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)

2026-02-15 · 75 min · 59 entities

episode page audio

Asserted relationships

→ references Winston Weinberg person

0.77

evidence rules-v4
Link in episode "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)": https://linkedin.com/in/winston-weinberg
→ references Ruth Porat person

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evidence rules-v4
Link in episode "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)": https://linkedin.com/in/ruth-porat
→ references glassdoor.com company

0.77

evidence rules-v4
Link in episode "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)": https://glassdoor.com/
→ references Jerry Garcia person

0.77

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Jerry_Garcia
→ references Bob Weir person

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evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Bob_Weir
→ references Phil Lesh person

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evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Phil_Lesh
→ references Ron "Pigpen" McKernan person

0.77

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan
→ references Marketing Lessons Grateful Dead Business book

0.77

evidence rules-v4
Link in episode "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)": https://amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520
→ hosted by Lenny Rachitsky person

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evidence rules-v4
Feed author/publisher: Lenny Rachitsky
→ founded HubSpot company

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evidence rules-v4
co-founded HubSpot
→ founded HubSpot company

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evidence rules-v4
co-founded HubSpot
→ recommended Marketing Lessons Grateful Dead Business book

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evidence rules-v4
Link in episode "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)": https://amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520
→ recommended Marketing Lessons Grateful Dead Business book

0.50

evidence rules-v4
Link in episode "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)": https://amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520
→ works at Shopify company

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evidence rules-v4
CEO of Shopify
→ works at Shopify company

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evidence rules-v4
CEO of Shopify
→ discusses Technology company

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evidence rules-v4
Feed category: Technology
→ discusses Business concept

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evidence rules-v4
Feed category: Business
→ discusses Entrepreneurship concept

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evidence rules-v4
Feed category: Entrepreneurship
→ references penname.co website

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evidence rules-v4
Link in episode "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)": https://penname.co/
→ references hubspot.com website

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evidence rules-v4
Link in episode "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)": https://hubspot.com/
→ references openclaw.ai website

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evidence rules-v4
Link in episode "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)": https://openclaw.ai/
→ references mckinsey.com website

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evidence rules-v4
Link in episode "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)": https://mckinsey.com/
→ references delphi.ai website

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evidence rules-v4
Link in episode "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)": https://delphi.ai/
→ references sonos.com website

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evidence rules-v4
Link in episode "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)": https://sonos.com/
→ references Bhalligan website

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evidence rules-v4
Link in episode "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)": https://delphi.ai/bhalligan
→ references Long Strange Trip person

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evidence rules-v4
Link in episode "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)": https://sequoiacap.com/series/long-strange-trip
→ references Scaling Entrepreneurial Ventures 15.392 company

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evidence rules-v4
Link in episode "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)": https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392
→ references Mens Basketball person

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evidence rules-v4
Link in episode "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)": https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159
→ references Dalai Lama 18 Rules For Living website

0.38

evidence rules-v4
Link in episode "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)": https://prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm
→ references The American Revolution person

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evidence rules-v4
Link in episode "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)": https://pbs.org/kenburns/the-american-revolution
→ references Redsox website

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evidence rules-v4
Link in episode "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)": https://mlb.com/redsox

Entities found in this episode

persons 20

mentioned Winston Weinberg person

0.90

evidence rules-v4
Link in episode "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)": https://linkedin.com/in/winston-weinberg
mentioned Ruth Porat person

0.90

evidence rules-v4
Link in episode "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)": https://linkedin.com/in/ruth-porat
mentioned Jerry Garcia person

0.90

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Jerry_Garcia
mentioned Bob Weir person

0.90

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Bob_Weir
mentioned Phil Lesh person

0.90

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Phil_Lesh
mentioned Ron "Pigpen" McKernan person

0.90

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan
references Winston Weinberg person

0.77

evidence rules-v4
Link in episode "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)": https://linkedin.com/in/winston-weinberg
references Ruth Porat person

0.77

evidence rules-v4
Link in episode "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)": https://linkedin.com/in/ruth-porat
references Jerry Garcia person

0.77

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Jerry_Garcia
references Bob Weir person

0.77

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Bob_Weir
references Phil Lesh person

0.77

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Phil_Lesh
references Ron "Pigpen" McKernan person

0.77

evidence rules-v4
Link in episode "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)": https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan
mentioned Lenny Rachitsky person

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evidence rules-v4
Feed author/publisher: Lenny Rachitsky
hosted by Lenny Rachitsky person

0.55

evidence rules-v4
Feed author/publisher: Lenny Rachitsky
mentioned Long Strange Trip person

0.45

evidence rules-v4
Link in episode "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)": https://sequoiacap.com/series/long-strange-trip
mentioned Mens Basketball person

