How I Invest with David Weisburd

What changes when wealth stops being about building and starts being about preserving? In this episode, I sit down with Jonathan Dane, CIO and Founder of Defiant Capital, to explore how family offices think about portfolio construction after a major liquidity event. Drawing on his experience at Goldman Sachs and Jefferies, Jonathan explains why independent advice matters and how families navigate the transition from wealth creation to long-term preservation. Highlights:

• Why large banks struggle to deliver fully independent advice
• The key psychological differences between Gen 1 and Gen 2 wealth
• Estate planning moves entrepreneurs should make years before a liquidity event
• Why gifting shares early can save millions in future estate taxes
• How portfolio construction changes once wealth becomes generational
• Why billion-dollar family offices are typically majority alternatives
• The critical importance of liquidity management before committing to private funds
• Why overcommitting to private equity can force families into bad financing decisions
• The growing frustration with long-dated venture funds and low DPI
• Why lower middle market private equity offers structural inefficiencies
• The operational alpha opportunity in Rust Belt manufacturing businesses
• How independent sponsors should demonstrate real skin in the game
• The biggest mistake $50–$500M families make: over-diversifying into too many managers
• Why AI should enhance diligence workflows but never replace human judgment

Guest Bio:

Jonathan Dane is the Chief Investment Officer of Defiant Capital, where he advises entrepreneurial families and multigenerational wealth on portfolio construction, liquidity management, estate integration, and alternative investments. He previously worked at Goldman Sachs and Jefferies, advising ultra-high-net-worth and institutional clients, and now focuses particularly on lower middle market private equity and operational value creation.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Jonathan Dane:

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

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 the Sell Side Gives Conflicted Advice (2:03) Why First-Generation Wealth Invests Differently (6:22) The Estate Planning Moves Entrepreneurs Miss (9:02) What Changes Once a Family Passes $50M (10:42) How Billion-Dollar Family Offices Build Portfolios (15:55) Building a Portfolio for a Newly Liquid $1B Family (19:20) Why Families Are Pushing Back on 15-Year Venture Funds (25:12) Why Lower Middle Market Private Equity Works (29:08) Independent Sponsors vs Traditional PE Funds (30:47) The #1 Portfolio Mistake Families Make

What if one of the most overlooked $700 billion pools of capital in the U.S. is quietly shaping private markets? In this episode, I sit down with Jennifer Mink, President of Investment Performance Services, an investment consulting firm overseeing roughly $70 billion in assets under advisement, to discuss how Taft-Hartley pension plans approach long-term investing. Jennifer shares how IPS designs portfolios that balance public and private markets, using disciplined asset allocation and diversification to improve overall portfolio efficiency and manage risk across market cycles. Highlights:

• How adding alternatives can reduce overall portfolio volatility through low correlation
• Why “double diversification” can dilute returns at the portfolio level
• The importance of grounding investments in a clear thesis to avoid emotional selling
• How IPS rebalanced aggressively during the 2020 market snapback
• What gets easier and harder when advising $70 billion across nearly 200 union plans
• Why emerging managers are typically tracked through three vintages before capital is deployed
• Red flags in early funds including team turnover, fee changes, and strategy drift
• The private equity distribution slowdown and pacing challenges facing LPs
• Structural requirements managers must meet to access Taft-Hartley capital, including ERISA fiduciary status
• The role of Responsible Contractor Policies in real asset mandates
• Why sometimes the best investment decision is the one you avoid
• How IPS tracks its own research process to ensure manager outperformance across cycles

Guest Bio:

Jennifer Mink is the President of Investment Performance Services (IPS), a 40-year-old investment consulting firm focused exclusively on the Taft-Hartley marketplace. IPS advises approximately $70 billion in assets and works with nearly 200 union plans nationwide. With more than two decades at the firm, Mink specializes in asset allocation, manager research, and private markets diligence, and leads a team that evaluates hundreds of managers annually while emphasizing disciplined structure, fiduciary responsibility, and consistency across full market cycles.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Jennifer Mink:

LinkedIn: https://www.linkedin.com/in/jennifer-mink-09057836b/

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 Job of Deploying $70B in Institutional Capital (0:52) Why Alternatives Can Reduce Portfolio Volatility (3:03) The Biggest Behavioral Mistake Investors Make (4:31) How Institutions Invest During Market Crashes (6:08) What Gets Easier (and Harder) Managing $70B (8:05) How Consultants Diligence 300–400 Managers a Year (10:13) Why Institutions Wait Until Fund IV to Invest (13:34) The DPI Crisis Breaking the Endowment Model (15:05) The Hidden Rules for Raising Taft-Hartley Capital (22:28) The Best Investment Is Sometimes Saying No

Why are private markets still managed in spreadsheets when hundreds of billions of dollars are at stake? In this episode, I sit down with Ryan Eisenman, Co-Founder and CEO of Arch, a platform supporting more than 550 clients and over $405 billion in alternative assets. Arch is building an operating system for private markets that helps investors manage the operational complexity of alternatives across private equity, venture, hedge funds, credit, and more, bringing modern infrastructure to a part of the financial system that has historically relied on manual processes and fragmented data. Highlights:

• What breaks when an LP scales from 10 to 50 fund commitments
• Why most private markets data is trapped in PDFs across 800+ portals
• The hidden operational chaos inside family offices and RIAs
• How poor liquidity visibility impacts re-up decisions
• Why venture fundraising has fallen dramatically since 2022 peaks
• The shift of capital from institutions to the wealth channel
• Growth in independent sponsor and deal-by-deal allocations
• Why private market data feeds often don’t match source documents
• The rise of secondaries and tightening discount spreads
• Why borrowing against private assets remains inefficient
• How Arch uses AI to extract key terms from 100-page LPAs
• Lessons Ryan learned building a venture-backed fintech company

Guest Bio:

Ryan Eisenman is the Co-Founder and CEO of Arch, a fintech platform that automates data aggregation, reporting, and analytics for alternative investments. Arch serves global banks, RIAs, family offices, and institutional allocators, helping them manage complex private market portfolios more efficiently.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Ryan Eisenman:

LinkedIn: https://www.linkedin.com/in/ryan-eisenman-21811246/

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) $405B in Private Market Assets — But LPs Still Use Spreadsheets (1:19) The Hidden Chaos of Tracking Private Investments (2:05) Why LPs Don’t Understand Their Own Liquidity (3:54) What Breaks When LPs Go From 10 to 50 Funds (5:17) The Manual Systems Behind Billion-Dollar Portfolios (7:00) Why Private Markets Data Is Completely Fragmented (9:11) The Shift From Institutions to Wealth Channel Capital (12:24) The DPI Crisis Reshaping Venture Capital (13:38) Why You Can’t Borrow Against Private Assets (15:40) How AI Is Finally Fixing Private Markets Data

What if the best private equity opportunities are the ones no one else is set up to pursue? In this episode, I sit down with Jeff Collins, Founder and Managing Partner of Cloverlay, to explore how he built a $2 billion firm by going where capital isn’t. After 14 years at Morgan Stanley Investment Management, Jeff spun out to focus on what he calls “uncorrelated private assets” - niche, often overlooked segments where return dispersion is wide and operator selection matters more than financial engineering. Highlights:

• Why “go where the money isn’t” only works if you build the right organization around it
• How Cloverlay built a sourcing flywheel through references and long-term reciprocity
• The importance of holding structured “kill calls” to preserve relationships
• Why broad dispersion of returns signals opportunity in overlooked markets
• How to evaluate niche segments like special mission aircraft, wireless spectrum, and IP
• The strategy behind assembling “portfolio premium” assets in industrial outdoor storage
• Why uncorrelated private assets can act as ballast in institutional portfolios
• How pensions think about completion portfolios and non-beta exposure
• The tradeoff between being an A+ specialist versus a well-rounded investor
• Why Jeff believes ego should be tied to performance, not AUM growth
• The cultural decision to remain focused instead of scaling into adjacent strategies

Guest Bio:

Jeff Collins is the Founder and Managing Partner of Cloverlay, a Philadelphia-based private investment firm managing approximately $2 billion in assets focused on uncorrelated private markets.

Before founding Cloverlay in 2015, Jeff spent 14 years at Morgan Stanley Investment Management, where he led investments across private market strategies and developed a focus on segments with high return dispersion and limited competition.

At Cloverlay, Jeff and his team specialize in niche asset categories ranging from intellectual property and aviation to industrial outdoor storage and other esoteric markets. The firm partners with highly specialized operators and seeks to generate performance through asset selection, structure, and disciplined portfolio construction rather than market beta or leverage.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Jeff Collins:

LinkedIn: https://www.linkedin.com/in/jeff-collins-76b7b54/

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 Strategy: Go Where the Money Isn’t (1:44) Why the Best Opportunities Take 291 Days to Close (3:20) Building Deal Flow Without Bankers or Auctions (7:59) Why Relationships Matter More Than Transactions (11:04) The Power of Proactive Deal Sourcing (14:48) How Small Markets Create Big Returns (19:17) The Role of Uncorrelated Assets in Portfolios (26:39) Why Investors Love Wide Dispersion of Returns (33:38) Turning Gravel Parking Lots Into Institutional Assets (47:27) Why Performance Matters More Than AUM

Why would an LP invest in the GP instead of the fund… and what problem is GP stakes really solving? In this episode, I sit down with Todd Owens, Managing Partner of Cantilever Group, to unpack the world of GP stakes. Todd explains what investors are actually buying when they take a minority stake in an alternative asset manager, why liquidity risk is the central challenge, and how structural innovation could reshape the asset class. Highlights:

• What you are really underwriting when you invest in a GP instead of a fund
• The hidden liquidity risk most LPs underestimate in GP stakes
• Why unpredictable exits are the defining challenge of minority GP investing
• How public listings could reshape liquidity for GP stakes funds
• Why lower middle market GP deals may offer structural advantages
• The three primary reasons GPs sell minority stakes and which one Todd likes most
• When growth capital meaningfully accelerates a manager’s trajectory
• Red flags when principals are taking money off the table
• How to distinguish between a durable firm and a single-founder platform
• Why venture capital can be “too volatile” for GP stakes investors
• The pricing discipline required to walk away from good businesses
• How strategic value creation works when you are a passive minority partner

Guest Bio:

Todd Owens is the Managing Partner of Cantilever Group, an investment firm that focuses on minority GP stakes in lower middle market alternative asset managers. The firm targets investments between $15 million and $75 million, partnering with managers seeking growth capital, capital restructuring, or solutions for generational transitions. Todd previously spent decades advising and working with asset management businesses, including serving as a Partner at Goldman Sachs, and at Cantilever Group he focuses on building a permanent capital model that aligns with GPs while addressing liquidity considerations for LPs.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Todd Owens:

LinkedIn: https://www.linkedin.com/in/todd-owens-401976160/

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 decision.

(0:00) Why GP Stakes Became a New Asset Class (0:36) What Investors Actually Buy in a GP Stake (1:22) Fund Returns vs. Owning the Management Company (2:09) The Biggest Risk: Unpredictable Liquidity (3:18) How GP Stakes Investors Create Liquidity (5:44) The Permanent Capital Model for GP Stakes (10:30) The 3 Reasons GPs Sell Stakes in Their Firm (11:56) How GP Stakes Capital Fuels Firm Growth (19:07) When GPs Take Money Off the Table (31:03) The Strategic Advantage of Investing at the GP Level

What separates elite venture LPs from everyone else… and why do most family offices underestimate the governance required to win? In this episode, I sit down with Michael P. Larsen, a longtime Partner at Cambridge Associates, to unpack nearly two decades of building venture and private equity portfolios for leading institutions and family offices. Michael shares why longevity may be the ultimate competitive advantage in asset management, how governance quietly determines venture outcomes, and why portfolio size can matter just as much as manager selection. We dive into power laws, spiky returns, growth equity’s overlooked role, co-invest best practices, and how benchmarking can help LPs stay disciplined during optically challenging cycles. Highlights:

• Why longevity in venture investing creates perspective most LPs never develop
• The hidden edge elite LPs have in portfolio sizing, not just manager selection
• Why governance may be the most underestimated driver of venture outcomes
• How to structure a venture allocation after a liquidity event
• The real reason venture portfolios feel “spiky” and why that is a feature, not a flaw
• Why waiting for obvious top managers often leads to second-tier access
• How fund cadence compression can quietly distort portfolio construction
• The importance of underwriting firms, not just individual funds
• Why benchmarking venture is especially challenging in Mag-7 dominated markets
• Growth equity as the “third bowl of porridge” between venture and buyout
• Co-invest adverse selection risks and how scale improves access
• Systematic vs opportunistic co-invest strategies and when each makes sense

Guest Bio:

Michael P. Larsen is a Partner at Cambridge Associates, where he has spent nearly two decades advising institutional investors and family offices on venture capital, private equity, and growth equity portfolio construction.

