E201: Top 10 Things LPs Look for in a General Partner w/Matt Curtolo

What does it take to be a truly great limited partner? In this episode, I spoke with Matt Curtolo, a veteran LP who’s worked with some of the most sophisticated institutional investors in the world—Hamilton Lane, MetLife, and Hirtle Callaghan. Today, Matt advises both LPs and emerging GPs, offering a rare perspective from both sides of the table. We dug deep into what separates elite LPs from the pack, how institutional incentives shape decision-making, the paradox of humility and self-promotion among GPs, and why the best partnerships are built on trust, EQ, and long-term thinking. If you're raising a fund—or allocating to them—this episode is a masterclass.

E200: 21 Harsh Truths Nobody Will Ever Tell You - Alex Hormozi

In this episode of How I Invest, I’m joined by Alex Hormozi — entrepreneur, investor, and founder of Acquisition.com — to unpack the mindset and methods that have fueled his success across multiple industries. We dive deep into why entrepreneurship is more a “game of the heart” than the mind, the power of compounding skills, the dangers of “ignorance debt,” and how to strategically decide whether to build skills yourself or bring in outside talent. Alex shares candid stories from his career — from building gyms to scaling software companies — and offers sharp insights on persistence, focus, and eliminating distractions to win long-term. We also explore the nuances of goal setting, why tiny incremental improvements matter when scaled to millions, and the art of building high-value peer networks. Whether you’re an aspiring founder, seasoned operator, or investor, you’ll walk away with concrete frameworks to increase your odds of success — and the conviction to keep playing the game long enough to win.

E199: How Rahul Moodgal Raised $99 Billion by Playing the Long Game

Most people pitch performance. Rahul Moodgal built a career on pitching relationships. In this episode, I go deep with Rahul Moodgal—Head of Investor Relations at Parvus Asset Management and one of the most trusted capital raisers in the hedge fund world. Over his career, Rahul has raised $99 billion across platforms like TCI and Parvus, building decades-long relationships with LPs, endowments, and mission-driven institutions around the globe. We explore how Rahul flips traditional fundraising on its head: opening with the negatives, focusing on long-term alignment, and avoiding the sales-y traps that doom many GPs. If you're a manager trying to understand how world-class LPs think—or an allocator looking to work with truly values-aligned capital—this is the playbook.

E198: How Family Offices Construct Portfolios in 2025 w/Scott Welch

In this episode of How I Invest, I speak with Scott Welch, Chief Investment Officer and Partner at Certuity, a multi‑family office managing over $4 billion in assets. Scott joined Certuity’s Board of Managers in 2020, and now leads the investment strategy and participates actively in risk management across all facets of the firm's investments, including portfolio architecture, asset allocation, investment due diligence, and manager selection We talk about what’s keeping him up at night in public markets, his views on the Fed and interest rate policy, and how Certuity builds globally diversified portfolios that balance risk factor, asset class, and geographic exposure. We also go deep into taxes, where Certuity aggressively harvests losses using market-neutral overlays to create "tax alpha" for their clients.

E197: Why Most Family Offices Fail—7 Lessons from Harvard Professor

Christina Wing is a Senior Lecturer at Harvard Business School, where she teaches the “Family Enterprise” course—a foundational class for the rising generation of family office leaders. She’s also the founder of Wingspan Legacy Partners, where she advises ultra-high-net-worth families on governance, talent, and legacy. In this episode, I sat down with Christina to unpack why most family offices are structurally flawed—and what to do about it. Christina shares insights from advising dozens of families and training hundreds of HBS students from Gen 1, Gen 2, and beyond. We explore the real reason most family offices fail, how to build a high-functioning investment operation, and why separating investment, concierge, and philanthropic functions is critical. Christina also walks me through what makes MSD Capital, the Koch family office, and others stand out—and how the next generation can step up and lead with clarity.

E196: Professor Steve Kaplan: Do Privates Really Outperform the S&P 500?

