Podcast
How I Invest with David Weisburd
Hosted by David Weisburd · EN
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
314episodes
Episodes
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E327: $7B CIO: The Right Way to Invest in Emerging Markets
Mar 1800:36:42Summary readyWhat 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
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E326: What Happens When AI Starts Replacing Analysts?
Mar 1700:30:47Summary readyWill 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
Summary
E325: Inside the $100B Continuation Vehicle Boom
Mar 1600:39:00Summary readyWhat 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
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E324: How The University of Cambridge Built Their Privates Portfolio
Mar 1300:31:58Summary readyWhat 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
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E323: How Billionaires Build Their Portfolios
Mar 1200:31:59Summary readyWhat changes when wealth stops being about building and starts being about preserving? In this episode, I sit down with Jonathan Dane, CIO and Founder of Defiant Capital, to explore how family offices think about portfolio construction after a major liquidity event. Drawing on his experience at Goldman Sachs and Jefferies, Jonathan explains why independent advice matters and how families navigate the transition from wealth creation to long-term preservation. Highlights: Why large banks struggle to deliver fully independent advice The key psychological differences between Gen 1 and Gen 2 wealth Estate planning moves entrepreneurs should make years before a liquidity event Why gifting shares early can save millions in future estate taxes How portfolio construction changes once wealth becomes generational Why billion-dollar family offices are typically majority alternatives The critical importance of liquidity management before committing to private funds Why overcommitting to private equity can force families into bad financing decisions The growing frustration with long-dated venture funds and low DPI Why lower middle market private equity offers structural inefficiencies The operational alpha opportunity in Rust Belt manufacturing businesses How independent sponsors should demonstrate real skin in the game The biggest mistake $50–$500M families make: over-diversifying into too many managers Why AI should enhance diligence workflows but never replace human judgment Guest Bio: Jonathan Dane is the Chief Investment Officer of Defiant Capital, where he advises entrepreneurial families and multigenerational wealth on portfolio construction, liquidity management, estate integration, and alternative investments. He previously worked at Goldman Sachs and Jefferies, advising ultra-high-net-worth and institutional clients, and now focuses particularly on lower middle market private equity and operational value creation. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Jonathan Dane: LinkedIn: https://www.linkedin.com/in/jonathandane/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why the Sell Side Gives Conflicted Advice (2:03) Why First-Generation Wealth Invests Differently (6:22) The Estate Planning Moves Entrepreneurs Miss (9:02) What Changes Once a Family Passes $50M (10:42) How Billion-Dollar Family Offices Build Portfolios (15:55) Building a Portfolio for a Newly Liquid $1B Family (19:20) Why Families Are Pushing Back on 15-Year Venture Funds (25:12) Why Lower Middle Market Private Equity Works (29:08) Independent Sponsors vs Traditional PE Funds (30:47) The #1 Portfolio Mistake Families Make
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E322: How $70 Billion Gets Allocated During Market Chaos
Mar 1100:27:07Summary readyWhat if one of the most overlooked $700 billion pools of capital in the U.S. is quietly shaping private markets? In this episode, I sit down with Jennifer Mink, President of Investment Performance Services, an investment consulting firm overseeing roughly $70 billion in assets under advisement, to discuss how Taft-Hartley pension plans approach long-term investing. Jennifer shares how IPS designs portfolios that balance public and private markets, using disciplined asset allocation and diversification to improve overall portfolio efficiency and manage risk across market cycles. Highlights: How adding alternatives can reduce overall portfolio volatility through low correlation Why “double diversification” can dilute returns at the portfolio level The importance of grounding investments in a clear thesis to avoid emotional selling How IPS rebalanced aggressively during the 2020 market snapback What gets easier and harder when advising $70 billion across nearly 200 union plans Why emerging managers are typically tracked through three vintages before capital is deployed Red flags in early funds including team turnover, fee changes, and strategy drift The private equity distribution slowdown and pacing challenges facing LPs Structural requirements managers must meet to access Taft-Hartley capital, including ERISA fiduciary status The role of Responsible Contractor Policies in real asset mandates Why sometimes the best investment decision is the one you avoid How IPS tracks its own research process to ensure manager outperformance across cycles Guest Bio: Jennifer Mink is the President of Investment Performance Services (IPS), a 40-year-old investment consulting firm focused exclusively on the Taft-Hartley marketplace. IPS advises approximately $70 billion in assets and works with nearly 200 union plans nationwide. With more than two decades at the firm, Mink specializes in asset allocation, manager research, and private markets diligence, and leads a team that evaluates hundreds of managers annually while emphasizing disciplined structure, fiduciary responsibility, and consistency across full market cycles. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Jennifer Mink: LinkedIn: https://www.linkedin.com/in/jennifer-mink-09057836b/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) The Job of Deploying $70B in Institutional Capital (0:52) Why Alternatives Can Reduce Portfolio Volatility (3:03) The Biggest Behavioral Mistake Investors Make (4:31) How Institutions Invest During Market Crashes (6:08) What Gets Easier (and Harder) Managing $70B (8:05) How Consultants Diligence 300–400 Managers a Year (10:13) Why Institutions Wait Until Fund IV to Invest (13:34) The DPI Crisis Breaking the Endowment Model (15:05) The Hidden Rules for Raising Taft-Hartley Capital (22:28) The Best Investment Is Sometimes Saying No
