

Long Strange Trip: CEO to CEO with Brian Halligan
Sequoia Capital
The CEO rulebook is getting rewritten. Brian Halligan, Sequoia partner and co-founder and longtime CEO of HubSpot, sits down with some of the CEOs who are defining the new one—from hypergrowth AI-native startups to 150-year-old behemoths. Whether you’re an early-stage founder or a scale-up CEO, Brian will be digging for advice you can use on the long strange trip of your own CEO journey.
Episodes
Mentioned books

Dec 11, 2025 • 57min
Hard Mode: Hypergrowth from Europe with Mati (ElevenLabs) and Anton (Lovable)
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.

26 snips
Nov 20, 2025 • 49min
Intuit CEO Sasan Goodarzi’s Grown-Up CEO Playbook
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.

77 snips
Nov 13, 2025 • 1h 17min
Parker Conrad’s Revenge Fantasy
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.

Nov 11, 2025 • 50sec
Long Strange Trip hosted by Brian Halligan
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.