Why do Harvard and Yale seem to be exiting private equity? What does the most rigorous data actually say about buyout and venture performance? And how should serious LPs think about real estate, hedge funds, and co-investments? In this episode, I’m joined with Steven Neil Kaplan—Professor of Entrepreneurship and Finance at the University of Chicago Booth School of Business, co-creator of the Kaplan-Schoar PME metric, and one of the most widely cited academics in private equity and venture capital. Steve breaks down decades of private market performance data, busts myths around IRRs and overmarking, and gives a rare, honest evaluation of asset class performance through multiple cycles. This conversation is a masterclass in understanding what the real numbers say—direct from the person who helped shape how performance is measured.

E195: 7 Lessons on Family Office Investing w/Stephan Roche

What does it take to manage the wealth of America’s most iconic families? In this episode, I spoke with Stephan Roche, Partner at BanyanGlobal, and former senior executive for the Gates and Walton families. Stephan has had a front-row seat to how some of the world’s most sophisticated family offices think about investing, governance, and multigenerational legacy. At Banyan, he now advises enterprising families on ownership strategy and purpose. We explore the frameworks ultra-wealthy families use to structure portfolios, co-invest alongside GPs, and prepare future generations for stewardship—not just of capital, but of mission and values. Whether you’re managing family wealth or building toward it, this is one of the most insightful conversations I’ve had on long-term investing.

E194: From Broke & Sleeping on the Floor to a $1 Billion Exit w/Tom Bilyeu

Tom Bilyeu went from sleeping on the floor to co-founding and selling a billion-dollar company, Quest Nutrition. Today, he's the force behind Impact Theory, a media studio with a bold mission: pull people out of the Matrix at scale. In this episode, Tom reveals the frameworks that helped him transform from a self-proclaimed “emotionally fragile” dreamer to a high-agency entrepreneur and truth-seeking machine. We cover everything from skill stacking and the physics of progress to first-principles thinking, radical candor in leadership, and how he’s building a real-world version of Ready Player One. If you're obsessed with performance, truth, and high agency thinking, this one’s for you.

E193: GLP-1s, AI & the End of Sick Care: The Next $10B Health Tech Giant

What if your healthcare wasn't about just treating sickness, but maximizing your potential? In today's episode on How I Invest, I spoke with Dr. Cameron Sepah, founder and CEO of Maximus, a performance medicine company pioneering a new paradigm in healthcare. Cameron previously helped build Omada Health, now a billion-dollar public company, and coined the term “digital therapeutics.” Now he's productized his unique medical expertise into a next-gen men's health platform. We talked about the evolution of performance medicine, why testosterone and GLP-1s are changing how Americans manage their health, and how AI is reshaping clinical decision-making. We also dug deep into the personal and systemic failures of the traditional healthcare model — and what the next 10 years will look like as proactive medicine goes mainstream.

E192: Lessons from a Top Pension Turnaround w/Anurag Chandra

In this episode, I spoke with Anurag Chandra, Chief Investment Officer of a single-family office and longtime trustee and former Investment Committee Chair of the San Jose Federated City Employees’ Retirement System (FSERS). Over the past decade, Anurag has helped transform FSERS from one of the worst-performing pension plans in the U.S. into a top-decile performer. He’s also an experienced operator, venture capitalist, and accidental allocator—with hard-won insight into everything from re-risking public portfolios to model delivery and tax-loss harvesting. In our conversation, Anurag shared how EQ, team dynamics, and governance structure often outperform raw IQ in investing—and how he helped rebuild a $2.2B pension plan through careful governance reform, luck, and great timing. We also covered how he now applies those same principles at a nimble family office, blending institutional rigor with operational agility.

E191: Randal Quarles: From Fed Vice Chair to Private Equity Trailblazer

Randal Quarles has been at the helm of some of the most influential institutions in finance and government. From his tenure as Vice Chair of the Federal Reserve and Under Secretary of the Treasury, to his leadership role at The Carlyle Group, Randal brings a rare blend of private market acumen and public sector insight. Today, he's the Chairman and Co-Founder of The Cynosure Group—an investment firm anchored by the Eccles family and built to solve the very structural misalignments that plague private equity for families and foundations. In this conversation, we explore the evolution of private equity, the mismatch between GP incentives and family office needs, the importance of long-duration compounding, and how Cynosure is creating a modern investment firm inspired by the early days of Lazard and Rothschild.

