Dharmesh Shah

Co-Founder & CTO at HubSpot

Co-founder and CTO of HubSpot; one of the most first-principled thinkers in tech; has zero direct reports by choice; known for defining HubSpot's culture code, measuring laughs per minute in keynotes, and deliberately contrarian product strategy.

The Operator The Visionary

Dimension Profile

Strategic Vision 80%

Execution & Craft 60%

Data & Experimentation 60%

Growth & Distribution 60%

Team & Leadership 70%

User Empathy & Research 50%

Key Themes

contrarian startup strategy culture definition by introverts laughs per minute metric zero direct reports CTO public company lessons first principles thinking

Episode Summary

Dharmesh Shah, co-founder and CTO of HubSpot, shares his deliberately contrarian approach to building: choosing to build a broad platform when everyone said to focus, being a CTO with zero direct reports, and having the company's biggest introvert define its culture code. He discusses lessons from 10+ years as a public company exec while remaining a startup person at heart, and his engineering approach to keynotes using custom software to measure laughs per minute.

Leadership Principles

→ One of our early zigs was doing exactly the opposite of 'focus on one thing' — HubSpot deliberately built a broad platform when conventional wisdom said to specialize
→ I could become passably okay at management with training, but I don't want to spend years becoming passably okay at something — play to your strengths instead
→ Culture shouldn't be defined only by extroverts — an introvert who doesn't like being around people can still codify culture through writing and systems

Notable Quotes

"Some of the best startup advice I've heard is startups should focus on one thing and be really, really exceptionally world-class at that one thing. And one of our early zigs is we are going to do exactly the opposite of that."
— On HubSpot's deliberately contrarian product strategy

"I could become passively okay at management with some training, with some coaching. I don't want to spend any years of my life becoming passively okay at something."
— On why he's never had direct reports as CTO

"My co-founder said, 'I hear this culture thing is really important. Can you go do that?' I'm like, of all the people in the company, I am the worst possible person. It's not that I don't like people, I just don't like being around them a whole lot."
— On the irony of an introvert defining HubSpot's famous culture code

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