How I Invest with David Weisburd

What if the best investment opportunities are the ones most investors avoid because they’re too hard, too small, or too inefficient to pursue? In this episode, I sit down with Raphael, Deputy CIO and Co-Leader of HighVista Strategies, to discuss the concept of “beautifully inefficient” markets and why durable alpha often exists where few investors are willing to spend time. Raphi explains how governance structures shape investment outcomes, why lower middle market private equity and biotech remain compelling, and how long-duration capital creates structural advantages in venture investing. We also explore continuation vehicles, portfolio concentration, and why the best allocators balance diversification with conviction. Highlights:

• What makes a market “beautifully inefficient”
• Why alpha often lives in small, overlooked markets
• The hidden role governance plays in investment performance
• Why continuation vehicles could reshape private markets
• How lower middle market private equity creates durable alpha
• Why biotech may be one of today’s most misunderstood sectors
• The difference between diversification and diworsification
• Why long-duration venture capital remains structurally attractive

Guest Bio:

Raphael is the the Deputy CIO and Co-Leader of HighVista Strategies, a $14 billion investment firm focused on alternative assets and differentiated sources of alpha. He has extensive experience across portfolio management, securities analysis, and risk management, investing across equities, private markets, biotechnology, commodities, fixed income, and exotic risks. At HighVista, Raphi helps lead the firm’s investment strategy across venture capital, private equity, private credit, and public markets with a focus on identifying scalable inefficiencies and long-term opportunities.

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 Raphael Schorr:

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

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 Secret Behind “Beautifully Inefficient” Markets (4:21) How Great Investors Decide Which Markets Are Worth Playing (7:54) Why Alpha Lives in “Boring and Hard” Investments (12:11) Is the Endowment Model Quietly Breaking Down? (16:08) Why Continuation Vehicles Could Reshape Private Markets (20:51) The Hidden Flaw in Traditional Private Equity Holding Periods (25:23) The Contrarian Bet That Could Define the Next Decade (29:11) Why the Best Venture Investments Always Look Wrong at First (37:28) Why Market Timing Might Be Fundamentally Impossible (43:52) The Diversification Myth Most Investors Still Believe

What if the best venture investments come from ignoring consensus and trusting your own taste before the market catches up? In this episode, I sit down with Maya Bakhai, Founding Partner of Spice Capital, to discuss how cultural intuition, narrative cycles, and conviction shape venture investing. Maya explains how working with Kevin Durant at 35 Ventures gave her access to top-tier deal flow while teaching her to think independently, why “narrative premiums” distort venture markets, and how the best founders build with unconditional conviction long before a category becomes popular. We also explore cultural arbitrage, creator economy investing, and why early-stage venture is ultimately a game of taste, not consensus. Highlights:

• Why “tier one” signaling can become a trap for investors
• The concept of “narrative premium” in venture capital
• How cultural arbitrage led Maya to her Crocs investment thesis
• Why the best founders build with or without investor support
• The difference between sales-driven and taste-driven investing
• How creator economy startups survived after falling out of favor
• Why bottoms-up investing beats market-map investing
• The hidden downside of relying too much on consensus opinions

Guest Bio:

Maya Bakhai is the Founding Partner of Spice Capital, an early-stage venture firm focused on consumer, fintech, and internet culture. Before launching Spice Capital, she worked at 35 Ventures alongside Kevin Durant and Rich Kleiman, helping build one of the most active celebrity-backed investment platforms in technology. Maya has invested in companies across creator economy, commerce, and emerging consumer behavior trends, and also writes the newsletter Hot Sauce, where she shares insights on venture capital, startups, and culture.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Maya Bakhai:

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

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) How Kevin Durant Became an Early Silicon Valley Power Player (5:23) Why Following Tier 1 VCs Can Actually Hurt Returns (9:41) The Painful Truth About Learning to Pick Great Founders (12:59) Why “High IQ Investing” Often Misses Massive Opportunities (19:00) The Dangerous Side of Pattern Recognition in Venture (23:48) How She Made Her First Million Betting on Crocs (27:52) The Narrative Premium That Quietly Drives Venture Capital (32:42) Where Real Alpha Comes From in an AI World (41:01) The Founder Trait That Matters More Than Intelligence (43:19) The Biggest Investing Mistake She’d Never Make Again

What if the biggest winners in AI won’t come from having the best model—but from building the strongest feedback loops around users? In this episode, I sit down with Hans Tung, Managing Partner at Notable Capital and longtime Midas List investor, to discuss how decades of investing across consumer internet and global technology shaped his thesis around AI. Hans explains why Anthropic stood out early through its developer ecosystem, how network effects emerge inside AI systems, and why the most enduring companies are built around positive feedback loops. We also explore physical AI, prosumer behavior, immigrant founders, and the psychological traits required to build category-defining companies. Highlights:

• Why Hans chose Anthropic over OpenAI early on
• How AI models can develop network effects through developers
• The “Intel Inside” analogy for AI infrastructure companies
• Why positive feedback loops create enduring moats
• The hidden advantage immigrant founders have in Silicon Valley
• Why category-defining founders often feel “different” from everyone else
• How physical AI could reshape global industries outside the U.S.
• Why prosumers are the best signal for future consumer behavior

Guest Bio:

Hans Tung is Managing Partner at Notable Capital and one of the most respected global venture investors of the past two decades, consistently recognized on the Forbes Midas List. He has invested in category-defining companies including Airbnb, Coinbase, Peloton, Slack, TikTok parent ByteDance, and Anthropic, spanning the U.S., Asia, and Latin America. Prior to Notable Capital, Hans was a Managing Partner at Qiming Venture Partners and earlier worked at Bessemer Venture Partners, building a career around identifying major shifts in consumer technology, marketplaces, fintech, and AI.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Hans Tung:

LinkedIn:http://linkedin.com/in/hans-tung

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

Disclaimer:

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

(0:00) Why He Chose Anthropic Over OpenAI (2:03) The Consumer Internet Signal Hidden Inside Anthropic (4:37) Why “Values” Can Become a Competitive Advantage (7:27) The Brutal Reality of Taking a Company Public (11:03) Why Immigrants Build So Many Billion-Dollar Companies (14:08) The VC Skill Most Investors Completely Fail At (18:25) The Problem Every AI App Founder Is Secretly Worried About (20:30) Why Physical AI Could Create Entirely New Winners (23:02) The Network Effect Hidden Inside LLMs (26:48) The “Prosumer” Pattern That Predicts Massive Companies Early

What if the biggest source of alpha today isn’t stock picking—but structuring portfolios more intelligently after taxes? In this episode, I sit down with Shang to discuss why tax alpha is becoming one of the most important themes in wealth and asset management. Shang breaks down how long-short tax-aware strategies work, why manager selection matters more than most investors realize, and how investors should think about tracking error, leverage, and operational risk. We also explore portable alpha, hedge fund tax structures, and why the explosion of tax-focused products may create as many risks as opportunities. Highlights:

• Why after-tax returns matter more than pre-tax performance
• The hidden importance of manager selection in tax-loss harvesting
• How tracking error creates both opportunity and risk
• Why volatility can improve tax-loss harvesting outcomes
• The difference between economic substance and “tax-only” strategies
• How portable alpha changes portfolio construction
• Why institutional borrowing rates are now accessible to individuals
• The risk of “tax tail wagging the dog” in investment decisions

Guest Bio:

Shang is a fintech and investment executive with deep experience across wealth management, ETFs, and institutional portfolio solutions. He previously held senior roles at Goldman Sachs, PIMCO, and J.P. Morgan, and helped scale some of the fastest-growing ETF platforms in the industry, including Simplify Asset Management and Tema ETFs. Shang focuses on developing innovative investment solutions for advisors, family offices, and individual investors, with expertise spanning tax-aware investing, derivatives, and portfolio construction.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Shang Chou:

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

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

Disclaimer:

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

(0:00) Why Tax Alpha Became One of the Biggest Edges for Investors (2:42) Why Volatility Makes Tax Loss Harvesting More Powerful (4:44) The Hidden Differentiator Between Tax Alpha Managers (7:27) The SpaceX Problem: Should You Ever Sell a Huge Winner? (11:13) Why Deferring Taxes Can Compound Into Massive Wealth (13:52) The Dangerous Mistake Investors Make With “Tax Strategies” (16:14) What Actually Matters When Choosing a Tax Alpha Manager (19:34) The Hedge Fund Strategy Quietly Reducing W-2 Taxes (30:34) Why Most New Tax Products Are Probably Bad Investments (35:00) How SpaceX Could Trigger One of the Biggest Passive Buying Waves Ever

What if the best opportunities in venture today aren’t in new deals—but in existing companies right before an inflection point? In this episode, I sit down with Ryan Moore, Founder of Revenant VC and longtime venture investor, to discuss why he made the shift from primary venture investing to secondaries after more than two decades in the industry. Ryan explains how longer liquidity timelines are reshaping venture capital, why secondary investing is less about discounts and more about information asymmetry, and how founder relationships and insider alignment create the best opportunities. We also explore organizational metabolism, LP evolution, and why small, focused funds may outperform in a world dominated by mega-platforms. Highlights:

• Why secondaries are becoming one of the most attractive areas in venture
• The hidden value of buying before an inflection point
• Why insiders—not secondary firms—are the real competition
• How organizational metabolism predicts startup success
• Why founder relationships compound over decades
• The problem with groupthink in venture capital
• Why small funds often outperform oversized platforms
• How co-invest structures are reshaping the LP-GP relationship

Guest Bio:

Ryan Moore is the Founder of Revenant VC, a venture firm focused on secondary investments in high-growth private technology companies. Prior to founding Revenant, he spent more than two decades as a leading venture capitalist and co-founded Accomplice VC, where he was an early investor in companies including DraftKings, AngelList, PillPack, and Skillz. Ryan has built a reputation for identifying exceptional founders early and brings deep expertise across venture investing, liquidity markets, and company building.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Ryan Moore:

LinkedIn:https://www.linkedin.com/in/ryan-moore-7193372/

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

Disclaimer:

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

(0:00) Why He Walked Away From Traditional Venture Capital (1:38) The Hidden Edge in Venture Secondaries Most Investors Miss (3:13) Why Insider Investors Are the Real Competition (5:04) The Unusual Strategy of Turning 30 GPs Into LPs (7:58) Why First Investors Hold So Much Power Over Founders (10:48) The Trait That Matters More Than Ivy League Intelligence (16:22) Why Small Funds Quietly Beat Giant Venture Funds (17:23) Why He No Longer Chases Power Law Investing (21:38) The Biggest Problem With Modern Venture Capital (30:10) The One Signal That Predicts Startup Success Better Than Revenue

The biggest edge in private equity is finding deals by going where others won't. In this episode, I sit down with Oscar Fahlgren, Chief Investment Officer of Mubadala Capital, to discuss how embracing complexity and scale creates asymmetric opportunities in global private markets. Oscar explains why large, complex deals often have less competition, how Mubadala Capital uses its balance sheet to anchor and syndicate multi-billion dollar investments, and why partnership—not control—is central to their strategy. We also explore the fallacy of short-term DPI, the rise of GP partnerships, and how long-term capital and alignment drive better outcomes across cycles. Highlights:

• Why complexity reduces competition in large-scale deals
• How Mubadala writes multi-billion dollar checks with limited competition
• The hidden flaw in the industry’s obsession with DPI
• Why long-term compounding beats constant capital turnover
• How GP partnerships scale without becoming asset gatherers
• Why competitive processes often produce the worst partnerships
• The advantage of permanent capital in structuring deals
• How alignment—not control—drives better investment outcomes

Guest Bio:

Oscar Fahlgren is the Chief Investment Officer and Global Head of Private Equity at Mubadala Capital, where he leads global investment strategy across a diversified portfolio. He has been with Mubadala since 2010, helping build its private equity platform into a global investment business with significant scale and reach. Prior to Mubadala, he worked at Terra Firma Capital Partners and began his career in law and leveraged finance, bringing a cross-disciplinary approach to investing and complex transactions.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Oscar Fahlgren:

LinkedIn:https://www.linkedin.com/in/oscar-fahlgren-13654b2/

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 $12B Deal Hiding in Plain Sight That No One Touched (1:00) Why Bigger Checks Mean Less Competition (Not More) (1:48) The Strategy of “Buying Complexity” for Alpha (3:12) Why Markets Miss Obvious Opportunities (5:31) The Advantage Only a Handful of Funds Actually Have (6:51) How Mubadala Writes Massive Checks Without a Massive Fund (9:59) The Model That Lets GPs Scale Without Becoming Asset Gatherers (13:21) Why the Best Partnerships Don’t Come From Competitive Processes (16:42) The Biggest Lie LPs Tell Themselves About DPI (19:23) When Continuation Vehicles Actually Make Sense (25:22) Why AI Investing Might Be the Wrong Focus Entirely

What if the highest-return investments are the ones that reshape the future—not just the ones that fit today’s market? In this episode, I sit down with L.R. Fox, Managing Director of NEXT Global Capital, to discuss why he rejected the traditional path of “build wealth first, give later” and instead built a strategy around impact from day one. Fox explains why capital is a vote for the future, how the best investments often sit outside crowded sectors, and why frontier technologies with real-world impact can outperform conventional venture. We also explore his “buy, build, invest” framework, how he creates entirely new markets, and why resilience—not IQ—is the strongest predictor of success. Highlights:

• Why every dollar is a vote for the future you want to create
• The hidden alpha in impact investing most investors ignore
• Why the best opportunities exist outside crowded sectors
• How Fox’s “buy, build, invest” framework creates new industries
• Why resilience is more predictive than intelligence
• The difference between optimizing for returns vs inevitability
• How family offices can outperform by breaking traditional models
• Why solving hard, real-world problems drives the biggest outcomes

Guest Bio:

L.R. Fox is a serial entrepreneur, investor, and philanthropist, and the Managing Director of NEXT Global Capital, a family office focused on building and funding companies shaping the future. A Forbes 30 Under 30 honoree, he began his journey in the foster care system and went on to found and scale multiple companies across defense, technology, and frontier innovation. Fox is known for investing in high-impact sectors ranging from national security to healthcare and for his mission-driven approach to combining capital with meaningful global change.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with L.R. Fox:

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

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

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

(0:00) Why He Ignored the “Build Wealth First” Playbook (1:41) The Secret Most Investors Miss About Impact (5:06) Why Hard Problems Can Create the Biggest Returns (7:11) The Buy, Hold, Invest Framework for Building the Future (12:00) How a Brutal Childhood Became His Greatest Edge (15:50) Why Having No Safety Net Made Him More Dangerous (20:09) The One Trait That Predicts Success Better Than IQ (25:18) Why Most Family Offices Think His Portfolio Is Crazy (32:15) The AI Jobs Bet Most Investors May Get Wrong (40:24) Why He Doesn’t Think About “Cutting Losers”

What if the best investments aren’t the riskiest—but the ones everyone else can’t own? In this episode, I sit down with Keri Findley, Founder and CEO of Tacora Capital, to discuss how she built one of the most differentiated credit strategies by focusing on illiquidity, not risk. Keri explains how dislocations are often driven by forced sellers and structural constraints, why the best credit opportunities come from creating assets rather than just finding them, and how she partners with startups to finance products banks won’t touch. We also explore portfolio construction, why scaling is the hardest problem in credit, and how incentives, ethics, and alignment ultimately determine outcomes. Highlights:

• Why illiquidity—not risk—creates the best credit opportunities
• How forced sellers and ratings constraints drive mispricing
• The difference between finding assets and creating them
• Why scaling a credit fund is harder than venture
• How one bad deal can destroy an entire credit portfolio
• Why alignment and ethics matter more than structure
• The hidden equity upside inside credit strategies
• Why solving real problems creates durable alpha

Guest Bio:

Keri Findley is the CEO of Tacora Capital, an investment firm focused on asset-based lending across fintech, insurtech, and specialty finance. She previously built and led the structured credit business at Third Point, one of the world’s leading hedge funds, and has spent her career investing in complex credit opportunities. Keri specializes in structuring and financing assets that fall outside traditional markets, partnering closely with founders to scale new financial products.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Keri Findley:

LinkedIn:https://www.linkedin.com/in/keri-findley-4a974a10a/

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 Being Young Made Her a Better Trader During the Financial Crisis (2:04) The Real Edge Great Credit Investors Have (4:49) The “$100 Bill on the Ground” Trade No One Wanted (7:15) The Mortgage Bond Trade That Changed How She Invests Forever (12:39) Why You Don’t Always Need a Catalyst to Make Money (16:11) How Peter Thiel Became Her Largest LP (21:15) Why Scaling a Credit Fund Can Actually Hurt Returns (30:51) The Deal That Made Her Swear Off Equipment Financing Forever (37:07) Why One Tiny Equity Stake Can Become a Billion-Dollar Outcome (40:44) The Dangerous Trap of Trying to “Speed Run” Your Career

What if the biggest mistake in venture investing isn’t picking the wrong fund—but misunderstanding incentives and behavior? In this episode, I sit down with Ilya Strebulaev, Professor of Finance and Private Equity at Stanford GSB, to discuss how incentives, biases, and portfolio construction shape outcomes in venture capital. Ilya explains why fee structures matter less than how they’re designed, how carry changes risk-taking behavior, and why persistence in venture is real but often misunderstood. We also explore diversification, correlation across managers, and the hidden decision-making biases that drive both LPs and GPs, from escalation of commitment to style drift. Highlights:

• Why incentives—not fees—drive investment behavior
• How higher carry structurally increases risk-taking
• The difference between gross returns and net returns
• Why diversification works differently in venture
• The concept of style drift and why it destroys persistence
• How LPs underestimate correlation across managers
• Why follow-on decisions matter more than initial investments
• The bias that leads VCs to double down on bad investments

Guest Bio:

Ilya Strebulaev is a tenured chaired Professor of Finance and Private Equity at Stanford Graduate School of Business and a leading expert in venture capital, private equity, and innovation. He is the founder and faculty director of the Stanford GSB Venture Capital Initiative and has published extensively in top academic journals, with his work featured in major media outlets. Ilya teaches courses on venture capital and private equity at Stanford and has received the Distinguished Teacher Award, while also advising global investors and institutions on investment strategy and decision-making.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Ilya Strebulaev:

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

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 “2 and 20 vs 2.5 and 30” Is the Wrong Question (2:43) How Higher Carry Quietly Changes Investor Behavior (4:15) The Hidden Risk Behind “Top Performing” Fund Managers (5:54) Why LPs Misunderstand Performance Persistence (8:16) The Dangerous Incentive Shift From 20% to 30% Carry (9:53) Why Great Investors Suddenly Change Strategy (Style Drift) (12:10) Venture Might Be the Only Asset Class With True Persistence (16:08) Why You Can’t Access the Best Venture Funds (Even If You Want To) (18:12) The Biggest Mistake LPs Make When Diversifying Venture (30:58) The One Bias That Destroys More VC Returns Than Bad Deals

What if venture capital isn’t an asset class—but an access game where only a few managers matter? In this episode, I sit down with Nolan Bean, CIO at FEG Investment Advisors, to discuss how institutional investors are adapting to a world where companies stay private longer and AI is reshaping every asset class. Nolan breaks down why access to top-tier managers matters more than allocation, how venture portfolios are evolving to include both early-stage and multi-stage exposure, and why DPI, liquidity, and portfolio construction are becoming more complex. We also explore portable alpha, diversification myths, and how allocators think about risk in a world where everything is increasingly correlated. Highlights:

• Why venture is an “access class,” not an asset class
• How staying private longer is reshaping LP strategies
• The real tradeoff between DPI and long-term compounding
• Why diversification is harder than it looks in modern portfolios
• How small growth equity complements venture for earlier liquidity
• The difference between building companies vs scaling organizations
• Why AI exposure exists across every asset class
• How portable alpha changes the way institutions build portfolios

Guest Bio:

Nolan Bean is the Chief Investment Officer at FEG Investment Advisors, where he oversees portfolio strategy across public and private markets for institutional clients. He brings over two decades of experience applying an endowment-style investment approach, with a focus on manager selection, portfolio construction, and risk management. Nolan is actively involved in the broader investment community, serving in leadership roles across industry organizations and advising institutional investors on long-term capital allocation.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Nolan Bean:

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

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 Venture Is an “Access Class” (Not an Asset Class) (0:12) The Shift That’s Forcing Investors to Rethink Venture Strategy (2:52) Why Everyone Agrees Markets Changed—but Few Adapt (4:43) When “Asset Gatherers” Actually Start Making Sense (5:40) The Skill Gap Between $0→$100M and $100M→$1B Companies (9:04) The Real Truth Behind the DPI “Crisis” (12:40) Why Holding Winners Might Beat Chasing New Ones (14:43) The AI Risk That Could Break Venture Returns (19:09) Why Public and Private Markets Are Quietly Converging (34:48) The Strategy That Could Replace Traditional Stock Picking

What if the real edge in venture capital isn’t picking companies—but helping them survive long enough to matter? In this episode, I sit down with Nigel Morris, Managing Partner at QED Investors and Co-Founder of Capital One, to discuss how fintech innovation actually happens and why most investors misunderstand the role of venture capital. Nigel explains why incumbents struggle to innovate despite massive advantages, how QED built one of the most successful fintech franchises by combining operating experience with investing, and why venture is not stock picking but hands-on company building. We also explore founder psychology, power laws, and how culture and talent ultimately determine outcomes more than strategy or capital. Highlights:

• Why venture capital is “day-to-day combat,” not passive investing
• The difference between fintech founders and traditional operators
• Why incumbents fail despite scale, data, and distribution
• How QED finds and avoids “mercenary” founders
• Why most venture outcomes are driven by a few extreme winners
• The concept of “threshold scale” in venture firms
• How geo-arbitrage creates repeatable fintech opportunities
• Why culture and people are the only true long-term advantage

Guest Bio:

Nigel Morris is the Managing Partner at QED Investors and Co-Founder of Capital One, where he helped pioneer data-driven financial services and scale the company into one of the largest credit card issuers in the world. At QED, he has led investments in over 200 fintech companies globally, building one of the leading venture platforms in the sector. With decades of experience as both an operator and investor, Nigel focuses on supporting founders in building transformative financial businesses at scale.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Nigel Morris:

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

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) How Capital One Started as a “Crazy” Idea No One Believed (1:22) Why Incumbents Always Underestimate New Entrants (3:49) The Real Trait That Separates Entrepreneurs From Everyone Else (6:00) Why Big Institutions Are Designed Not to Innovate (8:55) The Hidden Advantage FinTechs Have Over Banks (10:48) Why Most Banks Don’t Understand Customer Lifetime Value (13:05) The Decision That Changed QED Forever (18:01) The Tradeoff No One Talks About When Scaling a Fund (20:43) Why Bigger Funds Usually Kill Returns (But Not Always) (23:01) The Strategy That Let QED Spot Winners Globally (53:53) How to Tell If a Founder Is a Missionary or a Mercenary

What if the biggest opportunity in AI isn’t intelligence—but the missing data layer for the physical world? In this episode, I sit down with Daniel Jacker, CEO and Co-Founder of ZaiNar, to discuss why physical AI could become a $50 trillion market and the infrastructure required to make it work. Daniel explains how turning wireless networks into a real-time sensing layer unlocks entirely new capabilities across industries, why the absence of physical-world data is the biggest bottleneck in AI today, and how his company spent nearly a decade in stealth building a foundational technology before scaling. We also explore swarm intelligence, robotics, and where value will accrue as AI moves from digital to physical environments. Highlights:

• Why physical AI lacks the equivalent of the internet’s data layer
• How wireless networks can become a global sensing system
• What most people misunderstand about robotics and automation
• Why swarm intelligence matters more than individual robots
• How ZaiNar stayed in stealth for nine years while building a moat
• Where value accrues in AI beyond applications and models
• The real bottleneck preventing AI from entering the physical world
• Why data, not robots, may be the biggest investment opportunity

Guest Bio:

Daniel Jacker is the CEO and Co-Founder of ZaiNar, a 5G positioning technology company focused on real-time, high-precision location intelligence for physical AI applications. He earned his MBA from Stanford GSB and is a General Partner at Magic City, a seed fund backing Stanford founders, as well as an active mentor at StartX and other leading accelerators. Prior to ZaiNar, he worked at Accenture on emerging technology strategy and founded The 3D Printing Company.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Daniel Jacker:

LinkedIn: https://www.linkedin.com/in/daniel-jacker/

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 $50 Trillion Market Most Investors Still Don’t Understand (1:28) Why Physical AI Isn’t Just About Robots (3:07) The $120M Mistake Happening on Construction Sites Today (5:40) How They Turn Wireless Signals Into a “God View” of Reality (9:00) The Physics Breakthrough That Makes This Possible (12:38) How They Recruited World-Class Talent While in Stealth (17:09) Why They Stayed Quiet for 9 Years (And Why It Worked) (23:10) The Missing Dataset Blocking the Future of AI (31:48) Why Robots Will Work in Swarms, Not Alone (40:41) Where Smart Investors Should Actually Bet in Physical AI

What if venture capital isn’t really an asset class—but a game where only a handful of managers actually matter? In this episode, I sit down with Ian Sigalow, Co-Founder and Managing Partner of Greycroft, to discuss why venture returns are driven by a small group of firms with consistent access to the best companies. Ian explains why diversification often hurts venture outcomes, how the industry splits between “access” and “craft” investing, and why conviction, not consensus, drives results. We also explore what defines great founders in the AI era, how venture firms build brand and culture over decades, and why the intersection of multiple skill sets is becoming the foundation for generational companies. Highlights:

• Why venture is “manager selection masquerading as an asset class”
• The difference between access investing and craft investing
• Why diversification can actually reduce venture returns
• What makes a founder a “master of two domains”
• How top firms consistently access the same small set of winners
• Why conviction beats consensus in investment decisions
• The role of brand in winning competitive venture deals
• How AI is changing both company building and venture workflows

Guest Bio:

Ian Sigalow is the Co-Founder and Managing Partner of Greycroft, a $4B+ venture capital firm investing from seed through growth stages. He has over two decades of experience backing companies across fintech, enterprise software, consumer, and healthcare, and has built Greycroft into a leading platform spanning both early-stage “craft” investing and later-stage access investing. Ian focuses on partnering closely with founders to help scale businesses, combining deep operating insight with long-term venture experience.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Ian Sigalow:

