Compute Needs a Futures Market (4:13) The Five Layers of the AI Economy Explained (6:12) The Missing Compute Market Every AI Startup Needs (8:27) Is There Really a Data Center Bubble? (10:10) Why OpenAI Is Winning the Compute Race (12:36) Why Andreessen Backed a 22-Year-Old Founder (14:41) The AI Arms Race Between the U.S. and China (18:37) The Startup Lesson That Matters More Than Building Product

What happens when computers stop being tools and start behaving like collaborators? In this episode, I sit down with Russ d’Sa, Founder and CEO of LiveKit, to discuss why voice AI may become one of the most important computing platforms of the next decade. Russ explains how LiveKit powers AI experiences for companies including Tesla and xAI, why voice is emerging as the natural interface for AI agents, and what the rise of digital labor means for workers, founders, and society. Highlights:

• Why voice AI is becoming the next major computing interface
• The difference between voice-first and multimodal AI experiences
• How AI agents are already transforming customer service, healthcare, and financial services
• Why speed and conversational intelligence unlocked the voice AI revolution
• Russ’s view on whether AI will create or destroy jobs
• Why creativity may become more valuable as execution gets commoditized
• The types of careers most resilient to AI disruption
• Why reputation and relationships remain difficult to automate
• The importance of agency, adaptability, and learning velocity in an AI-driven world
• How companies should think about integrating AI across their organizations
• Why AI-native companies may outperform incumbents over the next decade
• Russ’s framework for choosing execution risk over market risk when building startups
• The long-term bet that computers will become increasingly human-like

Guest Bio:

Russ d’Sa is the Founder and CEO of LiveKit, the leading infrastructure platform powering real-time voice, video, and AI applications. LiveKit has become foundational infrastructure for the emerging voice AI ecosystem, serving companies including Tesla and xAI while helping developers build next-generation AI agents and multimodal experiences.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Russ d'Sa:

LinkedIn: https://www.linkedin.com/in/russelldsa/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Voice AI Could Become the Next Computing Platform (4:42) The Multi-Billion Dollar Industry AI Is Replacing First (9:16) The Two Breakthroughs That Made Voice AI Finally Work (14:15) Will AI Create More Jobs or Eliminate Them? (18:55) How to Avoid Getting Replaced by AI Over the Next Decade (23:30) Why Reputation and Relationships Become More Valuable in an AI World (30:12) The Two Traits Russ Looks for in Every New Hire (33:49) When Non-Engineers Will Be Able to Build Software (41:51) Why Most Companies Are Failing to Implement AI (46:24) The One Startup Lesson He Wishes He Learned Much Earlier

What if the biggest mistake LPs make in venture is backing the same managers over and over instead of constantly asking who they would invest in if they were starting from scratch today? In this episode, I sit down with Jamie Rhode, Partner at Screendoor, to discuss what separates the best emerging managers from the rest of the market. Jamie explains why so many venture funds look identical today, how LPs unintentionally create that dynamic, and why manager selection is really about finding GP-market fit. Highlights:

• Why so many emerging managers look exactly the same to LPs
• The concept of GP-market fit and why it matters more than ever
• What separates great investors from great fund managers
• Why endurance and adaptability matter more than early momentum
• The role of disagreement and respect in high-performing partnerships
• Jamie's framework for 90% rules-based investing and 10% "break-the-rule" investments
• Why fund one managers may have structural advantages over established firms
• How successful GPs refresh their networks before their edge disappears
• The founder flywheel effect and its impact on sourcing
• Why LPs should ask themselves: "Would I invest in this manager again today?"
• The hidden risks of strategy drift as venture firms mature
• Why sitting out a vintage year may be more costly than backing the wrong manager

Guest Bio:

Jamie Rhode is a Partner at Screendoor, a venture-focused fund-of-funds platform that anchors and supports the next generation of venture capital managers. Prior to Screendoor, she spent more than eight years at Verdis Investment Management, a single-family office where she focused on emerging venture managers, private equity, and hedge fund investments.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Jamie Rhode:

LinkedIn: https://www.linkedin.com/in/jerrcfa/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Most Venture Managers Sound Exactly the Same (1:41) The Hidden Framework Behind Great Emerging Managers (3:39) What It Actually Takes to Be a Top Seed Investor Today (5:47) Which Emerging Managers Will Survive the Extinction Event? (10:00) Why Great Venture Partnerships Need More Than Complementary Skills (14:29) The 10% Rule That Creates Venture Outliers (18:55) Why Fund One Managers Have a Structural Advantage (22:59) The One Trait Shared by Long-Term Winning Venture Firms (27:56) The Biggest Mistake LPs Make When Re-Upping Managers (35:18) How Emerging Managers Can Compete Against Mega Funds

What if the biggest edge in investing isn’t information, strategy, or even intelligence—but relationships? In this episode, I sit down with Ron Biscardi, Co-Founder and CEO of iConnections, to discuss what separates the world’s best allocators and investment managers from everyone else. Ron shares lessons from building the largest capital introduction ecosystem in alternatives, with more than 26,000 members across 80+ countries representing over $55 trillion in assets. We explore the role of EQ in investing, why relationships compound into investment advantages, how emerging managers should think about fundraising, and why some of the most successful investment firms are built by entrepreneurs rather than investors alone. We also discuss conviction, illiquidity, LP decision-making, manager selection, and the realities of navigating capital markets over decades. Highlights:

• What separates the top 1% of allocators and fund managers
• Why curiosity, humility, and continuous learning drive investment success
• The critical role of EQ and relationship-building in generating investment edge
• Why the best investors actively seek out viewpoints that challenge their own
• How emerging managers should approach fundraising and finding anchor investors
• The hidden psychology behind LP decision-making
• Why conviction must be balanced with adaptability
• The advantages of illiquidity and protecting investors from behavioral mistakes
• How LPs distinguish skill from luck in private markets
• Why many successful investment firms are built by entrepreneurs, not just investors
• Ron’s hardest lesson from decades in alternative investments and capital raising

Guest Bio:

Ron Biscardi is the Co-Founder and CEO of iConnections, the leading global capital introduction platform connecting investment managers, institutional allocators, and family offices. Under his leadership, iConnections has grown into the largest alternative investment ecosystem in the world, serving more than 26,000 members across 80+ countries that collectively represent over $55 trillion in assets under management.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Ron Biscardi:

