E363: How Nigel Morris Built QED into a Fintech Powerhouse

What if the real edge in venture capital isn’t picking companies—but helping them survive long enough to matter? In this episode, I sit down with Nigel Morris, Managing Partner at QED Investors and Co-Founder of Capital One, to discuss how fintech innovation actually happens and why most investors misunderstand the role of venture capital. Nigel explains why incumbents struggle to innovate despite massive advantages, how QED built one of the most successful fintech franchises by combining operating experience with investing, and why venture is not stock picking but hands-on company building. We also explore founder psychology, power laws, and how culture and talent ultimately determine outcomes more than strategy or capital.

E362: Why Jensen Huang Believes Physical AI will be a $50 Trillion Market

What if the biggest opportunity in AI isn’t intelligence—but the missing data layer for the physical world? In this episode, I sit down with Daniel Jacker, CEO and Co-Founder of ZaiNar, to discuss why physical AI could become a $50 trillion market and the infrastructure required to make it work. Daniel explains how turning wireless networks into a real-time sensing layer unlocks entirely new capabilities across industries, why the absence of physical-world data is the biggest bottleneck in AI today, and how his company spent nearly a decade in stealth building a foundational technology before scaling. We also explore swarm intelligence, robotics, and where value will accrue as AI moves from digital to physical environments.

E361: Why Venture Capital is Not an Asset Class

What if venture capital isn’t really an asset class—but a game where only a handful of managers actually matter? In this episode, I sit down with Ian Sigalow, Co-Founder and Managing Partner of Greycroft, to discuss why venture returns are driven by a small group of firms with consistent access to the best companies. Ian explains why diversification often hurts venture outcomes, how the industry splits between “access” and “craft” investing, and why conviction, not consensus, drives results. We also explore what defines great founders in the AI era, how venture firms build brand and culture over decades, and why the intersection of multiple skill sets is becoming the foundation for generational companies.

E360: The Hardest Lessons I Learned from Building 4 Unicorns

What if the biggest breakthroughs in biotech don’t come from more capital—but from building better systems for innovation? In this episode, I sit down with Errik Anderson, biotech entrepreneur and founder behind multiple billion-dollar companies, to discuss how building infrastructure, not just drugs, is reshaping the future of healthcare. Errik explains why most biotech companies fail the same way, how reducing the cost and time of experimentation unlocks more innovation, and why staying private longer enables better long-term decision making. We also explore compounding in biotech, the limits of scaling creativity, and how conviction, mission, and talent ultimately determine which companies change the world.

E359: What Charlie Munger Taught Me About Venture Capital

What if the real edge in venture isn’t price—but who you choose to partner with for a decade? In this episode, I sit down with Jamie Montgomery, Co-Founder and Managing Partner of March Capital, to discuss how long-term relationships, not transactions, drive venture outcomes. Jamie explains why asymmetric upside matters more than negotiating the last percentage point, how conviction and discipline shape follow-on decisions, and why understanding your own biases is critical when doubling down. We also explore capital cycles, liquidity dynamics, and how AI is forcing every company to either reinvent itself or fall behind.

E358: The Woman Behind the World's Top GP Brands | Jen Prosek

What if the biggest edge in investing isn’t capital or strategy—but how clearly the world understands you? In this episode, I sit down with Jennifer Prosek, Founder and Managing Partner of Prosek Partners, to discuss how branding, narrative, and communication have become core drivers of success in financial services. Jennifer explains why firms went from ignoring marketing to depending on it, how “efficiency and preference” directly impact fundraising and deal flow, and why owned media and the “digital blink” now shape first impressions. We also explore how founders should think about storytelling, differentiation, and building long-term trust in an increasingly competitive capital landscape.

E357: CalSTRS CIO: Where Do You Invest $390 Billion Today?

What if the biggest edge in managing $390 billion isn’t picking assets—but controlling risk and liquidity when markets break? In this episode, I sit down with Scott Chan, Chief Investment Officer of CalSTRS, to discuss how one of the largest institutional investors in the world is positioning for a period of massive structural change. Scott breaks down how AI, deglobalization, and the energy transition are driving a multi-decade investment cycle, why traditional diversification is breaking down, and how liquidity and dynamic allocation become critical in volatile markets. We also explore structural alpha, co-investing at scale, and how governance and partnerships enable CalSTRS to generate returns without taking incremental market risk.

E356: Why Co-Investments Are Taking Over Private Equity

What if the next source of alpha in private equity isn’t funds—but individual deals? In this episode, I sit down with Rohan Parikh, Vice President at Houlihan Lokey, to discuss the rapid rise of co-investments and why they are becoming a core part of institutional portfolios. Rohan explains how extended fundraising cycles, larger deal sizes, and slower distributions have created a “perfect storm” for deal-by-deal capital, why LPs are increasingly treating co-investments as a standalone asset class, and how independent sponsors are reshaping the market. We also explore underwriting frameworks, alignment, and how relationships, not just returns, drive long-term success in this segment of private markets.

