Podcast
How I Invest with David Weisburd
Hosted by David Weisburd · EN
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
314episodes
Episodes
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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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E396: The Future of Compute, Data Centers, and AI
Jun 2900:23:38Summary readyWhat if AI's most valuable commodity isn't software—but the computing power that makes intelligence possible? In this episode, I sit down with Kush Bavaria, Co-Founder and CEO of Ornn, to discuss why AI compute is becoming the next global commodity and how financial markets are evolving to support it. Kush explains why GPU capacity should trade like oil or electricity, how derivatives and futures markets could reshape AI infrastructure, and why access to compute may become one of the defining competitive advantages of the next decade. We also explore data centers, energy constraints, AI capital markets, and what it takes to build a venture-backed company at just 22 years old. Highlights: Why AI compute could become the world's next strategic commodity How Ornn is building a financial exchange for GPU capacity Why data centers need futures markets and price indices The growing importance of compute in the AI arms race Why energy, not capital, may become the biggest bottleneck for AI The investment opportunity behind data centers and AI infrastructure How America can maintain its competitive advantage in AI Building one of the fastest-growing AI infrastructure startups at age 22 Why customer obsession has become Ornn's biggest competitive advantage Kush's biggest lesson about hiring and scaling a startup Guest Bio: Kush Bavaria is the Co-Founder and CEO of Ornn, an AI infrastructure company building the financial markets for compute. Backed by Andreessen Horowitz, Ornn creates standardized price indices, exchanges, and derivatives that allow GPU capacity to be bought, sold, and hedged like traditional commodities. The company helps data centers monetize future compute capacity while enabling AI companies, developers, hedge funds, and enterprises to access computing power more efficiently. 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 Kush Bavaria: LinkedIn:https://www.linkedin.com/in/kush-bavaria/ 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 Compute Could Become the World’s Most Important Commodity (0:47) The $7 Trillion Market Most Investors Still Don’t Understand (2:03) Why AI Compute Needs a Futures Market (4:13) The Five Layers of the AI Economy Explained (6:12) The Missing Compute Market Every AI Startup Needs (8:27) Is There Really a Data Center Bubble? (10:10) Why OpenAI Is Winning the Compute Race (12:36) Why Andreessen Backed a 22-Year-Old Founder (14:41) The AI Arms Race Between the U.S. and China (18:37) The Startup Lesson That Matters More Than Building Product
Summary
E395: Russ d'Sa on AI, Agents, and the Future of Work
Jun 2600:45:40Summary readyWhat happens when computers stop being tools and start behaving like collaborators? In this episode, I sit down with Russ d’Sa, Founder and CEO of LiveKit, to discuss why voice AI may become one of the most important computing platforms of the next decade. Russ explains how LiveKit powers AI experiences for companies including Tesla and xAI, why voice is emerging as the natural interface for AI agents, and what the rise of digital labor means for workers, founders, and society. Highlights: Why voice AI is becoming the next major computing interface The difference between voice-first and multimodal AI experiences How AI agents are already transforming customer service, healthcare, and financial services Why speed and conversational intelligence unlocked the voice AI revolution Russ’s view on whether AI will create or destroy jobs Why creativity may become more valuable as execution gets commoditized The types of careers most resilient to AI disruption Why reputation and relationships remain difficult to automate The importance of agency, adaptability, and learning velocity in an AI-driven world How companies should think about integrating AI across their organizations Why AI-native companies may outperform incumbents over the next decade Russ’s framework for choosing execution risk over market risk when building startups The long-term bet that computers will become increasingly human-like Guest Bio: Russ d’Sa is the Founder and CEO of LiveKit, the leading infrastructure platform powering real-time voice, video, and AI applications. LiveKit has become foundational infrastructure for the emerging voice AI ecosystem, serving companies including Tesla and xAI while helping developers build next-generation AI agents and multimodal experiences. 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 Russ d'Sa: LinkedIn: https://www.linkedin.com/in/russelldsa/ 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 Voice AI Could Become the Next Computing Platform (4:42) The Multi-Billion Dollar Industry AI Is Replacing First (9:16) The Two Breakthroughs That Made Voice AI Finally Work (14:15) Will AI Create More Jobs or Eliminate Them? (18:55) How to Avoid Getting Replaced by AI Over the Next Decade (23:30) Why Reputation and Relationships Become More Valuable in an AI World (30:12) The Two Traits Russ Looks for in Every New Hire (33:49) When Non-Engineers Will Be Able to Build Software (41:51) Why Most Companies Are Failing to Implement AI (46:24) The One Startup Lesson He Wishes He Learned Much Earlier
