E256: What Fintech Will Look Like in 5 Years - Steve McLaughlin (FT Partners)
What does it take to build the most dominant FinTech investment bank in the world—starting from a $99 incorporation and a used laptop?
In this episode, I speak with Steve McLaughlin, Founder, CEO, and Managing Partner of FT Partners, widely regarded as the leading investment bank in FinTech. Steve has personally closed hundreds of the biggest M&A, capital raise, and IPO advisory transactions in the industry—while pioneering a completely different approach to value creation in investment banking.
We cover everything from the humble beginnings of FT Partners, to Steve’s philosophy of “never die,” to his groundbreaking thesis on AI, tokenization, defensibility in FinTech, and why he believes we’re entering a new era of trillion-dollar global financial technology companies. We also dive into the incentives model Steve built that has generated some of the largest fees in the history of investment banking—and why clients keep coming back.
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37:40
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37:40
E255: How to Hire the Top 0.1%
What does it take to recruit the top 0.1% of engineers in the world — and why has talent become the ultimate constraint in AI?
In this episode, I’m joined by Chris Vasquez, Founder & CEO of Quantum Talent, one of the most in-demand technical recruiting firms in the AI ecosystem. We discuss why elite engineering talent has become the core bottleneck in AI, how companies can actually attract S-tier builders, what founders get wrong about hiring, and why talent density—not headcount—is the strongest predictor of outcomes in today’s startup environment.
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35:05
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35:05
E254: How to Build a 100-Year Venture Firm
How do you balance power-law outcomes with real risk management while building a durable venture franchise?
In this episode, I speak with Mark Peter Davis (MPD) — Managing Partner of Interplay, entrepreneur, author, podcaster, and one of New York’s most active early-stage investors. We discuss how Mark’s philosophy of investing has evolved over 20 years in venture, why VC psychology is so different from other asset classes, and how he manages for both outliers and consistency across vintages.
Mark breaks down secondaries, constructing high-access portfolios, founder relationships, narrative risk, the role of operational support, and why grit compounds just like interest.
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42:49
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42:49
E253: How Great CIOs Think w/Bill Brown
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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47:00
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47:00
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.
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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