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Episodes from How I Invest with David Weisburd
E340: Why Family Offices Should Avoid 60/40 Portfolios
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. Highlights: How incorporating multiple, uncorrelated return streams...
E339: From Zero to $100 Million in 18 Months: Inside Legora
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...
E338: How I Invest $9 Billion into VC & Private Equity
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. Highlights: Why AI is both a major risk...
E337: How to Invest in a Post Singularity World
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. ...
E336: The Private Equity Firm of 2030
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. Highlights: Why performance should remain the core product in...
E335: Why the Best Investors Ignore “Capital Preservation”
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. <...
E334: Texas Tech CIO: How We Find Asymmetric Bets
Why buy an office when everyone else is selling? In this episode, I sit down with Tim Barrett, CIO of the Texas Tech University Endowment, to explore how he builds high-conviction portfolios across private equity, real estate, and hedge funds. Tim shares why governance, manager selection, and a generalist team structure drive consistent alpha, how he balances risk and upside with portable alpha, and why lower middle market investments can outperform flashy venture deals. He also dives into building team culture, aligning incentives, and using the endowment’s size and flexibility to access niche opportunities others can’t. Highlights: ...
E333: Why a $19B Allocator Is Betting on Lower Middle Market Buyouts
Why do most institutional investors still allocate heavily to large private equity funds? Alex Abell of RCP Advisors explains why the lower middle market has consistently outperformed, driven by less competition, faster exits, and stronger value creation. He breaks down the structural reasons LPs stay in large buyouts, including access constraints, manager selection difficulty, and career risk. The conversation also covers how top LPs evaluate managers, what actually predicts performance, and where alpha exists in private markets today. Highlights: Why lower middle market private equity often outperforms large buyouts over decades How manager selection, pattern recognition, and “superpowers” driv...
E332: Why Family Offices Must Go Risk-On or Go Broke
What if the best investors aren’t generalists at all, but operators who double down on the one place they truly have an edge? In this episode, I sit down with Nathan Cooper, Founder and Managing Partner of Barrel Ventures, to explore how a family with nearly a century in food transformed itself into a focused investment platform. From early mistakes outsourcing everything to building a differentiated edge in food and beverage, Nate shares how conviction, pattern recognition, and network-driven investing compound over time. Highlights: Why “money is fuel, not incentive” in operationally intense industries like food How early...
E331: Ron Biscardi, CEO of iConnections on the Biggest Mistakes Managers Make
What does it take for a GP to successfully raise capital in today’s venture and private markets? In this episode, I sit down with Ron Biscardi, co-founder and CEO of iConnections, to unpack the realities of LP relationships, fund-raising cycles, and scaling a global platform for capital introduction. Ron shares insights on how humility, patience, and responsiveness differentiate managers, why business risk matters more than returns for LPs, and how building trust over years compounds into large-scale success. Highlights: Why capital is abundant but only flows to managers who invest in relationships over time The trend from bl...
E330: EuropeanKid: The $32B Future of Influencer Marketing
What if influencer marketing isn’t about chasing mega-followers, but activating the creators who already love your brand? In this episode, I sit down with Aris Yeager, Founder of Storytime, to explore how he built a platform connecting brands with nano and micro creators to run highly targeted campaigns at scale. A creator himself known online as European Kid, Aris leverages his own social experience to help businesses automate gifting, engage loyal audiences, and measure campaign effectiveness while focusing on authenticity over follower count. Highlights: How Storytime turns influencer marketing into a scalable, data-driven platform Why nano and mi...
E329: How Oaktree Is Positioning $223 Billion for a Credit Cycle Shift
What if the best way to navigate credit markets is not about chasing yield but controlling risk? In this episode, I sit down with Danielle Poli, Co-Portfolio Manager of Global Credit at Oaktree, to explore how she manages a $20 billion portfolio within a $223 billion firm. Danielle shares how focusing on core income, rigorous underwriting, and a flexible toolkit allows her team to navigate complex markets while remaining defensive or opportunistic as conditions change. Highlights: Why a “core plus alpha” strategy balances steady income with opportunistic credit How to underwrite borrowers through leverage, cash flow, and sector fundamentals Why AI d...