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E394: How Great LPs Pick Venture Funds | Jamie Rhode
Jun 2400:38:40Summary readyWhat if the biggest mistake LPs make in venture is backing the same managers over and over instead of constantly asking who they would invest in if they were starting from scratch today? In this episode, I sit down with Jamie Rhode, Partner at Screendoor, to discuss what separates the best emerging managers from the rest of the market. Jamie explains why so many venture funds look identical today, how LPs unintentionally create that dynamic, and why manager selection is really about finding GP-market fit. Highlights: Why so many emerging managers look exactly the same to LPs The concept of GP-market fit and why it matters more than ever What separates great investors from great fund managers Why endurance and adaptability matter more than early momentum The role of disagreement and respect in high-performing partnerships Jamie's framework for 90% rules-based investing and 10% "break-the-rule" investments Why fund one managers may have structural advantages over established firms How successful GPs refresh their networks before their edge disappears The founder flywheel effect and its impact on sourcing Why LPs should ask themselves: "Would I invest in this manager again today?" The hidden risks of strategy drift as venture firms mature Why sitting out a vintage year may be more costly than backing the wrong manager Guest Bio: Jamie Rhode is a Partner at Screendoor, a venture-focused fund-of-funds platform that anchors and supports the next generation of venture capital managers. Prior to Screendoor, she spent more than eight years at Verdis Investment Management, a single-family office where she focused on emerging venture managers, private equity, and hedge fund investments. 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 Jamie Rhode: LinkedIn: https://www.linkedin.com/in/jerrcfa/ 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 Venture Managers Sound Exactly the Same (1:41) The Hidden Framework Behind Great Emerging Managers (3:39) What It Actually Takes to Be a Top Seed Investor Today (5:47) Which Emerging Managers Will Survive the Extinction Event? (10:00) Why Great Venture Partnerships Need More Than Complementary Skills (14:29) The 10% Rule That Creates Venture Outliers (18:55) Why Fund One Managers Have a Structural Advantage (22:59) The One Trait Shared by Long-Term Winning Venture Firms (27:56) The Biggest Mistake LPs Make When Re-Upping Managers (35:18) How Emerging Managers Can Compete Against Mega Funds
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E393: What 8,000 LPs and GPs Taught Him About Investing | Ron Biscardi
Jun 2200:41:40Summary readyWhat if the biggest edge in investing isn’t information, strategy, or even intelligence—but relationships? In this episode, I sit down with Ron Biscardi, Co-Founder and CEO of iConnections, to discuss what separates the world’s best allocators and investment managers from everyone else. Ron shares lessons from building the largest capital introduction ecosystem in alternatives, with more than 26,000 members across 80+ countries representing over $55 trillion in assets. We explore the role of EQ in investing, why relationships compound into investment advantages, how emerging managers should think about fundraising, and why some of the most successful investment firms are built by entrepreneurs rather than investors alone. We also discuss conviction, illiquidity, LP decision-making, manager selection, and the realities of navigating capital markets over decades. Highlights: What separates the top 1% of allocators and fund managers Why curiosity, humility, and continuous learning drive investment success The critical role of EQ and relationship-building in generating investment edge Why the best investors actively seek out viewpoints that challenge their own How emerging managers should approach fundraising and finding anchor investors The hidden psychology behind LP decision-making Why conviction must be balanced with adaptability The advantages of illiquidity and protecting investors from behavioral mistakes How LPs distinguish skill from luck in private markets Why many successful investment firms are built by entrepreneurs, not just investors Ron’s hardest lesson from decades in alternative investments and capital raising Guest Bio: Ron Biscardi is the Co-Founder and CEO of iConnections, the leading global capital introduction platform connecting investment managers, institutional allocators, and family offices. Under his leadership, iConnections has grown into the largest alternative investment ecosystem in the world, serving more than 26,000 members across 80+ countries that collectively represent over $55 trillion in assets under management. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Ron Biscardi: LinkedIn: https://www.linkedin.com/in/rbiscardi/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd 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) What Separates the Top 1% of Allocators From Everyone Else (2:04) Why EQ Matters More Than Most Investors Realize (4:02) The Relationship Strategy Behind a $2 Billion OpenAI Position (6:02) Why Conviction Can Be Dangerous Without This One Thing (8:17) How Antonio Gracias Built Extreme Conviction in SpaceX (10:06) If He Were Raising a First-Time Fund Today, Here’s What He’d Do (13:51) Why Anchor Investors Matter More Than Most GPs Think (18:23) The Private Markets Problem Nobody Talks About (23:27) The Behavioral Edge That Separates Great Investors (32:26) What the Most Successful Fund Managers All Have in Common
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E392: Jason Pritzker on Family Offices, Venture Capital, and Long-Term Investing
Jun 1900:25:36Summary readyWhat if the secret to building generational wealth isn’t finding the perfect investment—but finding the right people and holding great businesses for decades? In this episode, I sit down with Jason Pritzker, Managing Director and Vice Chairman of The Pritzker Organization and founder of 53 Stations, to discuss the investing principles that helped shape one of America’s most successful business families. Jason shares the story of how the Pritzker family built its fortune, why long-term ownership creates powerful advantages, and how partnering with exceptional leaders compounds value over time. Highlights: How the Pritzker family built a multi-generational investment empire Why finding the right partners matters more than finding the perfect deal The advantages of long-term ownership versus constant buying and selling Lessons Jason learned transitioning from private equity to venture capital Why great founders matter more than investment theses How 53 Stations developed its venture investing strategy The surprising similarities and differences between PE and venture investing Why board structure and governance can make or break a company The role of customer introductions as a venture capital value-add How family values and upbringing shaped Jason’s investing philosophy Guest Bio: Jason Pritzker is Founder and Managing Partner of 53 Stations, the venture arm of The Pritzker Organization, where he also serves as Vice Chairman. Backed by an inaugural $187 million commitment, 53 Stations invests in early-stage technology companies, bringing flexibility and scale to its founder partnerships, building companies that stand the test of time. 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 Pritzker: LinkedIn: https://www.linkedin.com/in/jasonpritzker/ 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 Forgotten Decision That Built the Pritzker Fortune (2:03) Why Picking the Right Partner Matters More Than Any Deal (5:27) The Hidden Flaw in the Traditional Private Equity Playbook (8:48) When Selling a Great Company Actually Makes Sense (11:21) Why Most Family Offices Lose Money in Venture Capital (15:14) The Private Equity Habits That Fail in Venture Investing (18:36) Why Great Founders Matter More Than Great Markets (21:09) The Surprising Advantage Behind 53 Stations’ Investment Strategy (25:04) The Boardroom Mistake That Weakens Startups (36:35) The Career Advice He Wishes He Learned a Decade Earlier
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E391: $17 Billion CIO on Taxes, Private Markets, and Building Wealth
Jun 1700:49:37Summary readyWhat if the biggest driver of long-term investment success isn't finding better investments, but helping investors avoid their own worst decisions? In this episode, I sit down with Ron Albahary, Chief Investment Officer at LNW, to discuss the unique challenges of managing wealth for taxable investors and why portfolio construction is as much about psychology as it is about finance. Highlights: Why managing investor behavior may be more important than picking investments The overlooked tax strategies that compound wealth over decades How framing risk in dollars instead of percentages changes decision-making Why fewer investment decisions often lead to better outcomes Lessons from three decades of market cycles and investment fads The role hedge funds and diversifiers play during periods of market stress Why some evergreen private market structures are misunderstood by investors The case for lower middle market private equity over mega-funds How AI is creating hidden concentration risk across portfolios Why humility may be one of the most underrated traits in investing Guest Bio: Ron Albahary is the Chief Investment Officer of LNW, where he oversees approximately $17 billion in assets and leads the firm's investment strategy across public and private markets. Over a career spanning more than three decades, Ron has served as both a Chief Executive Officer and Chief Investment Officer, helping oversee more than $175 billion in client assets. 