LinkedIn: https://www.linkedin.com/in/rbiscardi/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) What Separates the Top 1% of Allocators From Everyone Else (2:04) Why EQ Matters More Than Most Investors Realize (4:02) The Relationship Strategy Behind a $2 Billion OpenAI Position (6:02) Why Conviction Can Be Dangerous Without This One Thing (8:17) How Antonio Gracias Built Extreme Conviction in SpaceX (10:06) If He Were Raising a First-Time Fund Today, Here’s What He’d Do (13:51) Why Anchor Investors Matter More Than Most GPs Think (18:23) The Private Markets Problem Nobody Talks About (23:27) The Behavioral Edge That Separates Great Investors (32:26) What the Most Successful Fund Managers All Have in Common

What if the secret to building generational wealth isn’t finding the perfect investment—but finding the right people and holding great businesses for decades? In this episode, I sit down with Jason Pritzker, Managing Director and Vice Chairman of The Pritzker Organization and founder of 53 Stations, to discuss the investing principles that helped shape one of America’s most successful business families. Jason shares the story of how the Pritzker family built its fortune, why long-term ownership creates powerful advantages, and how partnering with exceptional leaders compounds value over time. Highlights:

• How the Pritzker family built a multi-generational investment empire
• Why finding the right partners matters more than finding the perfect deal
• The advantages of long-term ownership versus constant buying and selling
• Lessons Jason learned transitioning from private equity to venture capital
• Why great founders matter more than investment theses
• How 53 Stations developed its venture investing strategy
• The surprising similarities and differences between PE and venture investing
• Why board structure and governance can make or break a company
• The role of customer introductions as a venture capital value-add
• How family values and upbringing shaped Jason’s investing philosophy

Guest Bio:

Jason Pritzker is Founder and Managing Partner of 53 Stations, the venture arm of The Pritzker Organization, where he also serves as Vice Chairman. Backed by an inaugural $187 million commitment, 53 Stations invests in early-stage technology companies, bringing flexibility and scale to its founder partnerships, building companies that stand the test of time.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Jason Pritzker:

LinkedIn: https://www.linkedin.com/in/jasonpritzker/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) The Forgotten Decision That Built the Pritzker Fortune (2:03) Why Picking the Right Partner Matters More Than Any Deal (5:27) The Hidden Flaw in the Traditional Private Equity Playbook (8:48) When Selling a Great Company Actually Makes Sense (11:21) Why Most Family Offices Lose Money in Venture Capital (15:14) The Private Equity Habits That Fail in Venture Investing (18:36) Why Great Founders Matter More Than Great Markets (21:09) The Surprising Advantage Behind 53 Stations’ Investment Strategy (25:04) The Boardroom Mistake That Weakens Startups (36:35) The Career Advice He Wishes He Learned a Decade Earlier

What if the biggest driver of long-term investment success isn't finding better investments, but helping investors avoid their own worst decisions? In this episode, I sit down with Ron Albahary, Chief Investment Officer at LNW, to discuss the unique challenges of managing wealth for taxable investors and why portfolio construction is as much about psychology as it is about finance. Highlights:

• Why managing investor behavior may be more important than picking investments
• The overlooked tax strategies that compound wealth over decades
• How framing risk in dollars instead of percentages changes decision-making
• Why fewer investment decisions often lead to better outcomes
• Lessons from three decades of market cycles and investment fads
• The role hedge funds and diversifiers play during periods of market stress
• Why some evergreen private market structures are misunderstood by investors
• The case for lower middle market private equity over mega-funds
• How AI is creating hidden concentration risk across portfolios
• Why humility may be one of the most underrated traits in investing

Guest Bio:

Ron Albahary is the Chief Investment Officer of LNW, where he oversees approximately $17 billion in assets and leads the firm's investment strategy across public and private markets. Over a career spanning more than three decades, Ron has served as both a Chief Executive Officer and Chief Investment Officer, helping oversee more than $175 billion in client assets.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Ron Albahary:

LinkedIn: https://www.linkedin.com/in/ron-albahary-cfa/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Managing Humans Is Harder Than Managing Portfolios (2:19) The Highest-Conviction Ways to Create Wealth Without Taking More Risk (4:13) Why Taxable Investors Need a Different Portfolio Playbook (7:34) The Portable Alpha Mistake Investors Keep Repeating (11:01) The Simple Question That Reveals Someone’s True Risk Tolerance (15:56) Why Illiquidity Can Be a Feature, Not a Bug (20:23) The Counterintuitive Reason Great Investors Make Fewer Decisions (25:10) Will Retail Capital Destroy the Private Equity Illiquidity Premium? (33:40) Why Lower Middle Market May Be the Best Place to Find Alpha (42:54) How to Build a Portfolio That Isn’t Dependent on AI

What if the best venture investors aren’t chasing the hottest sectors—but the founders who would still be working on the problem long after the hype disappears? In this episode, I sit down with Ron Rofé, Co-Founder and General Partner of Rainfall Ventures, to discuss why founder quality matters more than industry trends, how non-consensus investing creates outsized opportunities, and what he has learned from backing over 120 startups and 230 founders. Ron shares the stories behind investments like Robinhood, Webflow, and Alma, explains why he prioritizes resilience over ideas, and discusses the founder traits that consistently predict success. Highlights:

• Why Ron avoids chasing consensus investment themes, including AI
• The founder traits that matter more than market size or industry
• How Rainfall backed Robinhood before it became a fintech giant
• Why resilience often matters more than the original business idea
• The surprising advantage of investing in non-consensus markets
• How great founders balance conviction with humility
• Why half of venture value is created before categories are fully recognized
• The networking philosophy that helped build Rainfall Ventures
• How helping founders creates long-term investing advantages
• Ron’s timeless advice: “Nobody knows anything”

Guest Bio:

Ron Rofé is the Co-Founder and General Partner of Rainfall Ventures, an early-stage venture capital firm that has backed category-defining companies including Robinhood, Webflow, Alma, and Harmonic. Over the past decade, Ron has invested in more than 120 startups representing over 230 founders, building a reputation for making non-consensus bets and identifying exceptional entrepreneurs before the market recognizes them.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Ron Rofé:

LinkedIn: https://www.linkedin.com/in/ronrofe/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why He Refuses to Be an AI-Only Investor (3:23) The Opportunity Cost Most Venture Capitalists Ignore (6:04) Why Half of Venture Returns Are Created Before a Market Has a Name (10:08) The Founder Trait That Matters More Than Intelligence (14:10) The Five Qualities He Looks for Before Writing a Check (17:32) How One Founder’s Humility Created a Billion-Dollar Outcome (22:28) The Unusual Way He Got Into Robinhood Before It Took Off (25:52) Why He Invested at a $300M Valuation When Everyone Thought He Was Crazy (31:46) The Hidden Flaw in Thesis-Driven Venture Capital (37:34) The Advice That Changed How He Thinks About Success

