Long Strange Trip: CEO to CEO with Brian Halligan

Tom Hale, CEO of Oura and hardware-software scaling veteran, reflects on the real pressures of leading a growing company. He discusses scaling through the 200–2,000 employee zone, the controversial move to subscriptions and handling backlash, tactics to prevent bureaucracy, keeping customer empathy alive, and the surprising lessons from a Gucci partnership.

Kaz Nejatian, former Shopify CTO turned Opendoor CEO known for product-driven leadership and a 16-day refounding of a public company. He discusses founder mode as owning outcomes, the mechanics of a fast turnaround, tying compensation to performance, making Opendoor AI-native, and the power of decisive life defaults and stewardship.

Ben Horowitz, Andreessen Horowitz partner and author known for tough operational lessons, lays out what breaks founder CEOs and what makes the great ones. He digs into founder mode, constructive confrontation, why bad news must travel fast, decision debt, and the pitfalls founders make hiring VPs of Sales. Brief, blunt, and focused on the hardest leadership choices founders face.

Bill Anderson, CEO of Bayer and transformation leader formerly at Roche/Genentech, explains how he flattened layers, expanded spans of control, and swapped annual budgets for 90-day planning. He talks about bureaucracy’s roots, running organizations like jazz not orchestras, peer-driven feedback, dynamic resource pools, and hiring mindsets that preserve speed as companies scale.

Vlad Tenev, co-founder and CEO of Robinhood known for steering the company through GameStop, outages, and steep market drops. He talks about leading with a constant wartime mindset. Short planning cycles, product events as forcing functions, giving urgent work to your busiest people, and practical ways to rebuild customer trust and keep tempo while scaling.

Winston Weinberg, Co-founder and CEO of Harvey, dives into the intense world of hypergrowth as his AI legal-software company skyrockets to a $190M run rate. He shares the audacious strategy of targeting the toughest law firms for initial sales and the chaos of rapidly evolving structures every few months. With insights on hiring leaders based on action bias, and the importance of clear ownership in decision-making, Winston’s drive for overcoming challenges reflects his unique journey from outsider to tech CEO, offering raw honesty and practical advice for founders.

Nikesh Arora, CEO of Palo Alto Networks and former Google executive, shares insights from his unique journey in tech. He discusses the importance of context switching as a CEO's superpower, blending quick decision-making with comprehensive problem-solving. Nikesh reveals why traditional M&A approaches may fail and champions the unconventional strategy of retaining founders post-acquisition. He emphasizes balancing customer feedback with visionary product development, while navigating the challenges of leadership and managing imposter syndrome in the fast-paced tech landscape.

David Solomon, Chairman and CEO of Goldman Sachs, shares insights from his extensive banking career. He argues that CEOs often face difficult '51/49' decisions, emphasizing the importance of experience over pure intelligence. Solomon reflects on mentorship from industry giants, highlights the value of resilience in hiring, and discusses how partnerships can succeed or fail based on alignment. He also explores how AI will influence the apprenticeship culture and recounts lessons from winding down Goldman’s consumer banking efforts. Plus, some unexpected twists about his passion for DJing!

In a captivating conversation, Mati, CEO of ElevenLabs, and Anton, founder of Lovable, share insights on building hypergrowth startups in Europe. They tackle the challenges of managing co-founder relationships and transitioning from founder to CEO roles. Themes include the need for effective delegation, hiring strategies, and adapting to rapid changes in AI. They highlight Europe's unique advantages like talent and cost while debating work culture intensity. Both offer practical advice for aspiring founders, emphasizing problem obsession and careful co-founder selection.

Sasan Goodarzi, CEO of Intuit, shares his journey transforming the company from boxed software to an AI-driven platform. He emphasizes the importance of curiosity and grit over raw talent while discussing how to maintain agility in a grown-up firm. Sasan elaborates on innovative customer engagement techniques like 'follow-me-homes' and the significance of solving high-value problems for SMBs. He also reveals strategies for successful channel partnerships and the lessons learned from transitioning to SaaS, showcasing how disruption keeps a 40-year-old company young.