E355: From Deal-by-Deal to a $6.5B Platform: Building a Real Estate Investment Empire

What if the best investments aren’t found in chaos—but in having the discipline to act when others can’t? In this episode, I sit down with Darren Fisk, Founder of Forum Investment Group, to discuss how he scaled from early syndication deals to a fully integrated multifamily investment platform managing billions. Darren breaks down how he leaned in during the 2008 financial crisis to acquire 9,000 units, why focusing on distressed capital structures rather than distressed assets created asymmetric opportunities, and how flexibility across the capital stack allows investors to generate returns in any market.

E354: Why Most VCs Misunderstand Peter Thiel’s Power Law

What if venture capital isn’t about finding unicorns—but about consistently making good investments? In this episode, I sit down with Eric Scott, Co-Founder and Managing Partner at Overlook Capital, to discuss how his approach to venture evolved from chasing power laws to focusing on fundamentals. Eric explains why most venture frameworks only make sense in hindsight, how thinking like a value investor can improve early-stage decision-making, and why founder quality is ultimately revealed through execution, not narratives. We also explore concentrated markets, late-stage venture dynamics, and how reputation, conviction, and timing shape outcomes across cycles.

E353: Why Biotech Is Struggling in Today’s Market (and the Future of Healthcare)

What if the biggest opportunity in healthcare isn’t new drugs—but reinventing how the entire system works? In this episode, I sit down with David Berry, Founder of over 20 companies including seven $1B+ businesses, to discuss why the traditional biotech model is breaking and where the next wave of innovation in healthcare is emerging. David explains how pricing pressure, rising costs, and global competition are compressing returns in drug development, while AI, data, and new business models are unlocking entirely new ways to deliver care. We also explore how technology is transforming clinical trials, why healthcare is shifting beyond pharmaceuticals, and how investors can find opportunity in mispriced parts of the market.

E352: JD Vance’s Co-Founder on Space Defense, Hard Tech, and the Biggest Opportunities Ahead

What if the best venture returns come from avoiding trends—not chasing them? In this episode, I sit down with Colin, Co-Founder of Narya, to discuss how he approaches investing in frontier sectors without falling into mimetic behavior. Colin explains why the best opportunities are often “hidden in plain sight,” how mission-driven investing can still generate venture-scale returns, and why concentration, not diversification, drives outcomes in venture. We also explore defense, space, and advanced manufacturing, and how timing, business model innovation, and founder quality ultimately determine success.

E351: Why Most Family Offices Fail (And How a16z Fixed It)

What if the biggest edge in investing isn’t picking better assets—but structuring them better for taxes, incentives, and control? In this episode, I sit down with Michel, Founding CIO of a16z Perennial, to discuss how institutional investing frameworks translate to individual portfolios. Michel breaks down why most wealth management fails at true investment management, how misaligned incentives shape outcomes, and why scale, access, and structure matter more than traditional asset allocation. We also explore concentrated portfolios, tax alpha, and how psychology ultimately determines whether a strategy succeeds or fails.

E350: How Family Offices Quietly Build Generational Wealth

Is the real edge in investing not picking assets but structuring how you allocate capital? Terence Thompson is a Vice President of Investments at DF Enterprises, about how single family offices think about portfolio construction, liquidity, and structural alpha. We break down why Terry uses a total portfolio approach, how family offices create edge through flexibility, and why being a liquidity provider during market stress is one of the most powerful strategies. We also discuss concentration risk in public markets, the evolution of private markets, and how allocators can think about illiquidity, secondaries, and niche opportunities.

E349: Built to Scale: The J.P. Morgan Growth Playbook

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.

E348: Why “Boring” Businesses Beat Venture Capital

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.

E347: The $26B CIO Who Turned Superforecasting Into Alpha

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.

E346: $7 Billion CIO: Why the Endowment Model is Changing

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.

E345: How I Raised $10 Billion in Venture Capital w/Scott Painter

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.

E344: How the Top Family Offices are Investing Today

What if the families with the largest fortunes generate the highest returns not by chasing hot sectors, but by pacing capital, managing liquidity, and investing with a multi-decade horizon? In this episode, I sit down with Douglas Evans, Chief Investment Officer & Partner at Callan Family Office, to explore how a $10B family office approaches private markets like an institutional investor. Doug shares how private capital pacing, vintage year diversification, and strategic GP partnerships drive consistent performance, why continuation vehicles and secondary markets are reshaping liquidity, and how focusing on underlying assets rather than labels helps families build repeatable, long-term returns.