How I Invest with David Weisburd

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 points, and the future of AI-powered enterprise solutions. If you’re curious about the intersection of AI and business strategy, this episode is a must-listen.

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 advantages in a hyper-competitive market.

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 lessons from success stories like Ryan Reynolds' Mint Mobile, Kim Kardashian's Skims, and George Clooney's Casamigos.

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, liquidity management, and identifying long-term supply-demand imbalances.

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 democracy, and how decentralized technologies are reshaping global power structures. Whether you're a crypto investor, a technology enthusiast, or someone curious about the future of governance, this episode is packed with thought-provoking insights.

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 education and technology. From the role of RIAs and wirehouses to the impact of digital wallets and tokens, Erik provides deep insights into what’s next for investors at every level. If you're curious about the future of investment opportunities and how they will change by 2030, this episode is a must-listen.

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 sourcing distressed assets to managing risk, Jackson offers a masterclass on investing in challenging environments.

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 can create game-changing opportunities. He also dives into the future of nuclear energy, the role of generalist investors in discovering new asset classes, and the long-term value of investment engagement.

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-making process, and his approach to alternative energy investments. Whether you're curious about pension fund management or the future of disruptive energy investments like nuclear fusion, this episode is a masterclass in strategic thinking and long-term investing.

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 law firm to navigating legal costs effectively, this episode is packed with actionable advice for entrepreneurs, venture capitalists, and investors.

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 masterclass on portfolio construction, risk management, and scaling a successful venture investment platform. Whether you’re an institutional investor, a fund manager, or simply intrigued by the inner workings of venture capital, this episode is packed with essential takeaways.

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 playbook for turning services into scalable software, and Henry's contrarian views on AI and leadership. This episode is packed with lessons for founders, investors, and operators navigating the evolving landscape of private capital.

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 learned from co-founding PowerSet, Lorenzo provides invaluable insights for investors and entrepreneurs alike.

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 approach to fostering relationships in venture capital and why community and authenticity are key drivers of success in this space. This episode is packed with actionable takeaways for emerging fund managers and anyone navigating the world of VC.

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 deep tech and computational biology, and why thesis-driven investing is the future of venture capital. Nick also discusses challenges like founder breakups, scaling value-added strategies, and his thoughts on the next big shifts in technology and bio-defense.

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 investment decisions, and the importance of building a culture of trust and innovation. Marcie also delves into CalPERS’ strategic focus on sustainable investments, diversity, equity, and inclusion initiatives, and how the organization is setting benchmarks in transparency and fiduciary responsibility.

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 challenges facing venture capital and private equity in today’s market, including liquidity bottlenecks and the hunt for alpha in a rapidly evolving landscape. Ken's personal story of resilience and his passion for innovation shine through in this inspiring conversation.

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 to private markets, the role of technology in scaling the alternatives industry, and the growing appetite for private equity and credit among high-net-worth investors. If you're curious about the future of wealth management and the intersection of technology and alternatives, this episode is a must-listen.

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 through tough times to becoming a leader in cutting-edge technology. A must-listen for anyone interested in semiconductors, AI, or transformative tech innovations.

In this episode of How I Invest, I connect with Matt Hougan, Chief Investment Officer at Bitwise Asset Management. Matt shares his expertise on Bitcoin and cryptocurrency investments, offering actionable insights on portfolio allocation, valuation, and the evolving crypto market. From the benefits of a 2–5% Bitcoin allocation to the potential of Bitcoin as a global settlement currency, Matt provides a compelling case for crypto as a transformative asset class. This episode is a must-listen for institutional investors, financial advisors, and anyone curious about the future of digital assets.

In this episode of How I Invest, I sit down with Alifia Doriwala, Co-CIO and Managing Director at RockCreek, a multi-asset and OCIO solutions firm managing $16 billion in assets. Alifia delves into RockCreek’s unique approach to managing customized portfolios for endowments, foundations, and pensions. She shares her perspectives on navigating public and private markets, the evolving role of hedge funds, and the outlook for IPOs and M&A activity in 2025. This conversation is packed with insights for asset managers, institutional investors, and anyone seeking a deeper understanding of market trends and investment strategies.

