Long Strange Trip: CEO to CEO with Brian Halligan
Sequoia CapitalThe 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.
| Publishes | Twice monthly | Episodes | 19 | Founded | 8 months ago |
|---|---|---|---|---|---|
| Number of Listeners | Category | Business | |||
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Latest Episodes
I had Kareem Amin all wrong. When Clay first crossed my radar, I thought he was too laid-back: no chip on his shoulder, not the hungry founder I expected to win. Clay has since exploded.
Kareem builds from what he calls "a place of wholeness" rathe... more
Tarek Mansour calls himself a paranoid risk manager - the guy who can list 20 ways a hot air balloon will go down before it leaves the ground. Then he bet his entire company on suing its own regulator.
Kalshi spent years walking through the desert. ... more
David Senra has spent a decade reading the biographies of 400+ founders for his podcast Founders - and lately he's started interviewing the living ones face to face. He joins me to share what all of them actually have in common, and it isn't what Sil... more
Ivan Zhao, founder and CEO of Notion, joins me to introduce a new contender in the founder mode debate: jazz mode. Ivan has a different take than Jack Dorsey's circular org chart or Brian Armstrong's player-coach approach. He thinks hierarchy is huma... more
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- Must-to-have for founders
It’s beyond my expectation. This pod reveals enormous amount of wisdom, insights and aspirations from established or scaled founders and CEOs. Each of this episode worth of listening many times to fully digest the context. It’s a lot to contain in one hour. And as a founder, listening to Brian’s Long Strange Trip, is absolutely one of the most refreshing, inspiring and enlightening time during our long strange entrepreneurial trip.
Apple Podcasts5HIL_GUO
United Statesa month ago - I love it! (+ feedback)
This is my favorite podcast! Obviously this is meant for CEOs/founders but as a VP level operator who reports up to a CEO at a high growth tech company (Sequoia backed!), I listen for insights into how CEOs make decisions so I can in turn be a more effective leader/direct report. I’m sure many other folks are doing the same. Would love more conversations around what CEOs need from their deputies so they can lead more effectively. Either way, I love this podcast and Go Sox!
Apple Podcasts5RoxWMUnited States4 months ago - Brian rules
Great pod
Apple Podcasts5SteveFoxPropUnited States5 months ago - More startup founders please
Winning concept - guest calibre is excellent and it’s cool that Brian can relate things back to his personal experience. Lean into the founder access afforded by Sequoia and Brian’s network. Way more interesting to hear from the next generation of legendary founders than from super established companies. Winston episode was the best. Wish the Mati and Anton episodes were two separate episodes
Apple Podcasts5Jack-HannahUnited States5 months ago - Great insights but flow could be better.
I recently started listening to this podcast and ripped through all of the episodes because of the good content. I do enjoy it a lot and I hope it continues with many other guest speakers. Some feedback, I did feel at times that answers were cut short from the CEOs, and it would be nice to hear their full answer. As well, the questions could be a bit more structured; the free-flow conversation is nice at times, but other times, as a listener, I’d prefer to hear as much useful information as poss... more
Apple Podcasts4Jesse DochertyUnited States6 months ago
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Apple Podcasts | #226 |  Norway/Business |
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Frequently Asked Questions About Long Strange Trip: CEO to CEO
What is Long Strange Trip: CEO to CEO about and what kind of topics does it cover?
The show features in-depth conversations with high-profile CEOs, founders, and leaders about the realities of scaling, refounding, and leading through disruption. Across episodes, topics include founder archetypes, AI-native transformations, crisis leadership, organizational design, culture, governance, and practical leadership tactics for both startups and long-established enterprises. A common thread is candid, experience-driven insight from leaders who have navigated rapid growth, complex transitions, and strategic pivots, often with a focus on the human side of leadership and decision-making. The format tends to blend personal stories with actionable takeaways, making it valuable for current and aspiring CEOs seeking tangible guidance a... more
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Which podcasts are similar to Long Strange Trip: CEO to CEO?
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How many episodes of Long Strange Trip: CEO to CEO are there?
Long Strange Trip: CEO to CEO launched 8 months ago and published 19 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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What guests have appeared on Long Strange Trip: CEO to CEO?
Recent guests on Long Strange Trip: CEO to CEO include:
1. Tarek Mansour
2. David Senra
3. Ivan Zhao
4. Dick Costolo
5. Sally Kornbluth
6. Jack Dorsey
7. Roelof Botha
8. Tom Hale
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