Podcast · 20 episodes
Long Strange Trip: CEO to CEO with Brian Halligan
by Sequoia Capital · English
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.
Latest episodes
Databricks’ Ali Ghodsi Never Wanted to Be CEO. Now He’s Among the BestAli Ghodsi (Databricks CEO) explains how he became CEO, what he learned about leadership and hiring, and how Databricks beat Snowflake by focusing on specific weaknesses and building the “lakehouse”…17 Sep 2026 · 1 h 14 min
The Philosopher CEO | Clay Co-Founder Kareem AminClay (go-to-market engineering) and Kareem Amin’s “philosopher CEO” approach—building from wholeness, committing to reality, creating categories/titles, and aligning teams through clarity while still…23 Jul 2026 · 1 h 9 min
Kalshi’s Tarek Mansour vs. the Federal GovernmentKalshi’s CEO/cofounder Tarek Mansour explains how the company built its “next-generation exchange” (Calci) and navigated years of regulatory resistance, then won a risky lawsuit against the federal…9 Jul 2026 · 1 h 3 min
All episodes
Databricks’ Ali Ghodsi Never Wanted to Be CEO. Now He’s Among the BestAli Ghodsi (Databricks CEO) explains how he became CEO, what he learned about leadership and hiring, and how Databricks beat Snowflake by focusing on specific weaknesses and building the “lakehouse”…17 Sep 2026 · 1 h 14 min · 28 chapters
The Philosopher CEO | Clay Co-Founder Kareem AminClay (go-to-market engineering) and Kareem Amin’s “philosopher CEO” approach—building from wholeness, committing to reality, creating categories/titles, and aligning teams through clarity while still…23 Jul 2026 · 1 h 9 min · 22 chapters
Kalshi’s Tarek Mansour vs. the Federal GovernmentKalshi’s CEO/cofounder Tarek Mansour explains how the company built its “next-generation exchange” (Calci) and navigated years of regulatory resistance, then won a risky lawsuit against the federal…9 Jul 2026 · 1 h 3 min · 33 chapters
David Senra: Mute the World and Build Your OwnDavid Senra argues that great founders share “focus” (his maxim: “mute the world and build your own”).4 Jun 2026 · 57 min · 25 chapters
Notion’s Ivan Zhao: The RefounderIvan Zhao (Notion co-founder/CEO) explains how Notion “refounded” twice—first in Kyoto (2015) to rebuild after missing product-market fit, and again in Cancun (2023) to become AI-native—then details…21 May 2026 · 1 h 3 min · 34 chapters
Surviving Twitter's Growing Pains: Ex-CEO Dick CostoloDick Costolo (Twitter’s third CEO) reflects on Twitter’s early “growing pains” and the leadership tactics he used to speed execution, reduce dysfunction, and manage scale—covering decision velocity,…7 May 2026 · 1 h 8 min · 33 chapters
What Founders Can Learn About Excellence From MIT President Sally KornbluthHow MIT president Sally Kornbluth sustains meritocracy and excellence while scaling a large institution, and what founders/CEOs can learn about leadership during crises, hiring standards, board…16 Apr 2026 · 44 min · 28 chapters
Jack Dorsey: Every Company Can Now Be a Mini-AGIJack Dorsey and Rulof Botha discuss transforming companies into “mini-AGI” organizations by replacing hierarchy with an AI “intelligence layer” over company artifacts, enabling real-time querying,…2 Apr 2026 · 1 h 4 min · 28 chapters
Oura’s Tom Hale: What People Don’t Tell You About Being CEOWhat it’s really like to be CEO of Oura (Aura Ring), especially in the “messy middle” (200–2,000 employees), building a non-hierarchical culture, managing international teams (Finland + US), and…26 Mar 2026 · 1 h · 27 chapters
The Most Founder Mode CEO Working Today Isn’t the Founder: Opendoor’s Kaz NejatianIn this episode, Brian Halligan interviews Kaz Nejatian, the new CEO of Opendoor.12 Mar 2026 · 1 h 3 min · 30 chapters
Ben Horowitz On What Makes a Great FounderIn this episode of "Long Strange Trip: CEO to CEO," Brian Halligan, co-founder of HubSpot and Sequoia partner, engages in a candid dialogue with Ben Horowitz from A16z.26 Feb 2026 · 49 min · 23 chapters
Bayer’s Bill Anderson: Turning a 168 Year-Old Tanker Like a SpeedboatIn this episode, Brian Halligan interviews Bill Anderson, CEO of Bayer, a historic pharmaceutical giant facing challenges typical of large organizations, such as bureaucracy and inefficiency.12 Feb 2026 · 1 h 13 min · 29 chapters
The Wartime CEO: Vlad Tenev of RobinhoodIn this episode, Brian Halligan interviews Vlad Tenev, co-founder and CEO of Robinhood, discussing what it takes to lead effectively during crises.29 Jan 2026 · 43 min · 17 chapters
Harvey CEO Winston Weinberg: Why You Should Reinvent Yourself Every 4 MonthsHarvey CEO Winston Weinberg discusses scaling a fast-growing company by “reinventing yourself every 4 months,” hiring for bias for action, building organizational “machinery” (product + GTM), and…15 Jan 2026 · 57 min · 25 chapters
Palo Alto Networks’ Nikesh Arora: Why Context Switching is a CEO’s Most Critical SuperpowerNikesh Arora (CEO of Palo Alto Networks) discusses CEO “context switching” as a superpower, how to swing big early, and how to build a cybersecurity platform through M&A, roadmap planning, and talent…8 Jan 2026 · 1 h 5 min · 31 chapters
Goldman Sachs CEO David Solomon: What Startup Founders Get Wrong About the CEO JobGoldman Sachs CEO David Solomon explains what founders and startups misunderstand about the CEO role, focusing on culture, decision-making (when to double down vs pull away), hiring for “smart…18 Dec 2025 · 57 min · 25 chapters
Scaling AI Rocketships: ElevenLabs’ Mati Staniszewski & Lovable’s Anton OsikaScaling AI startups with “founder mode” execution during hypergrowth—covering co-founder dynamics, delegation, building exec teams, planning under rapid model/platform change, and operating in Europe.11 Dec 2025 · 57 min · 22 chapters
Intuit CEO Sasan Goodarzi’s Grown-Up CEO PlaybookIntuit CEO Sasan Goodarzi’s “grown-up CEO playbook” covering how to run a company through curiosity, mechanisms for questioning strategy, customer “cold face” learning, SMB go-to-market, channel…20 Nov 2025 · 49 min · 23 chapters
Parker Conrad’s Revenge FantasyParker Conrad explains how Rippling was driven by a “revenge fantasy” after he was violently fired from Zenefits, then how he built and scaled Rippling through CEO “go and see” tactics,…13 Nov 2025 · 1 h 17 min · 30 chapters
Long Strange Trip hosted by Brian HalliganBrian Halligan (HubSpot co-founder/longtime CEO) introduces “Long Strange Trip,” focusing on how startup founders evolve into scale-up CEOs as leadership playbooks are “torn up” and rethought across…11 Nov 2025 · 1 min