E348: Why “Boring” Businesses Beat Venture Capital

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.

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.

What if the biggest edge in portfolio construction isn’t picking better assets but structuring a portfolio you can actually stick with through cycles? In this episode, I sit down with Chaya Slain, President and CIO at Virtera Partners LLC, to unpack how families can access institutional-quality investing without building a full family office. Chaya explains why alternatives are often the true driver of outperformance, how trend following can reshape risk and return, and why behavioral discipline matters more than perfect asset selection.

What if the real edge in venture isn’t picking the hottest companies, but structuring your portfolio, pacing capital, and building relationships in a way most investors never do? In this episode, I sit down with Jamie Melzer, Founder and Managing Partner of Altra Venture Partners, to break down how she built a firm focused on late-stage venture and secondaries at the height of market dislocation. We discuss why rising interest rates in 2022 created a rare entry point, how buying private tech companies at 40 to 80 percent discounts reshaped the opportunity set, and why transaction risk often matters more than company risk in secondary markets. Jamie explains her concentrated, power-law-driven portfolio strategy, how she sources deals in an opaque and relationship-driven ecosystem, and why access, not awareness, is the true barrier in private markets.

What if the best venture returns come from the LPs that are most patient and most strategic? In this episode, I sit down with Scott Voss, Partner at HarbourVest, to explore how the $150B multi-manager firm generates consistent outperformance across venture, growth equity, buyouts, and secondaries. Scott shares how consensus risk, vintage year timing, and strategic co-investing shape returns, why continuation vehicles and evergreen structures are transforming private markets, and how long-term relationships with GPs create first-look access to top deals.

What if building a portfolio for high-net-worth investors is more about managing downside risk than chasing returns? In this episode, I sit down with Damien Bisserier, Managing Partner and Co-CIO at Evoke Advisors, to explore how he constructs diversified portfolios for ultra-high-net-worth families. Damien shares why after-tax returns, alternative assets, and private markets matter more than concentrated US stock bets, and how behavioral insights and client-centered thinking drive long-term compounding. He also dives into venture capital, the importance of relationships, and the nuanced ways to identify managers who deliver repeatable alpha.