Speakers: Sam Parr (host), Shaan Puri (host)
Brian Halligan: We were constantly like, “Salesforce is going to crush us tomorrow. Did you see their announcement? We’re dead.” We said that so many times. I’m excited to be on your show.
Shaan Puri: It’s kind of our show, Brian.
Brian Halligan: Yeah, it’s true.
Shaan Puri: Do you consider yourself retired?
Brian Halligan: I don’t think I’ll ever retire.
Shaan Puri: But you’re not the CEO of a company.
Brian Halligan: No, I have a whole bunch of interesting stuff going on.
Happiness and the Scale of a Company [00:00:32]
Shaan Puri: 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? Where have your levels of happiness been? Because you’ve founded a company that now has 5,000, 6,000, or 7,000 employees and billions in revenue. Now you’re not retired, but you’re not running a company; you’re a bit of a VC and an adviser. Tell me about your happiness levels between each one.
Brian Halligan: Okay, I’m going to give you a grading system in my head for the number of employees. Zero to 10 employees: I was 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 an A. I felt like I knew what I was doing. I had been in scale-ups before. 100 to 1,000: maybe an A-minus. I felt like I knew what I was doing. 1,000 to 10,000: I didn’t enjoy it.
The secret of life is enjoying the passage of time. I wasn’t really enjoying the passage of time. It was a lot of working on 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.
Shaan Puri: You’re putting 100 to 1,000 in the same category. That’s astounding to me. It doesn’t seem like those should be in the same category. So, you enjoyed that whole range equally?
Brian Halligan: Yeah. When I had my first job out of school, I was the first BDR at a company called PTC. It’s a CAD software company. I joined when it was at $3 million in revenue, and when I left, it was billions in revenue. I saw that journey and I was part of that machine. I took a lot of that and brought it with me into HubSpot. I felt like I knew what I was doing there and I was working on things I really enjoyed.
There’s a lot that changes between 100 and 1,000. I just remember being quite motivated and happy with my day-to-day in there. There was very little worry in that phase about what the Nominating and Corporate Governance committee of the board thought. There was very little interaction with our compliance and legal folks. I was mostly just working on whether the employees were productive and happy and whether the customers were productive and happy. I really focused on that, and I like that type of work.
The Reality of Founder Life: 996 and Imposter Syndrome [00:03:15]
Shaan Puri: Can you go through your categories again? They 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 in terms of hours?
Brian Halligan: People talk about 996. That was at least that for both Dharmesh and me. We were pedal to the metal the entire time. 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 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. You’re married to your company and you’re full-on with the 996 thing. It’s at least that for founders. I work with a lot of founders today, and that’s a minimum for founders these days.
You guys said something on a tweet that I thought was interesting. You said that when you’re a founder, 90% of the time stuff is broken and you’re dealing with problems and things suck.
Shaan Puri: I’m angry. I’m angry most of the time.
Brian Halligan: 10% of the time it’s like, “We got this.”
Shaan Puri: “We got it. Everything’s going our way. The winds are back.” But it’s pretty rare. You live your day looking at your Slack, your inbox, and your texts, and it’s mostly bad news in there. Well, tell me, once a company gets to 100, 1,000, or 10,000 employees, does that emotion go away?
Brian Halligan: It’s the same. It’s the same ratio. It’s still mostly a sh*t sandwich in your inbox.
Shaan Puri: Do you feel existential threat? My business has plenty of money and is very profitable, but for some reason, I still feel an existential threat all the time where it’s like, “If we don’t do this well, we’re going out of business.”
Brian Halligan: Constantly. We were constantly like, “Salesforce is going to crush us tomorrow. Did you see their announcement? We’re dead.” We said that so many times. We tend to overestimate what 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. Maybe there’s no correlation, but there’s a correlation between people who start businesses because I noticed that I personally have very negative self-talk where it’s like, “You’re nothing. You have to prove them wrong. You are horrible. You barely grow. You can’t do this.” It wears people out, though, because I actually think that’s a pretty poor way to motivate people. But it motivates me.
Brian Halligan: I’m the same. People say you want to be very 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.
Shaan Puri: Really? Why?
Brian Halligan: Given all the success I’ve had, my confidence doesn’t even remotely compare to it. My inner monologue is like, “You’ve got so much to prove, dude. Don’t screw it up.”
Shaan Puri: Does Dharmesh feel the same way?
Brian Halligan: I can’t say for sure, but I think very much so.
Shaan Puri: You run in a circle with some of the best and most successful entrepreneurs on earth. Is that the common thread?
Brian Halligan: Yes, almost all of them. I interview all these CEOs and I ask them during the interviews if they have imposter syndrome. They hem and haw because they don’t want to say they do, but they do. Almost all of them.
Shaan Puri: Let me ask you one more question about all this, and then I want to know more about the Sequoia stuff because I think that’s super fascinating. Sometimes I think that with being an entrepreneur, the hard part—and I’ve been thinking about this a lot—is that 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 can land somewhere and be all right.
The hard part is the uncertainty and 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 looking back. Was dedicating all this time worth it? Do you look back at the last 20 years and think that was a life well-lived, or would you have changed anything?
Brian Halligan: No, I think it was. I’ll take the trade-off. It was a lot of fun. There was just a lot of joy. The people at HubSpot are amazing. The customers are amazing. Partners are amazing. There were so many happy times. A lot of down days, but the up days definitely outweigh it. I’m super proud of what we built. I wouldn’t trade it.
The thing I would say about HubSpot is that it was like two steps forward, one step back. Two steps forward, one step back. It looks like an easy ride if you look at the graphs, but it wasn’t. We had lots of issues, problems, and setbacks along the way. I think what good entrepreneurs do is they just stick with it. There are problems and issues and steps back, and they don’t fold. They just say, “We’re going to get through it. We’re going to rally the troops. We’re going to learn from that mistake and go forward.” Almost all the setbacks were self-inflicted.
The Pothole Report: Learning from Mistakes [00:09:45]
Shaan Puri: What would you have done differently to not make those mistakes?
Brian Halligan: One of the things we did that worked was a thing called the “Pothole Report.” We live in Boston, and this time of year, there are potholes everywhere. That was the analogy we used at HubSpot. We would create these potholes. Sometimes you bounce through the pothole and it hurts a little bit, and sometimes a pothole gets so big you drive your whole car into it. Oftentimes, there was a series of decisions or data where we could have avoided the pothole.
The Pothole Report was: every time we had a pothole, we looked back and asked how we should have handled this a year ago so that wouldn’t have happened, or what data do we wish we had? I’ll give you an example. We had a pothole in 2011. One of the things we did at HubSpot is we hired really good support people. Our secret sauce in hiring for support was that we would walk into an Apple store, buy an iPhone, and hire the kid who sold us the iPhone. They wouldn’t let me in the Apple store in Cambridge anymore because we hired so many people.
The value prop was great. It was like, “You make a little bit more money, but how would you like to sit down at work?” It was a really good value prop.
Shaan Puri: How many support people did you have?
Brian Halligan: We must have had 30 or 40. Then what we would do is use that support group to promote into CSMs, into sales, and into product. We fed the whole company with these Apple store people who were terrific. In this one particular period of time over a few months, we promoted a bunch of people out and congratulated them, but then we were a little behind on hiring and the customer numbers were way up.
We prided ourselves on answering the call within 30 seconds and staying on as long as they wanted. Suddenly, our wait