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.
309episodes
Episodes
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E412: UPENN Endowment: Why AI Will Create a New Generation of PE & VC Firms
2d ago00:59:45Summary readyAI isn't just changing technology—it is reshaping how investment firms create value, evaluate managers, and generate alpha. David sits down with Thomas Scriven, Managing Director University of Pennsylvania Office of Investments, institutional investor with experience across private equity, endowment management, and investment banking, to discuss why AI-native investment firms may outperform traditional firms, how great LPs evaluate GPs, why concentrated portfolios often outperform diversification, and the investing frameworks that separate elite allocators from everyone else. Highlights: Why AI-native private equity firms have a structural advantage. The framework Thomas uses to evaluate every GP. Why concentrated portfolios often outperform diversification. The hidden importance of incentives between LPs and GPs. How AI is changing operational value creation. Why thinking time is one of an investor's biggest competitive advantages. The mistake allocators make by overprotecting the downside. Why the best venture firms continue attracting elite founders. How secondaries have transformed institutional portfolio construction. The advice Thomas would give himself starting over today. Guest Bio: Thomas Scriven Managing Director University of Pennsylvania Office of Investments, institutional investor with more than 15 years of experience spanning private equity, endowment management, investment banking, mergers and acquisitions, portfolio construction, and special situations investing. During his career, he has helped build one of the world's leading university endowment private equity programs while partnering with top-performing venture and buyout firms globally. His investment philosophy emphasizes concentrated conviction, strong GP relationships, operational value creation, and long-term alignment between investors and managers. 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 Thomas Scriven: LinkedIn:https://www.linkedin.com/in/thomas-scriven-435281/ 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 Will Reshape Every Investment Firm (4:12) The AI Playbook That Wins Private Equity Deals (11:48) Why Most Investment Firms Don't Have Enough Thinking Time (18:02) The Hidden Incentives That Drive Every LP and GP (25:06) Frameworks Beat Rules in Investing (33:10) Why Concentrated Portfolios Win (41:02) What Actually Makes a Top Venture Firm (49:17) The Psychology Behind Elite Investors (56:28) AI Will Separate the Winners From Everyone Else (1:04:48) The Investing Lesson Thomas Learned Too Late
Summary
E411: How AI Is Creating a New Generation of Venture Firms
4d ago01:18:39Summary readyMost venture firms are using AI to save time. Earlybird is using it to generate alpha. David sits down with Andre Retterath, General Partner at Earlybird, to discuss how his firm built an AI-native venture platform, why proprietary data is becoming venture capital's biggest competitive advantage, how machine learning improves investment decisions, and why the future of venture belongs to investors who combine technology with exceptional judgment. Highlights: Why AI should automate venture capital—not replace investors. The hidden cost of missing great startups. How Earlybird built an AI-native investment platform. Why founder branding has become a competitive advantage. The surprising traits shared by successful AI founders. How machine learning improves venture capital decision-making. Why the best investors optimize for judgment, not activity. The framework Andre uses to evaluate every AI startup. How proprietary data creates lasting venture alpha. Why exceptional investors spend less time screening and more time thinking. Guest Bio: Andre Retterath is a General Partner at Earlybird, where he leads the firm's AI and infrastructure investment practice, focusing on frontier AI models, databases, developer tools, automation platforms, and AI infrastructure. He has led investments in companies including Aleph Alpha, Black Forest Labs, DeepCode, EthonAI, and Energy Robotics, while helping build one of Europe's leading AI-focused venture franchises. Before joining venture capital, Andre worked as a process automation engineer at ThyssenKrupp and as a management consultant at GE. He also earned a Ph.D. from the Technical University of Munich researching machine learning and the value of data in venture capital, research that continues to shape Earlybird's AI-native approach to investing. 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 Andre Retterath: LinkedIn:https://www.linkedin.com/in/andreretterath/ Website: https://earlybird.com/ Newsletter: https://datadrivenvc.io/ 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 Became Groupthink (3:34) The Portfolio Rule That Cost Them a 50x Winner (7:15) Why Great Fundraisers Keep Winning (10:09) The Founder Traits That Actually Matter (18:26) The Startup Patterns That Never Change (23:15) Why Founder Branding Became a Competitive Advantage (27:44) Inside EarlyBird's AI-Native Venture Platform (34:48) The Hardest Part of Bringing AI Into Venture Capital (1:01:10) Where Alpha Comes From in the AI Era (1:15:59) The Career Advice Andre Wishes He Learned Earlier
Summary
E410: How Relationships Built a $3.6B Venture Firm
