How I Invest with David Weisburd
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.
Episodes
July 16, 2025 • 42 mins
What if Berkshire Hathaway were built today, with the best of technology and long-term thinking baked into its DNA? That’s the question Matt Foran and his team at StoicLane are answering—by doing it.
In this episode, I speak with Matt Foran, co-founder of StoicLane, a holding company quietly building one of the most interesting portfolios in private markets. With over 70 acquisitions across four major verticals—accounting, PEO, ap...
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July 14, 2025 • 49 mins
What’s the playbook for building a resilient, multi-billion‑dollar venture firm that weathers every market cycle? In this episode, Abe Finkelstein, Co‑Managing Partner at Vintage Investment Partners, shares how they underwrite managers, navigate funds‑of‑funds and secondaries, and spot next‑gen innovation—all while maintaining LP confidence across turbulent times.
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July 11, 2025 • 35 mins
I spoke with Amy Rubenstein, CEO of Clear Investment Group, about how she built a thriving real estate platform by focusing on one of the most overlooked areas of the market: distressed C-class multifamily housing.
Amy didn’t come from institutional real estate — she taught herself everything from Excel to underwriting by reverse-engineering models, and built a company that now serves both high-net-worth and institutional LPs. Tod...
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July 9, 2025 • 62 mins
Philip Krim is best known as the co-founder and former CEO of Casper, one of the fastest-growing direct-to-consumer (DTC) startups in history. Under his leadership, Casper hit $100M in revenue in its first year, went public in early 2020, and was later taken private. Today, Philip is building again—this time through Montauk Climate, a platform innovating in what he calls the “electron economy.” We talked about lessons from hypergro...
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July 7, 2025 • 63 mins
Ron Biscardi is the Co‑Founder & CEO of iConnections, a fintech platform reshaping global capital introduction. With 25+ years in the alternative investment space, Ron has facilitated 36,000+ LP/GP meetings since launching iConnections in April 2020. He previously co-founded a boutique seeding firm, deploying over $600M in capital via 20+ deals.
From a philanthropic start—with Funds4Food raising $1.9M in 2020 targeting pandemic re...
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July 2, 2025 • 51 mins
In this episode, I speak with Tyler Sosin, founder of Villain Capital, a new fund focused on investing in vertical software businesses. Having grown up in the venture business for 17 years with storied firms Menlo Ventures and Accel Partners, Tyler brings a unique - and perhaps contrarian - perspective to venture investing. With Villain, Tyler's ambition is to help vertical focused founders efficiently scale their start-ups into d...
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June 30, 2025 • 50 mins
In this episode, I speak with T.C. Wilson, Chief Investment Officer of The Doctors Company (TDC Group), the nation's largest physician-owned medical malpractice insurer with $7 billion in assets under management. T.C. shares how he built an internal investment office, how insurance investing differs from endowment and foundation models, and why he treats surplus like an endowment portfolio.
We dive into his framework for portfolio...
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June 27, 2025 • 22 mins
What does it take to allocate billions in private markets—and what sets a top-tier LP apart?
In this episode, I speak with Patrick Miller, Executive Director and Portfolio Manager of J.P. Morgan Asset Management’s Private Equity Group, where he plays a central role in their alternatives platform, investing across venture capital and private equity. Patrick shares how a single energizing meeting with a Florida-based venture capital...
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June 25, 2025 • 64 mins
Michael Marvelli leads the private markets strategy at the UCLA Investment Company, managing a portfolio that spans private equity, real estate, and real assets. But his route to institutional investing wasn’t linear.
Before UCLA, he spent time at Prudential and The Irvine Company in real estate and mortgage finance, and even helped launch a venture-backed startup as COO and CFO. That operating experience gives him a unique lens w...
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June 23, 2025 • 44 mins
David Berry is one of the most prolific healthcare entrepreneurs of our time.
In this episode, we discuss his transition from scientist to founder to investor, what it takes to scale transformational health companies, and how his firm Averin is helping usher in the next wave of AI-enabled healthcare.
We also talk about his early experience launching a satellite at 14, how he's co-founded over 30 companies—including seven unicorns—a...
