Long Strange Trip: CEO to CEO with Brian Halligan

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.

Parker Conrad, founder and CEO of Rippling and former Zenefits leader, shares his journey from a public ousting to building a $17 billion enterprise. He discusses how revenge fueled his motivation and offers candid advice for founders, emphasizing the importance of operational speed and hiring mentality. Parker reflects on navigating capital raising after criticism and delves into a dramatic dispute with competitor Deel, revealing their investigative tactics. With insights on leadership and hiring philosophies, he tears up traditional CEO playbooks.

Discover the evolving role of the CEO in today's business landscape. Brian Halligan dives into insights from leaders of hot startups and established giants alike. He explores the new playbook for modern CEOs, tackling themes like hypergrowth and innovation. Learn how these executives navigate challenges in an ever-changing environment. This journey is packed with expert advice and transformative lessons for aspiring founders and seasoned leaders.