E190: $600 Billion Parametric CIO: Thomas Lee on Markets, Debt & Trust

In this episode of How I Invest, I spoke with Thomas Lee, Co-President and CIO of Parametric, a $600 billion asset manager within Morgan Stanley Investment Management. Tom walks us through how Parametric helps high-net-worth individuals access institutional-quality investment strategies, why customization is the future of asset management, and how their technology powers nearly a quarter million highly personalized accounts. We talk about inflation myths, the credibility of the Fed, and whether the U.S. will eventually inflate its way out of debt. Tom also shares how Parametric brings tax-efficient investing and direct indexing to portfolios as small as $25,000, explains why "investments as a service" is not just a tagline, and offers valuable insights on long-term leadership, scale, and innovation. Whether you're an institutional allocator, wealth manager, or an individual trying to understand the future of investing, this episode is packed with takeaways.

E189: Inside the Goldman Sachs Prop Desk: Lessons from a Top Trader w/Nancy Davis

Nancy Davis spent nearly a decade on Goldman Sachs’ legendary prop desk before founding Quadratic Capital, the firm behind the popular iVol ETF. In this episode, we dive deep into her options-based approach to investing, why she believes most investors manage risk backward, and how her firm is positioning for a potential return of stagflation. We also talk about her early days at Goldman, the psychological traps investors fall into, and why she thinks humility and coachability are underrated superpowers in finance. If you’ve ever wanted to understand volatility, inflation protection, or how to think like a derivatives trader—this episode is for you.

E188: The CAZ Way: Alignment, Access & Asymmetric Upside

Mark Wade leads strategy and investments at CAZ Investments, a Houston-based firm managing approximately $10 billion in assets. In this episode, we unpack the evolution of the alternatives landscape, the rise of evergreen funds, and what it means to lead with alignment—starting with $700 million of insider capital invested alongside clients. Mark gives a candid look at how CAZ sources differentiated deals, manages risk through the “CAZ Case” downside model, and builds trust by investing alongside 7,000+ LPs. We also dig into how the firm leverages NAV-based leverage, the growing appetite for alternatives from RIAs, and why humility is essential when allocating capital. If you're an allocator, an advisor, or simply trying to understand where private markets are headed, this episode is packed with insights from one of the most thoughtful voices in the space.

E187: Why Holding Companies Beat Private Equity w/Matt Foran

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, appraisal and mortgage services, and vacation rentals—StoicLane now manages $300M in TTM revenue and expects $60M in EBITDA this year. But it’s not just the numbers. StoicLane stands out for its permanent capital structure, seller-friendly integration approach, and deep use of technology and AI to transform old-school industries. We dive deep into how Matt thinks about company building, permanent capital advantages, competing with PE firms, and the cultural flywheels StoicLane is creating as they scale.

E186: Where’s the Alpha Opportunity in VC in 2025? w/Abe Finkelstein

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.

E185: Why Institutional Investors Invest into C-Class Real Estate w/Amy Rubinstein

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. Today, her firm consistently delivers 30%+ IRRs by stabilizing mismanaged assets and restoring them to market performance. We talk about her journey from buying a single six-unit property to leading a vertically integrated investment platform, her thoughts on risk and inflation, why C-class housing remains resilient, and how she thinks about scaling her team and her impact.

E184: How Casper Hit $100M in Year One: The Untold Startup Playbook

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 hypergrowth, managing through crisis, organizational design, and the future of climate investing.

E183: How to Raise Institutional Capital w/iConnections CEO Ron Biscardi

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 relief—to anchoring flagship “Global Alts Miami” events, Ron discusses the strategy of building trust, technology, and community in capital formation.

E182: Lessons from 17 Years at Menlo Ventures and Accel w/Tyler Sosin

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 dominant franchises that can compound their growth and relative market share over decades. The name of the firm, Villain, was inspired by a quote by Harvey Dent, a character in the Batman film The Dark Knight, who said to Batman, “You either die a hero or see yourself live long enough to become a villain.”