What happens when one investor sits at the intersection of venture capital, natural resources, AI, space infrastructure, and geopolitics? In this episode, I sit down with Rob Stephens, Director of Investments at Spider Management, to discuss how institutional investors are adapting to a world where private markets are capturing more value, AI is reshaping capital allocation, and the boundaries between asset classes are disappearing. Rob shares lessons from both the GP and LP sides of the table, explains why traditional portfolio construction frameworks may be outdated, and explores how themes like power generation, data centers, space infrastructure, and venture capital are becoming increasingly interconnected. We also discuss emerging managers, co-investments, continuation vehicles, concentration versus diversification, and the future of private markets. Highlights:

• How experience as both a GP and LP changes investment decision-making
• Why traditional asset allocation buckets may no longer reflect reality
• The growing divide between investors with access to elite private companies and everyone else
• Why Anthropic, OpenAI, and SpaceX are reshaping private market investing
• The rise of venture co-investments and SPVs
• How LPs evaluate alignment when reviewing co-investment opportunities
• Why references matter more than track records when evaluating spinout managers
• The debate between concentration and diversification in institutional portfolios
• How AI, power generation, natural resources, and venture capital are becoming deeply interconnected
• Why data centers, energy infrastructure, and even space-based computing may become major investment themes

Guest Bio:

Rob Stephens is Director of Investments at Spider Management, the University of Richmond’s $7 billion investment office and OCIO platform. He leads investments across venture capital, private equity, real assets, and thematic public market strategies, with a focus on deep tech, space, defense, AI, energy, natural resources, and China. Prior to joining Spider in 2022, Rob was a Managing Director at DAC Management in Hong Kong and New York, where he specialized in Chinese markets and cross-border investing.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Rob Stephens:

Spider Management Company: https://spiderinvests.com/ LinkedIn: https://www.linkedin.com/in/robstephens3/ X/Twitter: @robstephens_

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) What GPs Hide That Most LPs Never Notice (2:26) Why Traditional Asset Allocation Is Starting to Break (4:11) Will OpenAI, Anthropic, and SpaceX Fix Venture’s DPI Problem? (6:29) Why Emerging Managers May Struggle More Than Ever (9:05) The Capital Moat Protecting Tier 1 Venture Firms (11:08) The Unusual LP Model That Forces Extreme Alignment (15:08) Why Venture Firms Are Launching More SPVs Than Ever (24:23) Is Venture Capital Heading Toward an Extinction Event? (37:56) Why AI Is Turning Venture Capital Into a Natural Resources Bet (47:52) Can the Biggest Private Companies Stay Private Forever?

What if the biggest edge in investing today isn't having more information—but knowing how to turn information into conviction? In this episode, I sit down with Matt Wells to discuss how AI is reshaping the investment process, why investors are drowning in data but starving for conviction, and where information alpha still exists in increasingly efficient markets. Matt explains the evolution of expert networks, how the best investors use expert calls and channel checks to build differentiated insights, and why qualitative information often drives quantitative outcomes. We also explore decision-grade AI, conviction building, private market diligence, and how the role of the analyst is changing in an AI-driven world. Highlights:

• Why investors today are drowning in data but starving for conviction
• The difference between information and decision-grade intelligence
• How expert calls evolved from niche hedge fund tools into scalable research platforms
• Why qualitative signals often become quantitative outcomes
• The role of channel checks in forecasting company performance
• How AI can help identify patterns across thousands of expert conversations
• Why conviction matters more than information during periods of volatility
• The future of analysts as architects rather than spreadsheet builders
• How grounded AI differs from general-purpose AI models
• Why human relationships remain irreplaceable in investing and business

Guest Bio:

Matt Wells is a technology executive and entrepreneur focused on applying artificial intelligence and market intelligence tools to investment research and decision-making. Prior to joining AlphaSense, he founded and scaled multiple businesses, bringing a unique operator's perspective to financial technology and research workflows. Today, he works at the intersection of AI, expert intelligence, and investment research, helping institutional investors, corporations, and advisors turn overwhelming amounts of information into actionable insights and higher-conviction decisions.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Matthew Wells:

LinkedIn: https://www.linkedin.com/in/matthew-wells-932b6a2/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Investors Are Drowning in Data but Starving for Conviction (2:04) The Dangerous Problem With AI Nobody Talks About (4:17) How Expert Calls Became a Hidden Edge for Elite Investors (6:54) The SpaceX IPO Research Strategy Most Investors Won’t Use (11:17) How Top Funds Turn Hundreds of Expert Calls Into Alpha (15:58) Why Every Quantitative Model Starts With Qualitative Information (17:39) Where Investment Alpha Will Come From in an AI World (20:11) The Missing Ingredient Behind Every Great Investment Thesis (24:37) Why the Analyst Role Is About to Change Forever (31:34) The Career Advice That Applies to Investing, Sales, and Life

What if the best private equity opportunities are hiding inside businesses that everyone else thinks are too complicated to touch? In this episode, I sit down with Josh Adams, Partner at OpenGate Capital, to discuss why complexity has become one of the firm's greatest competitive advantages. Josh explains how OpenGate built a specialization around corporate carve-outs, why Europe offers more inefficiency than North America, and how operational improvements drive value creation in today's market. We also discuss sourcing, specialization, alignment, decision-making, and why focus has become increasingly important as private equity continues to evolve. Highlights:

• Why Europe has become a bigger opportunity than North America
• The hidden alpha inside corporate carve-outs and orphaned assets
• Why OpenGate thinks of itself as operational engineers, not financial engineers
• How complexity creates a sustainable competitive advantage
• The sourcing strategy that puts OpenGate in front of deals before they reach market
• Why speed and certainty consistently win transactions
• Lessons learned from Platinum Equity's operating model
• The dangers of chasing trends and losing strategic focus
• Why specialist firms may outperform as private equity consolidates
• How alignment changes investment behavior and decision-making
• The compounding power of relationships throughout a career

Guest Bio:

Josh Adams is a Partner at OpenGate Capital, where he is responsible for origination, execution, fundraising, and firm management, and serves as a member of the firm's Investment Committee. Since joining OpenGate in 2012, he has helped build the firm into one of the leading specialists in complex corporate carve-outs across Europe and North America. Prior to OpenGate, Josh was a Vice President at Platinum Equity, leading the firm's European business development efforts from London. He began his career as an accountant and is a member of the Association of Chartered Certified Accountants (ACCA).

Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/

Stay Connected with Josh Adams:

LinkedIn: https://www.linkedin.com/in/joshua-m-adams-70602126/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Europe Has Become a Bigger Opportunity Than the U.S. (1:30) The Alpha Hidden Inside Complex Corporate Carve-Outs (5:22) How a $30,000 401(k) Became a Billion-Dollar Firm (10:15) The Sourcing Strategy That Wins Deals Before Auctions Begin (15:22) Why Speed and Certainty Beat Bigger Funds (21:01) The Real Reason Platinum Equity Keeps Winning (23:29) Is Private Equity Quietly Turning Into Asset Management? (26:54) Why Smaller Funds Could Outperform for the Next Decade (30:40) The Alignment Test Every GP Should Pass (32:48) The Career Lesson That Compounds More Than Capital

What separates the venture investors who generate extraordinary returns from those who simply participate in the asset class? In this episode, I sit down with Jeff Diehl, Managing Partner and Head of Investments at Adams Street Partners, one of the world's largest private markets investors with more than $70 billion in assets under management. Jeff shares lessons from over four decades of venture investing, including why access to top managers matters more than almost anything else, what 14,000 realized venture exits have taught Adams Street about return generation, and why portfolio construction often matters more than stock picking. Highlights:

• Why access to top-quartile venture managers is the single most important factor in venture investing
• The data behind venture capital's unmatched persistence of returns
• What Adams Street learned from nearly 14,000 realized venture-backed company exits
• Why just 7% of companies generated 100% of venture gains
• The critical role of portfolio construction and time diversification
• How Adams Street uses co-investments and secondaries to increase exposure to breakout winners
• Why venture capital succession planning is notoriously difficult
• The relationship between incentives, culture, and long-term investment performance
• Whether venture capital is becoming more concentrated among a handful of mega-firms
• Why private markets continue to capture a growing share of global growth opportunities
• Jeff's most expensive investing lesson and why mistakes are essential for becoming a great investor

Guest Bio:

Jeff Diehl is the Managing Partner and Head of Investments at Adams Street Partners, a global private markets investment manager with more than $70 billion in assets under management across private equity and private credit strategies. He oversees the firm's investment activities and overall management while serving as Chairman of both the Portfolio Construction Committee and Executive Committee. Under his leadership, Adams Street has expanded its global footprint to more than 330 professionals across 14 offices worldwide.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Jeff Diehl:

LinkedIn: https://www.linkedin.com/in/jeffrey-diehl-63a0701/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) The Two Rules That Explain Almost Every Venture Outcome (0:43) Why Venture Capital Has More Persistence Than Any Other Asset Class (5:01) What 14,000 Exits Taught Him About Venture Returns (7:57) The Shocking Reality: 7% of Companies Create 100% of the Gains (9:22) Why Every Great Venture Co-Investment Starts With GP Relationships (10:33) The Hidden Reason Growth Investors Are Moving Into Private Markets (13:11) Why Succession Fails at Most Venture Capital Firms (16:23) The Culture and Incentive System Behind Top Investment Organizations (24:59) Can Size Become a Moat in Venture Capital? (33:53) The $12 Million Mistake He Still Keeps as a Reminder

What if the biggest opportunity in private markets isn’t finding the next startup—but owning the next public company years before it ever rings the bell? In this episode, I sit down with Matt Witheiler, Head of Late-Stage Growth at Wellington Management, to discuss how the line between public and private markets continues to blur. Matt explains why companies are staying private longer, why public investors are starved for growth, and how late-stage investing differs from both venture capital and public equities. We also explore IPO markets, valuation discipline, liquidity dynamics, and why the best companies often justify paying up for quality. Highlights:

• Why OpenAI, Anthropic, and SpaceX may reignite the IPO market
• The growing shortage of high-growth companies in public markets
• Why small-cap investing has fundamentally changed over the last decade
• How late-stage investors evaluate hype versus fundamentals
• Why founders optimize for partners, not the highest valuation
• The advantage Wellington brings as both a private and public market investor
• Why valuation discipline matters more than bargain hunting
• Matt’s biggest investing miss and what SpaceX taught him about exceptional founders

Guest Bio:

Matt Witheiler is the Head of Late-Stage Growth at Wellington Management, where he leads the firm’s private company investing activities across technology, healthcare, consumer, and financial services. Since joining Wellington in 2016, he has helped build one of the largest and most respected late-stage growth investing platforms, leveraging the firm’s deep public market expertise to identify future public company leaders. Prior to Wellington, Matt was a General Partner at Flybridge Capital Partners and earlier held operating roles in technology, including co-founding AnandTech.com. He has been named to the Forbes Midas List for six consecutive years and is widely recognized as one of the leading investors at the intersection of private and public markets.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/

Stay Connected with Matt Witheiler:

LinkedIn: https://www.linkedin.com/in/mwitheiler/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why the Biggest IPOs in History Won’t Break Public Markets (2:22) The Passive Buying Wave Coming for SpaceX, OpenAI, and Anthropic (3:15) Why Public Investors Are Desperate for New Growth Stories (5:22) How Investors Separate Real AI Companies From AI Hype (7:59) Why Pension Funds Are Buying Private Assets From Public Allocations (9:20) The Hidden Reason Small-Cap Investing Stopped Working (13:13) Why the Best Founders Want to Stay Private Longer (13:44) How Wellington Wins Deals Against Sequoia and Andreessen (18:38) The Secret to Getting Into the Hottest Rounds Before Everyone Else (24:42) The Billion-Dollar Mistake Wellington Made on SpaceX

What if the biggest edge in venture capital isn’t manager selection—but earning access to the managers everyone already knows are the best? In this episode, I sit down with Mark Anson, CEO, President, and CIO of Commonfund, to discuss what he has learned managing capital across some of the world’s most influential institutions, including CalPERS, the Bass Family Office, and Commonfund. Mark explains why venture capital remains one of the most persistent alpha-generating asset classes, how LPs earn access to top managers, and why relationships, responsiveness, and knowledge-sharing matter more than check size. We also explore performance persistence, the illiquidity premium, co-investments, and the lessons Mark has learned managing capital across multiple decades and market cycles. Highlights:

• The surprising story of how donuts helped unlock access to a top-tier VC fund
• Why venture capital has the greatest performance dispersion in investing
• The difference between average and top-quartile venture returns
• How Commonfund evaluates emerging managers before the market finds them
• Why access in venture is earned, not bought
• The case for a rules-based approach to venture investing
• Why innovation is completely uncorrelated with the business cycle
• Mark’s framework for managing “human capital” throughout a career

Guest Bio:

Mark Anson is the Chief Executive Officer, President, and Chief Investment Officer of Commonfund, where he oversees more than $35 billion in assets serving endowments, foundations, and institutional investors. Throughout his career, Mark has led investment organizations at some of the world’s most prominent institutions, including CalPERS, the Bass Family Office, British Telecom Pension Scheme, Hermes Pension Management, and Nuveen Investments. A prolific author, researcher, and educator, he has published more than 100 journal articles and several leading finance textbooks, including The Handbook of Alternative Assets.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Mark Anson:

LinkedIn:https://www.linkedin.com/in/mark-anson-7a9b4a75/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

Each of CF Private Equity, Inc. and Commonfund OCIO, Inc. (collectively, “Commonfund”) is a registered investment adviser under the Investment Advisers Act of 1940. This material is solely for informational purposes and should not be viewed as a recommendation or an offer to sell or the solicitation to buy securities or adopt any investment strategy. The opinions expressed herein represent the current, good faith views of the participants at the time of publication, are not investment advice, and should not be relied upon as such. The information discussed herein has been developed internally and/or obtained from sources believed to be reliable; however, Commonfund does not guarantee the accuracy, adequacy, or completeness of such information. There is no assurance that any events or projections will occur, and outcomes may be significantly different than the opinions stated herein. This information, including any projections concerning financial market performance, is based on current market conditions, which will fluctuate and may be superseded by subsequent market events or for other reasons.

(0:00) How a Box of Donuts Got CalPERS Into a Top VC Fund (2:35) Why Venture Capital Rewards Failure Differently Than Any Other Asset Class (4:20) The Power Law That Drives Nearly All Venture Returns (8:05) How Commonfund Wins Access to the Best Venture Managers (10:14) How Top LPs Can Approve Venture Deals in Just 48 Hours (11:50) The Secret Process for Finding Tomorrow’s Top VC Funds (15:10) Why Buying Into Carlyle Was Better Than Negotiating Lower Fees (18:37) Is Capital Still a Moat in Venture Capital? (24:38) Why the Biggest Investment Opportunities Happen Every 10 Years (33:31) The Hidden Cost of Companies Staying Private Too Long

What if the biggest investment opportunity of the next decade isn’t AI itself—but the companies building the infrastructure and workflows that allow AI agents to actually do work? In this episode, I sit down with David Blumberg, Founder and Managing Partner of Blumberg Capital, to discuss why he believes agentic AI is still in the first inning of a multi-decade transformation. David explains how AI agents will reshape productivity across industries, why vertical software companies with proprietary data have a major advantage, and how network effects are evolving through AI-powered data flywheels. We also explore the future of work, the rise of AI-native businesses, and why human relationships remain one of the few enduring advantages in an increasingly automated world. Highlights:

• Why agentic AI could become a larger market than software itself
• The hidden infrastructure needed for AI agents to transact autonomously
• How proprietary data creates durable AI moats
• Why vertical AI companies may outperform general-purpose models
• The concept of AI-powered data flywheels and compounding network effects
• How AI could dramatically increase productivity without eliminating opportunity
• Why the next generation of Fortune 500 companies is being built right now
• The enduring importance of relationships in a technology-driven world

Guest Bio:

David Blumberg is the Founder and Managing Partner of Blumberg Capital, an early-stage venture capital firm focused on backing visionary entrepreneurs building global B2B technology companies. Over a career spanning venture capital, operating leadership, and institutional investing, he has helped build and back category-defining businesses including Nutanix, Braze, DoubleVerify, Trulioo, and Check Point Software Technologies. Prior to founding Blumberg Capital, David held investment roles with Claridge, Apax Partners, Adler & Co., and T. Rowe Price, and was part of the early leadership team at Check Point. He is widely recognized for his focus on enterprise technology, cybersecurity, fintech, and the next wave of AI-driven innovation.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with David Blumberg:

LinkedIn:https://www.linkedin.com/in/davidjblumberg

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why AI Agents Could Become the Biggest Productivity Shift in History (0:43) Will AI Create More Jobs or Eliminate Them? (5:10) The B2B AI Opportunity Most Investors Still Underestimate (8:07) Why Almost Nobody Uses AI Agents Today (And Why That’s About to Change) (9:22) The $100 Trillion Market Hidden Behind White-Collar Work (12:16) The Infrastructure Layer Every AI Agent Will Need (18:49) The Data Flywheel That Makes AI Companies Hard to Compete Against (20:46) Why Vertical AI Could Beat the Largest LLMs (24:45) The Surprising Opportunity Emerging Managers Have in the AI Boom (28:17) The Career Prediction From the 1970s That’s Finally Coming True

What if the biggest opportunity in venture today isn’t finding the next unicorn—but solving the liquidity problem created by companies staying private twice as long as they used to? In this episode, I sit down with Ravi Viswanathan, Founder and Managing Partner of NewView Capital, to discuss how the venture ecosystem is evolving beyond the traditional fund model. Ravi explains why he left NEA to build a firm focused on liquidity solutions, how company-led secondaries are becoming a critical tool for founders and employees, and why the future of venture may depend on balancing long-term ownership with thoughtful liquidity. We also explore the DPI drought, continuation vehicles, cap table management, and why relationships remain the ultimate source of edge in venture capital. Highlights:

• Why companies staying private longer created a structural liquidity gap
• The rise of company-led secondaries and founder-controlled liquidity
• How employee liquidity can improve retention and long-term alignment
• Why the venture industry can no longer ignore DPI
• The tension between FOMO investing and long-term conviction
• How continuation vehicles may reshape venture portfolios
• Why capital often masks product-market fit during boom cycles
• The relationship-driven lesson Ravi wishes he learned earlier in his career

Guest Bio:

Ravi Viswanathan is the Founder and Managing Partner of NewView Capital, a growth-stage investment firm managing more than $3 billion and focused on primary, secondary, and hybrid investments in leading technology companies. Prior to founding NewView in 2018, Ravi spent 15 years as a General Partner at NEA, where he backed category-defining companies including MuleSoft, Braintree, Acquia, Cyence, and GlobalLogic. Over more than two decades in venture capital, Ravi has built a reputation for partnering with exceptional founders, identifying enduring technology businesses, and helping shape the evolution of liquidity and capital formation in private markets.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Ravi Viswanathan:

LinkedIn:https://www.linkedin.com/in/raviswanathan/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why He Left NEA to Launch a $1.3 Billion Venture Fund (1:02) Are the Best Venture Companies Already Obvious by Series B? (3:33) The New Secondary Market Trend Reshaping Venture Capital (5:02) Why Employees Need Liquidity Long Before an IPO (7:03) The Hidden Benefits of Letting Employees Sell Shares (11:38) Will OpenAI, Anthropic, and SpaceX Fix Venture’s DPI Crisis? (13:17) Why Venture Capital May Never Return to Historical DPI Levels (20:18) Are Continuation Vehicles the Next Big Venture Trend? (24:35) The One Thing That Compounded Most Over 25 Years in Venture (28:20) How Easy Money Created an Entire Generation of Zombie Startups

What if the biggest inefficiency in investing today isn’t asset selection—but the fact that most investors still optimize for pre-tax returns instead of after-tax outcomes? In this episode, I sit down with Jeff Bramel, Partner at a16z Perennial, to discuss why real assets remain one of the most misunderstood areas of institutional investing. Jeff explains how structural diversification works beyond traditional portfolio theory, why private real estate behaves differently from public markets, and how tax efficiency can dramatically reshape long-term returns for taxable investors. We also explore opportunistic investing, portfolio construction, risk management, and why real estate may offer one of the largest remaining pockets of structural alpha. Highlights:

• Why after-tax returns matter more than headline returns
• The hidden inefficiencies inside private real estate markets
• How depreciation transforms the economics of taxable investing
• Why structural diversification matters more than historical correlations
• The problem with overly rigid institutional asset allocation models
• How opportunistic investing can add hundreds of basis points annually
• Why higher-return assets often become safer over long time horizons
• The overlooked relationship between taxes, compounding, and alpha

Guest Bio:

Jeff Bramel is a Partner at a16z Perennial, where he focuses on real assets and institutional portfolio construction. He has more than 25 years of experience managing large and complex investment portfolios across public and private markets, with expertise spanning real estate, infrastructure, energy, agriculture, asset-backed investments, and alternative strategies. Jeff is known for applying first-principles thinking to portfolio management, combining deep quantitative analysis with a focus on structural diversification, cash-flowing assets, and after-tax optimization for long-term investors.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Jeff Bramel:

LinkedIn:https://www.linkedin.com/in/jeffbramel/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Billionaires Quietly Move Into Real Estate (1:22) The Structural Reason Real Estate Diversifies Tech Wealth (5:07) The Hidden Tax Advantage Most Investors Still Don’t Understand (9:53) Why Private Credit Looks Much Worse After Taxes (18:36) The Real Meaning of “Opportunistic” Real Estate Investing (21:15) How Rigid Asset Allocation Quietly Destroys Returns (27:11) How Much Alpha Exists in Picking the Right Real Estate Deals? (30:59) Why Higher Volatility Can Actually Create Better Long-Term Returns (38:26) The Diversification Myth Most Wealthy Investors Believe (45:50) Why Real Estate Is a Quant Nerd’s Dream Asset Class

What if the greatest threat to generational wealth isn’t bad investing—but the inability to think beyond the next liquidity event? In this episode, I sit down with Eric Becker, Founder and Chairman of Cresset, to discuss why he built a modern multi-family office after decades as an entrepreneur and investor. Eric explains the structural conflicts inside traditional wealth management, why most ultra-high-net-worth families lack true family office infrastructure, and how long-term thinking changes the way businesses, portfolios, and families compound over generations. We also explore governance, tax-aware investing, succession planning, and lessons from companies that have endured for centuries. Highlights:

• Why most wealth management firms fail entrepreneurs after liquidity events
• The hidden conflicts embedded inside traditional wirehouses
• Why family governance matters as much as investment performance
• The concept of “asset protection as compartments in a submarine”
• Why the next generation is often the greatest risk to family wealth
• How enduring companies survive across centuries and multiple crises
• Why building a business for the long term paradoxically accelerates growth
• The overlooked importance of stewardship in investing and leadership

Guest Bio:

Eric Becker is the Founder and Chairman of Cresset, a multi-family office and wealth management platform overseeing more than $250 billion in assets under management and advisement. Prior to founding Cresset, Eric built and invested in multiple businesses as an entrepreneur, beginning with a healthcare technology company he launched while attending the University of Chicago. He is also the author of The Long Game, a book exploring the lessons behind companies and families that have endured for generations, drawing on interviews with some of the world’s longest-lasting organizations and business leaders.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Eric Becker:

LinkedIn:https://www.linkedin.com/in/ebecker1/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Billionaire Founders Were Disappointed by Private Banks (3:45) The Hidden Conflicts Inside Traditional Wealth Management (7:16) How Crescent Avoids the Incentive Problems Most RIAs Have (9:30) What Family Offices Actually Do Beyond Investing (15:05) Why “Wealth Preservation” Often Fails by the Third Generation (18:13) The Most Underrated Alpha in Investing: Structure and Taxes (22:25) The Asset Classes Smart Family Offices Are Quietly Buying (28:40) What 200-Year-Old Companies Understand That Startups Don’t (37:56) Why Building for the Long Term Creates Faster Growth (41:21) The Strange Paradox Behind Great Founders and Wealth

What if the biggest problem in asset management today isn’t investment performance—but misalignment between managers and the investors they serve? In this episode, I sit down with Luke Sarsfield, Chairman and CEO of Ridgepost Capital, to discuss how incentive structures shape long-term outcomes in private markets. Luke explains why Ridgepost leaves most carried interest with underlying managers, how alignment creates better LP relationships, and why middle market specialists can offer diversification that many large-cap private portfolios lack. We also explore long-term thinking, public versus private market pressures, culture, mentorship, and why compounding relationships may be the most valuable asset in investing. Highlights:

• Why alignment matters more than asset gathering in private markets
• The hidden correlation risk inside large private equity portfolios
• Why Ridgepost focuses on management fee ownership over carry
• How long-term incentives improve investment decision-making
• The tension between public market short-termism and private market compounding
• Why culture and mentorship compound harder than capital
• The importance of building teams without creating groupthink
• Why relationships become the ultimate competitive advantage over time