1w ago00:59:21Summary readyConsumer startups may grab the headlines, but some of the most valuable companies are built by solving mission-critical problems for businesses. David sits down with Rick Heitzmann, Managing Director at FirstMark Capital, to discuss how he identifies high-growth technology-enabled business services, why sectors like data infrastructure, compliance, marketing technology, and information services continue to generate outsized opportunities, and what separates enduring enterprise businesses from short-lived trends. Highlights: Why B2B investing remains one of venture's biggest opportunities. The characteristics of exceptional enterprise software companies. How data has become a competitive advantage. Why compliance is creating entirely new categories of startups. The evolution of marketing and advertising technology. What makes technology-enabled business services highly scalable. How recurring revenue creates durable businesses. Where Rick sees the next wave of venture-backed winners. The investment frameworks FirstMark uses when evaluating founders. Why solving critical business problems creates lasting enterprise value. Guest Bio: Rick Heitzmann is a Managing Director at FirstMark Capital, where he invests in high-growth emerging media and technology-enabled business services. His investment focus includes data and information management, compliance and risk mitigation, marketing and advertising technology, and business process outsourcing. Rick has built his career identifying scalable enterprise businesses that become critical infrastructure for their customers and benefit from long-term technology adoption. 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 Rick Heitzmann: LinkedIn:https://www.linkedin.com/in/rickheitzmann/ 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) The Venture Capital Advantage Nobody Can Copy (1:51) Why Relationships Compound Faster Than Capital (8:06) The Hidden Framework Behind Every Great VC Investment (13:07) Why Most Relationships Never Compound (21:23) The AI Trend Almost Everyone Is Missing (25:13) Why the Best Venture Bets Always Look Wrong (35:01) The Founder Test That Predicts Billion-Dollar Companies (47:29) How FirstMark Survived the 2008 Fundraising Crisis (56:06) The Fundraising Lesson That Changed Everything (1:07:48) The One Piece of Advice Every Investor Needs
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E409: The Leadership Lessons That Built a $6.5 Billion Firm
1w ago01:01:57Summary readyMost investors chase what's exciting. Jason Koenig built a $6.5 billion firm by investing where almost nobody was looking. In this conversation, Jason explains why overlooked industrial assets can produce exceptional long-term returns, how ITE grew from $60 million to $6.5 billion in assets under management, why culture compounds just like capital, and the leadership lessons he learned while scaling an investment firm from startup to institutional platform. Highlights: Why the best investments are often hiding in overlooked industries. How Jason spotted a billion-dollar opportunity by watching trains. The founder mindset required to build conviction before everyone else. Why culture becomes a firm's biggest competitive advantage as it scales. The leadership framework behind hiring years before you actually need people. Why compensation should reward teamwork, not individual empires. The psychology every great investor must understand. Lessons from negotiating against Carl Icahn. Why entrepreneurs need both conviction and humility. The career advice Jason wishes he had followed much earlier. Guest Bio: Jason Koenig is the Founder, Managing Partner at ITE Management, an investment firm specializing in transportation infrastructure and industrial real assets. Since founding the firm in 2013, he has grown ITE from a startup into a platform managing $6.5 billion in assets, with approximately $13.5 billion of assets owned and managed. Before launching ITE, Jason held investing and legal roles at Avenue Capital, Hale Capital Management, Kirkland & Ellis, Latham & Watkins, and Cooley. He earned an MBA from the Wharton School and graduate degrees from the University of Michigan. 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 Jason Koenig: LinkedIn:https://www.linkedin.com/in/jason-koenig-goblue/ 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 Everyone Ignored a $6.5B Opportunity (2:46) From $60M to $6.5 Billion AUM (8:34) The Entrepreneur's V-Shaped Ego (15:17) Why Great Leaders Need Humility (25:13) The Hardest Part of Scaling a Firm (31:09) Hire 3 Years Before You Need Them (35:02) The Best Career Pattern for Leaders (43:37) How Great Cultures Police Themselves (46:19) Why Investing Is Really Psychology (57:02) The Career Advice Everyone Gets Wrong
Summary
E408: HarbourVest: Why Venture Capital Is Chasing Trillion-Dollar Companies
