Chapter 1: Are you happy with your journey as a founder?
We were constantly like, Salesforce is going to crush us tomorrow. Did you see their announcement? We're dead.
Chapter 2: Does the struggle of entrepreneurship ever stop?
We said that so many times. I'm excited to be on your show.
Chapter 3: How does imposter syndrome affect successful entrepreneurs?
It's kind of our show, Brian. Yeah, that's true. Do you consider yourself retired? I don't think I'll ever retire. But you're not the CEO of a company. No.
Chapter 4: Were the trade-offs in building HubSpot worth it?
I have a whole bunch of interesting stuff going on. Are you happier in this phase of your life than when you were running a $20 or $30 billion company? Or how about happier compared to when you were running a $10 million company?
Chapter 5: Is AI just a bubble in the tech industry?
Where's your levels of happiness been? Because you've founded a company that now has, I don't know, 5,000, 6,000, 7,000 employees, billions in revenue. Now you're retired and you're not retired, but you're not running a company and you're a
Chapter 6: Do you need to be liked to succeed as a founder?
So tell me about your happiness levels between each one. Okay. I'm going to give you like the grading system in my head for number of employees. Like two to 10 employees. I was like a C. I didn't really, I could write code, but no one wanted it. Like you don't add a lot of value at that phase. 10 to 100, I was like an A. I felt like I knew what I was doing.
I had been in, you know, scale-ups before. 100 to 1,000, you know, maybe A minus. Like, I kind of felt like I knew what I was doing. 1,000 to 10,000. I didn't enjoy the... The secret of life is enjoying the passage of time.
Chapter 7: What would you do if you had to start over in business?
I wasn't really enjoying the passage of time.
Chapter 8: What mistakes did you learn from in your entrepreneurial journey?
It was a lot of... I was just working on a lot of stuff I wasn't that interested in. So... Yeah. So it depended on where I was in the history of HubSpot. I had sort of CEO market fit between 10 and 1,000. That's like you're putting 100 to 1,000 in the same category. That's kind of astounding to me. That doesn't seem like those should be in the same category.
So you enjoyed that whole range equally. Yeah, I worked when I, my first job out of school, I was the first BDR at a company called PTC. It's a CAD software company. And I joined, it was like 3 million in revenue. And when I left, it was, you know, billions in revenue. So I sort of saw that journey and I was part of that machine.
And so, you know, I took a lot of that and brought it with me into HubSpot. And I just felt like I knew what I was doing in there and I was working on things I really enjoyed. There's a lot that changes between 100 and 1,000. I just sort of remember being quite motivated and happy with my day-to-day in there.
Very little wary in that phase about what the nom and gov committee of the board thought. Very little interaction with our compliance and legal folks, things like that. Mostly just working on, you know, are the employees productive and happy or are the customers productive and happy? Like really focused on that. And I like that type of work.
Can you go, okay, so your categories were 2 to 10, 10 to 100, 100 to 1,000, and then 1,000 to 10,000. What about how hard you were working, like in terms of hours? Yeah, people talk about 9, 9, 6. That was at least that for both Dharmesh and I. We were pedals to the metal the entire time. And if we weren't working, we were thinking about working. It's not for the faint of heart.
If you look at my life, it's kind of interesting. I'm 58 now. In the years I should have gotten married and had a bunch of kids, I had HubSpot. I'm still single. And yeah, you're kind of married to your company and you're full on. Like the 996 thing, it's at least that for the founders. And I work with a lot of founders today. That's a minimum for the founders, I would say these days.
And you guys said something on a tweet that I thought was, you said it. that I thought was kind of interesting. Like when you're a founder, like 90% of the time stuff's broken and you're dealing with problems and things kind of suck. I'm angry. I'm angry most of the time.
Most of the time.
I'm angry most of the time. 10% of the time it's like, we got this. We got it. Everything's going our way. The winds are back. But it's pretty rare. Like you live your day looking at your Slack and your inbox and your text and it's mostly bad news in there. Well, so tell me, once a company gets to 100 or 1,000 employees or 10,000 employees, does that emotion go away? Same. It's the same ratio.
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