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.
313episodes
Episodes
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E346: $7 Billion CIO: Why the Endowment Model is Changing
Apr 1300:34:43Summary readyHow 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
Summary
E345: How I Raised $10 Billion in Venture Capital w/Scott Painter
Apr 1000:17:45Summary readyWhat 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
Summary
E344: How the Top Family Offices are Investing Today
Apr 900:35:06Summary readyWhat 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
Summary
E343: The Death of the 60/40 Portfolio (And What Comes Next)
Apr 800:43:10Summary readyWhat 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
Summary
E342: The Rise of Venture Secondaries
Apr 700:34:32Summary readyWhat 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
Summary
E341: Why VC is Changing Forever ($150 Billion LP)
Apr 600:34:42Summary readyWhat 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
Summary
E340: Why Family Offices Should Avoid 60/40 Portfolios
Apr 300:31:50Summary readyWhat 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
Summary
E339: From Zero to $100 Million in 18 Months: Inside Legora
Apr 200:25:17Summary readyWhat 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
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E338: How I Invest $9 Billion into VC & Private Equity
Apr 100:41:21Summary readyIs 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
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E337: How to Invest in a Post Singularity World
Mar 3100:36:45Summary readyWhat 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
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