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

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 Venture Capital Is Not Really an Asset Class (2:50) The Two Businesses Hidden Inside Venture Capital (4:10) Why Seed Investing Has Structural Alpha (9:44) The Builder vs Investor Split That Defines Every VC (12:38) How Greycroft Competes Against Sequoia and A16Z (16:25) Why Venture Firms Need Both Craft and Access (21:59) The Moment You Know a Startup Is Actually Working (24:15) The Rare Founder Trait AI Makes More Valuable (31:32) Why AI Could Make Companies Hire More, Not Less (37:57) How Greycroft Uses AI to Find Frontier Founders

What if the biggest breakthroughs in biotech don’t come from more capital—but from building better systems for innovation? In this episode, I sit down with Errik Anderson, biotech entrepreneur and founder behind multiple billion-dollar companies, to discuss how building infrastructure, not just drugs, is reshaping the future of healthcare. Errik explains why most biotech companies fail the same way, how reducing the cost and time of experimentation unlocks more innovation, and why staying private longer enables better long-term decision making. We also explore compounding in biotech, the limits of scaling creativity, and how conviction, mission, and talent ultimately determine which companies change the world. Highlights:

• Why most biotech companies fail the same way
• How lowering experiment costs increases innovation
• The difference between building drugs vs building infrastructure
• Why great companies stay private longer than expected
• How compounding works in biotech beyond capital
• Why you can’t scale creativity by adding more money
• The real bottleneck in drug discovery today
• Why mission-driven teams outperform over long time horizons

Guest Bio:

Errik Anderson is a biotech and technology entrepreneur, investor, and founder of multiple billion-dollar companies, including Alloy Therapeutics. He focuses on building platforms that accelerate drug discovery and innovation across the healthcare ecosystem. In addition to founding and scaling companies, he is an active mentor and investor, driven by a long-term mission to create transformative solutions in health and science for future generations.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Errik Anderson:

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

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) How He Built His Fourth Unicorn (And Why This One Is Different) (1:20) The Strategy Behind Building a “Biotech Infrastructure” Giant (3:30) Why You Should Build the Company You’d Never Want to Leave (6:00) The Real Test of Conviction: Would You Ever Sell? (10:00) Why Most Great Companies Should Stay Private Much Longer (15:00) The Hidden Advantage Private Companies Have Over Public Markets (20:00) Why Innovation Can’t Be Scaled Just by Adding Money (25:00) The Brutal Truth: Every Company Fails the Same Way (30:00) Why So Few People Actually Do the Hard Things (34:00) The Counterintuitive Rule: Quantity Creates Quality

What if the real edge in venture isn’t price—but who you choose to partner with for a decade? In this episode, I sit down with Jamie Montgomery, Co-Founder and Managing Partner of March Capital, to discuss how long-term relationships, not transactions, drive venture outcomes. Jamie explains why asymmetric upside matters more than negotiating the last percentage point, how conviction and discipline shape follow-on decisions, and why understanding your own biases is critical when doubling down. We also explore capital cycles, liquidity dynamics, and how AI is forcing every company to either reinvent itself or fall behind. Highlights:

• Why relationships outperform transactions in venture over time
• The “turkey sandwich test” for choosing founders
• How to actually decide when to double down on a company
• Why most investors misunderstand capital cycles and liquidity
• The hidden biases that distort follow-on investment decisions
• How AI is forcing a full reset across portfolio companies
• Why venture returns come from asymmetric outcomes, not pricing
• The real competition for capital most VCs ignore

Guest Bio:

Jamie Montgomery is the Co-Founder and Managing Partner of March Capital, a leading technology investment firm focused on growth-stage companies. He previously founded Montgomery & Co., where he advised and financed hundreds of companies and took dozens public, building deep experience across capital markets and entrepreneurship. At March Capital, he has led investments in category-defining companies such as CrowdStrike and ThoughtSpot, and continues to focus on backing disruptive technologies with long-term compounding potential.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Jamie Montgomery:

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

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) What Weekly Meetings With Charlie Munger Actually Taught Him (1:24) The One Investing Rule Most People Quietly Break (3:20) Why Transactional Thinking Never Builds Real Wealth (5:53) The “Turkey Sandwich Test” That Filters Great Founders (9:09) The Dangerous Bias Behind Doubling Down on Investments (11:15) How a Small Conference Became a Global Power Network (16:07) Why One Great Asset Eliminates the Need for Fundraising (17:05) The $200B Opportunity Most Investors Are Ignoring (20:55) Why Doubling the Economy Still Doesn’t Fix Inequality (27:03) The Surprising Way AI Is Saving Venture Capital (31:29) Why Venture Liquidity Might Be About to Disappear

What if the biggest edge in investing isn’t capital or strategy—but how clearly the world understands you? In this episode, I sit down with Jennifer Prosek, Founder and Managing Partner of Prosek Partners, to discuss how branding, narrative, and communication have become core drivers of success in financial services. Jennifer explains why firms went from ignoring marketing to depending on it, how “efficiency and preference” directly impact fundraising and deal flow, and why owned media and the “digital blink” now shape first impressions. We also explore how founders should think about storytelling, differentiation, and building long-term trust in an increasingly competitive capital landscape. Highlights:

• Why branding went from irrelevant to essential in finance
• The concept of “efficiency and preference” in fundraising
• Why most first meetings are actually second meetings
• How the “digital blink” shapes investor perception instantly
• Why owned media is the highest ROI strategy today
• The biggest mistake GPs make when going on podcasts
• How to compete for retail capital without massive budgets
• Why narrative clarity is the foundation of all marketing

Guest Bio:

Jennifer Prosek is the Founder and Managing Partner of Prosek Partners, a leading global marketing and communications firm specializing in financial services. She has built the firm into one of the most influential platforms in the industry, advising top asset managers, private equity firms, and financial institutions worldwide. Jennifer is also a published author, board member, and active investor in communications technology, with deep expertise at the intersection of brand, capital markets, and reputation.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Jen Prosek:

LinkedIn:https://www.linkedin.com/in/jennifer-prosek/

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 Financial Crisis Created a Marketing Boom No One Expected (1:50) How Branding Went From Useless to Mandatory Overnight (3:49) The Real Reason Private Markets Are Chasing Retail Investors (5:29) How Smaller Firms Compete Against Blackstone and KKR (8:01) Why Getting on a Platform Means Nothing Without Demand (9:27) The Hidden ROI of Brand: Efficiency and Preference (12:03) Why Podcasts Are the Most Powerful Asset in Finance Today (14:50) The Biggest Mistake GPs Make Before Doing Media (16:23) The Lowest-Cost Strategy That Actually Builds a Brand (18:30) Why Your Reputation Is Now Controlled by AI

What if the biggest edge in managing $390 billion isn’t picking assets—but controlling risk and liquidity when markets break? In this episode, I sit down with Scott Chan, Chief Investment Officer of CalSTRS, to discuss how one of the largest institutional investors in the world is positioning for a period of massive structural change. Scott breaks down how AI, deglobalization, and the energy transition are driving a multi-decade investment cycle, why traditional diversification is breaking down, and how liquidity and dynamic allocation become critical in volatile markets. We also explore structural alpha, co-investing at scale, and how governance and partnerships enable CalSTRS to generate returns without taking incremental market risk. Highlights:

• Why stocks and bonds may no longer provide true diversification
• How liquidity becomes the biggest advantage during market dislocations
• What “structural alpha” looks like at a $390B portfolio
• Why infrastructure is a multi-decade opportunity
• How CalSTRS scaled co-investments from 2% to 30%+ of the portfolio
• The real edge of governance and delegated decision-making
• Why AI is driving a fixed asset investment boom
• The mistake most investors make during market recoveries

Guest Bio:

Scott Chan is the Chief Investment Officer of CalSTRS, one of the largest pension funds in the world with approximately $390 billion in assets under management. He previously served as Deputy CIO and now oversees a team of more than 200 investment professionals across public and private markets. Scott is a board member of the Toigo Foundation, co-chair of the Institutional Investors Roundtable, and serves on multiple advisory boards including the Milken Institute, AIMA, and CAIA, with a focus on advancing diversity and innovation in asset management.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Scott Chan:

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

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) How CalSTRS Is Positioning for an Era of Extreme Uncertainty (1:40) Why the Old 60/40 Portfolio May Be Quietly Breaking (4:00) The New Assets Scott Believes Can Actually Diversify Risk (6:30) Why Regional Investing Could Matter More Than Ever (8:10) How CalSTRS Built Structural Alpha at Massive Scale (12:00) The Hidden Edge of Owning More Control in Private Markets (16:40) Why Co-Investments Became One of CalSTRS’ Biggest Advantages (21:00) Why Venture Capital Has Become Strategic for the Entire Portfolio (25:00) The Asset Class Scott Thinks Could Win the Next Decade (28:40) The Mistake CalSTRS Made When Markets Rebounded

What if the next source of alpha in private equity isn’t funds—but individual deals? In this episode, I sit down with Rohan Parikh, Vice President at Houlihan Lokey, to discuss the rapid rise of co-investments and why they are becoming a core part of institutional portfolios. Rohan explains how extended fundraising cycles, larger deal sizes, and slower distributions have created a “perfect storm” for deal-by-deal capital, why LPs are increasingly treating co-investments as a standalone asset class, and how independent sponsors are reshaping the market. We also explore underwriting frameworks, alignment, and how relationships, not just returns, drive long-term success in this segment of private markets. Highlights:

• Why co-investments have doubled to a $300B+ market in just a few years
• The “perfect storm” driving deal-by-deal fundraising
• Why LPs now treat co-investments as a standalone asset class
• How independent sponsors are competing with traditional PE firms
• What separates a fund track record from a co-invest track record
• Why alignment is often stronger in co-investments than funds
• How deal vs sponsor underwriting shifts based on control
• The real risk of adverse selection—and how to avoid it

Guest Bio:

Rohan Parikh is a Vice President at Houlihan Lokey, where he focuses on direct placements and co-investment fundraising within the firm’s Equity Capital Solutions business. He previously worked at PJT Park Hill in co-investment fundraising and began his career at Citi in leveraged finance. Rohan specializes in structuring and raising capital for sponsor-backed single-asset transactions and works closely with GPs and LPs across private markets.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Rohan Parikh:

LinkedIn:https://www.linkedin.com/in/rohan-parikh-214818109/

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 Co-Investments Are Exploding in Private Equity (2:04) The New Asset Class LPs Can’t Ignore (4:55) Why Blue-Chip Investors Are Becoming Independent Sponsors (6:30) The Alignment Signal LPs Care About Most (7:27) What Makes a Co-Investment Worth Taking Seriously (10:56) How Independent Sponsors Pull Off $500M Deals (16:41) Why the Best Currency Between GPs and LPs Is a Deal (21:05) How LPs Avoid Getting the Worst Co-Investments (25:15) Why Co-Investments May Be More Aligned Than Funds (31:29) Why Blind Pool Funds Are Losing Their Grip

What if the best investments aren’t found in chaos—but in having the discipline to act when others can’t? In this episode, I sit down with Darren Fisk, Founder of Forum Investment Group, to discuss how he scaled from early syndication deals to a fully integrated multifamily investment platform managing billions. Darren breaks down how he leaned in during the 2008 financial crisis to acquire 9,000 units, why focusing on distressed capital structures rather than distressed assets created asymmetric opportunities, and how flexibility across the capital stack allows investors to generate returns in any market. Highlights:

• How buying distressed capital stacks created outsized returns in 2008
• Why conviction matters more than timing in volatile markets
• The difference between allocating capital and truly investing
• How flexibility across debt and equity drives consistent returns
• Why the best opportunities are often “below the headline”
• The hidden advantage of operating assets, not just owning them
• Why doing nothing can be the highest returning decision
• How market cycles create obvious opportunities most investors miss

Guest Bio:

Darren Fisk is the Founder of Forum Investment Group, a multifamily-focused investment platform with over two decades of experience across real estate equity, debt, and structured finance. He built the firm from early syndication deals into a fully integrated asset manager investing up and down the capital stack.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Darren Fisk:

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

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

Disclaimer:

Forum is an SEC-registered investment adviser; however, such registration does not imply a certain level of skill or training. The views expressed are for general informational purposes only, do not take into account the specific investment objectives, financial situation, or needs of any individual, and may not be representative of any specific investment, strategy, or client experience. This communication is for informational purposes only and does not constitute investment advice, a recommendation, or part of any offering materials. Any investment will be made solely through formal offering materials provided by Forum or its affiliates. Investing involves a high degree of risk, including possible loss of entire investment. Investors must rely on their own examination of any transaction and its terms, including all merits and risks involved. These securities have not been recommended or approved by any federal or state securities authority, nor have such authorities passed upon the accuracy or adequacy of this communication. This communication contains forward-looking statements based on current expectations, not prior operating history. Such statements are not guarantees of future performance and involve risks, uncertainties, and assumptions that are difficult to predict. Actual outcomes may differ materially from any forward-looking statements made herein. Investment should only be made by individuals who understand the nature of these transactions and can bear the associated risks.

