How I Invest with David Weisburd

Rip Reeves, CEO of Institutional Investor and former CIO of AEGIS, shares valuable insights from his 40-year career in investment management. He discusses his unconventional journey from Salomon Brothers to leading a major investment platform. Rip emphasizes the importance of building genuine relationships in finance, the flexible nature of endowment portfolio allocation, and the resurgence of fixed income. He also reveals how casual conversations can influence managerial evaluations and the evolving dynamics between investors and fund managers.

John Trammell, a seasoned institutional investor leading investments for the Episcopal Diocese of New York, dives into the changing landscape of endowment investing. He discusses why top universities are offloading assets in secondary markets and how this helps manage underperforming investments. Trammell argues that a concentration strategy has fueled great fortunes, while highlighting the critical role of liquidity today. He also examines Bitcoin's emerging role in portfolios and the importance of building conviction to navigate market challenges.

Aaron Jacobson, a partner at NEA with a rich background in AI, robotics, and cybersecurity, dives into the feasibility of Elon Musk's prediction of 10 billion humanoid robots by 2040. He discusses the significant technological hurdles that need to be overcome and contrasts the potential of consumer versus industrial robots. Jacobson also sheds light on the escalating cyber threats expected in the next five years, the importance of penetration testing, and how AI can revolutionize cybersecurity, making this conversation a treasure trove for tech enthusiasts and investors.

In this engaging discussion, Arjun Sethi, Co-Founder and Chairman of Tribe Capital and Co-CEO of Kraken, delves into the future of venture capital and crypto. He shares insights on investing in "N-of-1" companies and the critical differences that set them apart from market leaders. Arjun also discusses how traditional funding stages are evolving, the impact of tokenized equities on capital markets, and his bold predictions for humanoid robotics in defense. His unique perspective on using data-driven strategies reshapes the investment landscape.

Michael Loeb, founder and CEO of Loeb.nyc, shares his journey of resilience after being fired from Time Inc., sparking his path to innovative entrepreneurship. He reveals how he redefined subscription services and co-founded Priceline, one of the first online travel platforms. Loeb discusses the essential role of trust and adaptability in startups and cautions against the dangers of pattern-matching in venture capital. With humor and insight, he illustrates why successful entrepreneurs often thrive in uncertainty and embraces the unique challenges of the AI era.

Sasha Pieterse, actress and co-founder of Hippie Water, shares her journey from Hollywood to the beverage industry. She reveals how her personal health led her to create a hemp-derived THC drink, now in over 140 stores. The discussion dives into why Gen Z is turning away from alcohol, the stigma surrounding cannabis, and the challenges of being a celebrity founder. Sasha also emphasizes the importance of authenticity, strong leadership, and the balance between acting, entrepreneurship, and motherhood in her multifaceted career.

Brett Palmer, President of the Small Business Investor Alliance, advocates for unique capital structures in private markets, while David Demeter manages Davidson College’s endowment and focuses on diverse investments. They delve into the power of Small Business Investment Companies (SBICs), which have outperformed benchmarks by ~4% net IRR. The podcast highlights how SBICs can raise up to $175M with low refinancing risk, making them a pivotal tool for growth in the lower middle market, while also tackling the challenging landscape for small businesses in the U.S.

Andrew D’Souza, the visionary Founder/CEO of Boardy and former CEO of Clearco, discusses his groundbreaking AI super-connector. Boardy engages in over 50,000 conversations, optimizing connections in the venture capital space and facilitating multimillion-dollar deals. With the ability to identify overlooked talent and enhance decision-making, D’Souza reveals how this AI agent prioritizes relationships and judgment, redefining the landscape for startups and investors alike. Tune in to discover how tech can transform networking dynamics!

In this discussion, Alex Robinson, Co-Founder and CEO of Juniper Square, dives into the transformation of private markets through technology. He reveals how a FedEx delivery inspired the firm’s creation and shares the pitfalls of crowdfunding. The conversation highlights the blending of AI and human expertise in fund administration, the focus on building trust with GPs and LPs, and the unique challenges facing a fragmented industry. Robinson also addresses the evolving expectations for investor relations and the strategic importance of personal connections amid growing automation.

In this engaging discussion, Alexis John d'Amecourt, founder of the Mishory Method and a trusted coach to top Silicon Valley CEOs, shares golden insights on what separates remarkable leaders from the rest. He reveals how emotional intelligence transforms company culture and the vital role of coaching for navigating leadership challenges. Alexis delves into overcoming panic as a founder, the fine balance between managing and leading, and the common traits of top performers. He also discusses how childhood experiences can fuel a founder's drive, pairing personal anecdotes with powerful strategies.