E343: The Death of the 60/40 Portfolio (And What Comes Next)

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.

What happens when AI turns a $40B legal software market into a $1T opportunity? In this episode, I talk with David Eckstein, CFO of Legora, about scaling one of the fastest growing enterprise AI companies in history. David explains how Legora went from zero to $100M in 18 months, why AI is expanding markets rather than just disrupting them, and how the role of CFO is evolving into a strategic operator across every part of the business. We discuss vertical vs horizontal AI, why AI companies must focus on workflows instead of prompts, and how talent density and culture become the ultimate differentiators in high growth environments.

Is AI the biggest risk to equity portfolios or the biggest opportunity? In this episode, I talk with Christopher Vogt about how institutional investors think about risk, portfolio construction, and manager selection across public and private markets. We discuss AI disruption, why governance and structure matter more than asset labels, and how to evaluate managers using both quantitative and qualitative frameworks. Chris also shares lessons from building an endowment style portfolio from scratch, why patience matters in private markets, and how position sizing can make or break long term outcomes.

What does investing look like in a world dominated by AI? In this episode, David Weisburd talks with Alex Wissner-Gross about the profound implications of technological singularity and the evolution from LLMs to reasoning models. They discuss AI personhood, economic rights, and the rise of AI agents, as well as strategic investment approaches in a post-singular world. The conversation delves into Elon Musk's visions for massive compute capabilities, the role of science fiction in predicting technological advancements, and strategies to prevent technological unemployment. The episode concludes with a look towards the future and a call to action for listeners.

Is private equity becoming an asset gathering business instead of a performance business? In this episode, I talk with Sam Tidswell-Norrish, Partner at Access Holdings, about how private equity is evolving across sourcing, value creation, and distribution. We discuss why performance is still the core product, how AI is reshaping deal flow and portfolio operations, and why the lower middle market remains one of the best places to generate alpha. Sam also shares how culture, curiosity, and relationships drive long term success in an increasingly competitive and automated industry.

What if your family office could invest like a founder and a VC at the same time? In this episode, I sit down with Shane Neman, founder of a multi-entity family office with $850M AUM, to explore how he approaches venture investing, deep tech, and portfolio construction. Shane shares how his two decades as a SaaS founder shape his edge as an investor, why transparency and founder relationships matter more than fund mandates, and how he balances high-conviction bets with a rational family office lens. He also dives into frontier tech, co-invest structures, and building a diversified yet opportunistic portfolio.