Summary
E321: Why Most LPs Have No Idea What’s in Their Portfolio
Mar 1000:22:07Summary readyWhy are private markets still managed in spreadsheets when hundreds of billions of dollars are at stake? In this episode, I sit down with Ryan Eisenman, Co-Founder and CEO of Arch, a platform supporting more than 550 clients and over $405 billion in alternative assets. Arch is building an operating system for private markets that helps investors manage the operational complexity of alternatives across private equity, venture, hedge funds, credit, and more, bringing modern infrastructure to a part of the financial system that has historically relied on manual processes and fragmented data. Highlights: What breaks when an LP scales from 10 to 50 fund commitments Why most private markets data is trapped in PDFs across 800+ portals The hidden operational chaos inside family offices and RIAs How poor liquidity visibility impacts re-up decisions Why venture fundraising has fallen dramatically since 2022 peaks The shift of capital from institutions to the wealth channel Growth in independent sponsor and deal-by-deal allocations Why private market data feeds often don’t match source documents The rise of secondaries and tightening discount spreads Why borrowing against private assets remains inefficient How Arch uses AI to extract key terms from 100-page LPAs Lessons Ryan learned building a venture-backed fintech company Guest Bio: Ryan Eisenman is the Co-Founder and CEO of Arch, a fintech platform that automates data aggregation, reporting, and analytics for alternative investments. Arch serves global banks, RIAs, family offices, and institutional allocators, helping them manage complex private market portfolios more efficiently. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Ryan Eisenman: LinkedIn: https://www.linkedin.com/in/ryan-eisenman-21811246/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) $405B in Private Market Assets — But LPs Still Use Spreadsheets (1:19) The Hidden Chaos of Tracking Private Investments (2:05) Why LPs Don’t Understand Their Own Liquidity (3:54) What Breaks When LPs Go From 10 to 50 Funds (5:17) The Manual Systems Behind Billion-Dollar Portfolios (7:00) Why Private Markets Data Is Completely Fragmented (9:11) The Shift From Institutions to Wealth Channel Capital (12:24) The DPI Crisis Reshaping Venture Capital (13:38) Why You Can’t Borrow Against Private Assets (15:40) How AI Is Finally Fixing Private Markets Data
Summary
E320: Why Institutional Capital Avoids the Best Returns
Mar 900:45:33Summary readyWhat if the best private equity opportunities are the ones no one else is set up to pursue? In this episode, I sit down with Jeff Collins, Founder and Managing Partner of Cloverlay, to explore how he built a $2 billion firm by going where capital isn’t. After 14 years at Morgan Stanley Investment Management, Jeff spun out to focus on what he calls “uncorrelated private assets” - niche, often overlooked segments where return dispersion is wide and operator selection matters more than financial engineering. Highlights: Why “go where the money isn’t” only works if you build the right organization around it How Cloverlay built a sourcing flywheel through references and long-term reciprocity The importance of holding structured “kill calls” to preserve relationships Why broad dispersion of returns signals opportunity in overlooked markets How to evaluate niche segments like special mission aircraft, wireless spectrum, and IP The strategy behind assembling “portfolio premium” assets in industrial outdoor storage Why uncorrelated private assets can act as ballast in institutional portfolios How pensions think about completion portfolios and non-beta exposure The tradeoff between being an A+ specialist versus a well-rounded investor Why Jeff believes ego should be tied to performance, not AUM growth The cultural decision to remain focused instead of scaling into adjacent strategies Guest Bio: Jeff Collins is the Founder and Managing Partner of Cloverlay, a Philadelphia-based private investment firm managing approximately $2 billion in assets focused on uncorrelated private markets. Before founding Cloverlay in 2015, Jeff spent 14 years at Morgan Stanley Investment Management, where he led investments across private market strategies and developed a focus on segments with high return dispersion and limited competition. At Cloverlay, Jeff and his team specialize in niche asset categories ranging from intellectual property and aviation to industrial outdoor storage and other esoteric markets. The firm partners with highly specialized operators and seeks to generate performance through asset selection, structure, and disciplined portfolio construction rather than market beta or leverage. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Jeff Collins: LinkedIn: https://www.linkedin.com/in/jeff-collins-76b7b54/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) The Strategy: Go Where the Money Isn’t (1:44) Why the Best Opportunities Take 291 Days to Close (3:20) Building Deal Flow Without Bankers or Auctions (7:59) Why Relationships Matter More Than Transactions (11:04) The Power of Proactive Deal Sourcing (14:48) How Small Markets Create Big Returns (19:17) The Role of Uncorrelated Assets in Portfolios (26:39) Why Investors Love Wide Dispersion of Returns (33:38) Turning Gravel Parking Lots Into Institutional Assets (47:27) Why Performance Matters More Than AUM
