How I Invest with David Weisburd

What if the biggest edge in venture today isn’t picking companies—but owning the entire lifecycle of capital?

In this episode, I sit down with Paris Heymann, Co-Managing Partner of Technology Investing at J.P. Morgan Private Capital, to discuss how the boundaries between public and private markets are breaking down. Paris explains why companies are staying private longer, how value is increasingly accruing to private investors, and why multi-stage platforms are becoming the new model for capturing returns. We also explore how AI is shifting business models from selling software to selling work, why founder quality still drives outcomes, and how power laws continue to dominate both private and public markets.

Is private equity alpha really about picking great deals—or about executing the same playbook better than everyone else?

In this episode, I discuss with Monty Yort, Managing Partner at GenNx360 Capital Partners, about how disciplined execution and consistency drive long-term outperformance in private equity. We break down how GenNx360 approaches proactive sourcing, why lower middle market investing creates structural advantages, and how operational improvement and buy-and-build strategies compound value over time. Monty also shares lessons on leadership, mentorship, and why the best firms continuously refine their process rather than chase new strategies.

How do you manage a $26 billion public fund while keeping every investment decision disciplined, every team member calibrated, and every partner accountable?

In this episode, I sit down with Mark Steed, Chief Investment Officer of AZ Public Safety Personnel Retirement System, to explore how super forecasting and probabilistic thinking shape portfolio management. Mark shares how lessons from Dr. Phil Tetlock's the Good Judgment Project inform every investment decision, why intellectual humility and calibrated confidence drive better outcomes, and how simplifying portfolios into broad buckets creates flexibility and competition for capital. He also unpacks the role of co-investments, structural alpha, and first principles thinking in public markets.

How do you build a $7 billion portfolio that performs across decades while keeping every client aligned and every manager motivated?

In this episode, I sit down with Karen Welch, Chief Investment Officer at Spider Management Company, to explore the evolving role of a CIO in today’s complex investment landscape. Karen shares how lessons from Stanford’s endowment shaped her approach, why the best investment edge comes from people and relationships, and how Spider leverages both to generate top-tier returns. She also unpacks how to navigate private markets, assess the illiquidity premium, and structure portfolios to balance opportunity with risk.

What does it take to raise $270 million in a risk-off market while keeping your personal life, sanity, and team intact?

In this episode, I sit down with Scott Painter, Founder & CEO, TrueCar, to unpack the 21-month journey of taking a company private. Scott shares how persistence, strategic thinking, and mental resilience allowed him to navigate investor skepticism, market volatility, and personal stakes. He discusses the lessons he learned from fundraising in both up and down markets, why creating momentum and scarcity is critical, and how setting boundaries transformed the outcome for him and his team.