How I Invest with David Weisburd

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.”

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 construction, his views on innovation in asset management, the underrated value of evergreen structures, and the specific ways GPs can tailor their approach to win over insurance LPs. T.C. also shares why he’s cautious on large-cap private equity, how he thinks about downside protection, and what extreme ownership has taught him as a leader. If you want to learn how a CIO with decades of experience invests across public and private markets with an eye toward solvency, surplus growth, and long-term resilience, you’ll want to listen to this one.

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 capitalist sparked his interest in the asset class and how his team has since built a differentiated barbell strategy combining legacy tier-one firms and new emerging managers. We dive into what LPs can do to truly add value to GPs, why fund size and ownership matter, how AI is shifting capital dynamics, and what makes a venture firm truly “differentiated.” Whether you're a founder, a new VC, or an allocator, this episode is full of real LP insights from one of the most thoughtful voices in the game.

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 when evaluating managers today. In this episode, we talk about how UCLA builds conviction in lower-middle-market GPs, how they manage dry powder and fund pacing, and what it was like spinning out UCLA’s investment office into an independent entity.

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—and why patents, perseverance, and purpose are the trifecta behind lasting innovation.

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 he believes building authentic relationships matters more than ever in this industry. We also cover his deep ties to LSU, how he uses qualitative signals (like waiting room conversations) in manager evaluations, and the future of Institutional Investor in a changing GP-LP landscape.

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 portfolios, and why concentration—not diversification—created most of the great fortunes. This is one of the deepest conversations I’ve had on how the smartest long-term investors are thinking today.

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, cybersecurity, and cloud infrastructure. He’s backed companies like Databricks, Horizon3.ai and Veza, and previously worked in tech M&A at Qatalyst Partners. In this episode, we dive into what’s real vs. hype in AI, the future of humanoids, and where the biggest opportunities in infrastructure are emerging.

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 frameworks for scaling world-class companies, the evolution of crypto in a changing political landscape, and the big bets he’s making at the frontier—including humanoid robotics. Whether you're an allocator, founder, or just fascinated by the future of finance, this conversation is packed with sharp insights and original thinking.

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 Synapse back to Time, his early partnership with Jay Walker to incubate Priceline, and what makes a great entrepreneur. We also dive into how Loeb.nyc works, the role of trust and pivots in building companies, and why pattern-matching VCs often get it wrong. Michael doesn’t hold back. He’s honest, funny, and full of war stories from decades of building companies—and backing founders through multiple lives.

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 goes beyond cannabis — it’s about leadership, authenticity, and building brands with staying power.

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 result? LPs can access equity-like returns for credit-like risk, and fund managers gain scale without sacrificing strategy. Most people haven’t heard of it. That’s exactly why we did this episode.

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 goodwill and helping founders, fund managers, LPs, and executives find each other in real time. And here’s the wild part: Boardy is already responsible for over ten multimillion-dollar deals, including helping HF0 select 3 of its 10 portfolio companies, and facilitating LP meetings for emerging fund managers.

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 challenges of building a system of record in a fragmented industry.

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 his grandmother in D.C. after a turbulent childhood to becoming a three-time founder turned executive coach. This conversation is packed with tactical frameworks, powerful analogies, and a ton of heart.

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 shares his own personal playbook—from how he manages his time to the biggest lessons he’s learned over two decades in venture. If you're raising a fund, building a firm, or just curious about how top LPs think, this one is a must-listen.

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 companies, and why illiquidity can actually be a feature—not a bug. Brad also shares how he builds conviction in contrarian positions, what makes a great spinout manager, and why bigger private equity funds may still outperform. If you're building or managing portfolios across public and private markets, this episode is full of actionable insights.

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 and resources to build a purpose-driven business that could help tackle the e-waste crisis. This conversation covers everything from surviving the actor’s feast-or-famine cycle to the importance of storytelling, Stoic philosophy, and finding peace in a hyper-competitive world.

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 S-tier engineers, and instills an almost maniacal level of urgency and creativity across the organization. We talk about what it means to enter "founder mode," why professional managers may soon be obsolete, and how cultural memes shape everything from product design to company mission. If you’re building, investing in, or simply curious about the future of work and AI-native companies—this episode is a must-listen.

