Long Strange Trip: CEO to CEO with Brian Halligan
Episodes
Surviving Twitter's Growing Pains: Ex-CEO Dick Costolo
07 May 2026
Contributed by Lukas
Dick Costolo took over as CEO of Twitter in 2010, inheriting what he calls "the drama queen of hypergrowth companies." Hired as the adult in the room ...
Does Education Matter in the Age of AI? MIT President Sally Kornbluth
16 Apr 2026
Contributed by Lukas
Sally Kornbluth is president of MIT and one of the best crisis leaders I've come across. Within a year of starting the job, she got summoned – not ...
Jack Dorsey: Every Company Can Now Be a Mini-AGI
02 Apr 2026
Contributed by Lukas
Jack Dorsey (Block CEO) and Roelof Botha (Sequoia partner and Block board member) join to discuss a bold claim they wrote about recently: the traditio...
Oura’s Tom Hale: What People Don’t Tell You About Being CEO
26 Mar 2026
Contributed by Lukas
Tom Hale didn't originally set out to be a CEO - then he put it on his bucket list to prove something to himself. Now he runs Oura, the Finnish health...
The Most Founder Mode CEO Working Today Isn’t the Founder: Opendoor’s Kaz Nejatian
12 Mar 2026
Contributed by Lukas
Kaz Nejatian reveals how he left Shopify to pull off a highly unusual feat: refounding a struggling public company in just 16 days. From first attempt...
Ben Horowitz On What Makes a Great Founder
26 Feb 2026
Contributed by Lukas
A16z’s Ben Horowitz joins me for a raw, unfiltered conversation on what actually breaks founder CEOs, and what separates the great ones from the res...
Bayer’s Bill Anderson: Turning a 168 Year-Old Tanker Like a Speedboat
12 Feb 2026
Contributed by Lukas
Bill Anderson runs Bayer, a 160-year-old pharmaceutical giant that had 100,000+ employees when Bill took the helm. In just two years after becoming CE...
The Wartime CEO: Vlad Tenev of Robinhood
29 Jan 2026
Contributed by Lukas
In this episode, Vlad Tenev pulls back the curtain on what it takes to lead through the kind of crises that would break most CEOs. From waking up at 5...
Harvey CEO Winston Weinberg on Why You Should Tackle Your Hardest Problems First
15 Jan 2026
Contributed by Lukas
This might be my favorite episode yet. Harvey’s Winston Weinberg is the canonical 2026 hypergrowth CEO. He takes us inside what it's really like t...
Palo Alto Networks’ Nikesh Arora: Why Context Switching is a CEO’s Most Critical Superpower
08 Jan 2026
Contributed by Lukas
Nikesh Arora is one of the most fascinating CEOs in tech. He didn’t come up through cybersecurity. He wasn’t a founder. And when he took over Pal...
Goldman Sachs CEO David Solomon: What Startup Founders Get Wrong About the CEO Job
18 Dec 2025
Contributed by Lukas
David Solomon, CEO of Goldman Sachs, says that no easy decisions reach the CEO’s desk - only “51/49” decisions. When I was leading HubSpot, I de...
Hard Mode: Hypergrowth from Europe with Mati (ElevenLabs) and Anton (Lovable)
11 Dec 2025
Contributed by Lukas
This one’s a treat: two AI-native CEOs building some of the world’s fastest-growing startups from outside of Silicon Valley. Mati and Anton are...
Intuit CEO Sasan Goodarzi’s Grown-Up CEO Playbook
20 Nov 2025
Contributed by Lukas
When Intuit was born, the world ran on DOS. Forty years later it is a $180 billion powerhouse serving millions of small businesses, and Sasan Goodarzi...
Parker Conrad’s Revenge Fantasy
13 Nov 2025
Contributed by Lukas
I didn’t think Parker Conrad would get up off the mat when he got ousted from his previous startup, Zenefits. No one in Silicon Valley did. Instead,...
Long Strange Trip hosted by Brian Halligan
11 Nov 2025
Contributed by Lukas
Brian Halligan–Sequoia partner and co-founder and longtime CEO of HubSpot—is on a quest to uncover the new rules of CEO-ing from the best CEOs in ...