Long Strange Trip: CEO to CEO with Brian Halligan

Episodes

David Senra: Mute the World and Build Your Own

June 4, 2026

What do legendary founders have in common? David Senra reveals it's an intense, world-muting focus, a pattern seen from Rockefeller to Jobs.

Notion’s Ivan Zhao: The Refounder

May 21, 2026

Notion's CEO Ivan Zhao on refounding for the AI era. He discusses 'Jazz Mode' leadership, barbell-shaped hiring, and building a company.

Surviving Twitter's Growing Pains: Ex-CEO Dick Costolo

May 7, 2026

Ex-Twitter CEO Dick Costolo on scaling hyper-growth: drive velocity, push decisions down, and solve problems with people, not process.

Does Education Matter in the Age of AI? MIT President Sally Kornbluth

April 16, 2026

MIT President Sally Kornbluth on crisis leadership, sustaining excellence via meritocracy, and adapting education for the AI era.

Jack Dorsey: Every Company Can Now Be a Mini-AGI

April 2, 2026

Jack Dorsey explains his radical vision for companies as 'mini-AGIs,' using AI to eliminate hierarchy and drive decisions from customer data.

Oura’s Tom Hale: What People Don’t Tell You About Being CEO

March 26, 2026

Oura CEO Tom Hale on the CEO grind: navigating the messy middle (200-2k employees), managing global teams, and making tough business model pivots.

The Most Founder Mode CEO Working Today Isn’t the Founder: Opendoor’s Kaz Nejatian

March 12, 2026

Opendoor CEO Kaz Nejatian on his "founder mode" playbook: overriding defaults, building on first derivatives, and aligning family with mission.

Bayer’s Bill Anderson: Turning a 168 Year-Old Tanker Like a Speedboat

February 12, 2026

Bayer's CEO shares his playbook for dismantling bureaucracy: flattening hierarchy, adopting 90-day cycles, and empowering employees.

The Wartime CEO: Vlad Tenev of Robinhood

January 29, 2026

Robinhood CEO Vlad Tenev on navigating extreme crises, maintaining a perpetual "wartime" mentality, and rebuilding trust after public failures.

Harvey CEO Winston Weinberg on Why You Should Tackle Your Hardest Problems First

January 15, 2026

Harvey CEO Winston Weinberg on prioritizing action over perfection, tackling hard problems first, and the relentless intensity required for hyper-growth.

Palo Alto Networks’ Nikesh Arora: Why Context Switching is a CEO’s Most Critical Superpower

January 8, 2026

Palo Alto Networks CEO Nikesh Arora on M&A strategy, platformization, and why context switching is a CEO's most critical superpower.

Goldman Sachs CEO David Solomon: What Startup Founders Get Wrong About the CEO Job

December 18, 2025

Goldman Sachs CEO David Solomon on tough calls, valuing experience over slope, and why a firm's culture must be intentionally and constantly evolved.

Hard Mode: Hypergrowth from Europe with Mati (ElevenLabs) and Anton (Lovable)

December 11, 2025

CEOs of ElevenLabs & Lovable share hypergrowth secrets from Europe: balancing experience vs. potential, nimble planning, & a 996+ culture.

Parker Conrad’s Revenge Fantasy

November 13, 2025

Rippling CEO Parker Conrad on channeling a "revenge fantasy" into a $17B company, scaling intensity, and catching corporate spies.

Long Strange Trip hosted by Brian Halligan

November 11, 2025

HubSpot co-founder Brian Halligan explores the evolving CEO playbook, interviewing leaders to help founders transition to scale-up CEOs.