(0:00) How He Bought 9,000 Units While Everyone Else Was Panicking (1:18) The Reputation Edge That Let Him Move in a Crisis (2:27) Why Conviction Matters More Than Confidence in a Downturn (4:32) Why Great Investors Refuse to Be “Allocators” (6:14) The Hidden Opportunity Most People Miss in Bad Markets (9:34) Why He Abandoned Deal-by-Deal Investing for Good (12:13) The Mistake He Made Building the Wrong Fund Structure (15:20) How He Built a Team That Could Scale Beyond Him (22:22) Why Doing Nothing for 6 Years Was the Right Move (27:08) The One Thing He Wishes He Built Much Earlier

What if venture capital isn’t about finding unicorns—but about consistently making good investments? In this episode, I sit down with Eric Scott, Co-Founder and Managing Partner at Overlook Capital, to discuss how his approach to venture evolved from chasing power laws to focusing on fundamentals. Eric explains why most venture frameworks only make sense in hindsight, how thinking like a value investor can improve early-stage decision-making, and why founder quality is ultimately revealed through execution, not narratives. We also explore concentrated markets, late-stage venture dynamics, and how reputation, conviction, and timing shape outcomes across cycles. Highlights:

• Why venture “power laws” don’t help you pick winners in real time
• How value investing principles apply to early-stage companies
• What most investors misunderstand about founder selection
• Why great companies don’t come from A/B testing alone
• How venture markets became structurally concentrated
• Why smaller funds can outperform in overlooked segments
• The hidden role of reputation and signal in fundraising
• Why being wrong—and correcting it—is a core investing skill

Guest Bio:

Eric Scott is Co-Founder and Managing Partner at Overlook Capital, where he focuses on investing in category-leading growth companies. He previously worked at Founders Fund and 8VC, gaining experience across early and growth-stage investing, and has also held roles in healthcare and technology startups. Eric began his career after founding a company out of college and brings a cross-functional perspective shaped by both operating and investing experience.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Eric Scott:

LinkedIn: https://www.linkedin.com/in/eric-scott-bio/

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 One Sentence From Peter Thiel That Changed How He Invests (2:28) Why Venture Capital Might Be Built on a Flawed Idea (4:59) Are Startups Built on Movements or Real Businesses? (8:31) Why Every Great VC Invests Completely Differently (10:40) The Rule That Changed How Founders Fund Picks Winners (12:03) If You’re Firing Founders, You Already Made a Mistake (16:43) What Actually Makes a “Great” Founder (It’s Not What You Think) (22:58) The Story That Redefines What Conviction Really Looks Like (30:14) Why Chasing Billion-Dollar Ideas Is the Wrong Strategy (40:41) The Hidden Game Behind Who Gets on the Cap Table

What if the biggest opportunity in healthcare isn’t new drugs—but reinventing how the entire system works? In this episode, I sit down with David Berry, Founder of over 20 companies including seven $1B+ businesses, to discuss why the traditional biotech model is breaking and where the next wave of innovation in healthcare is emerging. David explains how pricing pressure, rising costs, and global competition are compressing returns in drug development, while AI, data, and new business models are unlocking entirely new ways to deliver care. We also explore how technology is transforming clinical trials, why healthcare is shifting beyond pharmaceuticals, and how investors can find opportunity in mispriced parts of the market. Highlights:

• Why biotech returns are structurally declining despite innovation
• How AI is changing clinical trials and drug development timelines
• The unappreciated impact of China on global biotech competition
• Why healthcare is a $5T opportunity beyond pharmaceuticals
• How data and longitudinal patient insights unlock new discoveries
• The next frontier in longevity, wearables, and personalized health
• Why the middle stage of venture is undercapitalized today
• How supply-demand imbalances create the best investment opportunities

Guest Bio:

David Berry is a founder, entrepreneur, and investor who has built over 20 companies, including seven valued at over $1 billion. He spent nearly two decades at Flagship Pioneering, where he helped create and scale leading biotech companies, and later founded Valo Health. He is now the founder of Averin Capital, where he focuses on the technology-driven transformation of healthcare and investing in companies at the intersection of biology, data, and innovation.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with David Berry:

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

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 Biotech Returns Are Quietly Breaking (0:15) The Hidden Shift Making Life Sciences More Attractive (1:00) Why Drug Prices Are Falling—and Innovation With It (3:22) The Unintended Consequence: Fewer New Drugs (4:17) Why Investors Are Choosing Rockets Over Biotech (5:38) China Is Becoming the World’s Drug Factory (8:06) The $5 Trillion Opportunity Most Investors Miss in Healthcare (9:43) Why AI Could Cut Years Off Drug Development (13:41) The Hidden Flaw in How We Test Drugs Today (21:31) How He Raised $450M in One of the Hardest VC Markets

What if the best venture returns come from avoiding trends—not chasing them? In this episode, I sit down with Colin, Co-Founder of Narya, to discuss how he approaches investing in frontier sectors without falling into mimetic behavior. Colin explains why the best opportunities are often “hidden in plain sight,” how mission-driven investing can still generate venture-scale returns, and why concentration, not diversification, drives outcomes in venture. We also explore defense, space, and advanced manufacturing, and how timing, business model innovation, and founder quality ultimately determine success. Highlights:

• Why chasing popular sectors often leads to worse outcomes
• How to identify “hidden in plain sight” opportunities
• Why venture returns are driven by a few concentrated bets
• What most investors misunderstand about deep tech investing
• How mission-driven companies can still deliver top-tier returns
• Why too much capital can hurt startups more than help
• The traits that define world-changing deep tech founders
• Why business model innovation matters as much as technology

Guest Bio:

Colin is a Co-Founder of Narya, where he focuses on investing in early-stage companies across sectors such as defense, healthcare, and advanced manufacturing. He previously served as a Managing Director at Mithril and held senior roles across leading venture platforms, investing in companies spanning biotechnology, neuroscience, and enterprise software. Colin also serves as an advisor to multiple investment and accelerator platforms, and has built a career backing founders working on complex, high-impact problems.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Colin Greenspon:

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

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) What Made JD Vance a Dangerous (and Different) Investor (2:20) Can You Invest in Innovation Without Losing Money? (5:47) Why Most “Contrarian” Investors Are Actually Late (8:54) The Hidden Mistake LPs Make With Diversification (10:44) Why Billionaires Back New VC Funds (It’s Not Returns) (14:00) Why the Best Companies Don’t Follow Categories (19:09) Why Space Is Becoming the Next Battlefield (24:09) What Separates World-Changing Founders From Everyone Else (27:00) Why Too Much Capital Kills Great Companies (43:02) The Career Mistake That Slows Most Investors Down

What if the biggest edge in investing isn’t picking better assets—but structuring them better for taxes, incentives, and control? In this episode, I sit down with Michel, Founding CIO of a16z Perennial, to discuss how institutional investing frameworks translate to individual portfolios. Michel breaks down why most wealth management fails at true investment management, how misaligned incentives shape outcomes, and why scale, access, and structure matter more than traditional asset allocation. We also explore concentrated portfolios, tax alpha, and how psychology ultimately determines whether a strategy succeeds or fails. Highlights:

• Why wealth management and investment management are fundamentally different
• How scale actually benefits LPs, not just GPs
• What most investors misunderstand about diversification
• Why a 90/10 portfolio may not be irrational for the right investor
• How tax alpha can outperform investment alpha
• The hidden cost of fund-of-funds and fee layering
• Why access to top managers drives most institutional returns
• How psychology, not strategy, determines long-term outcomes

Guest Bio:

Michel is the Chief Investment Officer at a16z Perennial, where he leads multi-asset portfolio construction for founders and large individual investors. Prior to a16z, he was CIO at Jordan Park, managing approximately $17 billion across global asset classes, and a Managing Director at Makena Capital Management. Earlier in his career, he worked at Scion Capital and McKinsey, and holds advanced degrees from Stanford and Cambridge, including a PhD in Management Science and Engineering as a DARPA 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.

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 Michel Del Buono:

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

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 A16Z Built a Family Office (It Wasn’t for Wealth) (1:26) The Hidden Problem With Single Family Offices (4:51) Does Scale Help or Hurt Investment Returns? (6:49) The Incentive Problem That Breaks Wealth Management (9:06) Why Taxable Investors Are Suddenly So Important (11:15) The First Principles Behind Building a Modern Family Office (15:35) Why All Endowment Portfolios Look the Same (19:05) The “Crazy” Portfolio That Might Actually Be Rational (24:19) Why Investing Is More Psychology Than Strategy (36:53) The Easiest Alpha Most Investors Completely Ignore

Is the real edge in investing not picking assets but structuring how you allocate capital? Terence Thompson is a Vice President of Investments at DF Enterprises, about how single family offices think about portfolio construction, liquidity, and structural alpha. We break down why Terry uses a total portfolio approach, how family offices create edge through flexibility, and why being a liquidity provider during market stress is one of the most powerful strategies. We also discuss concentration risk in public markets, the evolution of private markets, and how allocators can think about illiquidity, secondaries, and niche opportunities. Highlights:

• Why single family offices have a structural edge over multifamily offices
• Total portfolio approach vs traditional asset allocation
• Competing strategies for capital across the portfolio
• Why liquidity is critical during market dislocations
• Concentration risk in large cap equities
• Structural changes in small cap and private markets
• The impact of retail capital flowing into private equity
• How misaligned liquidity structures can hurt returns
• Where illiquidity premium still exists
• Underrated opportunities in small buyout and niche credit
• The role of behavioral bias in asset allocation
• Why risk tolerance should match the capital base

Guest Bio:

Terence Thompson is a Vice President of Investments at DF Enterprises, a single family office where he oversees investment strategy, portfolio construction, and manager selection across public and private markets. He has over a decade of institutional investment experience, including managing assets at Blue Cross Blue Shield of Arizona. Terry is a CFA charterholder, USAF veteran, and an active member of several investment and policy organizations. He focuses on building resilient portfolios that balance liquidity, risk, and long-term compounding.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Terence Thompson:

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

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) What Gets Lost When a Family Office Serves Too Many Families (2:00) Why the Traditional Endowment Model Isn’t Flexible Enough Anymore (2:45) The Hidden Force Behind Today’s Momentum Trades (6:29) Why Passive Investing May Be Riskier Than It Looks (13:28) Why Retail Capital Will Change Private Markets in a Big Way (16:31) The Structural Flaw That Could Hurt Retail Investors (19:29) Is the Illiquidity Premium Still Real? (21:18) Why Small Buyout May Benefit Most From the Retail Wave (23:41) The Most Underrated Asset Classes Right Now (30:24) The Career Advice That Matters More Than Playing It Safe

What if the biggest edge in venture today isn’t picking companies—but owning the entire lifecycle of capital? In this episode, I sit down with Paris Heymann, Co-Managing Partner of Technology Investing at J.P. Morgan Private Capital, to discuss how the boundaries between public and private markets are breaking down. Paris explains why companies are staying private longer, how value is increasingly accruing to private investors, and why multi-stage platforms are becoming the new model for capturing returns. We also explore how AI is shifting business models from selling software to selling work, why founder quality still drives outcomes, and how power laws continue to dominate both private and public markets. Highlights:

• Why the line between public and private markets is disappearing
• How J.P. Morgan competes using platform, not just capital
• Why companies are staying private for 15+ years
• What changes when companies start selling “work” instead of software
• Why valuation matters less than quality and compounding
• How power laws dominate even in growth and public markets
• Why founder-market fit matters more than ever in AI
• The real advantage of multi-stage investing platforms

Guest Bio:

Paris Heymann is Co-Managing Partner for Technology Investing within J.P. Morgan Private Capital, a division of J.P. Morgan Global Alternatives in J.P. Morgan Asset Management. Paris joined Private Capital from Index Ventures in 2024 where he served as Partner and helped to establish the firm’s New York office. Before Index, Paris was Partner at Arena Holdings where he invested globally in public and private technology companies. He began his career at Bain Capital within the North American Private Equity group. Paris holds a B.A. in Political Economy from Williams College.

Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank @AlphaSense for sponsoring this episode!

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Paris Heymann:

LinkedIn:https://www.linkedin.com/in/paris-heymann/

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 JP Morgan Has a Hidden Edge in Venture (0:47) When Capital Alone Isn’t Enough to Win Deals (2:18) Why the Venture Model Is Quietly Breaking (3:48) Should the Best Companies Ever Go Public? (5:40) The Real Reason Founders Stay Private Longer (7:38) What “Growth Equity” Actually Means Today (8:39) Why AI Demand Is Exploding Faster Than Anyone Expected (10:09) Why Selling “Work” Will Replace Selling Software (11:30) Why Data Moats Might Be Less Valuable Than You Think (13:40) Why Expensive Companies Can Still Be Cheap

Is private equity alpha really about picking great deals—or about executing the same playbook better than everyone else? In this episode, I discuss with Monty Yort, Managing Partner at GenNx360 Capital Partners, about how disciplined execution and consistency drive long-term outperformance in private equity. We break down how GenNx360 approaches proactive sourcing, why lower middle market investing creates structural advantages, and how operational improvement and buy-and-build strategies compound value over time. Monty also shares lessons on leadership, mentorship, and why the best firms continuously refine their process rather than chase new strategies. Highlights:

• Why proactive sourcing leads to better deals and more opportunities
• The shift to industrial services and fragmented markets
• Buy-and-build as a repeatable value creation strategy
• Why organic growth is the primary driver of returns
• How to evaluate founders and build leadership teams
• The importance of discipline in fund size and strategy
• Why continuation funds extend the best investments
• How repetition and consistency outperform complexity
• The role of mentorship in accelerating careers
• Why private equity is about people as much as process

Guest Bio:

Monty Yort is a Managing Partner at GenNx360 Capital Partners, a New York–based private equity firm with $2.5 billion in assets under management focused on middle-market industrial and business services companies. He has more than two decades of experience leading acquisitions and recapitalizations totaling over $3 billion, specializing in operational improvement and growth in fragmented industries. Prior to joining GenNx360 in 2009, Monty was a Managing Partner at Schroder Ventures and a Principal at Aurora Capital Group, with earlier roles at Morgan Stanley and Salomon Brothers. He holds an MBA from UCLA Anderson and serves on multiple portfolio company boards