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 Ron Albahary: LinkedIn: https://www.linkedin.com/in/ron-albahary-cfa/ 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 Managing Humans Is Harder Than Managing Portfolios (2:19) The Highest-Conviction Ways to Create Wealth Without Taking More Risk (4:13) Why Taxable Investors Need a Different Portfolio Playbook (7:34) The Portable Alpha Mistake Investors Keep Repeating (11:01) The Simple Question That Reveals Someone’s True Risk Tolerance (15:56) Why Illiquidity Can Be a Feature, Not a Bug (20:23) The Counterintuitive Reason Great Investors Make Fewer Decisions (25:10) Will Retail Capital Destroy the Private Equity Illiquidity Premium? (33:40) Why Lower Middle Market May Be the Best Place to Find Alpha (42:54) How to Build a Portfolio That Isn’t Dependent on AI
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E390: Ron Rofé on AI, Founder Obsession, and Venture Returns
Jun 1500:40:47Summary readyWhat if the best venture investors aren’t chasing the hottest sectors—but the founders who would still be working on the problem long after the hype disappears? In this episode, I sit down with Ron Rofé, Co-Founder and General Partner of Rainfall Ventures, to discuss why founder quality matters more than industry trends, how non-consensus investing creates outsized opportunities, and what he has learned from backing over 120 startups and 230 founders. Ron shares the stories behind investments like Robinhood, Webflow, and Alma, explains why he prioritizes resilience over ideas, and discusses the founder traits that consistently predict success. Highlights: Why Ron avoids chasing consensus investment themes, including AI The founder traits that matter more than market size or industry How Rainfall backed Robinhood before it became a fintech giant Why resilience often matters more than the original business idea The surprising advantage of investing in non-consensus markets How great founders balance conviction with humility Why half of venture value is created before categories are fully recognized The networking philosophy that helped build Rainfall Ventures How helping founders creates long-term investing advantages Ron’s timeless advice: “Nobody knows anything” Guest Bio: Ron Rofé is the Co-Founder and General Partner of Rainfall Ventures, an early-stage venture capital firm that has backed category-defining companies including Robinhood, Webflow, Alma, and Harmonic. Over the past decade, Ron has invested in more than 120 startups representing over 230 founders, building a reputation for making non-consensus bets and identifying exceptional entrepreneurs before the market recognizes them. 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 Ron Rofé: LinkedIn: https://www.linkedin.com/in/ronrofe/ 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 He Refuses to Be an AI-Only Investor (3:23) The Opportunity Cost Most Venture Capitalists Ignore (6:04) Why Half of Venture Returns Are Created Before a Market Has a Name (10:08) The Founder Trait That Matters More Than Intelligence (14:10) The Five Qualities He Looks for Before Writing a Check (17:32) How One Founder’s Humility Created a Billion-Dollar Outcome (22:28) The Unusual Way He Got Into Robinhood Before It Took Off (25:52) Why He Invested at a $300M Valuation When Everyone Thought He Was Crazy (31:46) The Hidden Flaw in Thesis-Driven Venture Capital (37:34) The Advice That Changed How He Thinks About Success
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E389: The Future of Investing: Data Centers, AI & the Next Trillion-Dollar Companies
Jun 1200:49:58Summary readyWhat happens when one investor sits at the intersection of venture capital, natural resources, AI, space infrastructure, and geopolitics? In this episode, I sit down with Rob Stephens, Director of Investments at Spider Management, to discuss how institutional investors are adapting to a world where private markets are capturing more value, AI is reshaping capital allocation, and the boundaries between asset classes are disappearing. Rob shares lessons from both the GP and LP sides of the table, explains why traditional portfolio construction frameworks may be outdated, and explores how themes like power generation, data centers, space infrastructure, and venture capital are becoming increasingly interconnected. We also discuss emerging managers, co-investments, continuation vehicles, concentration versus diversification, and the future of private markets. Highlights: How experience as both a GP and LP changes investment decision-making Why traditional asset allocation buckets may no longer reflect reality The growing divide between investors with access to elite private