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
96 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.