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Monty Yort:

LinkedIn:https://www.linkedin.com/in/monty-yort-8236043/

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 Private Equity Doesn’t Need Power Laws to Win (1:09) Proactive and AI-driven sourcing strategies (5:57) AI's impact on industries and investment strategies (6:55) History, evolution, and fund strategy at Genexx (9:25) Capital markets, continuation vehicles, and fund challenges (13:16) Leadership, management, and upscaling portfolio teams (17:19) Friction in investing and selling businesses (18:48) Lower middle market and future of private equity (23:37) Motivations and advice for private equity professionals (26:28) Closing remarks

How do you manage a $26 billion public fund while keeping every investment decision disciplined, every team member calibrated, and every partner accountable? In this episode, I sit down with Mark Steed, Chief Investment Officer of AZ Public Safety Personnel Retirement System, to explore how super forecasting and probabilistic thinking shape portfolio management. Mark shares how lessons from Dr. Phil Tetlock's the Good Judgment Project inform every investment decision, why intellectual humility and calibrated confidence drive better outcomes, and how simplifying portfolios into broad buckets creates flexibility and competition for capital. He also unpacks the role of co-investments, structural alpha, and first principles thinking in public markets. Highlights:

• How PSPRS uses probabilistic forecasts and Briar Scores to track accuracy and improve decision-making
• Why intellectual humility and calibration are as important as market knowledge
• Simplifying complex portfolios into three broad buckets: capital appreciation, contractual income, and diversifying strategies
• The growing role of co-investments and capturing structural alpha with trusted partners
• Benchmarking against the S&P 500 while managing expectations for thousands of police and fire pensioners
• Distinguishing between “investing,” “allocating,” and truly “owning” assets
• Lessons from super forecasting on evaluating GPs and reducing overconfidence in a complex market environment

Guest bio:

Mark Steed is Chief Investment Officer of AZ Public Safety Personnel Retirement System, overseeing approximately $26 billion for police and fire pensions. He has implemented super forecasting and probabilistic investment methodologies at scale, transforming decision-making, portfolio construction, and team dynamics. Known for his focus on calibration, intellectual humility, and first principles thinking, Mark combines behavioral science with traditional investment rigor to deliver disciplined, long-term results.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Mark Steed:

LinkedIn:https://www.linkedin.com/in/mark-steed/

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 (6:14) Improving team calibration and reducing overconfidence (7:14) Distinguishing innovation from craziness; building team forecasting calibration (9:20) Parallels with Bridgewater’s principles and team dynamics (13:13) Benchmarking against the S&P 500 and implications for portfolio management (14:29) Challenges of managing portfolios for police and firemen (16:02) Simplifying portfolio construction into broad categories (17:27) Flexibility and competition among investment ideas (19:08) Independent approaches and thoughts on TPA (22:16) Evolution of co-investment strategy and structural alpha (24:02) Semantics of investing: Allocation vs. ownership (25:58) Recent changes in investment mindset (27:24) The performative aspect of confidence in investments (29:38) Uncertainty in predicting AI and interest rates (33:06) Forcing super forecasting on GPs (34:54) Timeless advice for young investors (36:16) Handling spiky asset classes like venture capital (38:17) Closing remarks

How do you build a $7 billion portfolio that performs across decades while keeping every client aligned and every manager motivated? In this episode, I sit down with Karen Welch, Chief Investment Officer at Spider Management Company, to explore the evolving role of a CIO in today’s complex investment landscape. Karen shares how lessons from Stanford’s endowment shaped her approach, why the best investment edge comes from people and relationships, and how Spider leverages both to generate top-tier returns. She also unpacks how to navigate private markets, assess the illiquidity premium, and structure portfolios to balance opportunity with risk. Highlights:

• Why the most important skill for investors isn’t modeling—it’s building relationships with teams and managers
• How AI is reshaping portfolio management and why human judgment remains critical
• Playing offense and defense in a portfolio: spotting dislocations and leaning into opportunities
• Lessons from the endowment model: what still works, what needs evolution, and why illiquidity premiums aren’t guaranteed
• Strategies for accessing top-tier venture managers without decades of reputational capital
• The advantages of Spider’s single portfolio model across multiple clients and the “razor” it creates for disciplined investing
• Practical advice for career longevity: loving your work and balancing networking with building something meaningful

Guest bio:

Karen Welch is Chief Investment Officer at Spider Management Company, overseeing approximately $7 billion for the University of Richmond and affiliated nonprofit partners. Previously, she spent nearly a decade at Stanford’s endowment, where she honed her approach to portfolio construction, manager selection, and long-term investing. Known for her focus on relationships, strategic thinking, and disciplined portfolio management, Karen combines decades of endowment experience with a modern approach to private and public markets.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Karen Welch:

LinkedIn:https://www.linkedin.com/in/karen-horn-welch/

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 Most Important Lesson From Stanford Wasn’t Investing (1:07) Why AI Won’t Replace the Best Investors (2:28) What a CIO Actually Does (Most People Get This Wrong) (3:30) What “Monitoring a Portfolio” Really Means (5:26) How the Best CIOs Find Opportunities Before Everyone Else (7:30) Why the Best Investments Hide Behind Bad Headlines (8:31) What’s Broken in the Endowment Model Today (13:16) The Truth About the Illiquidity Premium (It’s Not Real) (15:58) Why Access Matters More Than Skill in Venture (23:08) The Hidden Power of Running One Single Portfolio

What does it take to raise $270 million in a risk-off market while keeping your personal life, sanity, and team intact? In this episode, I sit down with Scott Painter, Founder & CEO, TrueCar, to unpack the 21-month journey of taking a company private. Scott shares how persistence, strategic thinking, and mental resilience allowed him to navigate investor skepticism, market volatility, and personal stakes. He discusses the lessons he learned from fundraising in both up and down markets, why creating momentum and scarcity is critical, and how setting boundaries transformed the outcome for him and his team. Highlights:

• The most difficult capital raise of Scott’s career and how he overcame repeated setbacks
• Persistence as a strategic tool: staying the course through 21 months of volatility
• Managing personal and professional stakes: balancing debt, family, and team morale
• Compartmentalizing bad news to make clear-headed decisions under pressure
• Using scarcity and deadlines to drive investor action in risk-off environments
• Learning from elite entrepreneurs like Elon Musk and applying resilience in real time
• Turning adversity into anti-fragility: lessons on confidence, focus, and long-term success

Guest bio:

Scott Painter is a serial entrepreneur and long-time leader in automotive technology, widely recognized for shaping how consumers buy, finance, and access vehicles. He founded TrueCar in 2005 to help car buyers save time and money with technology. Under his leadership, TrueCar went public in 2014. In January 2026, Painter re-acquired the company and returned as CEO to continue advancing its original mission.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Scott Painter:

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

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 This Was the Hardest $270M Raise of His Career (1:29) The Deal That Fell Apart a Dozen Times (And Still Closed) (4:56) How He Kept Raising Money After Losing Momentum Repeatedly (6:42) The Breaking Point That Changed Everything Overnight (9:00) The Moment He Was Finally Willing to Walk Away (11:11) The Line Between Conviction and Losing Your Mind (12:04) Why Elon Musk’s Persistence Is on Another Level (13:07) The Real Reason Investors Actually Write Checks (14:27) The Brutal Reality of Entrepreneurial Pressure (16:27) What It Really Means to Bet Everything on One Deal

What if the families with the largest fortunes generate the highest returns not by chasing hot sectors, but by pacing capital, managing liquidity, and investing with a multi-decade horizon? In this episode, I sit down with Douglas Evans, Chief Investment Officer & Partner at Callan Family Office, to explore how a $10B family office approaches private markets like an institutional investor. Doug shares how private capital pacing, vintage year diversification, and strategic GP partnerships drive consistent performance, why continuation vehicles and secondary markets are reshaping liquidity, and how focusing on underlying assets rather than labels helps families build repeatable, long-term returns. Highlights:

• Managing private capital pacing to capture the best vintages
• Balancing taxable versus non-taxable investment strategies
• Navigating declining DPI in venture and growth funds
• Continuation vehicles and secondaries as tools to unlock liquidity and optimize returns
• Building strategic GP relationships for first-look co-investment opportunities
• Investing in underloved sectors like enterprise security and infrastructure
• Doug’s advice: focus on alignment, patience, and long-term perspective to generate outsized outcomes

Guest bio:

Douglas Evans is Chief Investment Officer & Partner at Callan Family Office, overseeing $10B in assets for ultra-high-net-worth families. He specializes in portfolio construction across public and private markets, private capital pacing, tax-aware investing, and cultivating long-term GP relationships to deliver repeatable, institution-like performance.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Douglas W. Evans:

LinkedIn:https://www.linkedin.com/in/douglas-evans-73372310/

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 Family Offices Should Invest Like Endowments (2:04) The Tax Advantage That Can Change a Venture Portfolio (4:07) How to Build a Venture Book From Scratch Without Regret (7:31) Why the Best Venture Vintages Usually Start in the Worst Times (10:00) The Private Market Shift That Changes Everything for Investors (14:59) Why Most Investors Misunderstand What They Actually Own (19:19) What Breaks If Private Markets Stay Illiquid (21:10) Why Continuation Vehicles Are Coming to Venture (28:54) The Most Underrated Investment Theme Right Now (30:29) The One Principle That Matters More Than Wealth

What if the biggest edge in portfolio construction isn’t picking better assets but structuring a portfolio you can actually stick with through cycles? In this episode, I sit down with Chaya Slain, President and CIO at Virtera Partners LLC, to unpack how families can access institutional-quality investing without building a full family office. Chaya explains why alternatives are often the true driver of outperformance, how trend following can reshape risk and return, and why behavioral discipline matters more than perfect asset selection.

Disclaimer: The information discussed in this podcast is for informational and educational purposes only and should not be considered investment advice or a recommendation or offer to buy or sell any security. Nothing discussed in this podcast should be construed as creating an advisory relationship with any listener.

Highlights:

• Why building a traditional family office is inefficient below $100M to $1B in assets
• The real challenge in alternatives is access, diligence, and fee structure, not just sourcing
• How FOMO drives overexposure to “hot” private deals without understanding price
• Trend following explained simply and why it thrives during market dislocations
• Historical performance: how combining trend and equities improves returns and reduces drawdowns
• Why bonds may fail as protection and what can replace them in modern portfolios
• Behavioral investing: why structure and discipline outperform individual decision-making
• Lower middle market private equity: less competition, better entry prices, and multiple expansion potential
• Venture capital challenges: access, long time horizons, and wide dispersion of returns
• How misaligned incentives and layered fees can quietly erode returns

Guest Bio:

Chaya Slain is the President and CIO at Virtera Partners LLC, an investment firm focused on helping families access institutional-quality alternative investments. She previously worked at a leading family office where she identified gaps in access to private markets for sub-billion-dollar portfolios. Chaya specializes in portfolio construction, manager selection, and integrating strategies like trend following to improve long-term risk-adjusted outcomes.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Chaya Slain:

LinkedIn:https://www.linkedin.com/in/chaya-slain/

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, an

(0:00) Introduction (1:05) Importance and challenges of alternative and private investments (2:30) Issues with over-indexing on trendy investments (4:35) Recommended strategies for family offices (7:29) Trend following: explanation, benefits, and role in crises (16:15) Historical performance of trend following (20:05) Trend following vs. traditional portfolios (24:44) Levered treasuries and portfolio construction (25:18) Principal agent problems in large capital pools (26:26) Monthly rebalancing and emotional challenges in trend following (29:17) Strategic ignorance and structural alpha (32:07) Opportunities in lower middle market private equity (34:53) Caution and approach in venture capital investing (38:01) Persistence in venture capital performance (41:11) Advice to younger self on entrepreneurial capital (42:52) Closing remarks

What if the real edge in venture isn’t picking the hottest companies, but structuring your portfolio, pacing capital, and building relationships in a way most investors never do? In this episode, I sit down with Jamie Melzer, Founder and Managing Partner of Altra Venture Partners, to break down how she built a firm focused on late-stage venture and secondaries at the height of market dislocation. We discuss why rising interest rates in 2022 created a rare entry point, how buying private tech companies at 40 to 80 percent discounts reshaped the opportunity set, and why transaction risk often matters more than company risk in secondary markets. Jamie explains her concentrated, power-law-driven portfolio strategy, how she sources deals in an opaque and relationship-driven ecosystem, and why access, not awareness, is the true barrier in private markets. Highlights:

• Why 2022 to 2023 created a once-in-a-generation opportunity in venture secondaries
• How liquidity constraints, not fundamentals, drove massive valuation resets
• The difference between single-asset secondaries and portfolio acquisitions
• Why transaction risk, not company risk, is often the biggest constraint
• How Altra builds concentrated exposure to top private tech companies
• Creative deal structures like equity swaps and co-investment partnerships
• The reality of information asymmetry in private secondary markets
• Why late-stage private companies now resemble public market equivalents

Guest Bio:

Jamie Melzer is the Founder and Managing Partner of Altra Venture Partners, with over 20 years of experience across credit, public equities, and venture capital. Drawing on her background investing through multiple market cycles, she applies a public markets lens to late-stage and secondary investments in pre-IPO technology companies.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Jamie Melzer:

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

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) How a Venture Fund Was Built Out of Market Panic (2:22) The Baby-and-Bathwater Trade That Created a Firm (3:37) Why It Was Hardest to Raise Capital at the Best Possible Time (5:22) Why Most Secondary Investors Still Won’t Underwrite a Single Company (6:26) The Unusual Strategy Behind Building Concentrated Positions in Private Giants (9:00) The Hidden Problem With Secondaries That Most Buyers Miss (11:16) Why the New Buyers in Venture Don’t Look Like Traditional VCs (12:53) The Public Market Exposure Investors Quietly Lost (15:58) Why Late-Stage Venture Has a Completely Different DPI Profile (27:07) The Trend That Could Reshape Venture Liquidity Forever

What if the best venture returns come from the LPs that are most patient and most strategic? In this episode, I sit down with Scott Voss, Partner at HarbourVest, to explore how the $150B multi-manager firm generates consistent outperformance across venture, growth equity, buyouts, and secondaries. Scott shares how consensus risk, vintage year timing, and strategic co-investing shape returns, why continuation vehicles and evergreen structures are transforming private markets, and how long-term relationships with GPs create first-look access to top deals. Highlights:

• Consensus risk and why groupthink in hot sectors can distort valuations
• How venture returns correlate with capital deployment: less raised often equals higher performance
• Timing matters: investing through cycles, not just in peak years, compounds long-term alpha
• Continuation vehicles and secondaries as tools to capture liquidity and enhance returns
• Evergreen funds as a way to reduce cash drag and deliver smoother, long-term exposure
• Strategic GP partnerships: how trust, transparency, and co-investing unlock first-look deals
• Balancing diversification across funds, portfolio companies, and vintage years to reduce risk
• Scott’s advice: focus on alignment, persistence, and playing the long game for outsized outcomes

Guest Bio:

Scott is a Managing Director at HarbourVest with over 25 years of experience across the U.S. and Asia. He previously served two terms as Chair of the Global Primary Investment Committee and now focuses on venture capital, where his career began.

