Why I’m Still Working as a Billionaire Founder

HubSpot co-founder Dharmesh Shah has no direct reports and rotates between three focus areas: brand, culture, and boldness. He spent 300 hours on the culture code deck and takes copywriting courses to master details, believing this beats traditional CEO work that doesn't suit him.
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HubSpot, 15 years old. It seems like you guys like grew pretty fast early on, but has it always felt like a grind? When I see you, I'm like, well, you don't have to do this. Like you could delegate this. You don't have to work here. You're set. You're good. Why are you still doing this? And does it still feel like a grind? And when has it stopped feeling like a grind?
So a couple of things. It's not widely known, but Brian and I as co-founders, we had a kind of heart-to-heart co-founder chat, which I encourage all founders to have. And we had this list of questions we're going to go through. Well, one of the things was around who's going to be CEO, and we decided he's going to be CEO. because I suck at being CEO. You know, I did that with my first startup for 10 years. I'm just not that good at it. So that was kind of decision one. But decision two, which is much, much more unconventional, is that I have no direct reports. So my agreement with Brian was I'm not going to have any management responsibilities in this company. I'm going to be in it 100%, but I'm not a good manager. Now, I'm a reasonably smart guy. If I spent a bunch of time, I could probably, with some coaching, get passably okay at management. Like, I think I could get there. I don't want to spend 10, 20, 30 years of my life getting passively good at something. I'm a big believer in take your strengths, whatever they are, and put all your energy into kind of amplifying those strengths and getting really, really good at that thing. And don't worry about your weaknesses all that much. So I don't want to worry about my weakness managing people. And so we have over 4,000 people at HubSpot. I have zero direct reports. I've never had direct reports in the 15 years. I don't think of it as a grind at all. It's completely discretionary and optional for me. Obviously, I have a lot of kind of vested interest in the company, but in terms of the work that I do, sort of whittled down my life at HubSpot. But I get it down to like 3 things I'm gonna work on, and that I will change those every few years. For a long time, it was like brand, culture, and what I call boldness, which is, is the organization taking on enough risk? Because the temptation is always like, once you start having customers and revenues are growing, things like that, is just the kind of what we call drag the spreadsheets. Like, oh, like here are the numbers, this is how it's growing, we're just gonna drag the spreadsheet and the numbers will flow. Basically, it's to push the organization so we don't do that. So what I do is I'll maniacally focus on whatever those 3 things are. And say no to pretty much everything else. Things will swap in and out. So I've had product in there. I've had platform in there. But on that thing, whatever it is I'm working on. So when I had culture on my list, it's like I spent 300 hours on the culture code deck at HubSpot. I'm going to do everything I can to learn everything I can to try and get culture to be a thing at HubSpot. I find it enjoyable. I get to kind of pick the things. So my three things are different, you know, from year to year. I like to dig into the details. I don't like kind of. floating at 50,000 feet in lofty ivory towers. If I'm gonna work on brand, I'm in there with the marketing team, like reviewing copy and going through the— and this is why I'm taking Sean's copywriting course. Like, I obsess over details. So anyway, yeah.
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