Over the course of his career, he has participated in thousands of GP meetings and helped design durable private market programs focused on governance, manager selection, and long-term discipline. His work emphasizes strategic allocation, benchmarking rigor, and building venture portfolios designed to withstand multi-decade market cycles.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Michael Larsen:

Michael Larsen: https://www.linkedin.com/in/michaelplarsen/

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 Longevity Advantage in Venture Investing (1:48) Why Venture Portfolios Behave Completely Differently (2:12) The Hidden Variable: Allocation Size Matters (4:30) Governance: The Least Sexy Alpha (6:15) Step One: Define Your Illiquidity Budget (8:33) Why Elite LPs Accept “Spiky” Returns (10:36) How Many Venture Funds You Actually Need (12:19) The Biggest Portfolio Construction Mistake (17:57) The Long-Term Game LPs Are Playing (20:54) The Real Risk in Venture Co-Investing

What if the biggest untapped source of alpha isn’t better investments… but better tax structure? In this episode, I sit down with Andrew Berman, Co-Founder and Managing Partner of Arqitel, to explore the overlooked power of tax-aware private real estate investing. After starting his career at AQR Capital Management and working closely with one of its co-founders inside a family office, Andrew saw firsthand how tax-aware strategies transformed public market investing. He realized private markets had yet to fully adopt the same discipline. We break down structural alpha, why many private real estate managers are incentivized to sell too soon, and how taxable investors can materially improve long-term wealth creation by aligning investment strategy with tax structure. In increasingly efficient markets, tax may be one of the few durable advantages left. Highlights:

• Why most private real estate investors underestimate how much taxes impact long-term returns
• How structural alpha can potentially exceed the dispersion between median and top quartile managers
• Why five-year hold periods may quietly erode after-tax wealth
• The mechanics of depreciation recapture and capital gains drag
• How manager incentives often conflict with after-tax optimization
• Why long-duration holds can enhance compounding for taxable investors
• When 1031 exchanges make sense and when they may introduce hidden costs
• Why taxable investors may be structurally under-allocated to private real estate
• How family offices think differently about liquidity, control, and tax efficiency
• Why after-tax return may become the defining metric for modern portfolio construction

Guest Bio:

Andrew Berman is the Co-Founder and Managing Partner of Arqitel. He previously began his career at AQR Capital Management and later worked within the family office of David Kabiller. His work focuses on maximizing after-tax returns for ultra-high-net-worth investors through tax-aware private real estate strategies.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Andrew Berman:

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

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 Real Estate Is the Most Tax-Advantaged Asset Class (1:22) The Hidden Returns Most Investors Leave on the Table (2:21) How Taxes Can Cut Your Real Estate Returns in Half (4:29) The Power of Depreciation and K-1 Pass-Throughs (5:28) Why Most Real Estate Funds Trigger Unnecessary Taxes (6:49) A Simple Example of 35% Tax Drag (9:08) The Truth About 1031 Exchanges (10:46) The Two Types of Family Office Investors (13:24) Why Tax Alpha Is the Next Big Investing Edge (14:47) Tax Strategy vs Picking Top Quartile Managers

What if the easiest alpha in public markets isn’t stock picking… but taxes? In this episode, I sit down with Zach Wainwright, Founder of Twin Oak ETF Company, to break down structural alpha, ETF tax efficiency, and how high-net-worth investors can compound capital more intelligently. Zach shares lessons from his time at Wellington, TIFF, and inside a single-family office — and why long time horizons, incentive alignment, and tax awareness may be more powerful than traditional stock-picking alpha. We also dive into tail-risk hedging inside an ETF wrapper and how families can design portfolios to survive extreme drawdowns without sacrificing long-term compounding. Highlights:

• Why “long-term” means something different for asset owners vs. traders
• Lessons from Wellington, TIFF, and investing in emerging managers
• Why fund one through fund three often generate the most alpha
• Incentive alignment and GP capital commitments
• Structural edges inside single-family offices
• The three levers of value creation: security selection, asset allocation, structural alpha
• Tax drag in mutual funds vs. ETFs
• How ETFs preserve tax alpha through in-kind redemptions
• Tail-risk hedging inside an ETF vs. private hedge funds
• Avoiding the 10 worst days — and capturing the 10 best
• Designing portfolios to reduce maximum drawdown
• Why tax deferral may be the most sustainable form of alpha

Guest Bio:

Zach Wainwright founded Twin Oak ETF Company with a singular focus: delivering innovative, institutional-quality, tax-efficient solutions to high-net-worth clients. Throughout his career at firms such as Wellington Management and TIFF, and later within a single-family office, Zach observed that taxable investors were often underserved — losing significant performance to unnecessary tax drag despite strong investment selection.

At Twin Oak, Zach focuses on what he calls “structural alpha” — leveraging time horizon, tax efficiency, and thoughtful implementation to unlock portfolio potential. His approach blends institutional rigor with family-office pragmatism, creating ETF-based solutions that aim to preserve compounding, reduce drawdowns, and optimize after-tax outcomes for long-term investors.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Zach Wainwright:

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

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) Introduction (0:13) Importance of long time horizon and differences in investing perspectives (1:16) Lessons from Wellington and transition to TIFF and early stage fund managers (2:25) Risk, incentives, and alpha generation with early fund managers (4:08) Risk-return tradeoffs and identifying traits in emerging managers (5:57) Transition to single family office (7:40) Structural advantages and unique investment strategies of family offices (10:25) Founding Twin Oak, investment philosophy, and tax strategies (13:48) Tail hedging strategies and costs/benefits of hedging (18:18) Optimizing portfolios: Long-only versus hedged performance (20:36) Client-driven innovation and optimal long-term public portfolio strategies (22:31) The evolving ETF ecosystem and the rise of taxable investors (24:51) Partnering with offices, hedge fund managers, and the importance of tax-aware investing (26:44) Advice for a younger self and the value of diverse experiences (28:14) Closing remarks

What if success isn’t about talent… but about multiplying your effort by 10? In this episode, I sit down with Grant Cardone, CEO of Cardone Capital, to break down the mindset behind the 10X Rule, omnipresence in marketing, raising billions from retail investors, and why quantity always precedes quality. Grant shares how he built a $5B real estate portfolio, scaled a media machine that sends hundreds of millions of emails per year, and combined Bitcoin with multifamily real estate to create a new hybrid investment vehicle. We also unpack why most people underestimate effort, why repetition builds self-esteem, and why illiquidity may be the real edge in investing. Highlights:

• Why people systematically underestimate how hard success actually is
• The real meaning behind the 10X Rule
• Quantity vs. quality — why reps create excellence
• How omnipresence builds brand power
• The psychology of follow-up and rejection in sales
• Raising over $2B directly from retail investors
• Why retail capital can be more powerful than institutional money
• The real estate + Bitcoin hybrid strategy
• Illiquidity as an investment advantage
• Tokenization vs. going public
• Lessons from addiction, ego, and resilience
• Why exceptional performance requires extreme repetition

Guest Bio:

Grant Cardone is the CEO of Cardone Capital, a private real estate investment firm managing over $5 billion in assets. He is the author of eight business books, creator of thirteen best-selling business programs, and CEO of seven privately held companies generating approximately $750 million in annual revenue. Over the past three decades, Grant has advised companies on sales expansion, profitability improvement, and operational scaling through disruptive marketing and training systems.

Recognized by Forbes as one of the top social media business influencers in the world, Grant built a global brand by embracing omnipresence, repetition, and relentless follow-up. Through Cardone Capital, he has raised billions from retail investors and continues to innovate with new financial structures, including real estate and Bitcoin hybrid vehicles and tokenized asset strategies.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Grant Cardone:

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

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) Introduction (1:30) The 10x rule, fear of being ignored, and underestimating effort (3:14) Schooling system, entitlement, and work ethic (5:52) Teaching practical skills and dealing with rejection (7:24) Analyzing top performers' strengths and weaknesses (9:14) Assets, liabilities, and misconceptions in finance (10:43) Marketing strategies and the rule of seven (16:15) Mastering persistence in sales and follow-up tactics (22:06) Media democratization and achieving excellence through repetition (26:11) Quantity vs. quality debate and embracing failure (33:57) Victim mentality and overcoming it (36:21) Raising capital and innovations in real estate funding (39:46) Tokenizing real estate and integrating Bitcoin investments (43:54) Illiquidity as a virtue and Bitcoin risks in real estate (48:26) Behavioral investing and creating anti-fragile portfolios (51:06) Real estate growth and scaling challenges (52:25) Property taxes and investment impacts (55:04) Migration patterns and economic effects on cities (57:42) Wealth accumulation strategies (1:00:25) Advice to younger self and life balance insights (1:02:54) Perspectives on public offerings and tokenizing assets (1:04:08) Expanding investor base and future aspirations (1:04:12) Closing remarks

If private equity generates alpha, why are investors still paying for beta? In this episode, I sit down with Roger Vincent, Founder and CIO of Summation Capital, to break down portfolio construction, co-investing, and fee alignment in private equity. After more than a decade leading Cornell University’s multi-billion-dollar private equity portfolio, Roger shares why diversification in PE actually increases expected return, how elite endowments use co-investments to systematically reduce fee drag, and why most allocators are misaligned with the capital they steward. We also unpack Summation’s industry-first structure—charging carry only on alpha over a public benchmark and offsetting fees through a no-fee, no-carry co-investment program. Highlights:

• Why portfolio construction is the most underrated driver of returns
• The false tradeoff between diversification and performance
• Venture capital’s cyclicality vs. buyout stability
• Why private equity beta is still expensive
• Benchmarking PE against public markets for compensation alignment
• Co-investments as a 600 bps fee arbitrage
• The dangers of under-diversified direct investing
• Behavioral finance and systematic co-investing
• “Gather a bunch of hawks” — diversified specialization
• Why double diversification destroys value
• Paying carry only on alpha over a public benchmark

Guest Bio:

Roger Vincent is the Founder and CEO of Summation Capital. Previously, he spent 12 years at the Cornell University endowment, where he managed private equity investments through multiple market cycles and helped construct a highly diversified institutional portfolio.

Earlier in his career, Roger was a GP, giving him direct experience in underwriting, syndicating, and executing investments. His work focuses on alignment, portfolio construction, and bringing endowment-style investing to a broader set of asset owners.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Roger Vincent:

LinkedIn: https://www.linkedin.com/in/roger-vincent-1a6423/

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) Introduction (0:42) Importance of portfolio construction and role of specific assets (2:26) Public vs. private market exposure (5:10) Influence of Professor Steve Kaplan and allocator incentives (7:38) Benchmarking and co-investment strategies (12:39) Diversification strategies for endowments (18:00) Overview of Summation Capital and misconceptions about diversification (24:14) Summation Capital's unique approach to aligning incentives (25:49) Closing remarks

Why does applying institutional investing frameworks often fail for taxable investors and families? David Weisburd speaks with Aneet Deshpande about adapting the endowment model to private clients, the rise of tax-aware private market investing, and why governance, pacing, and asset location matter more than product selection. Aneet explains how taxes, liquidity needs, and behavioral risks fundamentally change portfolio construction—and why clarity of objectives is the real edge. Highlights:

• Why institutional investing frameworks break down for taxable investors
• The rise of the taxable private-market allocator
• Asset allocation vs. asset location—and the cost of getting it wrong
• How taxes can erode 30–40% of gross returns
• Tax-efficient structures in infrastructure and private markets
• Applying the endowment model to families: what’s usually missing
• The three hardest problems: sizing, sourcing, and pacing
• Denominator and numerator effects in volatile markets
• Continuation vehicles, co-invests, and the evolution of fee structures
• Why governance and investment policy matter more than tactics
• Ranges vs. point targets in asset allocation
• Managing capital calls without forcing bad sales
• Why ad hoc investing quietly destroys portfolios
• Key-man risk, manager “genius,” and process vs. discretion

Guest Bio:

Aneet Deshpande is a senior investment professional and allocator with deep experience advising institutions and private clients on portfolio construction, private markets, and governance. His work focuses on adapting institutional frameworks—such as the endowment model—to the realities of taxable investors, with an emphasis on tax efficiency, pacing, liquidity management, and long-term wealth preservation across generations.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Aneet Deshpande:

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

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) Introduction (1:00) Taxable Investors and Private Market Investments (3:15) Endowment Model Challenges and Fee Trends in Alternatives (9:17) Managing Liabilities and Understanding the Denominator Effect (13:14) Governance and Best Practices in Wealth Preservation (17:48) Addressing Governance Issues and the Perils of Random Investments (21:37) Co-investment Trends and Algorithmic Approaches (23:00) Navigating SPV Layers and Investment Fees (24:05) Timeless Investment Principles and Intellectual Honesty (27:33) Unique Traits of Successful Investors (29:33) Analyzing Investment Manager Strengths and Strategic Planning (32:21) Closing remarks

Can ethics, generosity, and long-term relationships really outperform aggression in venture capital? David Weisburd speaks with David Hornik about why “nice guys finish first… eventually,” how power-law outcomes shape a venture career, and why reputation compounds more reliably than tactics. Hornik explains why backing unflinchingly ethical founders isn’t just moral—it’s a durable competitive advantage in an industry defined by uncertainty. Highlights:

• Why Hornik only backs founders who are “unflinchingly ethical”
• Ethics vs. culture: where pushing hard crosses the line
• Why venture capital is a business of disappointment—and patience
• How one out of ten investments defines an entire career
• The human cost of startup failure and why it never gets easier
• Why power laws make venture outcomes feel irrational
• Compounding reputation as the most valuable long-term asset
• The “transitive property of reputation” in deal sourcing
• Why founders should diligence investors as hard as VCs diligence founders
• Giving vs. taking—and why pure givers still need boundaries
• Media, conferences, and platforms as multiplicative ways to add value
• EQ vs. IQ: why emotional intelligence matters more than raw intelligence
• Why Hornik won’t invest without sharing a meal with founders

Guest Bio:

David Hornik is the Founder of Lobby Capital and a veteran venture capitalist with over 25 years of experience investing from seed to pre-IPO. He previously spent two decades at August Capital and was the first institutional investor in companies including Splunk. David is known for his emphasis on ethics, reputation, and long-term relationship-building as core drivers of venture success.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with David Hornik