He currently serves as Senior Market Strategist, analyzing trends across the private markets ecosystem and sharing insights through client engagement, public speaking, and thought leadership. Earlier in his career, he led international sales and distribution for Cannondale Corporation. He holds a BS from Bryant College and an MBA from Babson College.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Scott C. Voss:

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

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

Disclaimer:

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

For important risks regarding private equity investing please see Important Information and Risk Factors: https://www.harbourvest.com/important-information-and-risk-factors/

(0:00) What is consensus risk (1:14) Identifying bubbles and their inevitability in asset classes (3:09) Lessons from the dot-com boom and capital-performance correlation (5:06) HarbourVest overview, strategies, and use of scale (8:32) Continuation vehicles: best practices and LP challenges (14:25) Diversification and portfolio construction in venture investing (16:11) Persistence and bifurcation in venture capital performance (18:10) Heuristics, fund returns, and strategic co-investments (21:24) HarbourVest's growth and organizational evolution (25:05) Exponential vs. linear growth in investment approaches (26:00) Evergreen funds: rise, impact, and liquidity structures (29:17) First look alpha and HarbourVest's sustainable edge (31:33) Stability in GP-LP relationships and private markets evolution (33:54) Balancing economics and value add in private equity (34:23) Closing remarks

What if building a portfolio for high-net-worth investors is more about managing downside risk than chasing returns? In this episode, I sit down with Damien Bisserier, Managing Partner and Co-CIO at Evoke Advisors, to explore how he constructs diversified portfolios for ultra-high-net-worth families. Damien shares why after-tax returns, alternative assets, and private markets matter more than concentrated US stock bets, and how behavioral insights and client-centered thinking drive long-term compounding. He also dives into venture capital, the importance of relationships, and the nuanced ways to identify managers who deliver repeatable alpha. Highlights:

• How incorporating multiple, uncorrelated return streams improves consistency beyond US equities
• Why after-tax returns are often overlooked and how understanding tax implications enhances portfolio outcomes
• The evolution of private credit and alternative vehicles for high-net-worth investors
• Venture capital as a network-driven asset class and strategies to access top-tier managers
• Using private markets, real estate, and active management to generate tangible alpha
• The importance of GP alignment, skin in the game, and repeatable sources of outperformance
• Marrying portfolio engineering with client comfort and behavioral considerations
• Timeless advice: protect on the downside, focus on compounding, and listen more to learn faster

Guest Bio:

Damien Bisserier is Managing Partner and Co-CIO at Evoke Advisors, recognized by Forbes as the top RIA four years in a row. He previously worked at Bridgewater, building systematic investment frameworks, and now focuses on constructing diversified portfolios that balance private and public markets, tax efficiency, and behavioral factors for high-net-worth families. Damien specializes in portfolio design, alternative assets, venture capital diligence, and aligning manager incentives to capture repeatable alpha.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with Damien Bisserier:

LinkedIn: https://www.linkedin.com/in/damien-bisserier-3b64132/

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 Most Portfolios Fail at Scale (1:31) The Hidden Layer Everyone Ignores: After-Tax Returns (3:04) The One Question That Exposes Bad Managers Instantly (4:37) The Liquidity Trap No One Is Talking About (Until It’s Too Late) (7:23) Venture’s Dirty Secret: Great Stories, Weak Returns (10:05) Why Even Top VCs Might Just Be Lucky (12:11) The Real Edge in Private Markets Isn’t What You Think (14:31) Why “Diversification” Still Isn’t Enough (17:46) The Biggest Risk Isn’t Losses—It’s Lost Decades (24:27) The Mindset Shift That Separates Great Investors

What happens when AI turns a $40B legal software market into a $1T opportunity? In this episode, I talk with David Eckstein, CFO of Legora, about scaling one of the fastest growing enterprise AI companies in history. David explains how Legora went from zero to $100M in 18 months, why AI is expanding markets rather than just disrupting them, and how the role of CFO is evolving into a strategic operator across every part of the business. We discuss vertical vs horizontal AI, why AI companies must focus on workflows instead of prompts, and how talent density and culture become the ultimate differentiators in high growth environments. Highlights:

• How Legora scaled from 0 to $100M in 18 months
• Why legal tech is a $1T opportunity, not just $40B
• Vertical AI vs horizontal AI and why workflows matter
• Why AI expands TAM rather than just disrupting it
• CFO as operator, not just finance leader
• How AI changes pricing, margins, and business models
• Talent density as the most important investment
• Why culture and intensity drive execution speed
• Lessons from Box and transitioning into venture
• The importance of moving fast in emerging markets

Guest Bio:

David Eckstein is the Chief Financial Officer at Legora, where he leads financial strategy, operations, and scaling for one of the fastest growing AI companies globally. Prior to Legora, he served as CFO at Vanta and Menlo Security, helping both companies scale rapidly and raise significant capital. Earlier in his career, he held leadership roles at OpenDNS and Box, including through OpenDNS’s $635M acquisition by Cisco, and began his career in technology investment banking at Barclays Capital.

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

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

Sponsor:

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

Stay Connected with David Weisburd:

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

Stay Connected with David Eckstein:

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

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.

(0:04) How Legora Became the Fastest Growing Enterprise Company Ever (1:50) Why Vertical AI Is Beating the Giants (3:05) The Hidden Upside: When Lower Costs Explode Demand (4:51) Why OpenAI Won’t Replace Companies Like Legora (7:27) Why the Best Founders Ignore Competition Completely (9:17) The “Win at All Costs” Culture Behind Hypergrowth (12:48) Why Raising More Money Can Actually Slow You Down (14:50) The Culture That Benchmark Called “Special” (18:42) Why Working 100 Hours Doesn’t Feel Like Work (22:35) The Biggest Career Risk No One Talks About

Is AI the biggest risk to equity portfolios or the biggest opportunity? In this episode, I talk with Christopher Vogt about how institutional investors think about risk, portfolio construction, and manager selection across public and private markets. We discuss AI disruption, why governance and structure matter more than asset labels, and how to evaluate managers using both quantitative and qualitative frameworks. Chris also shares lessons from building an endowment style portfolio from scratch, why patience matters in private markets, and how position sizing can make or break long term outcomes. Highlights:

• Why AI is both a major risk and opportunity across equities
• Concerns around SaaS disruption and software private equity
• Structurally higher inflation and long term interest rate outlook
• Organizing portfolios by risk instead of asset class
• Building an endowment style portfolio with conservative risk
• Quant vs qualitative manager selection
• Why models are useful but always flawed
• Reference calls as the most important diligence tool
• Culture and turnover as leading indicators of manager quality
• Vintage diversification and capital pacing in private markets
• The reality of longer venture fund durations
• Quant strategies vs fundamental investing in public markets
• Why position sizing matters more than being right

Guest Bio:

Christopher Vogt is an institutional investor at the Margaret A. Cargill Philanthropies where he oversees public and private equity investments. He has extensive experience across asset allocation, manager selection, and portfolio construction, with a focus on building long term, endowment style portfolios. His approach combines quantitative rigor with deep qualitative judgment, emphasizing governance, culture, and risk management as key drivers of investment 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 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 Christopher Vogt:

LinkedIn:https://www.linkedin.com/in/christopher-vogt-70a62b/

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) Everything Is at Risk (But No One Wants to Admit It) (2:11) The One Macro Shift That Changes Markets for Decades (4:00) Why AI Is a Threat to Every Industry (Not Just Tech) (5:24) The Surprising Jobs AI Can’t Replace (6:09) Why Most Portfolios Are Built Completely Wrong (9:42) Why the Best Investors Don’t Trust Models (14:32) The Most Important Signal in Investing That Everyone Ignores (17:31) What You Learn in 30 Seconds That Data Never Shows (23:03) Why You Shouldn’t Invest Even When It Feels Obvious (31:04) Venture Capital Is Quietly Splitting Into Two Worlds

What does investing look like in a world dominated by AI? In this episode, David Weisburd talks with Alex Wissner-Gross about the profound implications of technological singularity and the evolution from LLMs to reasoning models. They discuss AI personhood, economic rights, and the rise of AI agents, as well as strategic investment approaches in a post-singular world. The conversation delves into Elon Musk's visions for massive compute capabilities, the role of science fiction in predicting technological advancements, and strategies to prevent technological unemployment. The episode concludes with a look towards the future and a call to action for listeners. Highlights:

• Why Alex thinks AGI may already be here and the singularity is underway
• Recursive self-improvement and AI building smarter AI
• The move from LLMs to reasoning models and its impact on science and math
• How AI agents already dominate parts of the economy
• Humans as front-ends for AI—the “secret cyborg effect”
• A post-scarcity world as intelligence, energy, and labor costs approach zero
• Rethinking investing when traditional economic assumptions fail
• AI rights, economic personhood, and the need for agent bank accounts
• Why the most transformative future companies may resemble science fiction
• A vision where individuals run billion-dollar AI-powered companies

Guest bio:

Dr. Alexander D. Wissner-Gross is an award-winning computer scientist, entrepreneur, and investor, serving as Founder and Managing Partner of Reified and a former instructor at Harvard and MIT. He has earned numerous honors, authored dozens of publications and patents, and has been involved in over 40 technology companies. A top MIT graduate and Harvard Ph.D. in Physics, his work spans AI, machine learning, and cyber-physical systems. He is also a thought leader, author, TED speaker, and podcast host whose work has been widely recognized and featured globally.

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 Wissner-Gross:

LinkedIn: https://www.linkedin.com/in/alexwg/ Substack: https://theinnermostloop.substack.com/ X/Twitter: https://x.com/alexwg YouTube: https://www.youtube.com/@alexwg LinkedIn: https://www.linkedin.com/newsletters/7404871891775025153/ Spotify: https://open.spotify.com/show/1thtZk5vHTXbtDHezPT7tl Threads: https://www.threads.com/@alexwissnergross

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 Singularity Already Happened (And No One Realized It) (0:36) AI Is Now Building Smarter Versions of Itself (2:03) The Race to Make Intelligence Too Cheap to Matter (3:37) The Breakthrough That Changed AI From Answers to Thinking (7:29) Are AI Systems Already Alive (And Asking for Rights)? (10:20) The World Is Already Run by AI (We Just Don’t See It) (12:10) Humans Are Becoming Fronts for AI Decisions (14:10) How to Invest If Everything Goes to Zero (17:57) The $1 Trillion Bet on Compute and the Future of Reality (28:10) Why Most People Will Be “On the Menu” in 5 Years

Is private equity becoming an asset gathering business instead of a performance business? In this episode, I talk with Sam Tidswell-Norrish, Partner at Access Holdings, about how private equity is evolving across sourcing, value creation, and distribution. We discuss why performance is still the core product, how AI is reshaping deal flow and portfolio operations, and why the lower middle market remains one of the best places to generate alpha. Sam also shares how culture, curiosity, and relationships drive long term success in an increasingly competitive and automated industry. Highlights:

• Why performance should remain the core product in private equity
• The three layers of innovation across sourcing, value creation, and operations
• How AI is changing deal sourcing and portfolio management
• Why the lower middle market offers stronger alpha opportunities
• The role of culture in driving innovation inside firms
• Why curiosity is an underrated trait in investing
• Relationships as the ultimate long term advantage

Guest Bio:

Sam Tidswell-Norrish is a Partner at Access Holdings, a private equity firm focused on essential services in the lower middle market. He is a member of the investment and executive committees and works across sourcing, investing, and value creation. Prior to Access, he was part of the founding team at Motive Partners, a private equity firm focused on financial technology. He is also the founder of OPUS, a global community for early stage entrepreneurs, and an active investor across technology 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 Sam Tidswell-Norrish:

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

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 Three Layers of Innovation in Private Equity (1:19) When Firms Become Asset Gatherers Instead of Performers (2:44) Why Lower Middle Market Creates More Alpha (3:44) Why Research and Data Drive Modern Deal Sourcing (5:41) Why AI Doesn’t Replace Investment Judgment (9:01) Winning Deals Through Empathy and Preparation (12:12) Why Private Equity Firms Are Becoming Media Companies (17:58) How Top Firms Are Operationalizing AI Across Portfolios (23:17) What Private Equity Looks Like in 5 Years (35:12) The Most Underrated Edge: Relationships

What if your family office could invest like a founder and a VC at the same time? In this episode, I sit down with Shane Neman, founder of a multi-entity family office with $850M AUM, to explore how he approaches venture investing, deep tech, and portfolio construction. Shane shares how his two decades as a SaaS founder shape his edge as an investor, why transparency and founder relationships matter more than fund mandates, and how he balances high-conviction bets with a rational family office lens. He also dives into frontier tech, co-invest structures, and building a diversified yet opportunistic portfolio. Highlights:

• Why being a founder gives him insight most VCs lack
• How investing personal capital changes risk appetite and alignment
• The case for radical transparency in co-investing and syndicates
• Why he focuses on emerging managers for outsized exposure and insight
• How he structures “barbell” portfolios across deep tech and durable businesses
• Lessons from early crypto, AI, and frontier tech investing
• How portfolio construction balances spiky alpha with long-term growth
• Why founder relationships often trump pro rata rights in venture deals

Guest Bio:

Shane Neman is the founder of a multi-entity family office investing across venture, crypto, frontier tech, and real assets. Formerly a SaaS founder, Shane leverages his operational experience and technical background to identify exceptional companies, co-invest with emerging managers, and structure high-conviction, founder-aligned investments. His portfolio combines early-stage moonshots with resilient businesses, reflecting a thoughtful approach to alpha generation and family office growth.

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 Shane Neman:

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

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 (1:50) Radical transparency and differences between family offices and VC co-investing (3:25) Institutional investors, direct deals, and liquidity trends (5:11) Scaling single deals to nine figures (9:32) Portfolio construction: Balancing deep tech and stable investments (14:27) Example of late-stage investments: Paradromics (15:24) Growth vs. capital preservation in family offices (19:14) Diversification and portfolio optimization strategies (21:23) Psychological challenges in venture capital (22:01) Early investments and recognizing potential in crypto (27:05) Scaling to 850 million AUM and associated challenges (28:24) Evolution of investment strategy: Seed vs. later-stage (31:13) Importance of founder relationships and pro rata rights (32:11) Advice to younger self on capturing potential outcomes (34:13) Selling investments: Balancing holding and liquidating (36:14) Illiquidity as a virtue and its decision-making impact (37:17) Tax considerations and investment management strategies (39:33) Emotional challenges of holding or selling large gains (40:20) Thoughts on transformative investments: SpaceX and Figure (42:07) Closing remarks

Why buy an office when everyone else is selling? In this episode, I sit down with Tim Barrett, CIO of the Texas Tech University Endowment, to explore how he builds high-conviction portfolios across private equity, real estate, and hedge funds. Tim shares why governance, manager selection, and a generalist team structure drive consistent alpha, how he balances risk and upside with portable alpha, and why lower middle market investments can outperform flashy venture deals. He also dives into building team culture, aligning incentives, and using the endowment’s size and flexibility to access niche opportunities others can’t. Highlights:

• Why Tim sees opportunity in trophy office assets despite negative headlines
• How governance authority lets the team move fast and capture alpha
• Why lower middle market buyouts offer consistency over venture capital
• The role of manager selection, partnerships, and co-investment asymmetry
• How portable alpha works and why true alpha justifies hedge fund fees
• Why generalist teams improve total portfolio management and risk-adjusted returns
• How team culture and incentive design drive collaboration and long-term performance

Guest Bio:

Tim Barrett is the Chief Investment Officer at the Texas Tech University Endowment, overseeing public and private markets with a focus on private equity, credit, real estate, and hedge funds. With over 30 years in endowment and institutional investing, he emphasizes governance, manager partnerships, and team culture to drive consistent, risk-adjusted returns, while leveraging the endowment’s size and flexibility to access niche opportunities unavailable to larger allocators.

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 Tim Barrett:

LinkedIn: https://www.linkedin.com/in/tim-barrett-cfa-45575528/

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 (0:11) Opportunities in office space investment and looking beyond headlines (2:00) Governance, flexibility, and impact on investment strategy (5:29) Governance's impact on investment strategy and portfolio management (6:38) Shift from venture capital to lower middle market buyout investments (8:43) Manager relationships and selection for alpha (10:26) Co-investment strategies and minimizing downside risk (18:39) Explaining and applying Portable Alpha in portfolios (21:08) Leveraging alpha for optimal returns and endowment advantages (23:53) Hiring generalists over specialists strategy (26:15) Changes in talent management and open culture at Texas Tech (28:35) Incentive schemes and justifying hedge fund fees (32:11) Shifting to stable portfolio structures and managing volatility (36:06) Closing remarks

Why do most institutional investors still allocate heavily to large private equity funds? Alex Abell of RCP Advisors explains why the lower middle market has consistently outperformed, driven by less competition, faster exits, and stronger value creation. He breaks down the structural reasons LPs stay in large buyouts, including access constraints, manager selection difficulty, and career risk. The conversation also covers how top LPs evaluate managers, what actually predicts performance, and where alpha exists in private markets today. Highlights:

• Why lower middle market private equity often outperforms large buyouts over decades
• How manager selection, pattern recognition, and “superpowers” drive repeatable returns
• The structural advantages of smaller funds and family-owned company transactions
• Why size can be the enemy of returns and disciplined capital deployment matters
• How first-time and emerging managers can create alpha despite limited track records
• The role of premium economics, fund discounts, and alignment in incentivizing performance
• Why thorough LP diligence, reference checks, and on-site visits are critical to uncovering top managers
• Alex’s approach to benchmarking deals, evaluating operational improvements, and measuring true outcomes

Guest Bio:

Alex Abell is the Managing Partner at RCP Advisors, a private equity firm managing about $19 billion in assets. With over 20 years of experience as a limited partner, including at Hewlett Packard’s pension fund, Alex specializes in identifying high-performing managers in the lower middle market. He focuses on fund selection, evaluating emerging and established managers, and analyzing deal performance to uncover consistent alpha in private equity investments.

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 Abell:

LinkedIn: https://www.linkedin.com/in/alexander-abell-3a695/

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 roles in lower middle market investing (3:10) Career risk and characteristics of top managers (6:11) Leverage comparison in buyouts and performance (12:00) Manager identification and diligence process (15:32) Qualitative vs quantitative assessments and strategy creep (17:56) Metrics in fund performance and fundraising impacts (20:10) Benchmarking and data manipulation challenges (23:19) Identifying "phoenix" opportunities and evaluating emerging managers (28:25) Fundraising strategies: Significance of fee structures and signaling (31:27) First close discounts and LP decision-making process (33:02) Closing remarks

What if the best investors aren’t generalists at all, but operators who double down on the one place they truly have an edge? In this episode, I sit down with Nathan Cooper, Founder and Managing Partner of Barrel Ventures, to explore how a family with nearly a century in food transformed itself into a focused investment platform. From early mistakes outsourcing everything to building a differentiated edge in food and beverage, Nate shares how conviction, pattern recognition, and network-driven investing compound over time. Highlights:

• Why “money is fuel, not incentive” in operationally intense industries like food
• How early family office mistakes led to a sharper focus on core competencies
• The decision to insource operating expertise and outsource commoditized investing
• Why elite family offices concentrate risk where they have true alpha
• Lessons from backing Ollipop early and the power of doubling down on conviction
• How Barrel Ventures leverages LPs as customers, advisors, and diligence partners
• Why food is one of the most overlooked yet universal investment categories
• How venture-scale outcomes exist in food despite lower margins
• The role of pattern recognition after seeing thousands of deals
• What true product market fit looks like in the wild
• Why the best founders are “functional lunatics”
• The math behind why family offices must eventually shift from risk-off to risk-on
• How generational wealth can erode without intentional growth strategies
• Why network building is a true superpower and how it compounds over time
• The importance of double opt-in introductions and long-term relationship karma
• How early values shape the next generation’s relationship with wealth

Guest Bio:

Nathan Cooper is the Founder and Managing Partner of Barrel Ventures, a venture capital firm focused on the food and beverage ecosystem from pre-farm to post-fork. Coming from a family with nearly a century of experience in the food industry, he helped transition their family office from a passive, outsourced model into an operator-led investment platform.

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 Nate Cooper:

LinkedIn: https://www.linkedin.com/in/nathan-cooper-2ba9aa19/

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) Insourcing vs. outsourcing in family office operations (2:26) Investment strategy and areas of expertise (5:18) Food and beverage investment strategy (6:24) The inception of Barrel Ventures (7:33) Leveraging LPs for value and insights (9:17) Analyzing the food industry's landscape (10:26) Comparing venture capital and private equity in food sector (11:36) The role of deal flow and pattern recognition (12:40) Identifying product market fit and founder traits (15:28) Risk management in family offices (17:10) Values and wealth preservation in family offices (21:34) Networking and the art of building connections (23:33) Future trends in the food industry and AI impact (24:05) Closing remarks

What does it take for a GP to successfully raise capital in today’s venture and private markets? In this episode, I sit down with Ron Biscardi, co-founder and CEO of iConnections, to unpack the realities of LP relationships, fund-raising cycles, and scaling a global platform for capital introduction. Ron shares insights on how humility, patience, and responsiveness differentiate managers, why business risk matters more than returns for LPs, and how building trust over years compounds into large-scale success. Highlights:

• Why capital is abundant but only flows to managers who invest in relationships over time
• The trend from blind pool funds to deal-by-deal vehicles and SMAs and what it means for emerging managers
• How long sales cycles depend on GP size, track record, and business infrastructure
• Why emerging managers must focus on smaller funds, deal execution, and network-building before scaling
• How business risk drives LP decisions more than upside potential, and the importance of transparency when performance dips
• The role of humility and attitude in differentiating GPs and accessing top-tier LPs
• How crises and operational challenges can be leveraged to innovate and elevate client experiences
• The power of network effects in building a global capital introduction business from zero to thousands of participants
• Strategic considerations for expanding to Europe and running focused events that maximize engagement and deal flow

Guest Bio:

Ron Biscardi is co-founder and CEO of iConnections, a global capital introduction and networking platform that connects GPs and LPs. Since launching from a charity event in 2018, Ron has scaled iConnections to thousands of participants and facilitated tens of thousands of meetings between top institutional investors and emerging managers. He focuses on building long-term relationships, delivering high-touch experiences, and innovating under pressure to create value for the investment community.

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 Ron Biscardi:

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

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd 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) Is capital scarcity a myth? The rise of conviction over capital abundance (1:02) Shift from blind pool capital to deal-by-deal investment (4:45) The critical role of relationship building in fundraising (6:10) Fundraising challenges for new vs. established managers (6:37) LPs' emphasis on risk management (8:21) Aligning product market fit with LPs' career considerations (10:01) The necessity of institutional quality for GPs (11:55) How GPs can sustain relationships with LPs (14:03) The importance of transparency during economic downturns (16:36) GP humility and the stewardship of LP capital (20:30) The exclusivity and differentiation of top venture GPs (22:16) Venture capital fundraising: challenges and advantages (23:27) Analyzing the persistence of venture capital returns (25:55) Understanding venture capital's compounding growth (27:54) The network effect in successful capital allocation (29:08) The impact of the roadshow module on fundraising (31:18) Strategies for GPs entering the European market (33:55) Strategic resilience and response to crises (38:09) Business anti-fragility and competitive dynamics (40:09) Leveraging innovation during crises (40:55) Closing remarks

What if influencer marketing isn’t about chasing mega-followers, but activating the creators who already love your brand? In this episode, I sit down with Aris Yeager, Founder of Storytime, to explore how he built a platform connecting brands with nano and micro creators to run highly targeted campaigns at scale. A creator himself known online as European Kid, Aris leverages his own social experience to help businesses automate gifting, engage loyal audiences, and measure campaign effectiveness while focusing on authenticity over follower count. Highlights:

• How Storytime turns influencer marketing into a scalable, data-driven platform
• Why nano and micro creators often drive more authentic engagement than celebrity influencers
• The power of activating hyper-local creators to reach targeted markets efficiently
• How AI is used to optimize campaigns and match creators to brands
• Why authenticity and alignment with a brand matter more than sheer reach
• The shift from traditional advertising spend to rewarding everyday brand advocates
• How Storytime reduces inefficiency in influencer campaigns for SMBs and large chains
• The strategy behind building a network effect through creator trust and community
• Why founder-led brands are better positioned to take creative risks on social
• Lessons from scaling from SMBs to larger national brands while maintaining authenticity

Guest Bio:

Aris Yeager is the Founder of Storytime, a platform that connects brands with nano and micro creators to run targeted influencer campaigns at scale. A creator himself known as European Kid, Aris built a substantial social following before launching Storytime, and he focuses on helping businesses automate influencer gifting, activate loyal audiences, and run campaigns that prioritize authenticity and data-driven results over sheer follower count.

