Latest Interviews
Showing 1–6 of 6 interview transcripts.
Clear all filters- Goldman Sachs18 min
Winning the Right to Invest: 20VC’s Harry Stebbings
Harry Cassell reframes media distribution as a critical weapon for securing investment rights, leveraging a data-driven content strategy that generated $6.1 million in 36 hours to differentiate his platform from traditional venture capital models. Critiquing the current market's saturation by large multi-stage funds, he emphasizes founder empathy, specific personality traits, and a robust LP network to navigate an environment where capital is commoditized and growth expectations have shifted. Looking toward Europe, Cassell predicts a decade of massive company creation driven by lower barriers to entry and increased founder resilience, citing early successes like Lovable as evidence of a reinvigorated ecosystem ready to compete globally.
Scooter Braun on Being Enough, Insecurity, Wealth, Investing, Fame, Marriage and Much More
Scooter Braun, Scott Braun, Harry Stebbings
Venture investor Harry Stebbins interviews Scooter Braun to explore the dissonance between external success and internal well-being, with Braun detailing his journey from a childhood "shame lie" to the transformative power of the Hoffman Process at age 39. Braun advises Stebbins to replace the pursuit of work-life balance with harmony, drawing on his own investment experiences and personal crises to illustrate that faith, rather than control, is essential for navigating fear and mediocrity. The conversation concludes with Braun emphasizing the critical importance of accountability, identity, and unconditional love for raising the next generation of leaders while dismantling the illusion that wealth guarantees happiness.
Rob Lacher: How I Scaled to $600M AUM; Hiring Tips for VCs; Venture Capital in Europe vs USA | E999
Visionaries deploys a €150M fund to bypass crowded Series A rounds, targeting Pre-Seed, Seed, and Series B/C stages by leveraging a unique network of 30 digital entrepreneurs and 25 family business leaders. The firm prioritizes long-term B2B value creation and founder alignment over momentum investing, utilizing a strategy that allocates 80% of seed capital for significant ownership stakes while rejecting early secondary sales to ensure sustained growth. Driven by a portfolio that previously returned 10x with multiple unicorns and decacorns, the organization aims to evolve into a self-sustaining ecosystem by 2028 where billionaire founders reinvest in the next generation of sustainable innovation.
Bill Ackman's Biggest Loss of All-Time
The speaker details the forced liquidation of Gotham Partners five years before the 2008 crisis following an MBIA white paper that triggered legal investigations and regulatory actions, alongside personal hardships during a 2015 to 2017 business downturn. Applying lessons from these structural failures regarding asset-liability mismatches, the founder established Pershing Square to invest exclusively in liquid large-cap companies while prioritizing rigorous internal reviews of both realized losses and missed opportunities like the Netflix position. Ultimately, the narrative emphasizes a resilience strategy combining physical health, supportive networks, and the discipline to reset after defeats, illustrated by a $2.8 billion interest rate hedge that remains regretted only for its insufficient capital allocation.
Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996
Jackie Reses, former Square executive, founded The Bank We Wanted to See to build a scalable fintech infrastructure targeting high-growth tech and crypto sectors that existing providers fail to serve. Her leadership philosophy prioritizes innate grit and honest feedback over resume pedigree, fostering a high-performance culture while she negotiates deals by focusing on regulatory speed and long-term partner value rather than immediate economic leverage. Reses aims to establish Lead Bank as a global innovator by 2028, leveraging her expertise in compliance and finance to guide the next decade of fintech through an anticipated market rationalization and return to first principles.
Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994
Dara Khosrowshahi, Harry Stebbings
Dara Khosrowshahi applies a philosophy of sustained excellence and calculated risk to guide Uber through its transformation from a crisis-ridden startup into a globally dominant logistics platform. By prioritizing marketplace technology over failed hardware ventures and correcting strategic missteps in delivery, he has successfully orchestrated complex supply-and-demand matching while shifting the board's focus from control to organizational success. His leadership approach emphasizes hiring for clarity of thought, maintaining a "plastic mind" to embrace mistakes, and allocating capital with a long-term perspective that balances Wall Street expectations with aggressive growth.