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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E406: Why AI Won't Transform Most Enterprises for 10 Years
4w ago00:57:11Summary readyMost companies use AI to make employees slightly more productive. Sushanth Raman believes AI should do the work instead. As the CEO of Pallet, Sushanth is building an AI workforce for the $12 trillion logistics industry, helping carriers, brokers, freight forwarders, and shippers automate mission-critical operations inside the systems they already use. He explains why reasoning-driven AI represents the next wave of enterprise software, why logistics is uniquely positioned for AI transformation, and how businesses can move from copilots to fully autonomous workflows. Highlights: Why AI should execute workflows instead of simply assisting employees. The biggest inefficiencies still holding back the logistics industry. How reasoning models differ from traditional AI automation. Why enterprise AI adoption depends on integrating with existing software. Lessons from building an AI company in a $12 trillion industry. How logistics companies can deploy AI without replacing their core systems. Why domain expertise matters as much as technical expertise in AI startups. The future role of human operators in an AI-native logistics ecosystem. What investors often misunderstand about enterprise AI adoption. Why logistics could become one of AI's largest commercial opportunities. Guest Bio: Sushanth Raman is the CEO of Pallet, an AI company building a reasoning-driven workforce for the logistics industry. He founded Pallet in 2021 after seeing how one of the world's largest industries still relied on manual, error-prone workflows. Since launch, the company has raised $50 million from investors including Bain Capital Ventures, General Catalyst, Bessemer Venture Partners, and Activant. Today, Sushanth combines deep technical expertise with his family's roots in shipping to help carriers, brokers, freight forwarders, and shippers automate mission-critical operations with AI. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Sushanth Raman : LinkedIn:https://www.linkedin.com/in/sushanth-raman/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why AI Won’t Transform Most Companies Anytime Soon (2:33) The #1 Trait of Companies That Actually Deploy AI (6:01) Why Employees Resist AI Even When They Believe in It (10:11) How Wall Street Could Force AI Adoption Overnight (17:27) Why the SaaS Apocalypse Is Being Misunderstood (20:23) The Future of Enterprise Software Is Hyper-Personalized (27:16) Why Supply Chain Is the Biggest AI Opportunity Nobody Sees (37:13) The Tiny Decisions That Compound Into Great Companies (44:13) Founder Mode vs Micromanagement Explained (55:50) The Advice Every Young Founder Needs to Hear
Summary
E405: Why AI Has Made Venture Capital Harder (Not Easier)
4w ago01:15:56Summary readyThe best venture investors don't just identify great markets. They recognize exceptional founders before everyone else does. Michael Gilroy shares lessons from investing at Coatue, Microsoft's M12, Battery Ventures, Insight Partners, and now Marathon Management Partners. He explains what separates extraordinary founders from everyone else, how venture investors evaluate conviction versus consensus, why AI is changing the investment landscape, and how decades of experience shaped his founder-first investing philosophy. Highlights: Why the best venture investments begin with founders instead of markets. The founder characteristics Michael consistently looks for before investing. Lessons from investing across Coatue, M12, Battery Ventures, and Insight Partners. Why consensus thinking often produces average venture returns. How AI is reshaping the next generation of technology companies. The difference between backing great businesses versus great founders. Why founder obsession matters more than polished presentations. How exceptional venture investors develop long-term conviction. The lessons Michael carried into launching Marathon Management Partners. Why founder-first investing continues to outperform market-first investing. Guest Bio: Michael Gilroy is the Founding Partner of Marathon Management Partners, where he invests in exceptional technology companies across venture and growth stages. Before launching Marathon, he was a General Partner at Coatue, investing across both private and public technology markets. Earlier in his career, he held investing roles at M12 (Microsoft's Venture Fund), Battery Ventures, and Insight Partners, developing deep expertise in enterprise software, AI, and technology investing. Today, Michael brings a founder-first perspective shaped by decades of experience backing category-defining companies alongside many of the industry's leading investors. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Micheal Gilroy: LinkedIn: https://www.linkedin.com/in/michaelbgilroy/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why the Best Venture Firms Think in Decades (2:17) The Biggest Mistake Founders Make When Building Boards (5:46) Why Great Board Meetings Aren't About the Past (9:12) The Simple Change That Makes Every Board More Valuable (13:41) How Incentives Quietly Shape Venture Capital (18:25) Why the Best Investors Measure People, Not Just Companies (23:08) The Hidden Cost of Growing Too Fast in Venture (28:16) The Framework Behind High-Performing Startup Boards (30:37) The Truth About Second-Generation Investors (36:45) The Leadership Trait That Separates Elite Investors
Summary
E404: Why This Billionaire Family Office Doesn't Rebalance Its Portfolio | Pincus Family CIO
Jul 1700:49:40Summary readyMost investors obsess over pre-tax returns. Scott Abookire argues they're measuring the wrong thing. As Chief Investment Officer of Pincus Capital, Scott oversees globally diversified public and private portfolios for multi-generational families. In this conversation, he explains why after-tax returns are the metric that truly matters, why he abandoned the traditional endowment model, and how sophisticated family offices think about risk, liquidity, and long-term compounding. Scott also shares the portfolio framework Pincus uses to manage drawdowns, why governance matters more than forecasts, and how the best investors stay disciplined when markets become emotional. Highlights: Why after-tax returns matter more than headline investment performance. The hidden cost taxes have on long-term wealth compounding. Why Pincus Capital moved away from the traditional endowment model. A better framework for portfolio construction based on liabilities instead of arbitrary asset allocation targets. How elite family offices manage risk without sacrificing long-term returns. The biggest mistakes investors make with private equity commitments. Why drawdown management is more important than volatility statistics. How long-term relationships create investment edge. Guest Bio: Scott Abookire is the Chief Investment Officer at Pincus Capital, a New York-based multi-family office that provides investment management and strategic advice to a select group of families with significant multi-generational wealth. Before joining Pincus Capital, he was a member of the investment team at the Metropolitan Museum of Art and previously worked at Cambridge Associates. Scott is a CFA Charterholder and earned his BS from Indiana University's Kelley School of Business. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Scott Abookire: LinkedIn: https://www.linkedin.com/in/scottabookire/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Most Investors Measure Returns Incorrectly (2:58) The Problem With Pre-Tax Performance (5:37) How Pincus Capital Calculates After-Tax Returns (9:54) Why Taxes Change Portfolio Construction (11:41) Why Scott Left the Traditional Endowment Model (17:54) The Drawdown Framework Every Family Office Should Know (31:52) The Hidden Risk of Private Equity Capital Calls (37:40) Why Great Portfolios Fail During Market Stress (42:43) Lessons From the 2022 Private Markets Reset (47:45) Why Venture Capital Is All About Pacing
Summary
E403: Why the Best Investment Firms Stay Small | Sound Point Capital Founder
Jul 1500:59:41Summary readyMost investors believe raising more capital is always a sign of success. Stephen Ketchum has spent nearly two decades proving the opposite. As Founder, CEO, and CIO of Sound Point Capital, Stephen built a $46 billion credit platform by resisting one temptation that destroys investment firms: deploying capital simply because it's available. Instead of maximizing assets under management, Sound Point limits fund sizes, turns away capital when opportunities aren't compelling, and prioritizes long-term trust over short-term fees. Stephen explains why excess capital weakens discipline, why incentives shape every organization, and why culture compounds just as powerfully as investment returns. This material does not constitute an offer to sell or a solicitation of an offer to buy any securities. It is being provided solely for informational and reference purposes only and is not intended to be, and must not be, the basis for any investment decision. Statements represent the subjective views of Sound Point as of the date of the recording and cannot be independently verified and are subject to change. All investing involves risks, including the risk of a total loss. Source for other lender software exposure: J.P. Morgan