Matt Holden wanted to be a math professor.
He studied abroad in France for a year when he was fifteen and went to a French high school there. That’s where he saw his first math proof.
“I had always liked math,” he says, “but when I saw proofs, I really glimpsed the transcendence of mathematics. I fell in love with it.”
He went on to study mathematics at Pomona College and the University of Cambridge before beginning a PhD at the University of Chicago.
Early on, he was excited by the expansiveness of the problems he could tackle in mathematics. But after his focus began to narrow in graduate school, he decided to seek out new challenges beyond academia.
“I was happy that I knew what my calling was in life,” he says, “but it turned out that wasn’t right. I left a profession that was charted for me and went out into the unknown. I didn’t know if it would work out.”
He spent a year as a software engineer in finance, before finding his way to product management at Google. Later he went on to co-found the startup TapEngage, which was acquired by Dropbox in 2012.
Matt hit the ground running as a product manager at Dropbox, shipping his first feature, two-factor authentication, in just five weeks.
“It was five weeks from the idea that we were going to do this to launching it across every platform—iOS, Android, Windows, Mac, Linux, our API, our website. There’s a lot of surface area to cover at Dropbox because we’re on so many different platforms.”
There were two key ingredients, he says, that made that first project so successful:
“We got a great team together, and we were really focused on our goal.”
Two years later, Matt is focused not only on making his team successful, but on pushing the boundaries of what’s possible for the product. Casual conversations about collaboration kicked off a prototyping effort that eventually became Project Harmony.
A talented engineer on the team was looking for ways to improve collaboration in applications many people already use with Dropbox, like Microsoft Office. The result, he says, came out of a true collaboration between engineering, product, and design.
“We didn’t actually know where we were going to end up,” he says. “We had a sense of the problem we were trying to solve, but it meandered in different ways between what we wanted to achieve and what the constraints were.”
Their process relied heavily on prototyping and research early on.
“There was a lot of back and forth,” he says, “between what’s technically possible and pushing the boundaries.”
It’s an approach he takes in his own life too, pushing the limits of what seems possible. In college, it led him to ballroom dance.
“I like to focus on things I’m not good at,” he says. “I had no idea how to dance, so I thought, ‘Well, I’ll sign up for ballroom dance classes.’”
He started out by stepping on people’s feet.
“I was the worst guy in the room,” he says, “but I just kept at it. I ended up really liking it, so then I joined the ballroom dance team.”
Looking back, Matt says he’s glad for the risks he’s taken. He’d always recommend choosing the harder path and maximizing for learning.
He says, “I’m happiest when I’m in over my head, I don’t know how to do whatever I’m supposed to be doing, and I’ve got to figure it out. I’ll probably make mistakes, and I’ll learn from them.”
When he’s not leading product teams or hitting up the occasional salsa or swing dance, Matt still returns to proofs on the weekend. It keeps him on his toes.
The Dropbox product team is growing. We’d love for you to join us.