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June 20, 2025 • 46 mins
In this episode, I speak with Rip Reeves, CEO of Institutional Investor and former CIO of AEGIS Insurance Services. Rip brings over four decades of experience across investment management, insurance, and endowments. We discuss his unconventional path from Salomon Brothers to leading one of the most iconic platforms in the investment world, his views on the OCIO model, portfolio construction, the “art” of manager selection, and why ...
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June 18, 2025 • 58 mins
John Trammell has been on the front lines of institutional investing for decades. He’s managed capital for some of the largest families and organizations in the world—from family offices to the Episcopal Church—and in this episode, he explains the seismic shifts happening in the world of endowment and foundation investing.
We talk about secondaries, collateralized fund obligations (CFOs), the future of Bitcoin in institutional port...
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June 16, 2025 • 27 mins
Aaron Jacobson is one of the most insightful thinkers at the intersection of AI, robotics, and cybersecurity—and in this conversation, he separates signal from noise. We explore the future of humanoids, the shifting threat landscape in cybersecurity, and why the next wave of industry-defining companies will be built on infrastructure, not just foundation models.
Aaron Jacobson is a Partner at NEA, where he invests in AI, cybersecu...
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In this episode of How I Invest, I speak with Arjun Sethi—Chairman and co-founder of Tribe Capital, Co-CEO of Kraken, and one of the sharpest thinkers in venture capital and crypto today. Arjun breaks down how he approaches investing in “N-of-1” companies, what most VCs get wrong about data, and why the traditional funding stages like “pre-seed” and “Series A” are being rewritten in real time.
We also go deep into Arjun’s framework...
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June 11, 2025 • 57 mins
What happens when you get fired from one of the most prestigious media companies in the world at age 36? For Michael Loeb, it meant inventing a new category in subscription services, launching one of the earliest venture studios, and incubating Priceline—one of the internet’s first great successes.
In this episode, I speak with Michael Loeb, founder of Loeb.nyc, about how getting fired from Time Inc. led to the $800M sale of Synaps...
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June 9, 2025 • 43 mins
Sasha Pieterse might be best known for her acting career — but behind the scenes, she’s been building a beverage empire.
In this episode, we dive deep into how Sasha's personal health journey led her to launch Hippie Water, a hemp-derived THC beverage brand that’s now in 140+ stores across 9 states. We talk about what it takes to transition from Hollywood to the CPG world, why Gen Z is drinking less alcohol, and how Sasha is redefi...
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June 6, 2025 • 34 mins
This episode is a masterclass on one of the most powerful — and under-the-radar — capital structures in private markets: Small Business Investment Companies (SBICs).
I’m joined by Brett Palmer, President of the Small Business Investor Alliance, and David Demeter, who helps manage Davidson College’s endowment. We dive deep into the SBIC program — a unique public-private partnership that lets private equity and credit funds access 2:...
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June 4, 2025 • 46 mins
What if your venture partner could talk to a thousand founders a day — and actually listen?
In this episode, I speak with Andrew D’Souza, the Founder/CEO (aka Creator) of Boardy and previously the founder and CEO of Clearco (formerly ClearBank). Andrew is building something entirely new: Boardy, an AI super-connector that lives across voice, chat, and email — and introduces people to each other.
He describes Boardy as a principal...
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June 2, 2025 • 69 mins
Alex Robinson is the Co-Founder and CEO of Juniper Square, a company transforming the private markets through technology and service. In this episode, we go deep into how he and his co-founders saw the opportunity to modernize fund administration, why the private markets are decades behind the public markets, and how Juniper Square is building for the future with AI agents. We also discuss how the best GPs scale trust with LPs, why...
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May 30, 2025 • 69 mins
Alexis John d'Amecourt is the coach behind some of the most iconic CEOs in tech today—including the founders of Substack, Eigenlayer, and Booksy. In this episode of How I Invest, I sat down with Alexis to explore what really makes great CEOs tick—and what causes them to fall apart.
We talked about how founders can build trust, navigate emotional turbulence, lead organizations as they scale, and get unstuck when things feel overwhel...
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