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

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) Introduction (1:18) Work-life balance in venture capital (3:31) Investment disappointments and startup failures (7:14) Power law outcomes and investment concentration (10:37) Compounding reputation and career effects (15:00) Long-term relationships and winning deals (19:07) Diligence and investment strategy contrasts (22:07) Role of luck and insights from Adam Grant (28:12) Building a network and leveraging media (30:27) Balancing IQ and EQ in startups (34:28) Advice and validation of relationship-based strategies (37:21) Understanding entrepreneurs and authenticity (38:41) Closing remarks

Why have continuation vehicles become one of the fastest-growing segments in private markets? David Weisburd speaks with Benjamin Carper about what’s driving record CV volume, how these transactions solve structural mismatches in private equity fund lives, and why both LPs and GPs hold mixed views on the strategy. Ben explains how continuation vehicles create liquidity, extend ownership of high-quality assets, and reshape portfolio management across buyout and venture markets. Highlights:

• Why continuation vehicles reached over $100B in annual volume
• How arbitrary fund life cycles created the need for CVs
• The shift from selling winners to compounding them
• Typical size ranges and asset profiles for continuation vehicles
• Why LPs both value and struggle with CV decision-making
• Continuation vehicles as a growing source of cash liquidity
• Pricing mechanisms: auctions vs. sponsor-led recapitalizations
• Best practices around LP rollover options and alignment
• What makes a high-quality CV asset attractive to investors
• How CVs function as “deal-level diligence” for LP–GP relationships
• Differences between buyout and venture continuation vehicles

Guest Bio:

Benjamin Carper is a senior member of Jefferies’ secondaries team, where he helps lead a large platform focused on continuation vehicles and private market liquidity solutions. He advises sponsors and institutional investors on structuring, pricing, and executing single-asset continuation transactions across buyout, growth, and venture portfolios. Ben has worked on some of the earliest and largest continuation vehicles in the market and is closely involved in the evolution of CVs from a liquidity solution into a core portfolio management tool.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Benjamin Carper:

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

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) Introduction to continuation vehicles and market focus (2:00) Increase in continuation vehicle volume and traditional hold period (5:40) Continuation vehicles' impact on company management and LP perspectives (9:09) Pricing and alignment in continuation vehicle deals (12:16) Attractiveness and due diligence in continuation vehicle transactions (16:57) Investor profiles and trends in continuation vehicles (19:01) Continuation vehicles' role in venture capital and long-term relationships (23:13) Notable deals and closing thoughts

Why has liquidity across private markets broken down and what does it mean for institutional portfolios? David Weisburd speaks with Alex Ambroz about collapsing distributions, the rise of continuation vehicles and secondaries, and why many allocators are facing a structural mismatch between models and reality. They explore whether “private is the new public,” how incentives shape GP behavior, and what LPs must change to adapt to a new normal of prolonged illiquidity. Highlights:

• Why private market distribution yields have fallen from ~25% to single digits
• How declining DPI drives the denominator effect across portfolios
• Continuation vehicles: why LPs both rely on and resent them
• Secondary sales as a liquidity tool—and their political costs
• The growing gap between private marks and realizable value
• Why IPOs are no longer a reliable liquidity release valve
• How incentives keep large companies private far longer than before
• Why private credit remains the lone exception on distributions
• Career risk and principal–agent problems on the LP side
• Where AI tools help allocators—and where judgment still matters
• Using factor models to distinguish alpha from disguised beta

Guest Bio:

Alex Ambroz is the Founder and CEO of the Allocator Training Institute, the first structured education platform dedicated to developing the next generation of institutional allocators.

Before founding ATI, Alex spent two decades in senior investment roles at Morgan Creek Capital, J.P. Morgan, Cleveland Clinic, and Aberdeen Standard Investments, where he built and managed multi-asset portfolios across public and private markets.

He has trained hundreds of analysts and investment officers globally and holds deep expertise in portfolio construction, factor modeling, and operational due diligence.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Alex Ambroz:

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

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) Introduction (1:25) DPI, distribution yields, and their historical context (4:38) Impact of reduced distributions on allocators and DPI trends for 2025 (7:06) Illiquidity in private assets and GP strategies (9:50) Role and challenges of secondary sales and CVs (17:34) Borrowing against private book and liquidity concerns (21:27) Preparing for the new normal in private asset distributions (25:24) Private market valuations and LP pressure on GPs (29:33) Principal-agent problem and the impact of AI on investment analysis (33:12) Quick assessment of investment factors (34:49) Closing remarks

What happens when AI stops assisting humans and starts replacing decision-making itself? David Weisburd speaks with Camilo Acosta about the rise of agentic AI, why incumbents still leave massive openings for startups, and how AI will reshape labor, venture capital, and entire asset classes. Camilo explains how investing ahead of regulation, betting on founders over ideas, and building for a fully agentic future define the next era of venture. Highlights:

• Why agentic AI replaces prediction, judgment, and action—not just tasks
• Lessons from building products at Meta and founding startups
• How incumbents’ scale creates opportunity rather than safety
• Why $10B outcomes are “too small” for Big Tech but ideal for VCs
• The danger of competing with platforms that control distribution
• Why copilots miss the point of where AI is going
• AI’s uneven impact across regulated vs. unregulated industries
• How AI will disrupt private equity, asset allocation, and the Yale Model
• The extinction-level event facing emerging VC managers
• Why building a firm is fundamentally a branding and marketing exercise
• Founder psychographics, ruthlessness, and investing pre-idea
• Why some of the best founders are the hardest to work with
• Audio-first interfaces as the next major compute platform shift

Guest Bio:

Camilo Acosta is the Founder and Managing Partner of Perceptive Ventures, an early-stage fund focused on agentic AI. He is a former startup founder and CEO whose company was acquired, and previously served as a senior AI engineering leader at Meta, where he helped run multi-billion-dollar product suites. Camilo invests with a thesis-driven approach centered on agentic systems, founder psychographics, and long-term technological disruption across industries.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Camilo Acosta:

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

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) Introduction (1:12) Distribution power and AI's disruptive potential (3:27) Framework for AI disruption and future opportunities (9:42) Conceptualizing an agentic AI future (10:53) AI's impact on asset classes and investment strategies (13:02) Strategies for emerging VC managers to survive (14:22) The significance of a strong LP network (17:14) Learning from investment misses: team vs. idea (18:44) Balancing AGI safety and national security (19:32) Founder ruthlessness and its effects (21:54) Ego and humility in venture capital (23:01) Managing relationships with challenging founders (25:05) Future of computing platforms (26:38) Career advice for aspiring tech professionals (28:29) Big tech vs. entrepreneurship for career start (29:36) Closing remarks

What happens when capital markets move from batch processing to real time? David Weisburd sits down with Yuval Rooz to discuss his path from Citadel and DRW to founding Digital Asset and building the Canton Network. Yuval explains why blockchain is less about crypto speculation and more about upgrading the infrastructure of global capital markets—unlocking 24/7 settlement, asset utility, and new forms of liquidity across public and private markets. Highlights:

• Yuval’s unconventional path from engineering to trading and entrepreneurship
• Citadel’s talent model and why technical skills scale faster than finance knowledge
• Building DRW’s ETF market-making desk from scratch
• How deep market structure knowledge creates asymmetric opportunities
• Early lessons from Bitcoin and crypto market infrastructure
• Why tokenization is really about financial rails, not hype
• The Canton Network and real-time settlement for capital markets
• Expanding asset utility beyond buy-and-hold investing
• Borrowing against assets vs. forced selling for liquidity
• Why inefficiency persists when it benefits incumbents
• Lessons on risk-taking early in one’s career

Guest Bio:

Yuval Rooz is the Co-Founder and CEO of Digital Asset, the company behind the Canton Network, a blockchain infrastructure designed for regulated capital markets. He began his career at Citadel before joining DRW, where he helped build its ETF trading and digital asset initiatives. Yuval brings deep expertise in market structure, trading, and financial infrastructure, with a focus on modernizing how assets are issued, traded, and settled across global markets.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Yuval Rooz:

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

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) Introduction (4:47) Tokenization, administrative efficiency, and blockchain in finance (9:59) Onboarding assets, transparency, and market inefficiencies (14:02) Closing remarks

How do you compete with Sequoia and Andreessen while running a $650M fund and still expect to outperform? In this episode, I sit down with Glenn Solomon, Managing Partner at Notable Capital, to break down how focused early-stage investing can outperform mega-platform venture funds. Glenn explains why 70%+ of venture dollars now go into mega-rounds over $100M, why Notable stays disciplined at seed and Series A, and how delivering “unscalable” founder support creates real edge. We also go deep on Anthropic, the so-called “software apocalypse,” AGI narratives, and where durable alpha exists in an AI-dominated world. Highlights:

• Why $350B in venture funding hides a barbell market structure
• How focusing on sub-$100M rounds creates structural edge
• Why size is often the enemy of return
• Building a 42-person team to serve 8–10 new founders per year
• The case for consistent top-quartile vs. volatile top-1% returns
• Anthropic’s enterprise-first positioning and labor market opportunity
• Why AI is attacking multi-trillion-dollar labor markets—not just software
• The pendulum effect behind the “software apocalypse”
• Why distribution and proprietary data still matter in SaaS
• AGI as a phase, not a binary event
• Where net-new opportunity sits above infrastructure
• The danger of chasing “shiny objects” without conviction

Guest Bio:

Glenn Solomon has been a venture capitalist for nearly 30 years and has spent the last 18 years building what is now Notable Capital, the U.S.-focused team that previously operated as GGV Capital before separating in 2023. Glenn invests in early-stage software companies across enterprise infrastructure, cybersecurity, data, and AI. A Stanford graduate and former three-time NCAA national championship tennis team member, Glenn brings a disciplined, team-first mindset to venture investing. He is known for deep sector expertise, strong founder relationships, and a focus on delivering consistent, high-conviction returns through concentrated early-stage ownership.

Our Podcast now receives more than 300,000 downloads a month. 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 market intelligence platform trusted by 85% of the S&P 100 that helps you make confident, data-driven decisions faster than your competitors. With powerful search capabilities designed for hedge funds, mutual funds, and private equity investors, AlphaSense gives you the edge to elevate your research. Visit: alpha-sense.com/howiinvest.

Stay Connected with David Weisburd:

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

Stay Connected with Glenn Solomon:

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

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) Introduction (1:35) Impact of the hot M&A and IPO market on investment strategies (2:43) Advantages and disadvantages of a $650 million fund and budget concentration for impact (5:38) Delivering unique value to founders and competing with large funds (9:40) Investment in Anthropic, AI market landscape, and opportunities (15:21) AI's disruption in the software market and incumbent adaptations (18:46) Investing strategies in a post-AGI world and AGI phase opportunities (24:58) Timeless career advice for investors and the importance of sector expertise (27:21) Closing remarks

Why does execution velocity matter more than pedigree at the earliest stages of company building? David Weisburd speaks with Eric Bahn about the concept of “hustle,” why early judgments about founders tend to persist, and how throughput, learning speed, and grit outperform traditional signals in pre-seed investing. Eric explains Hustle Fund’s wide-net strategy, its community-driven platform model, and how changing startup timelines are reshaping venture economics. Highlights:

• Why early founder rankings tend to persist over time
• Defining “hustle” as execution speed and learning velocity
• Why hustle is difficult to fake but easy to observe in practice
• Quantity of experimentation as a driver of quality outcomes
• The limits of pedigree and why it’s often priced into valuations
• Hustle Fund’s wide-net, low-ownership-sensitive portfolio model
• Combining diversification with selective concentration over time
• Building a venture fund as a media and community platform
• Staying small to preserve incentives and execution discipline
• Seed-strapping, delayed liquidity, and the growing role of secondaries
• Why venture fund timelines may need to extend beyond 10 years

Guest Bio:

Eric Bahn is the Co-Founder and Managing Partner of Hustle Fund, a pre-seed venture capital firm focused on backing founders with exceptional execution velocity. He began his career as a product manager at Meta and later worked at 500 Global, where he helped evaluate thousands of early-stage startups. Eric is known for his emphasis on hustle, learning speed, and building founder-focused platforms that combine capital, community, and distribution.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Eric Bahn:

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

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) Introduction (0:29) Identifying and differentiating true hustlers (1:30) Meta story and product management insights (2:31) Sprint-based evaluation model (5:31) Importance of throughput in success (7:06) Concentrated vs. diversified portfolios and HustleFund's strategy (11:07) Pedigree, grit, and emotional intelligence in founders (15:43) Media and community platform strategy at HustleFund (18:49) The impact of AI and alternate liquidity options in VC (23:59) The rise of secondaries and long-term fund dynamics (26:04) Cold outreach and advice to a younger self (28:54) Accepting limitations and finding satisfaction (30:04) Closing remarks

Why are vertical AI applications emerging as some of the most defensible opportunities in technology today? David Weisburd speaks with Nick Beim about why context—not raw intelligence—is becoming the key driver of AI performance, and how vertical software is reshaping wealth management, legal services, and defense. Nick shares how legacy infrastructure, industry economics, and human-centered workflows create enduring opportunities for AI-driven transformation. Highlights:

• Why vertical AI outperforms horizontal models through domain-specific context
• The limits of large LLM platforms in winning every application layer
• Structural failures in wealth management technology and custody systems
• Why advisors remain central despite advances in automation
• AI-driven tax-aware investing and personalization at scale
• The next wave of legal tech beyond basic research tools
• Why high legal costs suppress economic activity—and how AI changes that
• How AI is reshaping defense, intelligence, and modern warfare
• Low-cost autonomous systems vs. traditional defense contractors
• Why pattern recognition fails for the most disruptive venture investments

Guest Bio:

Nick Beim is a Partner at Venrock, where he has invested for over two decades across AI, wealth management, fintech, legal tech, and defense technology. He previously worked at McKinsey & Company and Goldman Sachs and serves on the Council on Foreign Relations. Nick is known for backing category-defining companies, focusing on vertical software, and investing in founders building highly contextual, defensible businesses.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Nick Beim:

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

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) Introduction (1:13) Limitations of horizontal LLMs and wealth management tech (5:34) Context in financial advising and rise of retail alternative investments (10:02) AI's future in tax-aware investing and legal tech (15:04) AI's impact on defense, national security, and next-gen warfare (21:36) Competition in defense tech and methodologies for diligencing AI investments (25:01) Pioneering companies and strategies for niche market investments (27:16) Advice for early career venture capitalists and understanding power law (31:32) Characteristics of successful founders and the role of personal drive (36:30) Founder magnetism, charisma, and the importance of transparency (38:31) Closing remarks

How should investors think about risk when traditional measures like volatility fall short? David Weisburd speaks with Jeff Blazek about portfolio construction across institutions and family offices, why drawdown matters more than standard deviation, and how allocators should balance public and private markets. Jeff shares first-principles thinking on liquidity, behavioral risk, and building resilient portfolios across market cycles. Highlights:

• Key differences between managing large institutions and smaller endowments
• Why drawdown is a more meaningful risk metric than volatility
• First principles for building an endowment-style portfolio
• The behavioral risks of over-allocating to private markets
• How liquidity enables rebalancing during periods of market stress
• Trade-offs between public and private investments
• Managing denominator effects and secondary market risks
• The role of liquid, uncorrelated diversifiers
• Why quality investing has overtaken pure value investing
• How allocators should think about AI, growth, and regime shifts

Guest Bio:

Jeff Blazek is Co-Chief Investment Officer of Multi-Asset Strategies at Neuberger Berman, a global asset manager overseeing approximately $550 billion in assets. He has held senior investment roles across endowments, pensions, and consulting, including NewYork-Presbyterian Hospital, Texas Teachers, and Cambridge Associates. Jeff brings over 25 years of experience in portfolio construction, asset allocation, and risk management across public and private markets.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Jeffrey Blazek:

LinkedIn: http://linkedin.com/in/jeffrey-blazek-cfa-a0a57212

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) Introduction (1:00) Impact of portfolio size on investment strategy and working with Britt Harris at Texas Teachers (3:01) Principles for building an endowment-like portfolio and defining risk tolerance (5:41) Understanding risk: Drawdown vs. standard deviation and stock market implications (8:48) Hidden risks in investment portfolios (10:19) Assumptions about volatility and endowments' role in venture capital (15:09) Multi-asset investing and managing public and private assets at Neuberger Berman (19:20) Volatility laundering, second-order effects, and risk of ruin (22:25) Ideal portfolio allocation strategies for unconstrained investors (25:47) Adjusting private and public equity allocations and implementing an 80/20 portfolio (33:24) Behavioral aspects of portfolio allocation and current asset class valuations (38:50) Fixed income vs. private credit and the evolution of investment philosophy (42:44) Staying cutting-edge and understanding market dynamics through bottom-up analysis (46:44) AI's impact on stock market pricing and future economic growth (48:59) Timeless career advice and comparing career paths (51:05) Closing remarks

Where does real edge still exist in public markets and how do you size risk when certainty doesn’t exist? In this episode, I talk with Ari Levy, Founder and CIO of Lakeview Investment Group, about applying probability theory, arbitrage, and disciplined position sizing to public equity investing. Ari explains how early lessons from card counting and game theory shaped his approach to risk, why small-cap markets remain structurally inefficient, and how activism, arbitrage, and management access can create asymmetric outcomes—without blowing up the portfolio. Highlights:

• Probability theory as the foundation of investing
• Why position sizing matters more than prediction
• Hidden risks in “risk-free” arbitrage trades
• Structural inefficiency in small-cap equities
• Passive flows as a tailwind for active small-cap investors
• Friendly activism and aligning boards with shareholders
• When public companies should be private
• Arbitrage vs. fundamental stock picking—and when each works
• Avoiding value traps in a tech-driven world

Guest Bio:

Ari Levy is the Founder, President, and Chief Investment Officer of Lakeview Investment Group, where he oversees portfolio construction, risk management, and investment decision-making across public equity strategies. A long-term, engaged owner, Ari frequently works with management teams and boards on strategy, capital allocation, and governance. Earlier in his career, he served as a Vice President and Share Partner at Advisory Research and was President of Levy Acquisition Corp., later serving on the board of Del Taco until its acquisition by Jack in the Box. Ari holds a B.A. in International Relations from Stanford University.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Ari Levy:

LinkedIn:https://www.linkedin.com/in/ari-levy-ab91254/

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) Introduction to probability theory and sports statistics (0:56) Running a blackjack team and risk management lessons (5:09) Idiosyncratic risk and ETF examples (6:33) Sponsor: AlphaSense channel research (7:44) Managing exposure in investments (8:17) Inefficiencies and opportunities in small cap companies (14:01) Activist investing strategies (18:13) Case study: Quipt Home Medical (20:15) Timeless investment advice for success (21:15) Historical performance and impact of tech on value investing (23:01) Closing remarks and call to action

What actually creates sustainable alpha in endowment portfolios and why do most investors mistake activity for edge? In this episode, I talk with Larry Kochard about building investment programs that endure across cycles. Drawing on his experience as CIO at Georgetown and the University of Virginia and later at Makena Capital, Larry explains why preparation before crises matters more than heroics during them, how governance and stakeholder buy-in reduce behavioral mistakes, and where real alpha still exists in increasingly efficient markets. We unpack liquidity discipline, rebalancing under stress, manager sizing, and why “people are upstream of everything.” Highlights:

• Preparing for downturns before they happen
• Why governance and buy-in reduce behavioral errors
• Rebalancing when it feels hardest
• Liquidity as the prerequisite to capturing great vintages
• Where alpha still exists—and where it doesn’t
• Size as the enemy of returns (and when exceptions apply)
• Underwriting people as the allocator’s true edge
• Playing to institutional strengths without overconcentration
• Passive as a smart default until real edge is built
• Why patience beats activity over decades

Guest Bio:

Larry Kochard is a veteran institutional investor and educator with decades of experience building and leading endowment-style portfolios. He served as CIO of Georgetown University, CEO and CIO of the University of Virginia Investment Management Company, and CIO and Partner at Makena Capital Management. Larry has taught institutional investing at UVA and Georgetown for many years and is widely recognized for his work on governance, portfolio construction, and long-term investing discipline. He holds a Ph.D. in Economics from the University of Virginia and is a CFA charterholder.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Larry Kochard:

LinkedIn:https://www.linkedin.com/in/larry-kochard-4a21b6b/

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) Introduction to Larry Kochard's career and experience at Georgetown (1:06) Crafting a new investment policy and advice from industry leaders (2:35) Rooted thesis and long term investing approach (4:00) Sustainability in investment programs (5:27) Managing endowments during financial crises (11:24) Preparing for and reacting to crises (13:08) Self-fulfilling prophecy in returns and sources of alpha (19:01) Mental model for picking managers and scaling challenges (21:52) Size as the enemy of returns and manager evaluation (24:05) Team management and multi-product offerings (27:32) Structural alpha and underwriting people (29:18) Institutional investment strategies and edge (34:14) Balancing strengths and allocation risks (37:10) Patience and pattern recognition in manager selection (40:14) Strategy communication and managing expectations (41:40) Co-investing, direct investing, and real estate portfolios (48:32) Borrowing against illiquid portfolios (50:46) Future of endowment investing and TPA model (55:42) Integrating best practices and personal advice (57:42) The importance of people, collaboration, and leadership (58:51) Closing remarks

After 300 interviews with the world’s top investors, what does alpha actually look like and why is it almost never what people think it is? In this special episode, the roles are reversed. David Weisburd, host of How I Invest and Co-Founder of Weisburd Capital, steps into the guest seat as his co-founder Curtis Pierce takes over as host. Together, they unpack the most important lessons David has learned from more than 300 conversations with CIOs, LPs, GPs, founders, and allocators representing trillions in assets. The discussion centers on why real alpha is hard, boring, and often low-status, how structural advantages drive sustainable outperformance, and why governance and portfolio construction matter more than any single trade.

Highlights:

• Why alpha is almost never a “stroke of genius”
• Hard and boring as the most reliable sources of outperformance
• Prestige as a contra-indicator to future returns
• Structural alpha vs. manager selection
• Portfolio construction as ~90% of long-term outcomes
• Co-investments and fee structure as embedded alpha
• Tax efficiency as one of the most powerful return drivers
• Why lower middle market investing passes the “cocktail cringe test”
• Governance as the true upstream driver of returns
• LP capture vs. LP empowerment
• Why reference calls are the most underrated investing skill
• Career alpha and choosing the right institution
• Focusing on activities that compound over decades

About David Weisburd: David Weisburd is the founder of Weisburd Capital and host of the How I Invest podcast.

He previously served as Partner and Head of Venture Capital at 10X Capital, leading investments in companies including Robinhood, HoneyBook, Palantir, Circle, and DraftKings. He also founded Growth Technology Partners, which was acquired by 10X Capital.

Earlier in his career, David was part of the founding teams of venture-backed startups iSocket (acquired by Rubicon Project) and RoomHunt (acquired by RentLingo). He has served on the boards of three publicly traded companies and holds an MBA from Tuck School of Business at Dartmouth and a master’s degree in psychology from Harvard University.

About Curtis Pierce: Curtis Pierce is a co-founder of Weisburd Capital and the How I Invest podcast.

He previously served as Senior Vice President at 10X Capital, where he led investment and capital markets activities across venture capital and other alternative asset classes. Notably, he led the firm’s investment in Cerebras Systems. He also served as CFO of a publicly-traded portfolio company, successfully executing a change of control transaction.

Pierce began his career at Wells Fargo Securities in the equity capital markets group covering technology, media, and telecom companies. He graduated magna cum laude from the University of Utah with an Honors BS in Finance and currently 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 Capital: https://www.weisburdcapital.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 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

(0:00) Introduction (1:36) Consistent compounding and portfolio construction (3:33) Achieving alpha through prestige and low status (5:36) Overcoming status games and examples of contrarian investors (9:05) Structural alpha and its examples (12:18) Co-investing and identifying alpha opportunities (16:15) Exploring lower middle market private equity (18:09) Principal-agent dynamics in institutional investing (20:28) Balancing returns and career management for CIOs (22:58) Leveraging corporate governance for institutional capital (25:59) Governance strategies for mid-career allocators (29:23) LP capture: risks and management (32:31) Fostering LP empowerment and avoiding capture (34:51) Evaluating institutional investing practices (36:16) Effective reference calls in investing (38:10) Career advice for recent graduates in finance (39:05) Closing remarks

Can institutional capital really afford to rush or is patience the ultimate edge in fundraising? In this episode, I sit down with Rahul Moodgal to unpack what it actually takes to build long-duration institutional relationships in today’s cautious capital environment. We talk about why capital raising is harder than it looks, how elite LPs think about alignment over performance, and why the best partnerships are often built over a decade—not a quarter. Highlights:

• Why raising capital today feels harder than ever—even at scale
• The difference between transactional LPs and long-term partners
• How trust, transparency, and integrity compound over time
• Why patience can outperform urgency in institutional fundraising
• What elite allocators look for beyond track record alone

Guest Bio:

Rahul Moodgal is a veteran institutional capital raiser with decades of experience working across pensions, endowments, foundations, and sovereign wealth capital. Known for his relationship-first philosophy, Rahul has helped managers build durable, long-term LP partnerships by prioritizing alignment, transparency, and trust over short-term performance chasing. His approach emphasizes patience, integrity, and the belief that the right capital—at the right time—matters more than fast capital.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Rahul Moodgal :

LinkedIn: https://www.linkedin.com/in/rahul-moodgal/

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) Introduction (2:08) Combining Rationality and Due Diligence in Investments (4:32) Building and Maintaining Long-term Investor Relationships (11:28) Scaling Challenges and Long-term Thinking in Investment Firms (15:21) Growth Strategies and Predictable Challenges for New Firms (18:15) The Pressures and Impacts of Rapid Firm Growth (19:20) Exploring Different Investment Strategies (25:02) The Importance of Early Backing and Loyalty in Investments (27:56) Best Practices and Relationship Building for Elite LPs (33:26) The Strategic Approach of Not Asking for the Sale (36:45) Retail Investors, Intermediaries, and Principal Agent Issues (41:04) The Significance of LP Quality and Alignment (43:00) Rahul Moodgal's Other Activities and Interests (45:00) Charity Work's Impact on Personal and Professional Life (45:50) Timeless Investment Lessons for GPs and LPs (48:27) Identifying Underrated Qualities in Successful Investors (50:41) Integrity and Exemplary Practices in the Investment Industry (53:38) Perspectives on AI and Its Evolving Role in Investments (55:34) The Value of Handwritten Notes in Professional Relationships (56:52) Closing remarks

What does it mean to be a true partner to lower middle market businesses? David Weisburd speaks with Peter Elliot Rothschild about building RF Investment Partners around listening first, designing bespoke capital solutions, and investing as the first institutional capital in family-owned companies. Peter discusses minority versus control investing, the role of trust and relationships, and why value creation in the lower middle market is driven less by financial engineering and more by people, incentives, and execution. Highlights:

• Building RF Investment Partners with a listening-first investment philosophy
• Why being first institutional capital creates unique opportunities
• Bespoke capital structures combining debt and equity
• Challenges of fundraising without fitting neatly into LP “buckets”
• Minority investing misconceptions and downside protection strategies
• Why lower middle market investing is fundamentally a people business
• The role of executive chairs and 180-day value creation plans
• Aligning employee incentives with tangible operating KPIs
• CEO summits as a value-creation and leadership tool
• Relationship compounding as a long-term competitive advantage

Guest Bio:

Peter Elliot Rothschild is the Founder and Managing Partner of RF Investment Partners, a private investment firm focused on providing flexible, bespoke capital solutions to lower middle market businesses. He has deep experience across both control and minority investments, with a focus on partnering with family-owned companies as their first institutional capital. Peter is known for emphasizing trust, alignment, and operational value creation over financial engineering, and for building long-term relationships with management teams, operators, and limited partners.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Peter Rothschild:

LinkedIn: https://www.linkedin.com/in/peter-rothschild-44a190/

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) Introduction (0:34) Benefits of being the first institutional capital and advantages of bespoke capital solutions (2:34) Challenges of fundraising and alignment with future investment philosophies (4:11) Misconceptions about minority investing and control dynamics (5:47) The role of being a therapist in family-owned businesses and underwriting risk (8:40) Flexible ownership stakes, advisory roles, and developing a 180-day plan (10:57) Value-add in sub $50 million enterprise companies and CEO Summit benefits (14:24) Compounding relationships and the importance of people in investment decisions (17:37) Balancing EQ and IQ with CEO psychology and background checks (19:27) Managing non-cooperative CEOs and the evolution of private equity (21:40) Critique of traditional buyout funds and benefits of having former CEOs as backers (25:08) Impact of personal relationships on investment approach (26:19) Closing remarks

How do tax efficiency, private markets, and structural change intersect in modern portfolio construction? David Weisburd speaks with Jeffrey Fulk about his career across hedge funds, fund-of-funds, and wealth platforms, and how AlTi Global approaches tax-aware investing, private credit, evergreen structures, and evolving access to private markets. Jeff shares insights on where opportunity is emerging as markets shift and why after-tax outcomes increasingly drive investment decisions.

