How do the best family offices consistently spot power-law opportunities and avoid the trap of “fake busy” work?
In this episode, I’m joined with William (Bill) Brown, CIO of the Terrace Tower Group, about the lessons he learned working for billionaire Leonard Stern, how he helped evolve a legacy real-estate portfolio into a globally diversified family office, and what pattern recognition looks like across trades like the Big Short, crypto, and private credit. We discuss how Bill thinks about decision-making, mental models, productivity, and the mindset required to survive long enough to capture asymmetric upside.
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E252: Inside the Mind of a 29-Year-Old Billion-Dollar Fund Manager
How do you scale from a $10M first fund to managing over $1.5B — all in one of the most capacity-constrained asset classes on earth?
In this episode, I talk with Eva Shang, Co-founder and General Founder of Legalist, about dropping out of Harvard, getting into Y Combinator, pivoting from legal analytics to litigation finance, and raising their first $10M fund long before they had any track record.
We discuss why Legalist chose the fund model over the venture-backed originator model, how they deployed their algorithm to find late-stage cases at scale, why litigation finance is capacity constrained, and how Legalist expanded into adjacent strategies like bankruptcy, mass torts, law-firm lending, and government receivables.
What does it actually take for an emerging manager to convince a top LP to invest?
In this episode, I’m joined by Alex Edelson, Founder of Slipstream, and one of the most respected LPs backing elite seed funds today. Alex pulls back the curtain on how LPs use AI, what “real talk” references look like, how he evaluates GPs, and why only a tiny percentage of funds ever make it through his screening.
We also dive into portfolio construction, picking and winning founders, why deep tech requires more shots on goal, and how Alex builds long-term trust with the world’s top institutions.
This conversation is a masterclass in LP underwriting and what separates good managers from truly exceptional ones
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E250: The GP Fundraising Playbook: From First Meeting to Final Close
What does it really take to raise a venture fund—and why does fundraising never get easier, even at Fund 5 or Fund 6?
In this episode, I talk with Yasmine Lacaillade, Founder of Sinefine and one of the most respected capital formation leaders in venture. Yasmine shares her journey from TPG Axon in London to joining Drive Capital at Fund I—years before it became consensus. We discuss why fundraising is always difficult, how LP sentiment shifts every 2–3 years, and why top fundraisers treat the process like enterprise sales rather than relationship maintenance.
Yasmine breaks down her market mapping framework, why the top of the funnel must always stay wide, how to qualify LPs quickly, and why “adding value first” is her core operating principle. She also explains how she evaluates new managers, how to identify true LP demand today, and why people, culture, and team cohesion matter more than anything else in venture.
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E249: How LPs Unlock Liquidity Without Selling
How do LPs unlock liquidity from private-fund positions without selling at a discount?
In this episode, I talk with Alex Simpson, Co-founder of Liquid LP, a platform that provides NAV loans backed by LP and GP interests in private funds. Alex explains how NAV loans work, how lenders underwrite illiquid portfolios, and when borrowing may be preferable to selling in the secondary market. We also discuss how different types of investors—high-net-worth individuals, family offices, and institutions—use these loans for personal liquidity, capital calls, tax needs, portfolio rebalancing, or simply as a liquidity backstop.
We also cover underwriting, LTV ranges, recourse structures, timing, advisory boards, and the origin story behind Liquid LP.
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
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