Latest Interviews
Showing 91–94 of 94 interview transcripts.
Clear all filtersCoinbase CEO Brian Armstrong Doesn't Know How to Vacation
Brian Armstrong, Harry Stebbings
Coinbase founder Brian Armstrong details his evolution from shyness and a fear of insignificance to a sustained drive fueled by the intrinsic joy of building, continuous learning, and solving large-scale meta problems. Following an existential crisis after his company reached a billion-dollar valuation, he reframed his success metrics to prioritize long-term progress over immediate celebration, rejecting small-scale impact as insufficient for fulfillment. Armstrong now advocates for "work-life harmony," describing his intense, decades-long commitment to building as a positive addiction where professional activities seamlessly integrate with travel and social connection.
Brad Gerstner: Why high interest rates mean low company valuations
Brad Gerstner, Harry Stebbings
The firm advocates for strict valuation discipline by applying a 20% discount to pre-pandemic multiples to ensure margins of safety against rising interest rates. It adjusts capital deployment inversely to market sentiment, expanding during panic but rejecting current growth stock corrections as fully priced rather than genuine opportunities. Looking forward, the strategy targets long-term value creation in cloud and AI sectors, contingent on a stabilized cost of capital and a return to predictable market conditions.
Mac the VC Answers a Quick Fire Round of Questions with host Harry Stebbings | 20VC
Mac the VC, Harry Stebbings, McKeever "Mac the VC" Conwell II
Rare Breed venture capitalist discussed the personal and professional challenges of balancing family life with the long-term demands of multi-fund operations during an appearance at the Harvard Club. The speaker advocated for increased diversity in venture capital and urged greater flexibility toward founders requesting non-disclosure agreements, while highlighting Unspun as a recent investment that leverages 3D printing to create zero-waste jeans. The conversation also emphasized the importance of founder conviction in deal-making and concluded with a call to return to pre-pandemic social norms through a public health message.
Chris Sacca Talks About His Fears For Kids Today & What Kind of Job Everyone Should Work | 20VC
Chris Sacca, Harry Stebbings, Crystal, Bill Gurley
The speaker critiques the hyper-anxious pursuit of elite education and early specialization in youth as drivers of a generational decline in empathy and basic social etiquette. To counteract the monoculture within the technology sector, their organization exclusively hires candidates with backgrounds in service industry or manual labor to foster real-world perspective and humility. Ultimately, the presentation argues that systemic pressures are producing entitled individuals disconnected from the human condition, necessitating cultural shifts in both family prioritization and corporate hiring practices.