The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Michael Mauboussin, Head of Consilient Research at Counterpoint Global and acclaimed author, shares insights on investment decision-making. He emphasizes creating safe environments for diverse opinions within teams to enhance decision quality. The discussion highlights the complexity of distinguishing luck from skill, encouraging investors to reflect on their biases. Mauboussin also stresses understanding economic models in venture capital and the importance of personal health practices for cognitive performance, while continuously learning from one’s experiences.

Rafael Illishayev, Co-founder and CEO of GoPuff, discusses his journey from student to leading a billion-dollar enterprise delivering essentials. He shares insights on the challenges of quick commerce, arguing that 10-15 minute delivery is unsustainable. Rafael outlines GoPuff's strategic shift towards profitability by 2024 and reflects on past mistakes in expanding to Europe. He also predicts the future of quick commerce, emphasizing the need for operational efficiency and solid customer retention strategies to thrive in a competitive market.

Brian Singerman, Partner at Founders Fund, shares his journey from Google engineer to a leading venture capitalist. He discusses the stark price mismatch between private and public companies, emphasizing the caution needed in today's investing climate. Brian advises young investors to focus on quality, not speed, during volatile times. He reveals his aggressive investment strategies, including a massive check into Anduril, and highlights the importance of understanding market dynamics. His insights provide a fresh perspective on navigating the ever-evolving venture capital landscape.

Wealth profoundly influences personal relationships and values, as stakeholders share their journeys from financial struggles to success. Insights reveal how successful figures teach their children the value of hard work amidst privilege. Discussions highlight the importance of approaching wealth with humility, essentialism, and a focus on experiences over materialism. Risk management in investing is explored, emphasizing passion over profit. Personal anecdotes illustrate the transformative impact of money on identity and relationships.

Vaibhav Sahgal, VP of Consumer Product at Reddit and former Head of Growth at Zynga, shares invaluable insights on scaling growth teams. He discusses the distinction between value connection and creation, emphasizing that growth is both an art and a science. Vaibhav advises on the right time to hire growth professionals and the common mistakes founders make in the hiring process. He also outlines his structured interview approach, highlighting the essential questions to ask and what to look for in candidates to foster an effective growth culture.

Emil Michael, former Chief Business Officer at Uber, shares his incredible journey from politics to Silicon Valley. He reveals the nuances of Uber's rapid growth, including raising $3BN from Saudi investors in just 60 days. Additionally, Emil offers insights on pivotal negotiations, including how he convinced Microsoft to triple their offer for TellMe. He discusses lessons learned from Uber's M&A challenges and emphasizes the emotional intelligence needed in high-stakes deals, making for a captivating conversation on the intricacies of venture capital and leadership.

Kyle Harrison, General Partner at Contrary and a seasoned venture capital expert, shares his insights on the shifting landscape of investment. He discusses the impending demise of 'so-so' venture firms, exploring what criteria lead to their downfall. Kyle highlights the emergence of dominant players reminiscent of Blackstone in venture capital and how increasing fund sizes impact returns. Additionally, his journey from filmmaking to tech investing reveals crucial lessons about market dynamics and the necessary evolution within VC firms.

Lauren Schwartz, VP of Enterprise Sales at Fivetran, has a rich history in scaling sales from her time at Google and Segment. She shares her journey from being rejected as an eighth grader to becoming a top sales leader. The conversation dives into the importance of a structured interview process for hiring sales reps, revealing common mistakes founders make. Lauren emphasizes the role of resilience in sales and discusses the value of a sales playbook and understanding customer pain points, crucial for startup growth.

Drew Houston, the co-founder and CEO of Dropbox, shares his journey from a college SAT prep startup to leading a cloud storage giant. He reveals the early challenges of joining Y Combinator and securing Sequoia's investment. Drew discusses his evolving leadership style, the impact of self-awareness, and lessons learned from hiring and firing decisions. He even reflects on a near acquisition by Steve Jobs. The conversation also touches on Dropbox's ambitious plans to transform into a comprehensive digital workspace.

Tristan Handy, the Founder and CEO of dbt Labs, shares insights from his journey in the startup world. He reflects on his early experiences at Squarespace and how they shaped his approach to building dbt, now valued at $4.2 billion. Tristan argues that our jobs aren't as hard as we think and emphasizes hiring for potential over experience. He discusses the challenges of remote work dynamics, including the necessity of physical interaction, and critiques the notion of the 'A-team,' advocating for communication and shared values instead.