Dharmesh Shah, HubSpot's founder, says his biggest mistake was not prioritizing culture and diversity early. Unlike technical debt, culture debt is nearly impossible to fix once a homogeneous team is entrenched. He urges founders to build diversity intentionally from the start, before scaling makes it much harder to change.
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So Dharmesh, if you were given a chance to go back in time and build HubSpot again, what would you do differently?
The one thing that jumps to mind, because this is on the list of like top 3 biggest professional mistakes I've made in my career, is I would start working on culture earlier. So it was several years in before that conversation with Brian happened where we started getting intentional about culture. And part B is recognizing the importance of diversity and building out the early team. Like, I— that candidly, that thought had just not even crossed my mind. We should have made a more deliberate effort. It's much easier to do that and solve for diversity, and it has long-range positive impact, as we're now learning as an industry, as a society, the importance of that. And it's really hard to fix later, right? Once you're at scale, say, okay, well, now we're going to try and go back and pay off what I think of as culture debt. When you have this homogeneous organization where everybody looks like everybody else. Mm-hmm. And technology debt, the good news is if you incur technology debt, most of the time you can refactor that piece of code that you took shortcuts on and you can kind of pay that debt off. Right. It's like, okay, well, I know we took a shortcut. We had to at the time. We needed the product out the door. Culture debt is much more insidious. There's no check you can write. There's no code you can rewrite. The roots of that are sometimes very deeply planted, right? It's like, then first you have to convince the organization that it's important. Then you have to say, well, what does that mean actually? Like, what do you actually do? And then you have to have the patience to say, okay, well, we spent a decade not being as mindful of this as we should have been. It's going to take decades, plural, to actually get it to likely where we want it to be. So my piece of advice would be, think about diversity early. Even though you may not actually get it, at least you plant the seed in your team's head that that's important. Otherwise, if you don't even talk about it, then everybody just assumes that that doesn't really matter.
