How I Invest with David Weisburd

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 less...

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...

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 foundati...

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 m...

In this episode of How I Invest, I sit down with Matt Fitzpatrick, CEO of Invisible Technologies and former head of McKinsey’s QuantumBlack Labs. Matt shares his deep insights on enterprise AI adoption, model fine-tuning, and the challenges businesses face when integrating AI into their workflows. We explore why only 8% of AI models make it to production, how enterprises can overcome friction poin...

In this episode of How I Invest, I interview Robert Cherun, an expert in search funds and small-cap investing. Robert shares his journey from launching his own search fund to building and exiting a highly successful business. We dive into the fundamentals of search funds, the economics of acquiring and scaling small businesses, and the key traits that make a successful searcher.

In this special solo episode of How I Invest, I break down one of the most powerful forces in investing: compounding. Over the course of 142 episodes, I’ve discovered that the best investors all leverage compounding—not just in their portfolios but in every aspect of their business. From relationships and reputation to proprietary information and top talent, compounding creates exponential advanta...

In this episode of How I Invest, I interview Scott van den Berg, an expert in celebrity-founded brands and the managing partner of Hotstar VC. Scott shares deep insights into how celebrities are leveraging their platforms to build billion-dollar businesses and why some partnerships thrive while others fail. We discuss the shift in celebrity investments, the rise of creator-led brands, and key less...

In this episode of How I Invest, I have a conversation with Scott Chan, Chief Investment Officer of CalSTRS, to explore how he oversees a staggering $350 billion in assets. Scott shares insights on CalSTRS’ collaborative investment model, their approach to private and public markets, and why they aim to be the "global partner of choice." We also discuss the importance of structural alpha, liquidit...

In this episode of How I Invest, I chat with Balaji Srinivasan—former CTO of Coinbase, General Partner at Andreessen Horowitz (a16z), and bestselling author of The Network State. Balaji shares his vision for how the internet could ultimately succeed America, the rise of network states, and the implications of Bitcoin's exponential growth. We discuss the future of digital governance, crypto democra...

In this episode of How I Invest, I sit down with Erik Hirsch, Co-CEO of Hamilton Lane, a global leader in private market investing. Erik discusses the evolving landscape of private markets and the integration of digital tools like tokenization in investments. He dives into how private markets are becoming more accessible to retail investors and the future of asset management, with a focus on educa...

In this episode of How I Invest, I engage with Jackson Craig, Managing Director and Co-Head of H.I.G. Bayside's U.S. Special Situations and Distressed Debt Strategy. With over 20 years of experience in private equity investing, Jackson shares his expertise on navigating distressed debt markets, building resilient portfolios, and uncovering hidden opportunities in complex financial situations. From...

In this episode of How I Invest, I speak with Jeremy Heer, Managing Director at the University of Illinois Foundation, about the art of networking, the power of super connectors, and the evolving landscape of institutional investing. Jeremy shares his insights on building relationships that drive investment success, the importance of strategic networking, and how attending conferences with intent...

In this episode of How I Invest, I dive deep into a discussion with John Skjervem, Chief Investment Officer at Utah Retirement Systems (URS), to uncover the unique governance and investment strategies behind one of the most innovative public pension funds in the United States. John shares his insights on governance structures, private equity allocations, the benefits of a "fishbowl-free" decision-...

In this episode of How I Invest, I interview Constantine Karides, a Lead Partner at Reed Smith, to discuss the critical role lawyers play in the startup and venture capital ecosystem. Constantine shares insights on what founders and investors should look for in legal counsel, the leverage model law firms use, and how AI is reshaping the legal landscape. From the importance of choosing the right la...

In this episode of How I Invest, I have a conversation with Mel Williams, Co-Founder and General Partner at TrueBridge Capital Partners. We dive into TrueBridge’s pivotal role as Forbes' data partner for the prestigious Midas List, its strategic approach to venture capital fund-of-funds investing, and how the firm consistently identifies and backs the top-performing fund managers. Mel provides a m...

In this episode of How I Invest, I dive deep into a conversation with Henry Ward, CEO of Carta, to discuss his journey building one of the most transformative companies in private market infrastructure. From cap table management to fund administration and beyond, Henry shares his insights on entrepreneurship, innovation, and the future of private equity. We delve into Carta's strategic pivots, its...

In this episode of How I Invest, I connect with Lorenzo Thione, Managing Director at Gaingels, one of the most active and inclusive venture syndicates in the world. Lorenzo discusses his philosophy on diversity, equity, and inclusion (DEI), the democratization of venture capital, and his thoughts on the AI revolution. From his experience building a portfolio of over 100 investments to lessons lear...

In this episode of How I Invest, I dive into a conversation with Nichole Wischoff, Founder and Managing Partner at Wischoff Ventures, to explore her remarkable journey of raising a $50 million fund during one of the toughest markets of 2024. Nichole shares her insights on fundraising strategies, the power of media in deal sourcing, and building a personal brand. She also discusses her unique appro...

In this episode of How I Invest, I sit down with Nick Shekerdemian, entrepreneur, investor, and founding partner of The Venture Collective (TVC). A former Oxford student turned Thiel Fellow, Nick shares his journey of dropping out of university to pursue big ideas and how the fellowship helped shape his path in venture capital. We explore TVC's unique approach to portfolio construction, investing...

In this episode of How I Invest, I sit down with Marcie Frost, CEO of CalPERS, the largest public pension fund in the United States. From her beginnings in public service to leading a $502.9 billion portfolio, Marcie shares her journey and offers insights into managing one of the most influential pension funds globally. We discuss the challenges of governance, integrating climate change risks into...

In this episode of How I Invest, I connect with Ken Smythe, founder of Next Round Capital, to discuss his journey in private markets, lessons from hedge fund management, and the future of thematic investing. Ken shares insightful stories about spotting talent, using key executive moves as signals for investment opportunities, and the rise of AI and defense technology. We also explore the challenge...

In this episode of How I Invest, I sit down with Lawrence Calcano, Chairman and CEO of iCapital, to explore the transformative potential of alternative investments in the wealth management space. Lawrence shares his journey from Goldman Sachs to building iCapital, a platform managing over $200 billion in alternative assets. We dive deep into the challenges and opportunities in democratizing access...

In this episode of How I Invest, I sit down with Felix Ejeckam, Co-Founder and CEO of Akash Systems. Felix discusses how Akash is leveraging synthetic diamond technology to revolutionize cooling for high-power microchips used in AI servers and satellite communications. He shares insights on their $68 million CHIPS Act funding, the importance of U.S. semiconductor manufacturing, and Akash’s journey...