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Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)

2/15/20261 hr 15 min

Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach.

We discuss:

1. His LOCKS framework for evaluating founders

2. Why you should build your team like the 2004 Red Sox

3. Why hiring “spicy” candidates beats consensus picks

4. Why enterprise sales will be the last white-collar job AI replaces

5. Some of my favorite “Halliganisms”

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Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been

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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

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Where to find Brian Halligan

• X: https://x.com/bhalligan

• LinkedIn: linkedin.com/in/brianhalligan

• Delphi: https://www.delphi.ai/bhalligan

• Podcast: https://sequoiacap.com/series/long-strange-trip

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Brian Halligan

(03:56) The perpetual state of constructive dissatisfaction

(05:25) Coaching CEOs

(07:49) The art of interviewing and hiring

(11:21) Getting the most out of reference calls

(13:10) Homegrown talent vs. big company hires

(16:31) Traits of successful CEOs

(19:40) Brian’s LOCKS framework for evaluating founders

(21:34) Are great CEO’s born or made?

(23:41) Giving effective feedback

(25:54) The future of go-to-market strategies

(31:56) Understanding forward deployed engineers

(34:17) How the CEO role has evolved over the last 20 years

(38:10) Halliganisms

(01:01:18) The CEO’s role in scaling a company

(01:02:41) Lightning round and final thoughts

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Referenced:

• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria

• HubSpot: https://www.hubspot.com

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad

• McKinsey & Company: https://www.mckinsey.com

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang

• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg

• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca

• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel

• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392

• OpenClaw: https://openclaw.ai

• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat

• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159

• Dalai Lama’s 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin

• Glassdoor: https://www.glassdoor.com

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a

• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia

• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir

• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh

• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution

• Delphi: https://www.delphi.ai

• Sonos: https://www.sonos.com

• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan

• The Boston Red Sox: https://www.mlb.com/redsox

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Recommended book:

• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

To hear more, visit www.lennysnewsletter.com

Clips

Snowmobile Crash Epiphany
Founders Work Every Day
The LOCK Algorithm
Build Teams Like ’04 Sox
Interview NDA Deck Hack
Two People Watering Plant

Transcript preview

First 90 seconds

  1. Brian Halligan· Guest0:00

    The thing about being a founder CEO is there's no one there to rescue you. Your parents aren't gonna rescue you, your VC's not gonna rescue you. That kinda hits you when you hit your first crisis.

  2. Lenny Rachitsky· Host0:08

    Starting a company has never been easier. Scaling one into a durable, high-impact organization has never been harder.

  3. Brian Halligan· Guest0:13

    The number of companies formed is going to mushroom over the next 10 years relative to the last 10 years. It's just gonna be hard to stand out and really accelerate.

  4. Lenny Rachitsky· Host0:20

    What's most different about what it was like to be a CEO maybe 10, 20 years ago versus today?

  5. Brian Halligan· Guest0:25

    There's a massive tax in optionality when you can move this fast and try a lot of things. It puts pressure on the CEOs to be faster and better decision-makers.

  6. Lenny Rachitsky· Host0:35

    A lot of people in the world want to be founders. They wanna be CEOs.

  7. Brian Halligan· Guest0:38

    I don't think anyone can do it. People talk about nine, nine, six, it's way more than that. Founders are seven days a week. They're always on. I text Sunday nights. It's full contact.

  8. Lenny Rachitsky· Host0:46

    Do you feel like there are specific profiles or traits to be successful?

  9. Brian Halligan· Guest0:50

    I look for four things. [chuckles] I call it my LOCK algorithm.

  10. Lenny Rachitsky· Host0:54

    [upbeat music] Today, my guest is Brian Halligan, co-founder and longtime CEO of HubSpot. I asked Brian to come on this podcast because he is, more than anyone I've met, a student of the job of a CEO. After leaving HubSpot last year, he became the in-house CEO coach at Sequoia, where he brings together dozens of top CEOs to learn from each other. He does one-on-one coaching with some of the world's top CEOs. He also hosts a popular podcast called Long Strange Trip, where he interviews some of the world's most successful CEOs. In this conversation, we unpack what it takes to be a successful

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