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 first principles thinking guide everything from product design to risk management. If you’re building in fintech, hiring in tech, or just obsessed with the craft of company-building, this episode is full of tactical insight.

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 at Goldman Sachs, and what he’s learned about investor behavior across cycles. This is one of the most insightful and entertaining conversations we’ve had on the podcast—and Cliff brings both humor and hard-earned wisdom to the table.

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.

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 why deep tech’s reputation for being overly capital-intensive is becoming outdated. Jamie shares firsthand stories from his time working under Elon Musk, his angel investments in companies like Boom Supersonic and K2 Space, and the founding principles behind Wave Function Ventures. If you're interested in the future of deep tech investing, how to identify category-defining founders, or how hardware startups can scale efficiently, this is a must-listen.

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 importance of institutional-grade operations from day one, and what it really takes to build a lasting venture firm.

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 talk about what’s changed in the last 20 years, how the best GPs handle crisis communication, and why building a brand as an investor matters more than ever.

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 Burkle at Inevitable Ventures, and why he believes biotech is the most exciting place to invest over the next decade. We also discuss how aesthetic intuition applies to investing, how to think in second and third order effects, and what it really means to be contrarian when contrarianism has gone mainstream.

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 still invest in niche, high-performing funds, how to manage investment committee dynamics, and why more isn't always better when it comes to diversification.

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 most influential investors.

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 and small hedge funds, and how they find and evaluate emerging managers.

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 hours before Y Combinator Demo Day. It’s a masterclass in high-agency entrepreneurship and building something audacious from first principles. From pitching billionaires to proving physics, from engineering emotional payoff for teams to raising capital from LPs directly, Blake unpacks how to build hard tech companies that actually work. If you’re a founder, builder, or dreamer, this one’s for you.

In this episode of How I Invest, Evan Fisher, Founder of Portal Ventures, shares his expertise in fundraising, venture capital, and deal flow. He discusses the key elements of successful fundraising, how to craft a compelling pitch, and what investors look for when evaluating opportunities. Evan’s insights provide valuable lessons for both founders seeking capital and investors looking for high-quality deals.

In this episode of How I Invest, Billy Libby, Co-Founder and CEO of Upper90, discusses how his firm is redefining venture capital through a hybrid investment model that combines equity and credit. He shares how Upper90 empowers founders to scale without excessive dilution and offers insights into navigating today’s venture landscape. Billy’s approach to alternative financing provides valuable lessons for entrepreneurs and investors alike.

In this episode of How I Invest, Aaron Hodari, Managing Director at Schechter, delves into the world of wealth management and alternative investments. He shares how his firm navigates market uncertainties, crafts resilient portfolios, and uncovers unique opportunities for high-net-worth clients. Aaron's insights provide valuable lessons for investors seeking to optimize their financial strategies.

In this episode of How I Invest, Logan Allin, Managing Partner and Founder of Fin Capital, shares how his firm uses AI-powered predictive models to evaluate startups. We explore how AI can assess founder DNA, predict billion-dollar outcomes, and transform the venture capital landscape. Logan also highlights the surprising traits that lead to startup success, the advantages of repeat founders, and what the future holds for fintech. This conversation offers valuable insights for investors, entrepreneurs, and anyone fascinated by the intersection of AI and venture capital.

In this episode of How I Invest, I speak with Brendon Parry, Head of Private Markets, Deputy CIO, and Managing Director at TIFF Investment Management. Brendon shares insights on TIFF’s mission to serve nonprofit institutions through tailored investment solutions. He discusses the importance of private market investments, the legacy of leaders like David Swensen, and how TIFF partners with foundations to achieve long-term financial goals. Tune in for actionable strategies and valuable perspectives from a seasoned investment professional.

In this episode of How I Invest, I dive deep into a conversation with Charlotte Zhang of Inatai Foundation. Charlotte shares her approach to managing a $2.4 billion private investment program, the importance of market inefficiencies, and how she strategically builds GP relationships. We explore how Inatai identifies top managers, why LPs are increasingly interested in fundless sponsors, and what makes a great investment philosophy. Whether you're an LP, VC, or just curious about institutional investing, this episode is packed with insights on capital allocation, conviction-based investing, and long-term partnership building.