How I Invest with David Weisburd

E392: The Investing Rule That Built the Pritzker Empire

What 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

E391: $17 Billion CIO on Taxes, Private Markets, and Building Wealth

What 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

E390: Ron Rofé on AI, Founder Obsession, and Venture Returns

What 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

E389: The Future of Investing: Data Centers, AI & the Next Trillion-Dollar Companies

What 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?

E388: The Future of Investing: AI, Expert Networks, and Information Alpha

What 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