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E319: GP Stakes Investing: Liquidity, Alignment, and the Real Risk
Mar 600:38:33Summary readyWhy would an LP invest in the GP instead of the fund… and what problem is GP stakes really solving? In this episode, I sit down with Todd Owens, Managing Partner of Cantilever Group, to unpack the world of GP stakes. Todd explains what investors are actually buying when they take a minority stake in an alternative asset manager, why liquidity risk is the central challenge, and how structural innovation could reshape the asset class. Highlights: What you are really underwriting when you invest in a GP instead of a fund The hidden liquidity risk most LPs underestimate in GP stakes Why unpredictable exits are the defining challenge of minority GP investing How public listings could reshape liquidity for GP stakes funds Why lower middle market GP deals may offer structural advantages The three primary reasons GPs sell minority stakes and which one Todd likes most When growth capital meaningfully accelerates a manager’s trajectory Red flags when principals are taking money off the table How to distinguish between a durable firm and a single-founder platform Why venture capital can be “too volatile” for GP stakes investors The pricing discipline required to walk away from good businesses How strategic value creation works when you are a passive minority partner Guest Bio: Todd Owens is the Managing Partner of Cantilever Group, an investment firm that focuses on minority GP stakes in lower middle market alternative asset managers. The firm targets investments between $15 million and $75 million, partnering with managers seeking growth capital, capital restructuring, or solutions for generational transitions. Todd previously spent decades advising and working with asset management businesses, including serving as a Partner at Goldman Sachs, and at Cantilever Group he focuses on building a permanent capital model that aligns with GPs while addressing liquidity considerations for LPs. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Todd Owens: LinkedIn: https://www.linkedin.com/in/todd-owens-401976160/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decision. (0:00) Why GP Stakes Became a New Asset Class (0:36) What Investors Actually Buy in a GP Stake (1:22) Fund Returns vs. Owning the Management Company (2:09) The Biggest Risk: Unpredictable Liquidity (3:18) How GP Stakes Investors Create Liquidity (5:44) The Permanent Capital Model for GP Stakes (10:30) The 3 Reasons GPs Sell Stakes in Their Firm (11:56) How GP Stakes Capital Fuels Firm Growth (19:07) When GPs Take Money Off the Table (31:03) The Strategic Advantage of Investing at the GP Level
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E318: The Biggest Mistake Investors Make When Building a Venture Portfolio
Mar 500:23:48Summary readyWhat separates elite venture LPs from everyone else… and why do most family offices underestimate the governance required to win? In this episode, I sit down with Michael P. Larsen, a longtime Partner at Cambridge Associates, to unpack nearly two decades of building venture and private equity portfolios for leading institutions and family offices. Michael shares why longevity may be the ultimate competitive advantage in asset management, how governance quietly determines venture outcomes, and why portfolio size can matter just as much as manager selection. We dive into power laws, spiky returns, growth equity’s overlooked role, co-invest best practices, and how benchmarking can help LPs stay disciplined during optically challenging cycles. Highlights: Why longevity in venture investing creates perspective most LPs never develop The hidden edge elite LPs have in portfolio sizing, not just manager selection Why governance may be the most underestimated driver of venture outcomes How to structure a venture allocation after a liquidity event The real reason venture portfolios feel “spiky” and why that is a feature, not a flaw Why waiting for obvious top managers often leads to second-tier access How fund cadence compression can quietly distort portfolio construction The importance of underwriting firms, not just individual funds Why benchmarking venture is especially challenging in Mag-7 dominated markets Growth equity as the “third bowl of porridge” between venture and buyout Co-invest adverse selection risks and how scale improves access Systematic vs opportunistic co-invest strategies and when each makes sense Guest Bio: Michael P. Larsen is a Partner at Cambridge Associates, where he has spent nearly two decades advising institutional investors and family offices on venture capital, private equity, and growth equity portfolio construction. Over the course of his career, he has participated in thousands of GP meetings and helped design durable private market programs focused on governance, manager selection, and long-term discipline. His work emphasizes strategic allocation, benchmarking rigor, and building venture portfolios designed to withstand multi-decade market cycles. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Michael Larsen: Michael Larsen: https://www.linkedin.com/in/michaelplarsen/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) The Longevity Advantage in Venture Investing (1:48) Why Venture Portfolios Behave Completely Differently (2:12) The Hidden Variable: Allocation Size Matters (4:30) Governance: The Least Sexy Alpha (6:15) Step One: Define Your Illiquidity Budget (8:33) Why Elite LPs Accept “Spiky” Returns (10:36) How Many Venture Funds You Actually Need (12:19) The Biggest Portfolio Construction Mistake (17:57) The Long-Term Game LPs Are Playing (20:54) The Real Risk in Venture Co-Investing
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