Global Alternative Investment Solutions, Goldman Sachs, J.P. Morgan Investment Bank Credit Research. February 2026. Past performance is not necessarily indicative of future results. Highlights: Why having more capital than ideas is one of investing's biggest risks. How Sound Point intentionally limits fund sizes instead of maximizing AUM. Why saying "no" to investors can strengthen long-term LP relationships. Why founder-led firms have an advantage in building trust with LPs. The hiring framework Stephen uses to avoid costly culture mistakes. Why incentives alone don't create great organizations. Why relationships, not money, have compounded the most over Guest Bio: Stephen Ketchum is the Founder, Managing Partner, CEO, and CIO of Sound Point Capital Management, a $46 billion alternative asset manager specializing in credit strategies. With more than 35 years in the credit markets, he previously led Media & Telecom Investment and Corporate Banking at Banc of America Securities and held senior investment banking roles at UBS and Donaldson, Lufkin & Jenrette. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Stephen Ketchum: LinkedIn:https://www.linkedin.com/in/stephen-ketchum-7174366/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why More Capital Can Hurt Investment Returns (1:44) Knowing When a Hot Market Has Peaked (6:19) How Sound Point Manages $46B Without Losing Discipline (10:25) Why Being "Long-Term Greedy" Wins (15:42) Warren Buffett's Lesson Beyond Financial Compounding (19:51) The Founder Advantage in Asset Management (27:30) The Culture Code Every Firm Should Learn (31:58) Scaling Culture From 5 to 210 Employees (39:27) What a Founder Actually Does All Day (47:31) Making Time to Build the Next Five Years (52:48) How AI Can Increase Alpha
Summary
E402: $92B Coatue: Where the Value in AI Will Accrue
Jul 1300:49:39Summary readyEveryone is asking which AI company will win. Lucas Swisher thinks investors are asking the wrong question. The biggest opportunities won't necessarily come from picking a single model or application. They'll come from understanding where durable advantages are created across the AI stack. Drawing on Coatue's investments in companies like OpenAI, Anthropic, Databricks, and SpaceX, Lucas explains why talent compounds, why data infrastructure may outlast today's application boom, why companies become harder—not easier—to disrupt as they scale, and how AI is reshaping the economics of software, semiconductors, and enterprise technology. Highlights: Why the AI application layer is far more resilient than many investors believe. The two AI infrastructure layers Lucas believes will generate the most enduring returns. Why companies above $10B may actually produce better venture outcomes than earlier-stage startups. How OpenAI and Anthropic continue extending their lead despite rapid industry innovation. Why talent has become the ultimate competitive moat in AI. How Coatue thinks about NVIDIA, custom silicon, and the next generation of chip companies. Why AI is making high-performing organizations more productive instead of replacing them. The biggest mistakes investors are making during today's AI investment cycle. Guest Bio: Lucas Swisher is a Co-Head of Growth Investing at Coatue Management, where he co-leads growth investing and software investing with a focus on AI, enterprise software, and cybersecurity. He has helped oversee Coatue's investments in OpenAI, Anthropic, SpaceX, and Databricks. Previously, he worked at Kleiner Perkins, Insight Partners, and Delivery Hero, and graduated from Harvard University. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Lucas Swisher: LinkedIn:https://www.linkedin.com/in/lucasswisher/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Who Captures the Value Created by AI? (0:38) Will Foundation Models Crush AI Applications? (2:01) How to Identify Durable AI Companies (5:29) Why Frontier Models Keep Pulling Ahead (11:13) Is the Mag Seven Already Dead? (16:40) The Two AI Layers Coatue Is Most Bullish On (19:24) Why OpenAI and Anthropic Are Growing So Fast (26:13) Will AI Replace Jobs or Create More? (35:17) The Surprising Data Behind 10x Companies (37:43) Why Talent Beats Technology (44:52) The Biggest Bottleneck Holding AI Back (48:00) Can Anyone Challenge NVIDIA? (53:44) The Biggest Mistakes AI Founders Are Making (57:26) Where AI Investors Are Most Likely to Lose Money (59:39) What Lucas Changed His Mind About in AI (1:01:05) Why Coatue's Public + Private Strategy Matters (1:02:36) The Career Advice Lucas Wishes He Learned Earlier
Summary
E401: Einstein Was Wrong About What Actually Compounds
