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)

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: B