Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO)

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. You have no direct reports, and I don't believe you've ever had direct reports at Hobspot. I could become passively okay at management with some training, with some coaching. I don't want to spend N years of my life becoming passively okay at something. What was that process like to define the culture? My co-founder and I were having one of our founders' meetings and he said, Oh, Darmesh, I hear this culture thing is really important. By the way, can you go do that? I'm like, Okay. Right. Well all the people and all me is like I am like the worst possible person. It's not that I don't like people, I just don't like being around them a whole lot. Something that's really unique and interesting about you is you're obsessed with comedy and keynote prep. It comes down to this metric that stand up comedians use called LPM laughs per minute. I have custom software that I've written that will say, Okay, here are the points at which the audience Laugh.

Today my guest is Darmesh Shaw. Darmesh is the co-founder and CTO of HubSpot, and also one of the most fascinating and first principled thinkers I've ever met. In our conversation, we cover a lot of ground. Darmesh's hilarious and ingenious approach to putting together a talk. Including measuring laughs per minute.

His biggest lessons from being a public company exec for over ten years now, especially while being a startup guy at heart. How he approached creating and scaling the culture of HopSpot, which you'll find both hilarious and inspiring. Why founders and product teams are all fighting the second law of thermodynamics, at a zig while everyone else is zagging, how and why Darmesh leans into his strengths, including never having a single direct report during his 18 years of running HubSpot. And so much more, this episode is so fun and will expand your mind in many ways. With that, I bring you Darmesh Shaw after a short word from our sponsors.

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