How I Invest with David Weisburd

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.

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.

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.

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lessons from both the GP and LP sides of the table, explains why traditional portfolio construction frameworks may be outdated, and explores how themes like power generation, data centers, space infrastructure, and venture capital are becoming increasingly interconnected.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.

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.