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PODCAST

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.

business investing

All Episodes

00:43:09

E172: How Cannabis Beverages are Disrupting the...

How I Invest with David Weisburd ·

2025/06/09

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 redefining what it means to be a “celebrity founder.” This conversation

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00:34:38

E171: SBIC Funds: How to Raise $175 Million for...

How I Invest with David Weisburd ·

2025/06/06

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 2:1 fixed-rate, non-recourse leverage from the U.S. government. The

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00:46:46

E170: How an AI Agent Is Outperforming VCs w/Andrew...

How I Invest with David Weisburd ·

2025/06/04

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, not an agent — a character with its own goals, who is building

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01:09:24

E169: How to Build an Enduring Private Equity...

How I Invest with David Weisburd ·

2025/06/02

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 the retail channel still hasn’t arrived in full force, and the

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01:09:36

E168: How I Coach The Top 0.1% CEO's in Silicon...

How I Invest with David Weisburd ·

2025/05/30

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 overwhelming. Alexis also opened up about his own story—from being raised by

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00:58:15

E167: The Hardest Questions Limited Partners Ask GPs...

How I Invest with David Weisburd ·

2025/05/27

Hunter Somerville helps allocate billions of dollars across venture capital at StepStone—and he’s one of the most thoughtful LPs I’ve ever met. In this episode of How I Invest, Hunter gives us a rare look into how top institutional investors evaluate funds, pick managers, and underwrite spinouts before they even happen.We go deep on what separates the best emerging managers from the rest, how LPs think about performance before DPI, and why some GPs win repeatedly while others fade. Hunter also

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00:58:47

E166: $20 Billion CIO: Why Small Cap Stocks Have...

How I Invest with David Weisburd ·

2025/05/23

Brad Conger has a rare view into the evolving dynamics of institutional portfolios—and how allocators can adapt. As Chief Investment Officer of Hirtle Callaghan, a $20B OCIO, Brad is responsible for investment decisions across public and private markets, and he's developed a highly nuanced view of what's working, what's broken, and where alpha really comes from.In this episode, we cover the structural decline of the small-cap index, how private markets have siphoned off the highest-quality growth

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01:05:41

E165: Hollywood Lessons on Risk, Reward, and...

How I Invest with David Weisburd ·

2025/05/20

Alexander Ludwig is best known for his breakout roles in The Hunger Games and Vikings, but behind the scenes, he’s a multi-hyphenate: a passionate actor, a devoted entrepreneur, and the co-founder of Their Jewelry—a sustainable, recycled gold and silver brand he runs with his wife.In this episode, Alexander opens up about the brutal realities of Hollywood, the myth of overnight success, and how ego and humility have shaped his 20-year career. We also dive deep into how he's channeling his platform

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00:33:18

E164: How I Built a Billion Dollar Company by Failing...

How I Invest with David Weisburd ·

2025/05/16

Howard Lerman has founded six companies and taken one public—he's a relentless builder with an obsession for speed, innovation, and execution. Currently the Founder and CEO of Roam, Howard is reimagining what the modern workplace looks like by building the “Office of the Future,” where AI agents work alongside humans to accelerate output.In this episode, Howard joined me in How I Invest Podcast to share the frameworks and mental models behind how he leads teams, scales product-market fit, recruits

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00:47:13

E163: How Thiel Fellows Build Billion-Dollar Startups...

How I Invest with David Weisburd ·

2025/05/13

Zaid Rahman is the founder and CEO of Flex, a breakout fintech startup that’s reinventing credit and payments for the middle market. Backed by the Thiel Fellowship and known for his “Delta 4” product philosophy, Zaid is building a multi-product platform that’s helping profitable, owner-operated businesses unlock capital and scale faster.In this conversation, Zaid breaks down how Flex is using AI to radically reduce underwriting time, why he’s obsessed with hiring 10x talent, and how “taste” and

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01:30:19

E162: Why Most Investors Quit Before Winning w/Cliff...

How I Invest with David Weisburd ·

2025/05/09

Cliff Asness is one of the most influential minds in quantitative investing and the Founder, Managing Principal and Chief Investment Officer at AQR Capital Management, which oversees over $100 billion in assets. In this wide-ranging conversation, we go deep into what makes a successful long-term strategy, how Cliff thinks about building portfolios, and why most investors misjudge both volatility and leverage.He also shares what it was like launching AQR after his early work on momentum strategies

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00:58:27

E161: The Death of Modern Portfolio Theory? w/John...

How I Invest with David Weisburd ·

2025/05/06

John Bowman, CEO of the CAIA Association, joins How I Invest to discuss the most important shift in institutional investing: the move from the traditional bucketed approach to the Total Portfolio Approach (TPA). In this episode, we go deep on how allocators are modernizing portfolio construction, why liquidity might be a hidden danger, and what the future of alternatives will look like as trillions of dollars flow from public to private markets.