Jul 1001:01:22Summary readyAfter more than 400 conversations with investors, founders, CIOs, and capital allocators managing over $10 trillion, the tables finally turn. In this special episode, Curtis Pierce, Co-Founder of Weisburd Pierce and the How I Invest podcast, interviews host David Weisburd about the biggest ideas that have permanently changed his thinking. David argues that the greatest compounding force isn't capital. It's relationships, reputation, access to information, and the ability to surround yourself with excellence early in your career. From venture capital and family offices to LP-GP relationships and organizational culture, he shares the principles shaping how Weisburd Pierce invests and builds enduring partnerships. Highlights: Why relationships compound faster than money The hidden advantage of brand and access How elite investors think about long-term partnerships Why the best opportunities rarely reach everyone Lessons from interviewing 400+ world-class investors Why culture becomes the only lasting competitive advantage How to build conviction instead of chasing consensus The investing philosophy behind Weisburd Pierce About David Weisburd: David Weisburd is a Co-Founder of Weisburd Pierce and host of the How I Invest podcast. Previously, he served as Partner and Head of Venture Capital at 10X Capital, leading investments in companies including Robinhood, HoneyBook, Palantir, Circle, and DraftKings. Earlier in his career, he helped build venture-backed startups iSocket and RoomHunt, both of which were acquired. He has served on the boards of three public companies and holds degrees from Dartmouth's Tuck School of Business and Harvard University. About Curtis Pierce: Curtis Pierce is a Co-Founder of Weisburd Pierce and the How I Invest podcast. Previously, he served as Senior Vice President at 10X Capital, where he led venture investing and capital markets initiatives, including the firm's investment in Cerebras Systems. He began his career at Wells Fargo Securities and serves as President of the New York City Chapter of the University of Utah Alumni Association. Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdpierce.com/ Stay Connected with Curtis Pierce: LinkedIn: https://www.linkedin.com/in/curtisapierce/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Einstein Was Wrong About Compounding (0:52) The Biggest Lesson From 400 Interviews (5:48) Why Excellence Changes Everything (10:27) Social Friction vs Intelligence (12:25) Why Relationships Compound (20:30) Building Long-Term Partnership Advantage (28:54) Culture Is the Ultimate Competitive Moat (40:00) Why Great LP-GP Relationships Matter (47:48) How David Thinks About Venture Investing (57:34) The One Lesson Every Investor Should Remember
Summary
E400: Anthony Pompliano on Power Laws, Conviction, and Compounding
Jul 801:10:00Summary readyMost investors spend their lives searching for more ideas. Anthony Pompliano thinks the real money comes from finding the rare idea and refusing to let go. Across public markets, private markets, Bitcoin, startups, and careers, Anthony argues that value follows power laws: a tiny number of companies, people, and decisions drive almost everything. The hard part is not effort. It is recognizing durable asymmetry early, pressing your winners harder, and resisting the temptation to sell simply because liquidity is available. The deeper lesson is scarcity. Great companies are scarce. Great investors are scarce. Great people are scarce. And when you find one, the job is not to constantly rotate into something new. The job is to understand what you own, build conviction, and let compounding do the work. The Numbers Behind This Episode 46 companies have created 50% of the $90T of stock market value since 1925. The NASDAQ has historically been viewed as a 13% return vehicle, while venture funds average around 17% to 18%. Antonio Gracias reportedly invested in SpaceX 30 times. Anthony describes one company with 11 employees serving $50B in assets on its software platform. Highlights: Why 5% of ideas can drive 95% of outcomes How durability, asymmetry, and volatility create exceptional investments Why selling may be harder than buying Why liquidity can become a behavioral disadvantage How SpaceX became the ultimate example of pressing a winner Why concentration is often a sign of conviction Why “luck” may be more psychological than real How winning cultures are built through standards, exposure, and mission Guest Bio: Anthony Pompliano is an entrepreneur, investor, and one of the most widely followed voices at the intersection of business, finance, and technology. He is the founder and CEO of Professional Capital Management, author of the daily Pomp Letter newsletter, and host of The Pomp Podcast, where he interviews many of the world's leading investors, entrepreneurs, and executives. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Anthony Pompliano: LinkedIn:https://www.linkedin.com/in/anthonypompliano/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Power Laws Rule Investing (1:15) Durability, Asymmetry, and Volatility (2:33) Building Portfolios Around Best Ideas (5:18) Buffett, Compounding, and Starting Early (7:25) Why Selling Is the Hardest Decision (10:04) Is Liquidity Actually a Problem? (14:06) Finding Non-Consensus Asymmetric Bets (18:02) Physical AI, Robotics, and the Next Big Theme (20:18) The SpaceX Conviction Test (21:33) Why 46 Companies Created Half the Wealth (26:05) Discipline in Venture Fund Construction (28:22) Why Luck Is Not Real (32:31) Attracting Success Instead of Chasing It (37:21) Turning Losers Into Winners (40:43) Building a Winning Culture (46:02) What Great Organizations Have in Common (50:50) Why Mission Creates Intensity (1:00:00) Scaling Culture With Small Teams (1:04:27) Go Bigger and Take Bigger Risks (1:05:59) Scarcity Is Value
Summary
E399: How General Catalyst Finds Billion-Dollar Startups
Jul 600:29:44Summary readyMost investors assume that once a venture firm reaches $43 billion in assets under management, the real opportunities shift toward writing larger checks. Yuri Sagilov believes the opposite. General Catalyst continues to push deeper into seed because that's where investment themes are born, founder relationships are formed, and category-defining companies are first recognized. Rather than optimizing for larger deployments, the firm optimizes for ownership, conviction, and seeing the future before everyone else. It's also why General Catalyst intentionally removed signaling risk from its seed strategy, giving founders confidence that early backing won't become a disadvantage later. Throughout our conversation, Yuri explains why AI-native founders think differently, why the best venture firms remain generalists, and why the next decade of venture may look very different from the last. Highlights: Why General Catalyst believes seed delivers some of venture's best returns. How the firm eliminated signaling risk without sacrificing ownership. Why Anduril changed the way investors think about defense startups. Why today's AI-native founders are building from a completely different starting point. The case for staying a generalist instead of launching sector-specific funds. Why ownership matters more than the size of the initial investment. How private markets could keep the best companies private much longer. The relationship philosophy Yuri says has compounded the most throughout his career. Guest Bio: Yuri Sagilov is a Partner at General Catalyst, where he focuses on seed investing across the firm's global platform. Previously, he founded Wayfinder Ventures, a first-check seed fund whose portfolio companies have created more than $23 billion in value. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Yuri Sagalov: LinkedIn: https://www.linkedin.com/in/yurisagalov/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why a $43B Firm Still Bets on Seed (2:39) Finding Categories Before They Exist (4:00) Learning From Founders Living in the Future (5:47) Why Great Seed Investors Stay Generalists (8:51) Eliminating Signaling Risk (12:08) Building General Catalyst's New Seed Strategy (13:27) Inside a 200-Company Seed Portfolio (14:40) Does Every Investment Need to Return the Fund? (16:05) Recognizing Power Law Companies Early (18:04) Why the Best Companies May Stay Private Longer (24:50) The Highest Compounding Asset in Venture (26:33) Why Yuri Became More Bullish on AI
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E398: Hamilton Lane ($1T AUA) on Venture Capital, AI, and Private Markets
Jul 200:43:09Summary readyWhat separates the venture investors who consistently outperform from those who simply get lucky? In this episode, I sit down with Miguel Luina, Co-Head of Global Venture Capital at Hamilton Lane, to discuss how one of the world's largest private markets investors evaluates venture managers, constructs portfolios, and thinks about the future of innovation investing. Miguel explains why venture and growth have become an essential allocation for institutional investors, how LPs distinguish skill from luck, and why conviction investing, secondaries, and portfolio construction may be the biggest drivers of long-term returns. Highlights: Why venture capital is entering a new liquidity cycle driven by AI and IPOs How Hamilton Lane distinguishes skill from luck when selecting venture managers Why sourcing, selection, and access are the three pillars of venture investing The importance of conviction investing—and doubling down on exceptional companies