How I Invest with David Weisburd

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.

Hunter Somerville, a Partner at StepStone Group, shares insights from his two decades in venture capital. He discusses the misconceptions about emerging managers and reveals what truly gets them funded. Hunter emphasizes the importance of metrics beyond DPI and TVPI, and how LPs assess performance pre-liquidity. He also outlines strategies for fund managers to distinguish themselves and dives into the critical nature of trust in financial partnerships. Plus, his unique time management techniques highlight the delicate balance between work and personal life.

Brad Conger, Chief Investment Officer of Hirtle Callaghan, oversees $20B in investments and shares his insights on small-cap stocks and their structural decline. He explains how private equity has shifted the market dynamics, siphoning off top growth companies. Brad discusses the appeal of illiquidity for investors and the importance of strong processes over predictions. He also reflects on a contrarian bet that paid off in Europe and shares his unique 'crazy trade' for his 90-year-old mother, illustrating creative thinking in investment challenges.

Alexander Ludwig, an award-winning actor from The Hunger Games and Vikings, shares his journey through Hollywood's ups and downs. He reveals the harsh truths behind the myth of overnight success and emphasizes the importance of persistence. Ludwig discusses his sustainable jewelry brand, Their Jewelry, co-founded with his wife, and their innovative plan to recycle e-waste into luxury pieces. He reflects on lessons from Stoicism, recognizing how humility can shape not just careers, but lives in the competitive entertainment industry.

Howard Lerman, the relentless founder and CEO of Roam, dives into the future of work by integrating AI into the modern office. He shares insights on being a 'cockroach' founder, emphasizing resilience as a key to survival. Discover how AI agents can drive productivity and the importance of company culture in recruiting top talent. Lerman explains his nightly 'founder mode' ritual and reflects on the adaptability required for success. Plus, he reveals how cultural memes influence product design and mission.