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00:41:26

E160: How a SpaceX Rocket Engineer Became a Top Deep...

How I Invest with David Weisburd ·

2025/05/02

Jamie Gull is the GP/Founder of Wave Function Ventures, a deep tech seed fund, and an engineer turned investor who previously worked at SpaceX during its early, intense years of scaling. In this episode, Jamie and I discuss the high-responsibility culture at SpaceX, how it shaped Jamie’s approach to company building and investing, and what makes a deep tech founder stand out. We also explore why fast iteration matters more than perfect planning, how techno-economics drive investment decisions, and

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00:35:21

E159:How a 24-Year-Old VC Landed Cendana Capital as a...

How I Invest with David Weisburd ·

2025/04/29

Paige Finn Doherty, Founding Partner of Behind Genius Ventures, joins the How I Invest podcast to share how she built one of the most distinctive brands in early-stage venture capital — all before turning 25. Paige talks about the power of content and community, how her engineering background shaped her investing style, and why being deliberate about media strategy can transform access to top founders and LPs. She also breaks down her investment thesis around AI in overlooked industries, the

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00:57:04

E158: How to Find the Right LPs for Your Next Fund...

How I Invest with David Weisburd ·

2025/04/25

Meghan Reynolds, Partner and Head of Capital Formation & Talent at Altimeter, has spent over 20 years at the intersection of GPs and LPs, helping some of the largest firms in the world raise capital, navigate investor relationships, and scale their strategies. In this episode, she breaks down what it takes to be a best-in-class capital raiser—how to expand into new strategies, find the right investors (not just any capital), and build enduring partnerships in a hypercompetitive environment.We also

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00:49:11

E157: DA Wallach: Spotting Genius in Elon & Zuck's...

How I Invest with David Weisburd ·

2025/04/22

D.A. Wallach’s journey is one of the most unconventional paths in venture capital. He went from fronting a rock band discovered by Kanye West and Pharrell, to investing in Spotify, SpaceX, and founding a biotech VC firm reshaping human medicine. In this episode, we dive into his evolution—from artist to investor—and what he’s learned from being in the room with Mark Zuckerberg, Elon Musk, and Ron Burkle.D.A. shares why great investing is an act of taste, how he earned his first big break with Ron

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01:11:47

E156: Inside the Mind of a $1.7B Endowment CIO w/Jim...

How I Invest with David Weisburd ·

2025/04/18

Jim Bethea oversees $1.7 billion at the University of Iowa’s endowment—and he does it with a team of just five people. In this episode, we cover how Jim thinks about asset allocation, governance, manager selection, and why Iowa has decided to specialize in certain asset classes like lower middle market private equity. This conversation is full of nuance, clarity, and hard-earned lessons that every allocator, GP, and fund manager will benefit from.Jim pulls back the curtain on how small teams can

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00:41:47

E155: Ben Horowitz: "The Classic VC Model Is Done”

How I Invest with David Weisburd ·

2025/04/15

In this thought-provoking debut episode of Turpentine VC, Erik sat down with Ben Horowitz, Co-Founder of Andreessen Horowitz, to explore the evolving landscape of venture capital, leadership, and the future of innovation. Ben shares his insights on navigating market cycles, building resilient companies, and the role of culture in long-term success. This conversation, recorded live at a16z’s Menlo Park offices in 2023, is packed with practical wisdom and candid stories from one of Silicon Valley’s

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00:43:35

E154: How a First-Generation Immigrant Became a Top...

How I Invest with David Weisburd ·

2025/04/11

Paul Chai’s journey from first-generation immigrant to Chief Investment Officer of a $1 billion endowment is anything but conventional. In this episode, we unpack how he transitioned from aerospace engineering to managing capital, his approach to investing in “outsiders,” and the delicate balance of taking risk in hedge funds, GP stakes, and tactical trades like TALF 2.0. Paul shares how Kansas State University's endowment supports the school’s mission, why they invest in lower middle market buyouts

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00:50:58

E153: Blake Scholl on Boom Supersonic: Learning from...

How I Invest with David Weisburd ·

2025/04/08

Blake Scholl started with a crazy idea: bring back supersonic flight. A decade later, Boom Supersonic pre-orders from the likes of Virgin, United, and American Airlines, and is building the fastest commercial jet since the Concorde—without the sonic boom.But what looks like an inevitable success now was, at the beginning, a nearly laughable dream. In this episode, we break down how Blake went from crashing a Virgin Galactic rollout to pitching Richard Branson over breakfast, to getting a “yes” 24

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