Why venture secondaries represent one of the most undercapitalized opportunities in private markets How continuation vehicles are reshaping venture liquidity Why institutional investors can no longer ignore venture and growth allocations The evolution of portfolio construction across funds, co-investments, and secondaries How the best venture managers compound relationships over decades Miguel's timeless advice on investing in people and letting relationships compound Guest Bio: Miguel Luina is Co-Head of Global Venture Capital at Hamilton Lane, where he oversees the firm's global venture, growth equity, and technology investment strategy. He leads investment sourcing, due diligence, and portfolio management across venture capital funds, co-investments, secondaries, and growth equity opportunities while serving as a member of the firm's investment committee. Hamilton Lane manages and supervises more than $1 trillion in assets across private markets, making it one of the world's largest private markets investment firms. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Miguel Luina: LinkedIn: https://www.linkedin.com/in/miguel-luina/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Why Venture Capital Is Entering a New Golden Age (1:06) How SpaceX, OpenAI, and Anthropic Could Reshape Venture (3:13) The Secret to Separating Skill From Luck in Venture Capital (6:05) Has Venture Capital Become a Consensus Trade? (11:41) Why Ignoring Venture Is Now a Massive Allocation Bet (16:10) The Portfolio Strategy Most Venture LPs Get Wrong (20:03) Why Continuation Vehicles Are Exploding in Venture (28:17) The Structural Alpha Hidden Inside Venture Secondaries (35:58) The Portfolio Construction Mistake That Kills Returns (40:56) Why the Best Investors Keep Doubling Down on Winners
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E397: Why Venture Capital Is a Relationship Compounding Machine
Jul 100:45:28Summary readyWhat if the greatest edge in venture capital isn't having the biggest fund—but building the strongest relationships? In this episode, I sit down with Elizabeth Weil, Founder and Managing Partner of Scribble Ventures, to discuss how emerging venture firms can outperform by staying focused, collaborative, and relentlessly founder-centric. Elizabeth shares how she built Scribble into a $280 million venture platform by backing exceptional founders at the earliest stages, why venture is fundamentally a network effects business, and why staying authentic has become one of her greatest competitive advantages. Highlights: Why venture capital is ultimately a network effects business How Scribble Ventures raised an oversubscribed fund in one of the toughest fundraising environments Why relationships compound more than almost anything else in investing Elizabeth's framework for identifying exceptional founders before consensus forms The importance of staying authentic with founders, LPs, and partners Why smaller venture funds can outperform larger platforms How Scribble approaches ownership, fund sizing, and portfolio construction differently The value of saying no—to both founders and LPs—when the fit isn't right Why breakout investing extends beyond simply finding companies at seed Lessons from Twitter's hypergrowth years and Andreessen Horowitz's rise The role of curiosity, consistency, and daily habits in long-term investing success Why every career ultimately compounds through relationships Guest Bio: Elizabeth Weil is the Founder and Managing Partner of Scribble Ventures, an early-stage venture capital firm managing approximately $280 million in assets focused on partnering with exceptional founders at the pre-seed, seed, and breakout stages. Over more than two decades in venture capital and technology, she has invested in more than 60 technology companies including SpaceX, Slack, Coinbase, Whatnot, Gusto, Grab, Calm, Envoy, Hipcamp, and Daily.co. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Elizabeth Weil: LinkedIn: https://www.linkedin.com/in/elizabethweil/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) How Elizabeth Raised an Oversubscribed Venture Fund in 2026 (1:47) The Network Effect That Separates Great Venture Firms (6:14) The Fastest Way to Build Judgment as an Investor (8:34) The Founder Traits That Matter More Than the Idea (12:34) The LP Fundraising Lesson Most Emerging Managers Miss (19:12) Why She Turned Down LP Capital on Purpose (22:25) What Elizabeth Looks for Before Writing a $3 Million Check (28:25) The Venture Capital Myth That Most LPs Still Believe (33:04) When Venture Firms Stop Being Investors and Become Asset Managers (38:47) The Career Advice That Compounds for Decades
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