The views expressed herein are those of Jeffrey Fulk and do not necessarily reflect the views of AlTi Global, Inc. or its affiliates (“AlTi”). This is for informational purposes only and does not constitute investment advice, an offer to buy or sell any financial product, a solicitation to become an advisory client of AlTi or an investor in any AlTi-advised fund, or an endorsement of AlTi, its advisory services, or investment strategies, including AlTi-advised funds. While the information and views presented are believed to be accurate and expressed in good faith, there is no assurance that they are correct, complete, or will not change over time. All investments carry risk, including loss of principal. Past performance is not indicative of future results.

Highlights:

• Jeff’s unconventional path into finance and early hedge fund investing
• Lessons from the LTCM collapse and market dislocations
• Why tax-aware strategies are reshaping wealth portfolios
• Mechanics and risks of long-short tax loss harvesting strategies
• The growing role of private credit and credit secondaries
• ETFs, correlation risk, and implications for portfolio construction
• Evergreen structures versus closed-end private funds
• Why operational simplicity matters for wealth clients
• Continuation vehicles and selective buyout opportunities
• The potential impact of private assets entering 401(k)s

Guest Bio:

Jeffrey Fulk is a senior investment professional at AlTi Global, a global wealth and asset management platform with approximately $100 billion in assets under management. He has held senior roles across hedge funds, fund-of-funds, and wealth management, including positions at Guggenheim Partners and Hightower. Jeff focuses on portfolio construction, tax-efficient investing, and integrating private markets into long-term wealth strategies.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Jeffrey Fulk :

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

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) Introduction (5:40) Key asset classes and strategies at Alti Global (9:56) Tax strategies in investing: Long short tax loss harvesting (17:54) Exploring the private credit market and secondaries (20:41) The rise of fixed income ETFs (24:07) 401(k)s and private assets: A new frontier (28:08) Innovations in investment structures (31:04) Evergreen structures vs. managing capital calls (34:35) Analyzing current trends in private equity (37:55) How to access top private companies (39:33) Reflections: Advice for the younger self (41:30) Closing remarks

Why do so many advisory boards look impressive on paper but fail to deliver real value when it actually matters? In his second appearance on the podcast, I sit down again with Matt Curtolo, a senior advisor to both GPs and LPs who has worked with more than 600 general partners across venture, growth equity, and private equity. Matt breaks down the biggest misconceptions around advisory boards and LP advisory committees, why “performative” governance quietly destroys trust, and how the best managers design advisory structures with real purpose. We get tactical on compensation, LPAC construction, advisor selection, and how great firms turn advisors into a true strategic weapon—not window dressing. Highlights:

• The critical difference between LPACs, boards of advisors, and independent advisors
• Why most advisory boards fail before they ever meet
• Purpose and clarity as the starting point for any advisory structure
• “Performative” advisors vs. functional advisors
• The value of truly independent, unconflicted feedback
• Advisor vs. full-time hire: how to decide
• Best practices for advisor compensation (carry, cliffs, and alignment)
• Why smaller LPACs outperform large, unwieldy committees
• How advisors can (and should) support fundraising
• Common LPAC construction mistakes GPs keep repeating
• Diversity of LP perspectives as a governance advantage
• Why transparency turns LPACs into long-term advocates

Guest Bio:

Matt Curtolo is a senior advisor to general partners and limited partners across venture capital, growth equity, and private equity. Over his career, he has worked with and advised more than 600 general partners, served on numerous advisory boards and LP advisory committees, and helped managers navigate fundraising, governance, and firm-building challenges. Today, Matt focuses on helping emerging and established managers design effective advisory structures, improve LP communication, and build durable franchises across private markets.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Matt Curtolo:

LinkedIn:https://www.linkedin.com/in/matt-curtolo-caia/

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) Introduction (2:36) Independent Advisers' Objective Feedback (5:52) Roles and Differences of Advisers vs. Full-Time Team Members (7:33) Compensation Frameworks for Advisory Board Members (10:34) Advisory Relationship Success Rate and Turnover (13:22) Building Advisory Boards from Scratch (16:03) Advisory Board Construction Based on Team Needs (17:14) Optics and Substance in Advisory Boards (19:19) LinkedIn Affiliations as Commitment Signals (20:34) Strategic Use of LP Advisory Committees (22:53) Leveraging Advisory Boards for Fundraising and LP Introductions (25:02) Mistakes in Constructing LP Advisory Committees (LPAKs) (27:40) Optimal LPAK Size (28:33) Venture Market Outlook for 2026 (32:40) Closing remarks

What actually separates great institutional investors from average ones and why does governance matter more than brilliance? In this episode, I talk with Christopher J. Ailman, former Chief Investment Officer of CalSTRS, about the decisions that shaped one of the largest and most successful public pension funds in the world. Chris reflects on more than two decades leading CalSTRS, why asset allocation and governance drive the vast majority of outcomes, and how building a resilient, low-cost, long-term portfolio matters far more than chasing the latest investment trends. We also discuss culture, decentralization, and what CIOs consistently get wrong when managing people and risk. Highlights:

• Why governance is the most underrated driver of returns
• Asset allocation as ~90% of long-term performance
• Borrowing from the Canadian pension model
• Building in-house capabilities to reduce costs
• Why chasing “shiny objects” destroys net returns
• Cost discipline as a competitive advantage at scale
• Culture as a hidden source of alpha
• Centralized vs. decentralized decision-making
• Portfolio resiliency and downside protection
• Why great investors come from wildly different backgrounds

Guest Bio:

Christopher J. Ailman is the former Chief Investment Officer of CalSTRS, where he served for more than 23 years and helped grow the fund into one of the largest and most respected institutional investors globally. Over a 30+ year career in institutional investment management, Chris became widely recognized as one of the world’s top CIOs. He is now the founder of Ailman Advisers, where he focuses on coaching and mentoring CIOs and institutional investors, as well as teaching and public speaking. He also serves as Chair of The 300 Club of global CIOs and is Chair Emeritus of the Milken Global Capital Markets Committee.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Christopher Ailman:

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

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) Introduction (0:06) Key decisions and achieving above median returns (2:18) Lowering investment costs and borrowing ideas (5:36) Avoiding fads and building a world-class culture (10:51) Governance and crisis anticipation in portfolio strategy (13:34) Hiring and unique due diligence strategies (17:37) Future of asset allocation and special GP encounters (21:18) Closing remarks

Why are humans — not models — still the biggest bottleneck to AI progress, and what happens when that bottleneck becomes a business? In this episode, I talk with Ali Ansari, Founder and CEO of micro1, about the hidden layer powering today’s AI breakthroughs: high-quality human intelligence. Ali explains how micro1 pivoted from an AI recruiting startup into a critical data infrastructure company for frontier AI labs, why expert-generated data is now the limiting factor in model performance, and what needs to change for AI agents to actually work in production. We also explore how focus, market timing, and ruthless prioritization enabled micro1 to scale more than 30× in a single year. Highlights:

• Why AI progress is still overwhelmingly driven by humans
• The shift from pre-training to expert-level post-training data
• Why AI agents fail in production despite great demos
• Evaluation frameworks as the missing layer for agents
• How micro1 serves frontier labs and Fortune 500 enterprises
• The hardest pivot: firing customers to focus on the right market
• Why market selection matters as much as product quality
• How investors are using AI to gain workflow-level edge
• Humans as operators of agents, not coworkers
• How focus became micro1’s biggest competitive advantage

Guest Bio:

Ali Ansari is the Founder and CEO of micro1, an AI platform for human intelligence that connects highly skilled experts — including PhDs, professors, and industry specialists — with leading AI labs to generate high-quality training and evaluation data. Under Ali’s leadership, micro1 rapidly transformed from an AI recruiting startup into a core data infrastructure provider for frontier models, scaling more than 30× in a year. Ali represents a new generation of AI-native founders building companies at the intersection of human expertise and machine intelligence.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Ali Ansari:

LinkedIn:https://www.linkedin.com/in/ali-ansari-7b240a18b/

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) Introduction to MicroOne and Customer Demographics (0:55) The Advancement of LM Models and Human Involvement (2:13) AI Agents in the General Market: Opportunities and Obstacles (5:57) AI Versus Human Intelligence in Performance (6:15) Identifying the Killer Application for AI Agents (7:06) AI Investment Strategies: Early Case Studies (8:28) The Journey of an AI Native Entrepreneur (9:21) AI's Impact on Venture Capital and Private Equity by 2030 (10:48) Human Roles in an AI-Dominated Future (12:13) AI Takeover Concerns and Safety Measures (14:17) Professional Growth Advice for AI Entrepreneurs (17:28) MicroOne's Market Focus and Strategic Reorientation (19:00) Insights on Adaptive Leadership in Tech (20:00) Extracting Ground Truth from Customer Feedback (20:54) Closing remarks

How should families think about portfolio construction when traditional diversification breaks down? David Weisburd speaks with Michael Phipps about building New Republic Partners, designing portfolios around growth, income, and diversification, and why open architecture matters in multifamily offices. Michael discusses common portfolio mischaracterizations, the role of alternatives and co-investments, and how families can better align risk, liquidity, and long-term objectives. Highlights:

• Building a conflict-free, open-architecture multifamily office
• Designing portfolios around growth, income, and diversification
• Why fixed income may no longer provide true diversification
• The role of absolute-return strategies as portfolio ballast
• How families should think about drawdowns and risk tolerance
• Separating hedged equity from true diversifiers
• Opportunistic use of secondaries in private markets
• Benefits and risks of co-investments
• Structural challenges facing sub-$250M family offices
• Endowment model versus total portfolio approach

Guest Bio:

Michael Phipps is a Partner at New Republic Partners, a multifamily office serving families, foundations, and endowments across the Southeast. He has extensive experience in portfolio construction, manager selection, and alternative investments, and previously worked in institutional investing roles including at university endowments. Michael’s work focuses on aligning portfolios with long-term objectives, risk tolerance, and liquidity needs through an open-architecture approach. Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Michael Phipps:

LinkedIn: https://www.linkedin.com/in/michael-phipps-unc2004/

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) Introduction (1:02) Overview of assets under management and company structure (2:07) Open architecture and due diligence in multifamily offices (4:59) Portfolio building strategies for sizable clients (8:35) Diversification and income-generating assets (11:30) Asset roles and strategic allocation in portfolios (16:51) Co-investment opportunities and selection challenges (18:43) Special considerations for smaller family offices (21:29) Comparing portfolio construction philosophies (23:29) Timing markets and investment cycles (25:33) Lessons from Davidson and UNC Endowments (29:10) Reflective advice for future investors (30:31) Closing remarks

How do experienced LPs evaluate venture managers in an increasingly crowded and bifurcated market? David Weisburd speaks with Kate Simpson about her career as a venture allocator, her move to GEM to lead venture investing, and how institutional LPs assess sourcing, portfolio construction, and power-law dynamics. Kate explains how reference calls, fund sizing, access, and long-term relationships shape conviction in venture manager selection. Highlights:

• Kate’s path from the UNC Endowment to leading venture at GEM
• Lessons learned from fund-of-funds investing and institutional due diligence
• Why asking the right questions matters more than having the right answers
• Differentiating between “good” and “glowing” references
• Evaluating venture funds through sourcing, picking, and winning
• The role of portfolio construction and reserve strategy in venture returns
• Why venture has become two distinct games: access vs. discovery
• How fund size impacts the ability to capture power-law outcomes
• Signals LPs use to evaluate managers before liquidity
• The evolving role of LPs as long-term partners in venture ecosystems

Guest Bio:

Kate Simpson is a senior venture allocator at GEM, where she leads venture investing across the firm’s OCIO and discretionary platforms. She has spent her career as an institutional LP, with prior experience at the UNC Endowment and multiple fund-of-funds, focusing on venture manager selection, portfolio construction, and long-term partnerships. Kate brings a deep understanding of both qualitative and quantitative diligence across early-stage and multi-stage venture strategies.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Kate Simpson :

LinkedIn:https://www.linkedin.com/in/kate-simpson-159796/

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) Introduction (0:40) Kate's career and venture investing insights (3:49) Effective reference checks and venture investing strategies (9:50) Fund math and spotting industry shifts (13:25) Evaluating venture funds and market bifurcation (17:24) Sourcing competitive advantages at Gem (20:41) LP vs. GP perspectives in venture capital (22:19) Identifying signs of successful investors (24:14) Challenges with DPI and LP value add (26:29) Building LP pipelines and JEM's approach to relationships (28:35) Active participation and current venture investing difficulties (30:56) Venture returns and the role of solo GPs (34:08) Managing key man risk and long-term GP partnerships (38:17) Career advice and advocating for oneself in investments (39:30) Closing remarks

How does one of the world’s largest pension funds shift its culture, governance, and investment process at scale? David Weisburd speaks with Nicole about her transition from Ontario Teachers’ Pension Plan to serving as CIO of CalPERS, implementing a total portfolio approach, and leading organizational change during a period of market and operational disruption. Nicole shares lessons on governance, board alignment, co-investing, and building long-term investment institutions. Highlights:

• Transitioning from Canadian pension governance to leading CalPERS
• Implementing a total portfolio mindset within a large, complex organization
• Why culture and governance matter more than asset allocation labels
• Breaking down silos across asset classes and investment teams
• Aligning incentives, compensation, and accountability
• Building trust and transparency with pension boards
• The role of co-investing in improving net returns
• Lessons from managing private markets at scale
• Moving from institutional allocator to founding a private credit firm

Guest Bio:

Nicole is the Founder and Managing Partner of Square9 Capital and previously served as Chief Investment Officer of CalPERS, where she oversaw one of the largest pension portfolios globally. Earlier in her career, she spent nearly two decades at Ontario Teachers’ Pension Plan and also worked as a GP in private markets. Nicole has extensive experience across public and private investments, pension governance, and portfolio construction, with a career focused on long-term capital stewardship and mission-driven investing.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Nicole T Musicco:

LinkedIn: https://www.linkedin.com/in/nicole-t-musicco-293620101/

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) Introduction (1:19) Total portfolio approach and cultural changes at CalPERS (12:08) Building trust and governance at CalPERS (15:44) Co-investment strategies and GP partnerships (19:39) Energy transition, diversity, and structural alpha (23:25) Capital deployment challenges and credit strategies (24:45) Launching Square Nine Capital (29:45) Allocator and GP dynamics (32:26) Challenges of starting a new investment firm (37:24) Empathy in investment and leadership (40:33) Nicole Musicco's legacy and closing thoughts (42:20) Closing remarks

Why have consumer startups fallen out of favor and why might that be the biggest opportunity of the next decade? In this episode, I talk with Brian O’Malley, founder of Tactile Ventures, about why consumer investing is deeply misunderstood and how AI is unlocking a new wave of products that improve everyday American lives. Brian shares lessons from two decades investing at Accel, Battery, and Forerunner, why incentives—not talent—drive venture outcomes, and how the best consumer companies blend technology, business models, and human behavior. We also explore why AI is moving out of its “toy phase,” why humans still need to stay in the loop, and how early-stage investors win by giving founders something large platforms can’t: time. Highlights:

• Why consumer investing has declined despite driving most historic IPO winners
• The difference between “seven deadly sins” products and durable everyday utilities
• Why consumer companies are often less capital-intensive than people assume
• How to invest in consumer startups before traction exists
• Why AI is leaving its “toy phase” and moving into real-world applications
• The power of human-in-the-loop models for trust and adoption
• How incentives inside VC firms shape decision-making and returns
• Why large venture platforms struggle as they scale
• How Tactile competes with mega-funds by showing up earlier and more prepared
• The rise of AI-powered services and digitally native franchises
• Why the best early-stage investors act like “the second-and-a-half cofounder”

Guest Bio:

Brian O’Malley is the founder of Tactile Ventures, an early-stage venture capital firm backing founders who combine emerging technologies with new business models to solve everyday problems for Americans. Before launching Tactile, Brian spent more than 20 years investing in consumer and technology companies as a managing partner at Forerunner Ventures, an early-stage partner at Accel, and a general partner at Battery Ventures. He has partnered with founders behind companies spanning travel, commerce, healthcare, and financial independence, and previously helped build multiple startups that were acquired by Motorola, Oracle, and IBM. Brian is a frequent writer and contributor to Fortune, Forbes, and LinkedIn, and a regular guest on leading investment podcasts. He is a graduate of the Wharton School at the University of Pennsylvania.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

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 Brian O’Malley:

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

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) Introduction (1:39) The seven deadly sins and inevitability of consumer tech solutions (4:15) Investing in consumer tech pre-traction and understanding alternatives (7:13) Facebook's strategic growth and the transition from toy to serious AI applicationsse (11:39) Early use cases and the challenge of near-perfect AI performance (19:10) AI versus cardiologists and generational trust differences (22:12) Views on large multistage VC platforms and growth incentives (28:16) Aligning incentives in large firms and complexity in venture incentives (39:56) Marking valuations and incentive biases (40:58) Tactile's new fund and interest categories in AI and consumer applications (45:27) Differentiating against large firms and value of early-stage investor involvement (50:14) Unique aspects of Tactile VC and building a successful investment organization (52:02) Closing remarks

Why does today’s venture market feel increasingly untethered from historical precedent? David Weisburd speaks with Narayan Chowdhury about structural shifts in venture capital, the limits of data-driven decision-making, and how founders and investors navigate an unusually noisy and fragmented market. Narayan shares how access, trust, and long-term relationships are becoming more important as traditional signals lose reliability. Highlights:

• Why the current venture market feels unprecedented and difficult to underwrite
• Structural gaps in venture data and challenges in finding ground truth
• The role of access and founder selection in venture outcomes
• How regime shifts reduce the usefulness of backward-looking analysis
• Why founder trust and long-term relationships matter more than branding
• The risks of overfished strategies and consensus thinking
• Differences between generalist and specialist venture approaches
• How institutional LPs evaluate manager behavior through market cycles
• Why small teams can now build and scale faster than ever

Guest Bio:

Narayan Chowdhury is a Co-Founder and Partner at Franklin Park, a Philadelphia-based investment firm overseeing approximately $21 billion in assets. He has over two decades of experience allocating capital across venture and private markets, with a focus on manager selection, long-term partnerships, and disciplined portfolio construction amid evolving market regimes.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Narayan Chowdhury:

LinkedIn: https://www.linkedin.com/in/narayan-chowdhury/

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) Introduction (0:14) The unpredictable nature of the current investing landscape and the bipolar market (5:19) The reliability of data and the importance of channel checks in venture capital (9:00) Untethered investments, founder's equity, and long-term investor relationships (13:33) Maintaining investment discipline and the role of media in venture capital (16:29) Balancing high expected returns with operational stability (19:23) The importance of references and continuous market engagement (24:00) Continuous market engagement with Bright Mind in cybersecurity (27:30) Impact of high-velocity capital deployment on firm strategies and venture dynamics (33:15) The importance of long-term relationships and high conviction beliefs in venture capital (36:54) Conclusion and final thoughts from Narayan Chowdhury (37:05) Closing remarks

Why did private credit secondaries emerge, and what problem do they solve for investors? David Weisburd speaks with Rakesh Jain about building one of the world’s largest private credit secondary platforms at Pantheon, the mechanics of liquidity in private markets, and how seasoned portfolios differ from primary credit origination. Rick explains how diversification, underwriting discipline, and alignment shape risk-adjusted outcomes across cycles.

Disclaimer: This episode was recorded in 2025. Market conditions, data, and opinions discussed reflect that time period.

Highlights:

• How Pantheon identified the need for credit secondaries
• Defining the investor value proposition in a nascent market
• Key differences between credit and private equity secondaries
• Sources of value in seasoned credit portfolios
• Managing diversification across thousands of underlying loans
• LP versus GP-led secondary transactions and trade-offs
• Mitigating adverse selection through sourcing and diligence
• Misunderstood risks and correlations in private credit
• The role of credit secondaries in institutional and wealth portfolios

Guest Bio:

Rakesh Jain is Global Head of Private Credit at Pantheon, where he oversees one of the largest private credit secondary platforms globally. He has extensive experience across credit investing, portfolio construction, and platform building, and has played a central role in developing Pantheon’s approach to liquidity solutions, diversification, and risk management in private credit markets. Earlier in his career, he held senior roles at Morgan Stanley, Goldman Sachs, and Citigroup.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

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 Rick Jain

LinkedIn:https://www.linkedin.com/in/rakesh-j-6b539/

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) Introduction (1:19) Developing investment process and scaling at Pantheon (3:16) Evolution of the private credit market (5:37) Diversification strategies in private credit (9:00) Credit secondaries: use cases and investor benefits (10:56) Strategies in LP and GP-led investing (14:01) Addressing adverse selection in credit secondaries (18:29) Building a $12 billion private credit franchise (21:13) Enhancing GP relationships as a secondary investor (22:27) Risks and misconceptions in the private credit market (26:16) Innovations and institutional products in private wealth (28:17) Tax efficiency and capital appreciation strategies (31:30) The future of private credit at Pantheon (33:03) Career advice for finance professionals (35:37) Incorporating private credit secondaries in portfolios (37:57) Utilizing evergreen funds for investment (39:17) Closing remarks

How do you raise $875M in one of the hardest fundraising markets in decades and still outperform on DPI, IRR, and culture? In this episode, I sit down with Jesse D. Serventi and Atif Gilani, Founding Partners of Renovus Capital Partners, to unpack what actually compounds in private equity over 15+ years. We break down why staying in the lower end of the lower middle market creates structural advantage, how talent density became their real edge, and why portfolio construction—not deal hype—is the hidden driver of net returns. Jesse and Atif also share how Renovus evolved from three founders doing everything into a scaled firm built to last decades, not cycles. Highlights:

• How Renovus raised $875M while many peers struggled
• Why sub-$10M EBITDA businesses create more “at bats”
• Purchase price discipline and playing the game on “easy mode”
• Talent density as the true compounding advantage
• Boomerang CEOs and the Renovus ecosystem effect
• Evolving from deal makers to firm builders
• Recycling capital to invest ~120% of LP commitments
• Why holding great businesses longer beats forced exits
• “Invest and investigate” as a portfolio construction edge
• Choosing LPs as long-term partners, not one-off capital

Guest Bio:

Jesse D. Serventi and Atif Gilani are Founding Partners of Renovus Capital Partners, a private equity firm focused on founder-owned businesses in the lower middle market. Prior to Renovus, Jesse was an investment professional at Leeds Equity Partners and began his career at Citigroup in investment banking and private equity. Atif was a Managing Director at Leeds Equity Partners and started his career in M&A at Merrill Lynch. Together, they have spent more than 15 years building Renovus into a scaled, culture-driven firm known for strong DPI, disciplined portfolio construction, and long-term alignment with founders, executives, and LPs.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

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/

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) Introductions (2:47) Playing in the lower middle market and growth perspectives (8:42) Team dynamics and hiring talent with potential (14:32) Evolution of LP mix and portfolio strategy (22:01) Managing short-term orientation and founder partnerships (24:29) Invest and investigate philosophy with business examples (27:15) Fund investment sizing, durability, and advice for longevity (29:19) Closing remarks

What separates enduring investment firms from those that quietly break as they scale? In this episode, I talk with Chris Brimsek, Managing Partner of CAB Advisory, about the unseen mechanics behind building durable alternative investment firms. Drawing from his experience working directly with David Rubenstein and former COO of Carlyle’s $15B Infrastructure & Energy business, Chris explains why culture, judgment transfer, and succession—not deal mechanics—are the true bottlenecks to long-term performance. We unpack how elite leaders create environments without intellectual hierarchy, why forgiveness builds trust faster than perfection, and how emerging managers can avoid the most common traps as they scale. Highlights:

• Why the best firms eliminate intellectual hierarchy, not decision hierarchy
• How great leaders use mistakes to build confidence and trust
• “Expect what you inspect”: using questions to shape culture
• Why most GPs underestimate the challenge of running a business, not a fund
• The difference between managing deals and building a firm
• Succession as knowledge and judgment transfer—not titles or economics
• Lessons from fighter pilot debriefs applied to investment decision-making
• Why non-economic factors dominate talent retention
• How GP stakes are reshaping incentives and firm-building
• The biggest silent risk facing emerging managers today

Guest Bio:

Chris Brimsek is the Managing Partner of CAB Advisory, where he serves as a trusted advisor to founders and leadership teams of alternative investment managers. Previously, he was Chief Operating Officer of The Carlyle Group’s Infrastructure & Energy business and a member of Carlyle’s Global Private Equity Operations team. Chris began his career working directly with David Rubenstein and was part of the executive group during Carlyle’s IPO. He holds an MBA from Harvard Business School and a bachelor’s degree from Washington & Lee University.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Chris Brimsek :