2w ago00:43:10Summary readyVenture capital isn't about avoiding losses. It's about owning the handful of companies that change everything. Scott explains why HarbourVest has built its venture strategy around power laws, why secondaries have become essential to modern venture investing, and how institutions evaluate managers, partners, and companies across thousands of investment opportunities. Highlights: Why accepting losses is the price of capturing venture's biggest winners. The data behind why 10% of companies generate 90% of industry returns. How secondaries allow LPs and GPs to stay invested in generational companies. Why some of the best venture funds intentionally extend beyond their original 10-year life. Why great venture investments almost always look "too expensive" at the time. How HarbourVest evaluates individual partners instead of just venture firms. The subtle signals Scott looks for when conducting GP references. Why diversification across vintages matters more than trying to time venture cycles. How HarbourVest believes venture investing will evolve over the next decade. Guest Bio: Scott Voss is a Partner at HarbourVest, a $160B multi-manager private equity firm, where he leads venture and co-investment strategies. With 27 years at the firm, he has helped scale HarbourVest from $150M to $160B AUM, pioneering the firm’s secondary, direct, and continuation vehicle strategies. Scott specializes in portfolio construction, private market diversification, and building long-term strategic GP relationships to generate 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 Pierce: 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. Nothing herein should be construed as a solicitation, offer, recommendation, representation of suitability, legal advice, tax advice, or endorsement of any security or investment and should not be relied upon by you in evaluating the merits of investing in HarbourVest funds or in any other investment decision. (0:00) Why Venture Capital Is a Power Law Business (2:08) The Liquidity Decision That Can Make or Break a Fund (5:33) Why Great Investors Keep Underestimating Their Biggest Winners (8:54) The Hardest Truth Every Venture Investor Must Accept (12:49) Why Consensus Investing Rarely Creates Outlier Returns (15:20) The Secret Behind HarbourVest’s Three-Pronged Venture Strategy (21:04) Why HarbourVest Tracks Individual Partners Instead of Just Firms (29:54) How Elite Venture Firms Quietly Lose Their Edge (33:49) What to Do If You Can’t Access Top-Tier Venture Funds (36:20) What Venture Capital Will Look Like in 10 Years
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E407: Why Venture Capital is Becoming a Winner-Take All Market
2w ago01:07:48Summary readyVenture capital has never been more competitive. Aram Verdian argues it has also never been more concentrated. Drawing on Accolade Partners' research across more than 3,000 U.S. venture firms, Aram explains why fewer than 20 firms have consistently produced 3x net returns, what separates the firms that keep winning, and why venture is increasingly becoming a winner-take-all business. From portfolio construction and manager selection to AI, late-stage investing, and fund sizing, he shares the framework his team uses to identify the next generation of exceptional venture firms. Highlights: Why fewer than 1% of venture firms consistently outperform public markets. The data behind venture capital's winner-take-all dynamics. Why seed investing has become more competitive than ever before. The "right to win" framework Aram uses to evaluate emerging managers. Why many successful seed firms struggle after raising larger funds. How LPs should think about concentration versus diversification. Why AI has fundamentally changed venture fundraising and company building. How private markets continue to delay IPOs and reshape venture returns. Why great LPs become long-term strategic partners instead of capital providers. The importance of relationships and culture in building enduring investment firms. Guest Bio: Aram Verdian is a Partner at Accolade Partners, where he focuses on venture capital fund investments, growth equity, and digital assets. Previously, he invested at Andreessen Horowitz and earlier spent several years at Accolade before returning as Partner. Today, he helps oversee more than $3 billion in assets under management while leading the firm's blockchain initiatives and identifying emerging venture managers capable of generating long-term, top-decile returns. 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 Aram Verdiyan: LinkedIn:https://www.linkedin.com/in/aram-verdiyan-8099186/ 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 Only 20 Venture Firms Consistently Win (3:42) The 3X Rule Every LP Should Know (9:07) Why Seed Investing Has Never Been Harder (16:20) The VC Math Behind Billion-Dollar Returns (23:05) Why Great Investments Are So Rare (33:16) Why Consistency Beats One Lucky Fund (38:23) The Secret Behind a VC's "Right to Win" (50:18) Why AI Broke Venture Capital (1:02:09) The Biggest Mistake Investors Make in AI (1:16:25) The Career Advice That Changed Everything
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E406: Why AI Won't Transform Most Enterprises for 10 Years
2w 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
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E405: Why AI Has Made Venture Capital Harder (Not Easier)
3w 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
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E404: Why This Billionaire Family Office Doesn't Rebalance Its Portfolio | Pincus Family CIO
3w ago00:49:40Summary 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
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E403: Why the Best Investment Firms Stay Small | Sound Point Capital Founder
3w ago00:59:41Summary 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
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