MEET David

David Cancel is the founder and CEO of Drift, the world’s leading conversational marketing platform. He is the author of the newly released book, Conversational Marketing, an entrepreneur-in-residence at Harvard Business School, and was previously chief product officer at HubSpot. He says growing up as the son of a builder and a seamstress fueled a lifelong “obsession with making things,” from the five companies he’s founded to the perfect homemade pizza.

What is something you’ve learned that you lean on daily?

I think I lean most on systems thinking, which is something I learned early in my career, when I was an engineer. I still use it a lot in my own decision-making, and I also try to teach it to the team at Drift. I’ve realized systems thinking doesn’t come naturally to all of us—not everyone is robotically logical like me! Most people are more linear. They observe something, choose option A or B, and that’s the end of it. But I’ve found it really valuable to think through various causes and effects, and to think about when and why you might have to reevaluate. When we consider a change that would affect our customers, for example, whether it’s pricing or product or positioning, we’ll game out what the possible impacts could be, and spend time talking with some of those customers before we make a decision.

What one piece of advice would you give someone starting a company?

Your company’s stage is super important—it adds context about what you need for where you are. With hiring, for example, I used to think only in terms of the quantitative and qualitative traits. Quantitative meaning what skills a person has, which companies they’ve worked at, which industry they come from; qualitative meaning their cultural fit and personality. I wasn’t thinking about the third dimension, which is stage.

We’d hire people who were great on the quantitative and qualitative dimensions, and then they’d struggle. I couldn’t figure it out. I’d think, “Their skills are perfect. Who they are is perfect. Why does this keep happening?” Eventually, I realized there was nothing wrong with the people or what they were doing. They just had trouble in our environment because their only experience was with companies four or five stages ahead of where we were. Sometimes you can apply that background in a new context, but it’s difficult, and definitely something you need to be conscious of. Now, we’re very deliberate about considering stage and discussing it with candidates. We try to forecast what the company’s growth will look like and where we’ll be by the time a new hire is really up and running, and then we look for people who are a good fit.

What small change has made a big difference in your life?

I decided to go all-in on being a morning person. For a long time, some days I’d get up early and some days I’d stay up late, and I always felt like I was failing at one or the other. So I decided to develop a consistent, deliberate practice in the morning. I spend time with my kids and drive them to school, I do yoga, I read—all before I open my email. And I’m always cycling through different rituals to see which ones work for me and which ones don’t. I’ve tried several forms of meditation, for example, and haven’t landed on one so far. The most valuable practices for me are the ones I naturally come back to, so I’ve gotten better at listening to myself. I’ve learned to accept it and move on when something doesn’t work, and to lean into the things that feel right.

What don't you know that you wish you knew?

I wish I knew what I think I’ve mastered, but actually haven’t. As time goes on, I’ve realized that many of my most important lessons were things I thought I already knew—but I didn’t truly know them or live them until I learned the hard way. Some are things my mom used to say to me growing up, like “el flojo trabaja doble,” which means “the lazy person does the work twice.” As a kid, that might have been something simple, like not taking the time to put food away correctly. As an adult, I like to think I take the easy way out less often, but I still catch myself sometimes—I haven’t truly learned that lesson. At work, for example, we all know how important it is to backchannel and get as much context as possible about a person before you hire them, but when you’re already enamored with someone, it’s so easy to shortchange that part of the process. If you don’t do it right, though, you may end up doing it again.

What books are on your nightstand right now?

This one’s tough, because I’m addicted to learning and usually read at least five books at once. Right now I have Yuval Noah Harari’s book 21 Lessons for the 21st Century; The Obesity Code, by Jason Fung; Wooden, by John Wooden; and about seven others. The podcast I host with our VP of Marketing, Dave Gerhardt, actually started because I’m such an avid reader. We talk a lot about the books we’re reading, and the podcast is named after Peter Bevelin’s book Seeking Wisdom, which has been on my nightstand for years. It’s a compilation of these age-old lessons on things like decision-making and mental models—how to be more logical and avoid the traps of our biases.

I loved reading as a kid, but at some point during school, I started to hate it, because I somehow got the idea that I had to read every book cover-to-cover, one at a time. That took all the fun out of it for me. Then I started reading multiple books at once, and suddenly ideas began to cross-pollinate. Even with two books on radically different topics, I could see patterns emerge. I also have no guilt now about putting down a book if it’s not right for me. One day, in another context, I might pick it up again. I reread a lot of books, too, for the same reason—at a different time in my life, I’m coming in with a different context and can pull out different lessons.

When did you realize you were wrong about something?

I was probably 10 years into my career before I started saying, “I don’t know.” Part of that was fear of being vulnerable. Part of it was that I kept trying to take my lessons from the books that existed at the time—which were mostly from leaders of big, Fortune 500 companies. I’d try to follow conventional wisdom when it often wasn’t relevant, and wouldn’t get the results I thought I should. Eventually I got frustrated enough to say, “I don’t know how to do this. Let’s just start fresh and figure it out.” That’s when the learning began, and I started to accelerate.

What unit of time matters the most and why?

I live in the moment—probably to an extreme degree. I never look at a calendar or anything to see what’s happening tomorrow, and by Monday morning, I’m not even thinking about how I spent my weekend. I only think in terms of today. I know I can’t control the past or the future; I can only control right now. For me, it’s about how I can make this moment as good as it can be. I think that mindset is especially valuable when you’re creating something. It could be writing or sculpting. It was definitely true for me when I was an engineer. You get in the zen state where you’re entirely focused on making whatever you’re doing the best experience possible.

Hard-won advice