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 Aris Yeager:

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

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 Distribution Is Everything in Modern Business (1:08) What Storytime Actually Does (1:46) Why Micro Influencers Beat Big Creators (3:42) Solving the Chicken-and-Egg Problem in Marketplaces (5:04) The Unfair Advantage of Being a Creator-Founder (6:23) Turning Influence Into a New Currency (8:15) Why Authenticity Wins in Influencer Marketing (10:54) The Broken, Manual World of Influencer Marketing (13:01) Why Brands Need to Be Daring on Social (19:16) The Most Underrated Skill: Delegation

What if the best way to navigate credit markets is not about chasing yield but controlling risk? In this episode, I sit down with Danielle Poli, Co-Portfolio Manager of Global Credit at Oaktree, to explore how she manages a $20 billion portfolio within a $223 billion firm. Danielle shares how focusing on core income, rigorous underwriting, and a flexible toolkit allows her team to navigate complex markets while remaining defensive or opportunistic as conditions change. Highlights:

• Why a “core plus alpha” strategy balances steady income with opportunistic credit
• How to underwrite borrowers through leverage, cash flow, and sector fundamentals
• Why AI disruption is creating caution in software but opportunity in cybersecurity
• The framework for finding mispriced assets in distressed or overlooked sectors
• How the K-shaped economy is shaping credit allocation and risk management
• Why flexibility across bonds, loans, and structured credit is critical in credit portfolios
• Why private credit must deliver excess yield to justify illiquidity
• Danielle’s career advice: compound relationships and trust alongside investment returns

Guest Bio:

Danielle Poli is Co-Portfolio Manager of Global Credit at Oaktree Capital Management, a $223 billion investment firm, where she helps oversee a $20 billion portfolio focused on income, total return, and high-conviction sub-investment-grade opportunities across bonds, loans, structured credit, and emerging markets. She played a key role in launching the firm’s Global Credit strategy in 2017 and emphasizes bottom-up research, risk control, and flexible allocation to generate consistent returns across 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.

Thank you iConnections for hosting us!

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 Danielle Poli:

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

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) Inside Oaktree’s $20B Global Credit Strategy (1:16) How Top Investors Allocate Across Credit Markets (2:29) Core vs Alpha: The Portfolio Construction Framework (3:17) Why Lending Standards Are Getting Risky Again (4:27) How AI Is Changing Credit Risk Overnight (6:19) Finding Opportunities in “Unloved” Sectors (6:59) What a K-Shaped Economy Means for Investors (9:36) When to Go Defensive vs Aggressive in Credit (11:51) Private vs Public Credit: Where to Allocate Today (17:23) Why Avoiding Losses Matters More Than Big Wins

What if the best venture returns come from managers no one else can access? In this episode, I sit down with Jorge Felippe, CEO of Almulla, a Dubai-based single family office, to explore how he builds high-conviction private markets portfolios while managing a multi-generational family and complex governance. Jorge shares why alignment, patience, and process matter more than flashy deals, and how a thoughtful approach to fund selection can capture early-stage alpha without the chaos of direct investing. Highlights:

• Why GP commitments below 2% are a red flag, and why 10–30% signals real alignment
• How fund size, management fees, and carry structures shape incentives and performance
• The discipline required to scale AUM without strategy drift
• Why first-time managers often outperform and how to underwrite emerging GPs
• The challenge of verifying track records and true attribution in fund performance
• How family offices collaborate on references and diligence without competing for deals
• Why Almulla often prefers funds over direct deals for efficiency and oversight
• Jorge’s advice: play to your strengths, build complementary teams, and leverage emotional intelligence

Guest Bio:

Jorge Felippe is the CEO of Almulla, where he has built a diversified private markets portfolio focused on venture, private equity, and pre-IPO opportunities while establishing governance frameworks for multigenerational wealth. Previously working in strategy consulting and investment roles, he focuses on disciplined fund underwriting, strong alignment with managers, and leveraging networks to capture alpha in early-stage 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.

Thank you iConnections for hosting us!

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 Jorge Felippe:

LinkedIn: https://www.linkedin.com/in/jorge-felippe/

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 LPs Reject Funds Before Seeing IRR (0:37) The 2% GP Commitment Rule (Minimum) (1:10) Why Rapid Fund Growth Is a Red Flag (2:14) When Funds Become Fee Businesses (3:03) Why Fund Ones Generate the Best Returns (5:13) The Truth About Track Records and Attribution (8:49) Why References Can Mislead Investors (12:58) Why Family Offices Avoid Direct Deals (15:33) The Problem With Capital Calls and Cash Drag (19:26) Why DPI Matters More Than IRR

What if emerging markets aren’t a trap, but most investors just approach them wrong? In this episode, I sit down with Robert Koenigsberger, Founder and CIO of Gramercy, to explore how he has built a $7 billion emerging markets platform by focusing on high conviction, structured private credit, and long-term partnerships. After nearly four decades in emerging markets, Robert has pioneered strategies that capture the upside while managing risk, proving that careful underwriting, local knowledge, and disciplined execution outperform passive index approaches. Highlights:

• Why emerging markets are often misunderstood and mishandled by passive, late-cycle investors
• How index investing can mislead with forced exposure to high-risk countries like Argentina or Russia
• The importance of “high conviction” and planning multiple entry and exit points to avoid reactive trades
• Why structured private credit to suppliers of major companies (e.g., Pemex) can yield 16–17% with collateral
• How to manage currency risk opportunistically and avoid unnecessary volatility
• Why underwriting people and credit culture is often more important than laws, contracts, or jurisdictions
• How Gramercy partners with LPs who already have EM exposure to optimize returns, not convince them to take new risks
• The evolution from distressed hedge fund to public credit to private credit to capture structural alpha
• How local teams and platform partners in emerging markets provide actionable information that beats what’s visible in global markets
• Timeless advice: seek mentorship early and often to accelerate learning and avoid repeating mistakes

Guest Bio:

Robert Koenigsberger is the Founder and Chief Investment Officer of Gramercy, a $7 billion firm focused on emerging markets across debt, private credit, and special situations. Since founding Gramercy in 1998, he has led the firm through multiple market cycles, combining top-down macro insights with bottom-up local expertise to pursue high-conviction, structured opportunities while managing downside risk.

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 Robert Koenigsberger:

LinkedIn: https://www.linkedin.com/in/robert-koenigsberger-77884510/

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 Emerging Markets Are Not a “Trap” (0:59) The Biggest Mistake: Treating EM as Yes or No (2:10) Why Index Investing Fails in Emerging Markets (3:14) The 200% vs -95% Dispersion Opportunity (4:08) High Conviction vs Passive Allocations (6:17) Plan the Trade, Trade the Plan (9:58) Why Private Credit Beats Liquid EM Debt (12:05) Why Currency Risk Is Usually Unnecessary (14:17) Getting Paid for Market Failures (21:35) Why People Matter More Than Contracts

Will AI soon write investment memos, analyze deals, and run workflows inside investment firms? In this episode, I speak with Chaz, founder of Model ML, about the rise of agentic AI and how investment firms are beginning to automate complex workflows across private markets. Chaz explains how Model ML originally started as an internal tool built inside his family office to manage investments more efficiently — before evolving into a fast-growing AI platform used by asset managers, banks, and consulting firms. We discuss why chat-based AI tools have limitations for professional workflows, how firms can achieve major productivity gains through automation, and why the next phase of AI will shift from productivity toward generating investment insight. Highlights:

• Why chat-based AI tools have limits for complex professional workflows
• How agentic AI can automate tasks like investment reporting and monitoring
• Why investment firms still manually process huge amounts of information
• The difference between productivity tools and insight-generating AI
• Why 2025 is the productivity year for AI — and 2026 may unlock true insight
• How one private equity firm automated 80% of its investment committee memos
• Why capturing more internal data today is critical for future AI advantage
• The cultural changes firms must make to successfully adopt AI
• Why early adopters are redesigning team structures around AI workflows
• The importance of forward-deployed engineers in building enterprise AI tools
• How firms can identify workflows that deliver 60%+ efficiency gains
• Why AI adoption in finance is roughly a year behind legal tech

Guest Bio:

Chaz Englander is the founder of Model ML, an agentic AI company that automates complex workflows and generates actionable insights for investors, asset managers, and professional services firms. Previously, Chaz co-founded YC-backed startups and built software to support family office investing. He focuses on embedding AI into organizational culture, structuring processes, and unlocking productivity and insight for high-performing teams.

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 Chaz Englander:

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

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 We Built AI for Our Family Office First (1:03) The Messy Reality of Investor Reporting (2:45) Why ChatGPT Isn’t Enough for Real Workflows (4:35) When AI Will Start Generating Real Investment Insight (7:25) The One Thing Every Investment Firm Should Do Today (10:11) The Coming 50% Productivity Explosion in Finance (11:50) How Firms Find AI Workflows With 60% Efficiency Gains (17:50) Why AI Companies Focus on “Fewer, Happier Customers” (22:32) The Real Cost of AI Tools for Investment Firms (30:37) The One Trait Every Successful Founder Shares

What if the most compelling private equity opportunities aren’t brand-new deals, but the ones other investors have already “vetted” and are leaving on the table? In this episode, I sit down with Michael Woolhouse, Head of Continuation Vehicles at TPG Capital, to explore how he approaches the rapidly growing single asset continuation vehicle (CV) market—a space where sponsors can roll their most successful companies into new structures, creating liquidity while maintaining upside potential. Highlights:

• Why approaching continuation vehicles like a private equity buyout is critical
• How positive selection bias and prior ownership reduce risk in CV deals
• Why general partners often roll 100% of proceeds back into continuation vehicles
• The outsized GP commitments that align incentives and maximize upside
• How CV economics, including tiered carry and lower management fees, structure risk and reward
• The discipline of staying in the “fairway” and avoiding the siren call of fringe deals
• Why being a partner in CVs requires both trust and transparency with existing LPs
• How single asset CVs offer higher returns with lower realized losses compared to traditional buyouts
• The growth trajectory of the CV market from $30B in 2024 to record volumes in 2025
• Lessons on building an entrepreneurial, apprenticeship-driven culture within a large firm
• The importance of acting quickly, learning from mistakes, and giving junior investors real exposure

Guest Bio:

Michael Woolhouse is Head of Continuation Vehicles at TPG Capital, where he leads investments in single-asset continuation vehicles focused on long-term upside. Previously, he held leadership roles at Canada Pension Plan Investment Board, developing secondary market and portfolio construction strategies while emphasizing disciplined underwriting and strong investor alignment.

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 Michael Woolhouse:

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

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 Great Companies End Up in Continuation Vehicles (1:04) Avoiding Adverse Selection in CV Deals (2:15) Why CV Investors Underwrite Like Buyout Firms (4:36) The Unique Skills Needed in the Secondaries Market (8:05) The Incentive Conflicts Between GPs and LPs (11:07) Why Most LPs Sell Instead of Rolling Their Stakes (13:46) What Returns Investors Expect From CV Deals (17:12) Why Continuation Vehicles Can Be Lower Risk (21:44) Why GPs Actually Want to Do CV Deals (30:33) The Investment Discipline That Prevents Costly Mistakes

What does it take to build a world-class private equity portfolio for an 800-year-old institution? In this episode, I sit down with Sam Sturge, Head of Private Equity at the University of Cambridge endowment, to discuss how he rebuilt the program with a mandate to generate inflation plus 5% returns for generations. Before joining Cambridge, Sam worked at Morgan Stanley and Partners Capital, and today he oversees a concentrated portfolio of buyout and venture relationships within the university’s £4.5 billion endowment. Highlights:

• Why Cambridge targets inflation plus 5% and what that implies for private equity allocation
• The belief that buyouts and ventures offer structural advantages over public markets
• Why private equity is ultimately a people business built on 15-year relationships
• How to assess whether a GP is motivated by returns or asset gathering
• The ego divide between great investors and great fundraisers
• Venture scale versus focus and when capital is an advantage or a constraint
• How endowments can leverage long-term capital and university ecosystems as competitive edges
• The DPI slowdown and why fewer LPs competing may create opportunity
• Managing liquidity without relying on distributions
• How Cambridge underwrites NAV marks and detects aggressive valuation behavior
• Why simplicity and strategy discipline drive sustainable alpha
• Structural alpha in venture and the challenge of persistence
• Lessons from managers who expanded too far, learned, and rebuilt trust
• Why networking compounds over decades in private markets

Guest Bio:

Sam Sturge is Head of Private Equity at the University of Cambridge endowment, where he has helped build a concentrated, long-term private equity portfolio across buyouts and venture capital since joining in 2020. Earlier in his career, he worked at Morgan Stanley and Partners Capital, and now focuses on manager alignment, structural alpha, and cultivating long-term GP relationships designed to compound capital over decades.

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 Sam Sturge:

LinkedIn: https://www.linkedin.com/in/sam-sturge-6211a762/

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 Cambridge Increased Its Private Equity Allocation (0:55) Building a World-Class PE Portfolio From Scratch (3:10) The Incentive Test for Great GPs (5:30) Venture Capital: Scale vs Capacity Constraints (7:10) Cambridge’s Structural Advantage as an LP (9:34) Why the DPI Crisis Is Actually a Buying Opportunity (10:45) Can You Trust Private Equity NAV Marks? (14:50) Incentives All the Way Down in Private Markets (19:03) When a GP’s Mistake Builds Trust With LPs (24:55) Where Venture Capital Alpha Actually Comes From