Grit

Josh Silverman, CEO of Etsy, shares his transformational journey at the company, where he initially hesitated but accepted leadership during turbulent times. He discusses the importance of energy management and effective delegation, emphasizing a shift in leadership style towards thoughtful decision-making. Silverman also reflects on the emotional toll of layoffs and balances work-life dynamics. Additionally, he addresses the role of AI in the future of handmade artistry, debating innovation versus traditional craftsmanship. His insights reveal a deep commitment to Etsy's community.

In this engaging conversation, Varun Mohan, CEO and Co-founder of Codeium, delves into the importance of hiring exceptional talent over familiar résumés. Leigh Marie Braswell, a partner at Kleiner Perkins, adds her insights into venture capital and the AI landscape. They discuss the transformative impact of AI on coding efficiency and the challenges of achieving genuine product-market fit. Varun also shares the advantages of building in Silicon Valley, emphasizing the need for ambitious and innovative teams to navigate the fast-paced tech sector.

In this engaging discussion, Sal Khan, founder of Khan Academy, shares his journey from hedge fund analyst to educational innovator. He highlights the transformative potential of AI in personalized learning and emphasizes the need for education to disrupt itself continuously. Sal delves into the ethical challenges of monetizing educational resources while maintaining a nonprofit mission. He also introduces Khanmigo, an AI tutor designed with empathy to enhance learning experiences, and reflects on the meaning of grit in his work.

Matt MacInnis, COO of Rippling and a former Apple executive, shares insights on operational leadership and the importance of understanding a company’s mechanics. He likens executive roles to piloting an airplane, emphasizing the need for expertise to troubleshoot issues. Matt discusses overcoming challenges in his entrepreneurial journey, the innovative use of AI for employee evaluation, and the lessons learned from the Silicon Valley Bank crisis. He reflects on grit, teamwork, and the balance between personal and professional life, offering a compelling look at modern leadership.

Jason Kilar, former CEO and co-founder of Hulu and WarnerMedia, reflects on his remarkable career in media. He shares his early obsession with Disney and the invaluable lessons learned during his time at Amazon. Kilar discusses the inception of Hulu, highlighting the innovative spirit needed in today’s streaming landscape. He also tackles the idea of identity, exploring how labels can limit personal growth. With insights on leadership and navigating challenges, Kilar emphasizes the importance of resilience and staying true to one’s values.

Joe Thomas, CEO and co-founder of Loom, shares insights on the emotional journey of selling his video communication company to Atlassian for $975 million. He reflects on the bittersweet reactions from his team and the importance of preserving Loom's culture post-acquisition. Ilya Fushman, a partner at Kleiner Perkins and involved in Loom's funding, discusses the strategic shifts in a rapidly evolving tech landscape. They also delve into the role of AI in future development and the vibrant startup community in Atlanta, emphasizing the essence of grit and resilience.

Rony Abovitz, founder and CEO of SynthBee, has a remarkable background in innovative technology, particularly spatial computing. He shares his vision of a more benevolent AI future, challenging the current powers that control data. Rony dives into the resilience required during the pandemic, his intriguing encounters in tech, including a memorable day with Shaquille O’Neal, and navigating the challenges of leadership transitions. He emphasizes the need for a human-centric approach in tech, blending ambition with empathy to empower individuals.

Sebastian Siemiatkowski, CEO and co-founder of Klarna, shares insights from the fintech landscape and his journey as an immigrant entrepreneur. He reveals his strategic decision to meet with Sam Altman from OpenAI, emphasizing the gap between European startups and Silicon Valley giants. The discussion delves into AI's role in reshaping customer service, tackling growth amidst uncertainty, and the importance of resilience formed through personal and professional challenges. Siemiatkowski's reflections on comfort zones encourage stepping into the stretch zone for true growth.

Kyle Hanslovan, CEO and co-founder of Huntress, shares insights from his journey to building a $1.5 billion cybersecurity firm. He emphasizes the importance of integrity and transparency in leadership, advocating for open communication and even sharing personal finances to foster trust. Partner at Kleiner Perkins, Ev Randle, highlights the rarity of deep diligence in founder-investor relationships. The duo discusses the evolution of leadership in tech, the significance of resilience, and the core values that drive success in high-growth environments.

Mark Fields, former president and CEO of Ford Motor Company, shares his unique journey in the automotive industry. He candidly discusses the challenges of leading Ford during economic downturns and the impact of his family dynamics while commuting. Fields reflects on his transition to retirement, emphasizing purpose and connection after leadership. He also dives into the complexities of the electric vehicle shift and the strategic efforts behind Ford's Le Mans legacy, highlighting both successes and lessons learned in a rapidly evolving market.