7 Brutal Questions for a $20B Founder

**SPEAKER_1** (0:00)
We were constantly like, Salesforce is going to crush us tomorrow. Did you see their announcement?

**SPEAKER_2** (0:05)
We're dead.

**SPEAKER_1** (0:06)
We said that so many times.
I'm excited to be on your show. It's kind of our show, Brian. Yeah, it's true. You couldn't see yourself retired? I don't think I'll ever retire. But you're not the CEO of a company? No. I have a whole bunch of interesting stuff going on. Are you happier in this phase of your life than when you're running a 20 or $30 billion company? Or how about happier compared to when you're running a $10 million company? Where's your levels of happiness been? Because you've founded a company that is now has, I don't know, 5, 6, 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 little bit of a VC and advisor. So, tell me about your happiness levels between each one. Okay. I'm going to give you like a grading system in my head for number of employees. Like 2 to 10 employees. I was like a C.
I could write code but no one wanted it. 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 scale-ups before. 100 to 1,000, maybe A minus. I felt like I knew what I was doing. 1,000 to 10,000, the secret of life is enjoying the passage of time. I wasn't really enjoying the passage of time. I was just working on a lot of stuff I wasn't that interested in. So it depended on where I was in the history of HubSpot. I had 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, my first job out of school, I was the first BDR at a company called PTC. It's CAD software company. And I joined, it was like 3 million in revenue. And when I left, it was billions in revenue. So I sort of saw that journey and I was part of that machine. And so 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 to 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 NAM 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 the customers productive and happy? Like really focused on that. And I like that type of work. Can you go to, 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 are working? Like in terms of hours? Yeah, people talk about 996 That was at least that for both Darmesh and I. We were peddled to the metal the entire time. And if we weren't working, we were thinking about working. It's not for the fain of heart. If you look at my life, it's kind of interesting. I'm 58 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. 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 most of the time. Most of the time. 10% of the time it's like, we got this. We got it. Everything's going our way. The wins are back. But it's pretty rare. 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. It's still mostly a shit sandwich in your inbox. Do you feel existential threat? Like my business, we have plenty of money and very profitable, whatever, but for some reason, I still feel like an existential threat all the time. Whereas if we don't do this well, we're going out of business. Constantly. We were constantly like, Salesforce is going to crush us tomorrow. Did you see their announcement? We're dead. We've said that so many times. Yeah, we tend to overestimate where our competitors do and underestimate what we do. Maybe there's a correlation between how shitty you think you are and how good of an entrepreneur you make because maybe there's no correlation, but there's a correlation between people who start businesses because I noticed that I have like, I personally have very negative self-talk where it's like, you're shit, you're nothing, you have to prove them wrong, you are horrible, you barely growed, you can't do this, you have to, like, and it wears people out, though, because I actually think that that's negative, that's a pretty poor way to motivate people, but it motivates me. I'm the same and that people say, you know, you want to be very positive and positive and motivate the people. I tend to be paranoid. I still, after all these years, have imposter syndrome. I'm a little nervous talking to you today, believe it or not. Really? Why? Yeah, I'm not. Given all the success I've had, my confidence doesn't even remotely help me to bear to it. And my inner monologue is like, you got so much to prove, dude. Don't fuck it up. Does Darmash feel the same way? Yeah, I can't say for sure, but I think very much so. Do most other, so you run in a circle with some of the best entrepreneurs on earth, most successful entrepreneurs on earth. Is that the common thread? Yes, almost all of them. I interview all these CEOs and I ask them during the interviews, do you have imposter syndrome? And they have them on hot because they don't want to say they do. They do. Almost all of them. Let me ask you one more question about all this. And then I want to know about what you're like more of the Sequoia stuff, because I think that's super fascinating. Sometimes I think that with being an entrepreneur, the hard part, I've been thinking about this a lot and I've talked about it a lot, which is the hard part emotionally isn't the risk taking. The risk taking is actually not that challenging, because in a lot of cases, the risk is not that big. And you could like, even if you go big, you can kind of land somewhere and be all right. The hard part is the uncertainty. And like asking yourself, am I spending time for the next six or 24 months on this thing? And will it actually make my life better or get me to where I think I want to go? That uncertainty part is quite challenging.