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 | 17 | Founded | 7 months ago |
|---|---|---|---|---|---|
| Number of Listeners | Category | Business | |||
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Latest Episodes
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
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 behind founders Jack Dorsey and Ev Williams, Dick spent five years dragging Twitter from a chaotic c... more
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 invited – to testify before Congress alongside the presidents of Harvard and UPenn. You know how that w... more
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Reviews
- 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 Podcasts5RoxWM
United States3 months ago - Brian rules
Great pod
Apple Podcasts5SteveFoxPropUnited States3 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 States3 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 States5 months ago - Good Questions
I have really enjoyed listening. One thing Brian does good at is probing answers and really getting down to root cause or experience. However, Brian could improve by letting guests finish their thoughts before asking thoughtful follow up questions
Apple Podcasts5NakentnsooswnnrntifUnited States5 months ago
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Apple Podcasts | #155 |  Poland/Business |
Apple Podcasts | #184 |  Singapore/Business |
Apple Podcasts | #215 |  New Zealand/Business |
Apple Podcasts | #248 |  Sweden/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 candid conversations with CEOs and founders about leading companies through growth, disruption, and transformation. Episodes frequently cover pragmatic leadership lessons, scaling from startup to scale-up, maintaining culture across geographies, and managing risk, with a strong emphasis on decision-making, transparency, and building resilient organizations. Guests range from AI-native startups to century-old enterprises, often discussing product strategy shifts, go-to-market partnerships, and the realities of guiding a company through crises, M&A, or public markets. Listeners can expect actionable takeaways on hiring, leadership style, and sustaining momentum on the long road from early traction to sustained impact.
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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 7 months ago and published 17 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. Ivan Zhao
2. Dick Costolo
3. Sally Kornbluth
4. Jack Dorsey
5. Roelof Botha
6. Tom Hale
7. Kaz Nejatian
8. Ben Horowitz
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