In this episode of the How I Invest Podcast, I interview David Clark, CIO of Vencap, to discuss the venture capital landscape. We discuss assumptions about small vs. large venture funds, unpack survivorship bias in performance data, and explore the power law dynamics in early-stage and growth funds. David Clark shares Vencap's strategy for identifying top-performing managers, insights on fund size limits, and the implications of political and economic shifts on venture capital. A must-listen for investors seeking a data-driven perspective on navigating the venture ecosystem.

In this episode of How I Invest, I connect with Gregor von dem Knesebeck, Co-Founder and Managing Partner of Blue Future Partners. Gregor shares the story of building a successful fund-of-funds focused on venture capital, emphasizing brand building, portfolio construction, and navigating the unique challenges of venture investing as a family office. This episode provides insights into venture capital portfolio strategies, the power law of returns, and best practices for fund allocation. A valuable listen for emerging fund managers, family offices, and anyone exploring fund-of-funds strategies.

In this episode of How I Invest, I sit down with Elizabeth Browne, Managing Director and Co-Head, Sponsor Solutions Group & Elevate at GCM Grosvenor. Elizabeth shares her deep expertise in GP seeding—a niche yet growing area in private equity—covering topics such as structuring deals, the challenges of building institutional-grade asset management firms, and how to identify and support future industry leaders. This episode is a must-listen for anyone intrigued by the nuances of private equity, the intersection of investing and firm-building, and the future of the seeding market.

In this episode of How I Invest, David Weisburd speaks with Ron Diamond, a renowned expert in the family office space and the founder of Diamond Wealth. Together, they explore the transformative role family offices are playing in private markets, the impending $84 trillion wealth transfer, and the challenges of professionalizing family office operations. Ron also shares his insights on governance, structural alpha, and strategies for raising grounded, ambitious children in wealthy families. A must-listen for anyone interested in the future of family offices and their potential to disrupt private equity and venture capital.

In this episode of How I Invest, David Weisburd is joined by Teddy Gold, the Founder and CEO of 3i, a membership-based platform that connects elite investors. Teddy discusses key insights into private equity, venture capital, and niche investing strategies. He shares his experiences with scaling asset management, navigating the complexities of private credit, and the power of leveraging networks to uncover investment opportunities. A must-listen for those interested in the intersection of high-level investment strategies and the value of relationship-driven networks.

Najada Kumbuli, Vice President, Head of Investments at Visa Foundation sits down with David Weisburd to discuss what makes a first-time fund manager a breakout success, why storytelling matters in impact investing, and why this is the most challenging fundraising market since 2001.

In this episode of How I Invest, we’re joined by Michael Kakenmaster, Director of Investments at Loyola University Chicago. Michael shares his journey and expertise in managing university endowment portfolios, with a focus on private markets and hedge fund strategies. He offers valuable insights on how to build sustainable, diversified portfolios and the strategies that have led to success in his role. We also discuss the evolving landscape of venture capital and how institutions like Loyola are adapting to market changes.

Hansen Ringer, Managing Director at Sepio Capital sits down with David Weisburd to discuss the asset class that delivers equity-like returns without the market risk, what distressed credit reveals about market cycles and investor behavior, and what happens when stocks and bonds move together.

Victor Mayer, Managing Director, Head of Private Wealth at Pantheon sits down with David Weisburd to discuss why top GPs are rushing to evergreen funds, how Pantheon balances small-cap potential and large-cap stability, and the benefits of Pantheon’s no-cost co-investment deals.

James Langer, Chief Executive Officer and Chief Investment Officer at Redmont Wealth Advisors sits down with David Weisburd to discuss how Reason small cap stocks are crushing large caps, the academic approach to outperforming with small cap strategies, and the history of top stocks since 1926.

Chris Dion, Co-Chief Investment Officer and Managing Partner at Brockenbrough sits down with David Weisburd to discuss what makes small buyout funds resilient, how small buyouts outperform big private equity deals, and why the deal leader matters more than the firm.

Christopher Zook, Founder, Chairman, & Chief Investment Officer at CAZ Investments sits down with David Weisburd to discuss the cost of keeping the wrong person on the team, the crucial mistake CEOs make when building a strong culture, and the secret behind faster growth and success.