0.45

evidence rules-v4
Link in episode "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)": https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159
mentioned The American Revolution person

0.45

evidence rules-v4
Link in episode "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)": https://pbs.org/kenburns/the-american-revolution
references Long Strange Trip person

0.38

evidence rules-v4
Link in episode "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)": https://sequoiacap.com/series/long-strange-trip
references Mens Basketball person

0.38

evidence rules-v4
Link in episode "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)": https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159
references The American Revolution person

0.38

evidence rules-v4
Link in episode "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)": https://pbs.org/kenburns/the-american-revolution

websites 18

mentioned penname.co website

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evidence rules-v4
Link in episode "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)": https://penname.co/
mentioned hubspot.com website

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evidence rules-v4
Link in episode "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)": https://hubspot.com/
mentioned openclaw.ai website

0.45

evidence rules-v4
Link in episode "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)": https://openclaw.ai/
mentioned mckinsey.com website

0.45

evidence rules-v4
Link in episode "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)": https://mckinsey.com/
mentioned delphi.ai website

0.45

evidence rules-v4
Link in episode "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)": https://delphi.ai/
mentioned sonos.com website

0.45

evidence rules-v4
Link in episode "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)": https://sonos.com/
mentioned Bhalligan website

0.45

evidence rules-v4
Link in episode "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)": https://delphi.ai/bhalligan
mentioned Dalai Lama 18 Rules For Living website

0.45

evidence rules-v4
Link in episode "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)": https://prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm
mentioned Redsox website

0.45

evidence rules-v4
Link in episode "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)": https://mlb.com/redsox
references penname.co website

0.38

evidence rules-v4
Link in episode "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)": https://penname.co/
references hubspot.com website

0.38

evidence rules-v4
Link in episode "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)": https://hubspot.com/
references openclaw.ai website

0.38

evidence rules-v4
Link in episode "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)": https://openclaw.ai/
references mckinsey.com website

0.38

evidence rules-v4
Link in episode "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)": https://mckinsey.com/
references delphi.ai website

0.38

evidence rules-v4
Link in episode "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)": https://delphi.ai/
references sonos.com website

0.38

evidence rules-v4
Link in episode "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)": https://sonos.com/
references Bhalligan website

0.38

evidence rules-v4
Link in episode "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)": https://delphi.ai/bhalligan
references Dalai Lama 18 Rules For Living website

0.38

evidence rules-v4
Link in episode "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)": https://prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm
references Redsox website

0.38

evidence rules-v4
Link in episode "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)": https://mlb.com/redsox

companys 12

mentioned glassdoor.com company

0.90

evidence rules-v4
Link in episode "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)": https://glassdoor.com/
references glassdoor.com company

0.77

evidence rules-v4
Link in episode "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)": https://glassdoor.com/
mentioned HubSpot company

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evidence rules-v4
co-founded HubSpot
mentioned Shopify company

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evidence rules-v4
CEO of Shopify
founded HubSpot company

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evidence rules-v4
co-founded HubSpot
founded HubSpot company

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evidence rules-v4
co-founded HubSpot
mentioned Technology company

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evidence rules-v4
Feed category: Technology
works at Shopify company

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evidence rules-v4
CEO of Shopify
works at Shopify company

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evidence rules-v4
CEO of Shopify
mentioned Scaling Entrepreneurial Ventures 15.392 company

0.45

evidence rules-v4
Link in episode "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)": https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392
discusses Technology company

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evidence rules-v4
Feed category: Technology
references Scaling Entrepreneurial Ventures 15.392 company

0.38

evidence rules-v4
Link in episode "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)": https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392

concepts 5

mentioned Business concept

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evidence rules-v4
Feed category: Business
mentioned Entrepreneurship concept

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evidence rules-v4
Feed category: Entrepreneurship
discusses Business concept

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evidence rules-v4
Feed category: Business
discusses Entrepreneurship concept

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evidence rules-v4
Feed category: Entrepreneurship
mentioned CEO concept

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evidence rules-v4
CEO

books 4

mentioned Marketing Lessons Grateful Dead Business book

0.90

evidence rules-v4
Link in episode "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)": https://amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520
references Marketing Lessons Grateful Dead Business book

0.77

evidence rules-v4
Link in episode "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)": https://amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520
recommended Marketing Lessons Grateful Dead Business book

0.50

evidence rules-v4
Link in episode "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)": https://amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520
recommended Marketing Lessons Grateful Dead Business book

0.50

evidence rules-v4
Link in episode "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)": https://amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520

Episode description as stored

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” — Brought to you by: Sentry —Code breaks, fix it faster: http://sentry.io/lenny Datadog —Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny WorkOS —Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — 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 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — 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 — 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/w