Grit

Jay Kreps, Co-founder and CEO of Confluent and a key creator of Apache Kafka, discusses the pivotal role of real-time data in modern business. He shares insights on how companies like Expedia and eBay leverage this technology as their 'central nervous system.' Kreps also addresses the reality behind the myth of AI-driven efficiency, highlighting the long journey to building transformative businesses. The conversation includes personal anecdotes about navigating the challenges of entrepreneurship, balancing work and life, and the evolving dynamics of tech leadership.

Howie Liu, Co-Founder & CEO of Airtable—an AI-native platform trusted by over 500,000 organizations—discusses the challenge of reinventing a no-code giant in the face of AI advancements. He reflects on his entrepreneurial journey, from his early days and Salesforce acquisition to the emotional complexities of scaling. Liu shares insights on the importance of agility, the impact of conversational AI, and the idea of 'refounding' Airtable. He emphasizes how AI can empower everyone to build software and the significance of continuous innovation in the tech landscape.

Bill McDermott, the optimistic CEO of ServiceNow and former SAP leader, shares captivating stories from his diverse career. He recalls his high school deli venture competing against 7-Eleven and the pivotal job interview at Xerox that fueled his ambition. The discussion reveals his unwavering positivity and the importance of resilience, shaped by personal loss and family support. McDermott also reflects on transformative experiences, including a life-altering accident, and how these trials have deepened his connection to his work and ambitions for the future.

In this conversation, Drew Houston, Co-founder and CEO of Dropbox, shares his journey from coding on a bus stop to challenging tech giants. He discusses the vital role of grit in entrepreneurship and how it means embracing discomfort. They explore the impact of AI on remote work, emphasizing collaboration between humans and machines. Drew reflects on leadership challenges in tech, from startup dynamics to solo CEO experiences, highlighting the importance of self-awareness and personal growth in navigating a competitive landscape.

In this engaging discussion, Dan Lee, CEO and Co-founder of Nooks, shares his vision for enhancing sales efficiency through AI automation. He emphasizes that even in a tech-driven world, genuine human connection remains key to sales success. Leigh Marie Braswell, Partner at Kleiner Perkins, provides insights into the future landscape of sales technology. They tackle the revival of cold calling, revealing how innovative tools can modernize traditional methods and enhance team performance. Expect a blend of innovation, friendship, and entrepreneurial wisdom!

Shishir Mehrotra, co-founder of Coda and CEO of Grammarly, shares his journey from YouTube to creating innovative productivity tools. He discusses how the collaboration between Coda and Grammarly redefines context in workflows. Mehrotra reflects on the evolution of digital advertising, navigates the challenges of startup culture, and reveals the importance of data in AI advancements. He also hints at a future where tools become intuitive allies in our work, paving the way for AI-driven communication and seamless digital interactions.

Ivan Zhao, co-founder and CEO of Notion, dives into the power of minimalist design as a differentiator in a crowded software market. He discusses the slow arrival of AI agents in productivity and how Notion's modular system aims to bridge that gap. Reflecting on his journey from Canada to Silicon Valley, Zhao shares insights on mentorship and innovation. He also touches on the art of hiring, emphasizing casual conversations to find the right cultural fit and the balance between work and personal well-being in today's tech landscape.

Steve Kaufer, co-founder and former CEO of TripAdvisor, shares the story behind its rise as a travel giant built on billions of user reviews. He discusses early challenges, the importance of timing, and the transformative power of AI in travel planning. Kaufer reflects on learning from failures and his journey toward creating a browser extension focused on charitable donations. He emphasizes the necessity of social proof in decision-making while also highlighting how technology is reshaping the way travelers find information and make choices.

Garrett Lord, co-founder and CEO of Handshake, and Mamoon Hamid, a partner at Kleiner Perkins, dive into the evolution of AI and career opportunities. They discuss how Handshake is reshaping job recruitment through a high-trust expert network, emphasizing the transition from generalists to domain experts in AI model training. Their personal stories of entrepreneurship highlight the significance of relationships and adaptive business strategies. The duo also explores the balance of job shifts in the AI era, revealing how technology drives efficiency while creating new demands for skilled professionals.

Zach Perret, Co-founder and CEO of Plaid, shares insights from his journey in fintech, including leading Plaid through a failed $5.3B acquisition by Visa. He discusses the emotional challenges of the setback and the pivotal lessons learned about communication and trust. Zach emphasizes the delicate balance between rational and emotional decision-making in high-pressure situations. He also reflects on how Plaid navigates market changes and maintains user obsession—transforming setbacks into a foundation for innovative growth.