Jake Paul and Joey Levy, Co-Founders of Betr, sits down with David Weisburd to discuss Jake Paul’s bold vision for the future of sports betting and how the company seeks to become the market leader in the space.

Dean Duchak, Chief Investment Officer at KFF sits down with David Weisburd to discuss the lessons learned from 13 years at KFF, how to create a culture of collaboration in endowments, and Dean’s perspective on diversifying investment strategies.

David Sawyer, Chief Operating Officer & Managing Partner at Legacy Knight : Multi-Family Office sits down with David Weisburd to discuss the top mistakes investors make in GP stakes, why middle-market GP stakes could be a game-changer for investors, and how GP stakes outperform traditional investments in 2024.

Ben Challgren, Principal at Top Tier Capital Partners sits down with David Weisburd to discuss what makes a top-performing fund, the surprising role of local managers in European venture success and the secrets to spotting a winning startup before it’s big.

Charles Hudson, Managing Partner at Precursor Ventures sits down with David Weisburd to discuss how to support first-time fund managers, innovative strategies for sourcing deals in venture capital and tips for success on building relationships with limited partners.

Scott Richland, Chief Investment Officer at Caltech sits down with David Weisburd to discuss key portfolio secrets inside Caltech’s $4.5B endowment strategy, the importance of strategy discipline in asset management and how direct investments are chosen behind Caltech's opportunistic bucket.

Kunal Sood, Managing Director at Pantheon sits down with David Weisburd to discuss how US institutional investors can access Indian venture capital and private equity, key trends shaping India's unicorn startup ecosystem for global investors and how to leverage local expertise to navigate asia-pacific private markets.

David Weisburd speaks with Ryan Serhant, founder and CEO of Serhant, about the explosive growth following the Netflix debut of *Owning Manhattan*. They discuss how the show has transformed the business, increasing market diversification, website traffic, and lead engagement. Ryan also shares his insights on scaling a real estate business, the importance of culture in a distributed workforce, and why he sees Serhant as more than a brokerage—defining it as a sales as a service company with an innovative approach to training and technology. Throughout the conversation, Ryan reflects on his personal journey, the challenges of transitioning from broker to CEO, and the responsibility of building a brand tied to his own name.

Justinas Milašauskas, Investment Manager at Willgrow sits down with David Weisburd to discuss the risks and rewards of investing in spinouts, top lessons learned from investing in venture and private markets and lessons on investing in emerging managers and navigating fragmented markets.

Alex Hormozi, entrepreneur and founder of Acquisition.com, joins David Weisburd to share his journey of building a $150 million net worth. He discusses the lessons learned from losing his fortune twice, the importance of controlling revenue streams, strategic risk-taking in business, insights into scaling businesses, and the mindset required for long-term success. Hormozi also explains how he leverages his social media presence to drive deal flow and growth for Acquisition.com.

Francesca Cornelli, Dean at Northwestern University - Kellogg School of Management sits down with David Weisburd to discuss how private equity firms handle CEO turnover, why private equity firms benefit from enlightened disagreement and diverse opinions, and the importance of mentorship in private equity.

Mark Shoberg, CIO & Partner at Capital Creek Partners sits down with David Weisburd to discuss the keys to successful institutional investing, how large should an endowment be for optimal returns, and how to build the perfect investment platform for family offices and endowments.

Travis Shore, CIO at University of Illinois Foundation sits down with David Weisburd to discuss how CIOs can adapt to the next big change in time, the critical mistakes made in mastering risk in uncertain markets, and identifying which strategy may save your endowment in the next crisis.

Albert Azout, Managing Partner at Level Ventures sits down with David Weisburd to discuss how to spot unicorn founders early in Venture Capital, what separates great fund managers from the rest, and digging deep into the role of data in unpacking venture fund performance.

Rob Rahbari, Senior Investment Officer and Assistant Treasurer at University of Rochester sits down with David Weisburd to discuss the hidden potential that diverse fund managers offer, the missing ingredient in a successful investment strategy, and what role will diversity, equity, and inclusion play in the future of institutional investing.

Drew Myers, Co-Founder and Managing Partner at CrossLayer Capital sits down with David Weisburd to discuss the key to small funds thriving in pre-seed investing, how time diversification tame crypto volatility, and identifying persistent top quartile crypto funds.