Guest Bio:

Luke Sarsfield is Chairman, Director, and Chief Executive Officer of Ridgepost Capital, an investment platform focused on partnering with specialized alternative asset managers. Prior to Ridgepost, he spent more than two decades at Goldman Sachs, where he served in several senior leadership roles including Global Co-Head of Goldman Sachs Asset Management and Chief Commercial Officer of Asset and Wealth Management. Across his career, Luke has focused on building enduring investment businesses, aligning incentives between managers and LPs, and helping scale world-class investment platforms with a long-term orientation.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Luke Sarsfield:

LinkedIn:https://www.linkedin.com/in/luke-sarsfield/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) The Asset Management Incentive Problem Ridgepost Is Trying to Fix (1:31) Why Carry Creates Better Investors Than Management Fees (3:03) The Hidden Correlation Risk Inside Private Equity Portfolios (4:45) Why Public Markets Assign Almost Zero Value to Carry (7:09) The Surprising Reason Great Managers Eventually Scale Anyway (9:38) Why Finance Quietly Rewards Short-Term Thinking (12:33) How a Public Company Can Still Think in Decades (17:57) What Asset Management Firms Are Actually Worth Today (23:33) The Common Pattern Across Every Great Asset Manager (31:53) The Most Important Career Decision Most People Get Wrong

What if the biggest opportunity in private equity today isn’t buying companies—but buying liquidity from investors who are forced to sell great assets for reasons unrelated to performance? In this episode, I sit down with Ryan Levitt, Co-Head of LP Secondaries at ICG, to discuss why secondaries have evolved into one of the most attractive areas in private markets. Ryan explains how LP secondaries can outperform traditional buyouts with lower downside risk, why DPI pressures are reshaping institutional portfolios, and how rules-based allocators create structural inefficiencies. We also explore return dispersion, continuation vehicles, GP relationships, and why access and information matter more than sourcing in modern secondaries investing. Highlights:

• Why secondaries have historically outperformed most buyout funds
• The growing return dispersion inside private equity
• How DPI pressures are fueling record secondary market activity
• Why LPs often sell their best assets instead of their worst
• The hidden inefficiencies created by rules-based allocators
• Why access and information matter more than sourcing in secondaries
• How continuation vehicles are changing private markets liquidity
• Why culture and mentorship compound harder than compensation early in a career

Guest Bio:

Ryan Levitt is Co-Head of LP Secondaries at ICG, a global alternative asset manager with more than $126 billion in assets under management across private equity, credit, structured capital, and real assets. At ICG, Ryan focuses on originating and leading LP secondary transactions, co-investments, and primary fund commitments globally. Prior to joining ICG, he was a Partner and Portfolio Manager at Pomona Capital, where he helped build the firm’s private wealth interval fund platform, and earlier in his career he invested across direct equity and debt transactions at GE Capital.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Ryan Levitt:

LinkedIn:https://www.linkedin.com/in/ryan-levitt/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Secondaries Quietly Outperform Traditional Buyouts (2:22) The Hidden Problem Breaking Modern Buyout Returns (4:14) The DPI Crisis Forcing LPs Into the Secondary Market (7:45) Why LPs Sell Their Best Assets Instead of Their Worst (9:27) The Incentive Problem Quietly Driving Secondary Deal Flow (11:33) Where the Best Secondary Opportunities Exist Right Now (14:18) The Real Source of Alpha in Secondaries: Information and Access (18:37) Why There Still Isn’t Enough Capital in the Secondary Market (22:03) How ICG Scaled to $127B Without Burning GP Relationships (25:16) The Career Advice That Matters More Than Compensation

What if the biggest venture returns are already gone by the time a category has a name? In this episode, I sit down with Niko Bonatsos, Founder and Managing Partner of Verdict, to discuss why the best venture opportunities emerge before consensus exists. Niko explains why “50% of the profits are made before a vertical even has a name,” how he identifies “freak” founders with extreme rates of learning, and why most VCs are structurally incentivized to follow momentum instead of creating conviction. We also explore why consumer and gaming are deeply undervalued today, how AI is changing company formation, and why relationship-building compounds harder than capital in venture investing. Highlights:

• Why the biggest venture profits are captured before categories are named
• The definition of a “freak” founder and why rate of learning matters most
• Why most VCs optimize for markups instead of outcomes
• How AI is compressing company-building timelines dramatically
• Why consumer, gaming, and crypto are deeply underappreciated today
• The hidden advantage of immigrant and neurodivergent founders
• Why “small thinking” competes with breakthrough ideas
• How relationship-building became General Catalyst’s long-term edge

Guest Bio:

Niko Bonatsos is the Founder and Managing Partner of Verdict, an early-stage venture firm focused on backing unconventional founders building entirely new categories. Prior to launching Verdict, he spent 15 years at General Catalyst, where he helped expand the firm from an emerging venture platform into one of the world’s leading investment franchises. Niko is known for investing early in overlooked markets, partnering with highly technical founders, and developing a reputation for identifying “freak” entrepreneurs with exceptional rates of learning and conviction.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Niko Bonatsos:

LinkedIn:https://www.linkedin.com/in/bonatsos/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why 50% of Venture Profits Are Made Before a Market Has a Name (2:27) Why Most VCs Are Just Following the Herd (3:30) The Brutal Reality of Scaling Early-Stage Venture (5:14) How He Finds Markets Before Anyone Else Believes (6:26) What Makes a Founder a “Freak” (8:43) Why Most Smart VCs Don’t Take Enough Risk (12:41) Why AI and American Dynamism Are Already Overhyped (16:51) The Contrarian Founder Archetype Most VCs Ignore (21:30) Why Nobody Wants to Fund Gaming Right Now (36:13) The Biggest Problem Inside Venture Capital Today

What if the biggest opportunity in venture today isn’t funding new companies—but solving the liquidity crisis created by companies staying private for 20 years? In this episode, I sit down with Jared Carmel, Founder and Managing Partner of Manhattan Venture Partners, to discuss how venture secondaries evolved from a gray market into critical infrastructure for private capital markets. Jared explains why nearly $3 trillion is now trapped in aging venture funds, how DPI became the defining metric for LPs, and why secondary liquidity is now essential for founders, employees, and venture firms alike. We also explore continuation vehicles, cap table management, institutionalization of the secondary market, and why trust compounds faster than capital in private investing. Highlights:

• Why companies staying private for 20+ years changed venture forever
• The $3T liquidity problem sitting inside venture capital
• Why DPI matters more than IRR for LPs today
• How secondaries became institutionalized after years as a “gray market”
• Why trust compounds faster than capital in private markets
• The hidden risks inside retail SPVs and secondary hype cycles
• How continuation vehicles are reshaping venture fund liquidity
• Why “land and expand” became MVP’s core investment strategy

Guest Bio:

Jared Carmel is the Founder and Managing Partner of Manhattan Venture Partners, a leading venture secondary investment firm managing billions across primary and secondary private market investments. He has spent more than a decade helping institutionalize venture secondaries, building liquidity solutions for founders, employees, and investors in many of the world’s most valuable private technology companies. Through MVP’s “Land and Expand” strategy, Jared has invested across category-defining businesses including SpaceX, Anthropic, Databricks, xAI, and Coinbase, while helping shape the modern private liquidity ecosystem.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Jared Carmel:

LinkedIn:https://www.linkedin.com/in/carmel/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) The $3 Trillion Problem Locked Inside Venture Capital (1:18) Why Great Companies Stay Private for 20 Years (2:41) Why DPI Suddenly Matters More Than IRR (5:16) How the Secondary Market Became Institutional (7:48) The Hidden Risk in Retail Secondary SPVs (12:29) How MVP Competes in One of the Hardest Markets (14:45) Why Continuation Vehicles Could Fix Venture’s DPI Problem (19:04) The Trust That Built a $3B Secondary Platform (26:47) What MVP Could Become in 10 Years (28:12) The Advice That Would Have Changed Everything

What if the biggest source of alpha for taxable investors isn’t stock picking—but minimizing friction inside the portfolio itself? In this episode, I sit down with Brent Sullivan, independent tax analyst and author of one of the leading research platforms on tax-aware investing, to discuss why tax alpha has become one of the fastest-growing themes in wealth management. Brent explains how long-short tax-loss harvesting strategies evolved from niche institutional products into mainstream planning tools, why tracking error is often misunderstood, and how sophisticated investors think about balancing risk, leverage, and after-tax returns. We also explore trader funds, operational risk, and why tax management may matter more than active management for many investors. Highlights:

• Why tax alpha can matter more than active management returns
• How long-short portfolios create recurring tax-loss harvesting opportunities
• The hidden risks behind aggressive tax-loss harvesting strategies
• Why tracking error is often a feature, not a flaw
• The operational complexity most investors underestimate
• How trader funds generate ordinary losses
• Why the best tax strategies are tied to assets investors already want to own
• The difference between tax planning and “the tax tail wagging the dog”

Guest Bio:

Brent Sullivan is an independent tax analyst, software developer, and writer focused on tax-aware investing and portfolio construction. He publishes widely followed research on tax alpha, long-short investing, and advanced wealth management strategies through his platform Tax Alpha Insider. Brent specializes in analyzing the mechanics, risks, and implementation details behind sophisticated tax planning strategies used by advisors, family offices, and institutional investors.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Brent Sullivan:

LinkedIn:https://www.linkedin.com/in/brntsllvn/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Tax Alpha Became the “Boring” Edge Investors Miss (4:03) The Strategy Making Tax Loss Harvesting Explode (7:03) Where These Massive Tax Losses Actually Come From (12:28) The Biggest Players in Tax Loss Harvesting 3.0 (14:36) The Hard Part No One Talks About: Unwinding the Trade (19:39) Why Some Families Never Unwind These Strategies (23:12) The Hedge Fund Tax Strategy Quietly Gaining Momentum (29:15) How Tax Alpha Strategies Can Fail (36:54) Why Tracking Error Isn’t Always a Bad Thing (43:11) Why He Wishes He Went Independent Much Earlier

What if the key to outperforming isn’t taking more risk—but building a portfolio strong enough to survive volatility without breaking? In this episode, I sit down with Doug Hanly, CIO of the Louisiana State Police Retirement System, to discuss why liquidity, simplicity, and process are the foundations of durable investing. Doug explains why he views short-term government credit as the “supply depots” of a portfolio, how preparation during calm periods creates opportunities during crises, and why avoiding mistakes matters more than chasing complexity. We also explore governance, manager selection, portfolio construction, and how small incremental improvements compound into long-term outperformance.

Disclaimer: The thoughts and opinions expressed in this material and oral presentation are the author's and not necessarily those of the Louisiana State Police Retirement System, the Board of Trustees of the Louisiana State Police Retirement System, or the State of Louisiana. The statements and conclusions in this material and oral presentation are not binding on the State of Louisiana and its agencies, officers, and employees and do not alter the law of the State of Louisiana or policies of the Louisiana State Police Retirement System. In the event of a conflict between the material contained in this document and the applicable law, regulation, or policy, then the law, regulation, or policy is controlling.

Highlights:

• Why liquidity creates optionality during market dislocations
• The hidden risk of fragile portfolios during crises
• Why simplicity often outperforms complexity in investing
• How governance shapes long-term investment outcomes
• The importance of “killing weak ideas early”
• Why smaller specialist managers often outperform larger funds
• How incremental improvements compound into durable alpha
• The role of preparation and psychology during drawdowns

Guest Bio:

Doug Hanly, CFA, CAIA, is the Chief Investment Officer of the Louisiana State Police Retirement System, where he oversees total portfolio strategy across public and private markets for the $1.5 billion pension fund. He previously held investment roles at Atala Financial, Windrose Advisors, Mass General Brigham, and the Washington University Investment Management Company. Doug also teaches hedge funds at LSU, founded the Next CIO Institute, and is known for his disciplined approach to governance, risk management, and institutional portfolio construction.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank AlphaSense for sponsoring this episode!

Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Doug Hanly:

LinkedIn:https://www.linkedin.com/in/doughanly/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why Short-Term Government Bonds Are His Favorite Asset Class (3:41) The Contrarian Advantage of Holding Cash During Crashes (7:17) Why Asset Management Is Basically Exposure Therapy (10:01) The Slow-Motion Strategy That Protects LPs From Disaster (13:06) Why Smaller Funds Often Generate More Alpha (17:43) The Hidden Power of Simplicity in Investing (20:14) Why Quantity Quietly Creates Better Investors (22:25) The Surprising Benefits of a “Boring” Portfolio (25:10) The Consultant Strategy Most LPs Completely Miss (26:56) The One Simple Question That Can 10X Results