David Cancel has founded five startups, but he says this one feels different. The 45-year-old chief executive of marketing company Drift recently received votes of confidence from some of the biggest names in venture capital. Fresh off a funding round that included General Catalyst, Sequoia Capital, CRV, and his former employer HubSpot, Cancel sat down with the Globe’s Andy Rosen to talk about his path into entrepreneurship, his New York upbringing in an immigrant family from Ecuador, and Puerto Rico, and why he doesn’t always see physical fitness as a good thing.
1. He’s a proud college dropout. Cancel left Queens College in New York before he earned his degree, but he did learn something important while he was there.
“I just knew that people went to college, but I didn’t know anything about it, and so at the very last minute I applied for a school that was just, like, there. Why that school? I don’t know. It was there. I didn’t have a good experience because I didn’t feel like any of my professors — now, looking back — were that passionate about what they were teaching. I felt like I wasn’t learning anything interesting.
“I’ve always been obsessed with reading, and I still am, and I would spend most of my time in the library. We had the early Internet, and that became my rabbit hole that I’m still in right now.”
2. He knew it was time to leave HubSpot when he people started complementing him on his fitness habits.
“I got to a point where we did a lot of great things — we were going public, it was awesome — but that last year I felt I wasn’t learning anymore. I had a bunch of people who were reporting to me and they did stuff, and they felt like they could do it on their own.
“I was in the best shape in my life, probably, that last year because I would go to the gym twice a day. So other people would be like, ‘Oh, that’s amazing,’ and I would be like, ‘No, I went to the gym to get through the day.’ Even though on paper it looked like a dream job, I was dying because of it.”
3. You can often find Cancel walking around the mall at Copley Place, near his office.
“When we do meetings — when I do one-on-ones — I almost always try to walk. I don’t like standing still. So we’ll walk outside, but this location is good because in the winter, we could just walk around the mall forever. We don’t have to go outside in the rain and the snow. “
4. He makes it a point not to talk business at home, but his 12-year-old daughter seems to have caught the entrepreneurial bug anyway. (Cancel also has a 6-year-old son.)
“I came home one day, and she said, ‘I’m going to start a business. I’m going to sell baked goods at the farmer’s market.’ So I don’t know where this is going, and she says, ‘I’d like to come to your office tomorrow.’ At this point, she had never been to my office. She said, ‘I’m bringing in samples of my baked goods.’ And I’m like, ‘You know you can’t sell baked goods at my office,’ and she said, ‘I’m going to give this away for free, because I’m running a pricing study.’
“She came in, she printed up her menus, and that’s when I saw her with the business cards. I had never seen them before. She set up a table. She got everyone at the office to come and she gave them treats. We went home, I didn’t ask anything about it, and everyone told me she had e-mailed them all to survey them and send thank you notes.”
5. His companies have been bought out before, but don’t expect that to happen this time.
“We want to build a public company in Boston. All my other companies, I’ve sold at some point, and so that was the end of the journey. Part of building those companies was we kind of only focused on one thing, which was building the software, getting that going. We weren’t thinking: Do we care about building a brand? Do we care about representing something more than the software? Do we care about everyone’s progression within the team? I’m sure we did a little bit, but that was all in pursuit of building the software. Now we feel like we want to create this lasting thing, so it changes your perspective.”Andy Rosen can be reached at firstname.lastname@example.org. Follow him on Twitter at @andyrosen.