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

(instrumental music plays) 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 HubSpot.

I could become passably okay at management with some training, with some coaching. I don't want to spend N years of my life becoming passably okay at something.

What was that process like to define the culture?

My co-founder and I were having one of our founder's meetings and he said, "Oh, Dharmesh, I hear this culture thing is really important. By the way, can you go do that?" I'm like, "Okay, Ryan, of all the people in all of

(laughs)

... company, it's 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 laughed."

(instrumental music plays) Today my guest is Dharmesh Shah. Dharmesh 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. Dharmesh'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 10 years now, especially while being a startup guy at heart, how he approached creating and scaling the culture of HubSpot, which you'll find both hilarious and inspiring, why founders and product teams are all fighting the second law of thermodynamics, how to zig while everyone else is zagging, how and why Dharmesh 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 Dharmesh Shah after a short word from our sponsors. And if you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and it helps the podcast tremendously. This episode is brought to you by Explo, a game changer for customer facing analytics and data reporting. Are your users craving more dashboards, reports and analytics within your product? Are you tired of trying to build it yourself? As a product leader, you probably have these requests in your roadmap, but the struggle to prioritize them is real. Building analytics from scratch can be time-consuming, expensive and a really challenging process. Enter Explo. Explo is a fully white-labeled embedded analytic solution designed entirely with your user in mind. Getting started is easy. Explo connects to any relational database or warehouse and with its low-code functionality, you can build and style dashboards in minutes. Once you're ready, simply embed the dashboard or report into your application with a tiny code snippet. The best part? Your end users can use Explo's AI features for their own report and dashboard generation, eliminating customer data requests for your support team. Build and embed a fully white-labeled analytics experience in days. Try it for free at explo.co/lenny. That's E-X-P-L-O.co/lenny. This episode is brought to you by Vanta. When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers and automate compliance for SOC 2, ISO 27001, HIPAA and more with a single platform, Vanta. Vanta's market-leading trust management platform helps you continuously monitor compliance alongside reporting and tracking risks. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's V-A-N-T-A.com/lenny. (instrumental music plays) Dharmesh, thank you so much for being here and welcome to the podcast.