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

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) Introduction (1:15) Intellectual curiosity and leadership at Carlyle (4:51) Best practices for engaging junior personnel and creating a culture of open communication (8:51) The role of incentives in retaining talent and differences between banking and asset management (13:02) Challenges and strategies for emerging managers in investment firms (18:52) Trends in alternatives and basics for LPs evaluating managers (20:29) Intentionality, innovation, and succession in investment firms (24:23) Challenges in launching new products and managing distraction costs (28:00) Importance of honest communication and common problems GPs hide from LPs (34:51) Role and impact of GP stakes in the market (38:00) Addressing LP skepticism and misconceptions about GP stakes (41:39) Industry changes and timeless career advice (45:26) Strategic thinking and the value of intellectual curiosity in career development (47:41) Closing remarks

How well do venture capital returns really reflect skill versus structure? In this episode, David Weisburd speaks with Abe about what large-scale AngelList data reveals about seed investing, power-law returns, and why traditional assumptions around expected value, conviction, and diversification often break down. Abe explains how adverse selection shapes outcomes, why access matters more than insight, and where data-driven strategies may — and may not — apply in venture capital. Highlights:

• Why venture capital behaves differently across seed, Series A, and later stages
• How power-law dynamics challenge the idea of expected value
• The role of adverse selection in early-stage investing
• Why diversification can outperform concentrated conviction at seed
• What AngelList data reveals about pricing, dilution, and markups
• Why small checks often outperform large checks
• The limits of quantitative models in startup selection
• How common signals outweigh idiosyncratic insight
• Using data to evaluate venture fund managers rather than startups

Guest Bio:

Abe is a consulting researcher at AngelList and CIO of Strawberry Tree Management Company which recently got renamed to AngelList Asset Management LLC, an independent RIA affiliated with AngelList. He works with large-scale venture data to study early-stage investing behavior, power-law returns, and fund performance, with a focus on understanding how structure, pricing, and access influence outcomes across the venture ecosystem.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.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 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) Introduction (2:28) Insights from AngelList data and importance of share price (9:28) Investment strategies and market efficiency in early-stage investing (14:32) Power law distributions and their practical implications (20:15) Seed stage investing and LP perspectives (23:15) Quantum mechanics analogy and diligence strategies (27:36) Portfolio strategies and management fees impact (30:54) Specialized fund managers and adverse selection (37:08) Check sizes and signal in seed investing (42:15) Valuation, signal, and GP style drift (45:02) Strawberry Tree Management Company strategy (46:45) Quantitative GP selection and fund of funds approach (50:38) Pricing power and variability in VC funds (53:45) Broad investing in seed stage venture (55:35) Key signals and the role of DPI (58:12) Distinguishing skill from luck in early exits (1:00:05) Following Abe Othman’s work and advice from Mike Maples (1:01:50) Closing remarks

What does it take to build an investment firm outside the traditional private equity model? David Weisburd speaks with Jeff Schwartz about founding Corbel Capital Partners, identifying opportunities in the lower middle market, and why structured capital fills a gap left by banks and large buyout firms. Jeff discusses the operational realities of scaling an investment platform, fundraising challenges, and how market inefficiencies continue to shape strategy selection. Highlights:

• The market gap that led Jeff to launch Corbel Capital Partners
• Why traditional banks retreated from lower middle market lending
• The difference between growing a firm horizontally versus vertically
• How managing an investment firm differs from being an investor
• Fundraising challenges for emerging and mid-sized managers
• Using multiple strategies without outgrowing a core market focus
• The role of SBIC leverage in enhancing return profiles
• Why special situations investing is increasingly attractive
• Aligning incentives across teams and strategies

Guest Bio:

Jeff Schwartz is the Founder and Managing Partner of Corbel Capital Partners, a private investment firm focused on structured capital solutions for lower middle market businesses. He is a senior private equity investment professional with extensive experience raising capital and executing leveraged buyouts, distressed debt-for-control investments, and structured equity transactions across multiple industries, with a focus on consumer products and retail, specialty manufacturing, and business services. Prior to founding Corbel in 2014, Jeff held senior roles at Ares Management.

Our Podcast now receives more than 300,000 downloads a month. 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 Capital: https://www.weisburdcapital.com/

Stay Connected with Jeff Schwartz:

LinkedIn:https://www.linkedin.com/in/jeff-schwartz-corbel-capital

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) Introduction (1:30) Building a new investment firm and Transition from player to manager (7:11) Building investor base and Scaling the team (11:34) Recruiting, retention, and Leveraging SBIC capital (18:46) Current market interests and Special situations competency (23:26) Insights from Ares to Corbel and Building relationships in distressed markets (25:39) Delivering capital on a timely basis and Accelerating success (27:43) Closing remarks

How do family offices approach investing differently from institutional capital? David Weisburd speaks with Robert about building Align, identifying gaps between capital and resources in family offices, and why downside protection shapes every investment decision. Robert discusses private credit, opportunistic investing, shorter-duration strategies, and how collaboration among families creates a distinct and disciplined investment ecosystem.

All investment advisory services are offered through Align Private Capital LLC (“Align”). Align is an investment advisor registered with the Securities and Exchange Commission (SEC). Information presented herein should not be construed as investment advice. All investments involve some degree of risk, including the potential loss of principal. The opinions expressed in this podcast are those of the speakers and do not necessarily wholly represent the opinions of Align.

Highlights:

• The market gap that led to the creation of Align
• Why family offices often lack institutional-scale resources
• How Align evolved into an opportunistic investment platform
• The role of private credit in generating risk-adjusted returns
• Why inbound deal flow differs between families and institutions
• A downside-first approach to evaluating all investments
• The benefits of shorter-duration, mid-term investments
• Why family offices collaborate rather than compete
• Viewing alternatives as a portfolio rather than isolated bets

Guest Bio:

Robert is the Founder and CIO of Align, an investment firm serving family offices and managing an opportunistic investment platform focused on absolute returns. He has extensive experience overseeing alternative investments across private credit, public and private markets, and structured transactions, and previously served as CIO for multiple family offices. His work emphasizes capital preservation, disciplined risk management, and collaborative investing.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#venturecapital #vc #startups #openlp #assetmanagement

Stay Connected with David Weisburd:

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

Stay Connected with Robert Blabely:

LinkedIn: https://www.linkedin.com/in/robert-blabey-260202/

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) Introduction (2:30) Opportunities and discipline in the alternatives market (6:14) Family office co-investment dynamics and risk management (14:00) Investment strategy and comparison to legendary investors (19:04) Investment opportunities in uranium and nuclear energy (22:46) Themes in the alternatives universe and yield curve control (25:53) Career advice: Investing in networks and learning from experiences (29:04) Conclusion and appreciation (29:14) Closing remarks

What happens when the marginal cost of intelligence approaches zero? David Weisburd speaks with Richard Socher about building U.com, the evolution of AI search and agents, and why infrastructure—not hype—will determine AI’s real economic impact. Richard shares a first-principles view on where AI creates value, how enterprises are deploying agents today, and what long-term shifts in labor, productivity, and education may follow. Highlights:

• Building You.com and focusing AI search on accuracy and data quality
• Why AI agents depend on strong search and infrastructure layers
• Early enterprise use cases across coding, legal, healthcare, and research
• The idea of intelligence becoming cheap and its second-order effects
• Why AI adoption is gradual but structurally inevitable
• Jobs, agency, and the fallacy of fixed labor supply
• How AI changes access to tutoring, healthcare, and personal assistance
• Investing in AI from first principles: data availability and timing
• Where regulation matters and where it risks overreach
• Why computer science remains foundational in an AI-driven world

Guest Bio:

Richard is the Co-Founder and Managing Director at AIX Ventures and Co-Founder and CEO of You.com, the leading AI search infrastructure for enterprises. At AIX Ventures, he has led early investments into several fast growing and category defining AI startups including Hugging Face, Weights and Biases, Athelas, Profluent, Parallel Bio, and Assured Robot Intelligence (ARI).

Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016. Richard received his Ph.D. in computer science from Stanford University in 2014 and later served as an adjunct professor. He is widely recognized as having brought neural networks into the field of natural language processing, inventing the most widely used word vectors, contextual vectors, and prompt engineering. He is one of the top-five most-cited researchers in NLP, with over 230,000 citations.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Richard Socher:

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

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) Introduction (1:05) AI in enterprises and its impact on job markets (4:22) Predictions for the economic impact of AI agents (7:34) AI's role in evolving local news and early enterprise use cases (8:49) AI investment strategies and Richard Socher’s fund principles (14:06) AI regulation, comparison with crypto, and geopolitical aspects (18:45) AGI, ASI, and AI's influence on math and programming (21:14) Balancing AI optimism with potential risks and existential concerns (25:01) Preparing future skills for AI-driven industries (26:15) Interdisciplinary approach combining computer science (27:09) Richard Socher's personal life insights (28:13) Closing remarks

What role do independent sponsors play in today’s lower middle market private equity ecosystem? David Weisburd speaks with Tom Duffy about how TIFF partners with independent sponsors, why deal-by-deal investing can improve alignment, and what differentiates high-quality sponsors in a rapidly growing market. Tom explains how sourcing, economics, and hands-on diligence shape long-term GP relationships and inform future fund commitments. Highlights:

• TIFF’s dual business model: OCIO services and private market strategies
• Growth of the independent sponsor market and what’s driving it
• Why deal-by-deal investing can improve alignment and diligence
• Key attributes that define high-quality independent sponsors
• How flexibility and economics attract experienced PE professionals
• Fee structures and GP commitment in sponsor-led transactions
• Using early deals to underwrite long-term GP partnerships
• The importance of sourcing differentiation and resilience
• How sponsor relationships can evolve into fund investments

Guest Bio:

Tom Duffy is a Director on TIFF’s Private Market Investment Team, where he focuses on lower middle market private equity and early stage venture capital strategies. TIFF is an outsourced chief investment officer and private markets platform managing over $10 billion* in assets, with a long-standing focus on alternatives and private markets. Tom works closely with independent sponsors and emerging managers, underwriting both deals and long-term partnerships across the lower middle market.

*TIFF assets under management (AUM) is as of 9/30/25 and includes discretionary and non-discretionary client assets for which TIFF affiliates provide investment management or advisory services. The private markets portion of TIFF AUM is calculated based upon fund net asset value plus unfunded commitments. Calculation of TIFF AUM differs from the calculation of regulatory assets under management in TIFF’s Form ADV filings with the SEC and may differ from the AUM calculation methodologies used by other investment managers.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Tom Duffy :

LinkedIn: https://www.linkedin.com/in/tom-duffy-cfa-cfp/

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) Introduction (3:03) Independent sponsor market growth and saturation concerns (7:25) Fee structures and long-term partnership benefits with TIFF (10:54) Diligencing managers and alignment of interests (15:57) Opportunities for non-pedigree sponsors and market state (21:41) Closing remarks

Why do some venture-backed companies struggle to survive despite strong technology and teams? In this episode, David Weisburd speaks with Trey Ward about the structural differences between software and hard-tech businesses, the predictable “Death Valley” many startups face, and what recent data suggests about the future of venture funding. Trey shares how capital intensity is often misunderstood, why graduation rates are declining, and how profitability can create a path forward when fundraising stalls. Highlights:

• Why strong conviction matters most when the market disagrees
• How hardware and software revenue curves fundamentally differ
• The misconception around capital intensity in deep-tech businesses
• What “Death Valley” looks like for hard-tech startups
• How investors distinguish failed companies from those with unmet potential
• Data showing declining Series A–to–Series B graduation rates
• Why a post-2022 venture funding hangover is accelerating failures
• Acquiring venture-backed assets at a fraction of historical R&D spend
• Using profitability as a strategy to give founders more time

Guest Bio:

Trey Ward is the Founder of Rook, an investment firm focused on acquiring venture-backed technology companies that have strong fundamentals but lack access to continued venture funding. He has spent his career investing in and operating across hardware, software, and deep-tech businesses, with a focus on capital discipline, long-term value creation, and paths to profitability outside the traditional venture model.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Trey Ward:

LinkedIn:linkedin.com/in/thomasvwardiii

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) Introduction (4:04) Challenges and differentiators for hard tech startups (7:46) Venture capital downturn and strategies for struggling assets (14:07) Investment structures and management retention in acquisitions (16:17) Closing remarks

Why do the best investors spend more time preparing for what can go wrong than forecasting what might go right? In this episode, I talk with Mark Sotir, President of Equity Group Investments, about what it really means to invest with an owner’s mindset. Mark shares lessons from working alongside Sam Zell for nearly two decades, why staying alive matters more than maximizing any single outcome, and how long-term capital changes behavior inside portfolio companies. We break down why protecting downside creates asymmetry, how adaptability beats prediction, and why value creation comes from operating discipline, not transaction timing. Highlights:

• The difference between being an owner vs. a trader
• Why “the hundred-year storm happens every ten years”
• Preparing instead of predicting in volatile environments
• Staying alive as the core compounding strategy
• Why long holding periods create better outcomes than fast flips
• Cash flow discipline as risk management
• Why control enables transformation, not micromanagement
• How flexibility inside companies prevents brittleness
• Why value is created operationally, not transactionally
• The danger of rigid planning in dynamic markets

Guest Bio: Mark Sotir is the President of Equity Group Investments, the private investment firm founded by Sam Zell, where he oversees the firm’s investment portfolio and works closely with portfolio companies to improve strategy and operations. He also serves as Chair of the investment committee at Chai Trust Company, the corporate trustee for the Zell family trusts. Mark joined EGI in 2006 and has held senior leadership roles across operating companies, including as CEO of Sunburst Technology and President of Budget Group, with earlier experience at Coca-Cola. He holds an MBA from Harvard Business School and a BA from Amherst College.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

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 Sotir:

LinkedIn: https://www.linkedin.com/in/mark-sotir-02577b4/

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) Introduction (0:28) Owner's mindset and risk management in private equity (1:35) Adapting investment strategies and the "hundred year storm" concept (2:22) The importance of capital structure and not over-leveraging (3:42) Navigating unpredictable market changes and staying in business (6:13) Dedicated capital base and long-term value creation (11:41) Cash flow generation and disciplined investing (12:20) Control in portfolio companies and leveraging multiple strategies (16:07) Avoiding attachment and the importance of team diversity (17:34) Balancing empathy with business decisions and founder transitions (21:01) Founder readiness and adapting to company culture (24:43) Business development, CRM strategies, and succession planning (27:40) Leadership transition, trust, and optimizing operations (29:23) Sourcing deals and the evolving landscape of private equity (30:23) Closing remarks

Why does venture capital break when liquidity disappears and what actually creates alpha when markets get hard? In this episode, I talk with Logan Allin, Founder and Managing Partner of Fin Capital, about why private markets are structurally changing, how secondaries are becoming a primary liquidity mechanism, and why discipline — not optimism — is what separates enduring managers from zombies. Logan explains how Fin Capital built a full-lifecycle platform across venture and late-stage secondaries, why fund size is the enemy of performance, and how contrarian positioning creates real structural alpha over time. Highlights:

• Why venture “breaks” without liquidity
• How secondaries are replacing IPOs as the main exit
• Why fund size destroys returns past a threshold
• The rise of zombie funds and asset gatherers
• How Fin Capital uses secondaries as a risk buffer
• Why competition — not fundamentals — drives private market pricing
• Why retail capital is dangerous for blind-pool venture funds
• How contrarian investing actually works in practice
• Why orchestration and application layers win in AI
• Why alpha comes from doing the work others avoid

Guest Bio:

Logan Allin is the Founder and Managing Partner of Fin Capital, a global venture and growth equity firm focused exclusively on enterprise software for financial services. He previously served as Vice President at SoFi Ventures and has held operating and advisory roles across fintech and financial services, including leadership positions at Atlantic Trust, City National Bank, and several venture-backed startups. Logan holds degrees from Duke University and Stanford Graduate School of Business, where he was a Sloan Fellow.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Logan Allin:

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

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) Introduction (1:07) Challenges and dynamics in the current venture market (2:17) Opportunities in the secondaries market and institutional capital (7:02) Diligence process for late-stage pre-IPO opportunities (9:09) Discussion on fund lifespan and size constraints (14:05) Retail investors and OpenAI's business model concerns (19:36) Howard Marks' insights and second-order thinking in investments (22:40) Investment strategies in AI and avoiding LLMs (24:02) LP communication and the cost of being a contrarian (27:08) Conversations with LPs and focus on specific tech sectors (28:32) Emerging spaces in technology investments (32:22) FinCapital's approach to investment and market relations (34:09) Closing remarks

What if the most powerful investment strategy isn’t optimization but making one truly great decision each year? In this episode, I talk with Joshua Browder, Founder and CEO of DoNotPay and a solo pre-pre-seed investor, about how momentum, conviction, and first-belief investing create outsize outcomes. Joshua shares how DoNotPay became a profitable, dividend-paying AI consumer company with a team of 14, why he focuses on backing founders before they look credentialed, and how acting decisively on binary choices can matter more than years of incremental improvement. We also explore why grit beats IQ, how momentum keeps startups alive, and what it really takes to be a founder’s first believer. Highlights:

• Why “one big decision per year” matters more than constant optimization
• How DoNotPay scaled to millions of users with a tiny team
• Why profitable companies can still be venture-scale
• Grit vs. IQ in predicting founder success
• The power of being the first believer, not the fastest follower
• How momentum determines survival at pre-seed
• Why binary decisions beat marginal improvements
• How Joshua creates momentum for founders operationally
• Why founders should build for meaning, not resumes
• How portfolio construction changes at pre-pre-seed

Guest Bio:

Joshua Browder is the Founder and CEO of DoNotPay, an AI consumer rights platform that has automated over 200 legal and financial processes and won more than two million cases for users. He founded the company while studying computer science at Stanford before leaving to join the Thiel Fellowship. Joshua is also an active early-stage investor, backing first-time founders before they become obvious, and has invested in over 150 companies including Figma, Mercury, and Owner.com. His work focuses on helping people fight institutional friction while building profitable, mission-driven businesses.

Stay Connected with David Weisburd:

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

Stay Connected with Joshua Browder:

LinkedIn: https://www.linkedin.com/in/joshua-browder-b0b573116/

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) Introduction (0:39) Business model, profitability, and startup myths (2:56) Transition to venture capital and Thiel Fellowship experience (6:02) Reflecting on investment decisions and philosophy (9:47) Evaluating founders and the one-person accelerator approach (14:23) Traits of successful entrepreneurs and startups as momentum machines (18:16) Founders’ roles and commitment evaluation (23:43) Portfolio construction and key decision-making in early-stage investing (27:22) Productizing tasks and balancing tactical vs strategic thinking (30:36) Closing remarks

Why is the hardest discipline in growth equity not finding great companies but refusing to grow past the point where returns break? In this episode, I talk with Deepak Sindwani, Co-Founder and Managing Partner of Wavecrest Growth Partners, about why fund size discipline, culture, and integrity matter more than optics in building a great investment firm. Deepak explains why Wavecrest capped Fund III at $450M despite excess demand, how staying in the sub-$50M equity check range preserves alpha, and why being a true growth partner — not a financial engineer — creates better outcomes for founders and investors alike. Highlights:

• Why Wavecrest refused to raise a larger fund despite strong demand
• The break point where growth equity becomes overly competitive
• Why consistent strategy beats chasing milestones
• The “treasure hunting” model for finding overlooked growth companies
• Why profitable, 30–50% growth companies are the sweet spot
• How direct sourcing creates better founder relationships
• Why culture and “no-asshole” policies increase expected value
• Selling capital to founders who don’t need it
• The real reasons founders take growth capital
• How adversity builds better long-term investors

Guest Bio:

Deepak Sindwani is the Co-Founder and Managing Partner of Wavecrest Growth Partners, a growth equity firm focused on profitable B2B software and technology-enabled services companies. Prior to Wavecrest, Deepak was a Partner at Bain Capital Ventures and a Principal at Comcast Ventures, where he led early- and growth-stage investments across the technology sector. He began his career in technology investment banking at Credit Suisse and later worked in product management, marketing, and business development at several technology companies, including his own startup. Deepak holds a B.S. in Electrical Engineering and Economics from the University of Pennsylvania.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Deepak Sindwani:

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

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) Introduction (2:22) Balancing Fund Growth with Investment Strategy (3:33) Market Competitiveness and Portfolio Construction (6:12) Identifying and Investing in Growth Opportunities (9:45) The Role of Passion in Growth Equity (14:00) Building a Positive Company Culture (15:46) Challenges of Selling Capital to Self-Sufficient Companies (21:01) Wavecrest's Growth Strategies and Value Addition (25:13) Leveraging Portfolio Strengths to Win Deals (29:36) Personality Assessments in Talent Management (31:57) Deepak Sindwani's Reflections and Advice for Aspiring Investors (33:57) Bootstrapping a Fund: Strengths and Challenges (35:13) Embracing Challenges for Building Resilience (37:15) Closing remarks

Why do the biggest investing breakthroughs come not from complexity, but from simplicity and why is that so hard for smart people to accept? In this episode, I talk with Britt Harris, one of the most experienced institutional investors in the world, about what really drives long-term investment success inside large pools of capital. Britt explains why simplicity beats complexity, how scale creates negotiating power and structural advantage, and why engagement — not intelligence — is the true separator of performance. We discuss how innovation in investing is usually recombination, not invention, why empowered teams outperform credentialed ones, and how leaders can systematically create cultures that compound. Highlights:

• Why simplicity is the highest form of reliability
• How scale changes negotiating power and opportunity access
• The “four-minute mile” effect in organizational change
• Why fully engaged people outperform smarter but disengaged peers
• The 30–50–20 rule of engagement inside organizations
• Why innovation is usually recombination, not invention
• How to avoid complexity syndrome in investing and management
• Why keeping your word is the foundation of trust and leadership
• How empowerment is earned, not granted
• Why culture compounds faster than strategy

Guest Bio:

Britt Harris is a veteran institutional investor and executive who has served as Chief Investment Officer for some of the largest pools of capital in the world, including the University of Texas Investment Management Company (UTIMCO), the Texas Permanent School Fund, and the Texas Teachers Retirement System. Over a career spanning more than four decades, he has overseen and advised on portfolios totaling hundreds of billions of dollars and is widely recognized for his contributions to institutional investing, governance, and organizational leadership.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Britt Harris:

LinkedIn:https://www.linkedin.com/in/britt-harris-6678477/

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) Introduction (2:27) Overcoming impossibilities and full engagement in organizations (6:38) Empowerment and success in the workplace (12:06) Innovation in financial instruments and trends (16:12) Complexity syndrome and the importance of simplicity in investments (17:32) Closing remarks

Why do the people who build the most meaningful things almost always choose the hardest path and what does that unlock in the long run? In this episode, I talk with Larsen Jensen, Founding General Partner of Harpoon Ventures, about why deliberately choosing difficult problems builds the resilience, clarity, and long-term edge required to create category-defining companies. Larsen shares lessons from his time as an Olympic medalist and Navy SEAL, how those experiences shaped his investing philosophy, and why venture capital is ultimately a power-law game driven by rare outliers. We explore how founders develop mental toughness, how conviction is formed under uncertainty, and why great investors learn to trust teams more than models. Highlights:

• Why hard things produce disproportionate personal and professional growth
• How resilience is built only through adversity, not theory
• The role of mental conditioning in elite performance
• Why venture returns come from rare exceptions, not rules
• How founders choose investors more than the reverse
• What it really takes to find product–market fit
• Why 10x solutions and desperate customers matter most
• The difference between vitamins and painkillers in startups
• Why the best teams are upstream of product and market
• How humility and mission matter more than ego

Guest Bio:

Larsen Jensen is the Founding General Partner of Harpoon Ventures, a venture firm focused on investing in companies that serve the national and economic interests of the United States and its allies. Before venture, Larsen was an Olympic medalist in swimming and served as a U.S. Navy SEAL, experiences that shaped his emphasis on resilience, mission, and long-term thinking. At Harpoon, he backs founders building frontier technologies across defense, cybersecurity, AI, and critical infrastructure, and is known for his founder-first, conviction-driven approach to early-stage investing.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#venturecapital #vc #startups #openlp #assetmanagement

Stay Connected with David Weisburd:

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

Stay Connected with Larsen Jensen:

LinkedIn: https://www.linkedin.com/in/larsen-jensen/

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) Introduction (0:14) Larson Jensen's background and embracing challenges (1:56) Benefits and importance of overcoming adversity (4:38) Parallels between parenting, self-coaching, and mental toughness (7:33) Resilience across multiple careers and challenging environments (10:22) Mental toughness in venture capitalism and adapting to market changes (13:41) Harpoon Ventures' investment strategy and collaboration with major funds (16:30) Mentorship, servant leadership, and characteristics of successful founders (21:43) Distinguishing high beta vs. low beta investment ideas (24:06) Defining venture capital as an access class (27:27) Startups: Achieving product-market fit and the importance of team (34:38) Building mental toughness in founders and venture capitalists (38:57) Overcoming challenges for meaningful success (42:05) Advice for aspiring fund managers and the pitfalls of rigid VC rules (44:46) Resilience in successful individuals (45:46) Closing remarks

What if the biggest barrier to earning returns in alternatives isn’t access, fees, or performance but friction, complexity, and behavior? In this episode, I talk with Brett Hillard, Founder and CEO of GLASFunds, about why infrastructure matters more than selection in alternative investing. Brett explains how GLASFunds helps wealth managers implement alternatives at scale, why K-1 friction keeps investors out of high-return asset classes, and how thoughtful design around vintages, liquidity, and reporting can dramatically improve long-term outcomes. We also explore why “alternatives” is an overused label, how to build portfolios across vintages, and why illiquidity can actually protect investors from themselves. Highlights:

• Why infrastructure, not product, is the bottleneck in alternatives
• How GLASFunds solved the K-1 problem for multi-fund portfolios
• Why most investors fail simply by not being invested at all
• The behavioral value of minimizing friction and complexity
• Why “alternatives” is a misleading and overused category
• How to build private market exposure across vintages
• Why secondaries and private credit are ideal entry points
• The virtue of illiquidity and why it protects against bad behavior
• Why risk is often misunderstood as discomfort
• How emotional intelligence matters more than technical skill in investing

Guest Bio:

Brett Hillard is the Founder and CEO of GLASFunds, an infrastructure platform that enables wealth managers to build, customize, and implement alternative investment portfolios at scale. GLASFunds provides legal, operational, and reporting infrastructure that allows advisors to offer hedge funds and private capital strategies while dramatically reducing administrative friction, tax complexity, and behavioral barriers for investors. Brett is widely recognized for his first-principles approach to portfolio construction, risk, and behavioral finance in private markets. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

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

Stay Connected with Brett Hillard:

LinkedIn:www.linkedin.com/in/brett-hillard-caia-cfa-40729725/

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) Introduction (3:18) Model portfolio for high-net-worth clients and endowment strategies (9:39) Risk tolerance, liquidity, and the misinterpretation of "alternatives" (11:44) Crafting an alternatives portfolio and private credit secondaries insights (18:04) Wealth manager advantages and behavioral investing in alternatives (22:23) Selecting general partners and evaluating hedge funds (24:27) Value creation and risk-reward in private capital and fund vintages (28:32) Investing in first-time funds and assessing risk perception (32:12) Timeless investment advice and the benefits of illiquidity (35:59) Closing remarks