companies and everyone else Why Anthropic, OpenAI, and SpaceX are reshaping private market investing The rise of venture co-investments and SPVs How LPs evaluate alignment when reviewing co-investment opportunities Why references matter more than track records when evaluating spinout managers The debate between concentration and diversification in institutional portfolios How AI, power generation, natural resources, and venture capital are becoming deeply interconnected Why data centers, energy infrastructure, and even space-based computing may become major investment themes Guest Bio: Rob Stephens is Director of Investments at Spider Management, the University of Richmond’s $7 billion investment office and OCIO platform. He leads investments across venture capital, private equity, real assets, and thematic public market strategies, with a focus on deep tech, space, defense, AI, energy, natural resources, and China. Prior to joining Spider in 2022, Rob was a Managing Director at DAC Management in Hong Kong and New York, where he specialized in Chinese markets and cross-border 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 Rob Stephens: Spider Management Company: https://spiderinvests.com/ LinkedIn: https://www.linkedin.com/in/robstephens3/ X/Twitter: @robstephens_ 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) What GPs Hide That Most LPs Never Notice (2:26) Why Traditional Asset Allocation Is Starting to Break (4:11) Will OpenAI, Anthropic, and SpaceX Fix Venture’s DPI Problem? (6:29) Why Emerging Managers May Struggle More Than Ever (9:05) The Capital Moat Protecting Tier 1 Venture Firms (11:08) The Unusual LP Model That Forces Extreme Alignment (15:08) Why Venture Firms Are Launching More SPVs Than Ever (24:23) Is Venture Capital Heading Toward an Extinction Event? (37:56) Why AI Is Turning Venture Capital Into a Natural Resources Bet (47:52) Can the Biggest Private Companies Stay Private Forever?
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E388: The Future of Investing: AI, Expert Networks, and Information Alpha
Jun 1100:34:05Summary readyWhat if the biggest edge in investing today isn't having more information—but knowing how to turn information into conviction? In this episode, I sit down with Matt Wells to discuss how AI is reshaping the investment process, why investors are drowning in data but starving for conviction, and where information alpha still exists in increasingly efficient markets. Matt explains the evolution of expert networks, how the best investors use expert calls and channel checks to build differentiated insights, and why qualitative information often drives quantitative outcomes. We also explore decision-grade AI, conviction building, private market diligence, and how the role of the analyst is changing in an AI-driven world. Highlights: Why investors today are drowning in data but starving for conviction The difference between information and decision-grade intelligence How expert calls evolved from niche hedge fund tools into scalable research platforms Why qualitative signals often become quantitative outcomes The role of channel checks in forecasting company performance How AI can help identify patterns across thousands of expert conversations Why conviction matters more than information during periods of volatility The future of analysts as architects rather than spreadsheet builders How grounded AI differs from general-purpose AI models Why human relationships remain irreplaceable in investing and business Guest Bio: Matt Wells is a technology executive and entrepreneur focused on applying artificial intelligence and market intelligence tools to investment research and decision-making. Prior to joining AlphaSense, he founded and scaled multiple businesses, bringing a unique operator's perspective to financial technology and research workflows. Today, he works at the intersection of AI, expert intelligence, and investment research, helping institutional investors, corporations, and advisors turn overwhelming amounts of information into actionable insights and higher-conviction decisions. Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Pierce: https://www.weisburdcapital.com/ Stay Connected with Matthew Wells: LinkedIn: https://www.linkedin.com/in/matthew-wells-932b6a2/ 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 Investors Are Drowning in Data but Starving for Conviction (2:04) The Dangerous Problem With AI Nobody Talks About (4:17) How Expert Calls Became a Hidden Edge for Elite Investors (6:54) The SpaceX IPO Research Strategy Most Investors Won’t Use (11:17) How Top Funds Turn Hundreds of Expert Calls Into Alpha (15:58) Why Every Quantitative Model Starts With Qualitative Information (17:39) Where Investment Alpha Will Come From in an AI World (20:11) The Missing Ingredient Behind Every Great Investment Thesis (24:37) Why the Analyst Role Is About to Change Forever (31:34) The Career Advice That Applies to Investing, Sales, and Life
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