Drew Houston: “No one is born a CEO”

September 04, 2025

Dropbox founder Drew Houston reflects on feeling insecure in the CEO role when he first started the company:

“What I didn’t know was if I should be CEO. The more I learned about business, the more I realized I didn’t know. I was concerned — maybe I should find a more business-minded co-founder and be the CTO.”

Drew recalls asking the CEO of another startup for advice at the time:

“He told me to give it a shot — it doesn’t have to be permanent. If you like it, keep going. If you don’t, you don’t have to be CEO. He was very practical, but I think it’s totally rational to have imposter syndrome — especially if you’re in your early 20s — and recognizing that there’s a whole world of stuff you need to know beyond the technology and product. I wasn’t fully aware then that all of that is learnable.”

He continues:

“No one is born a CEO. Everyone is a first-time CEO at some point. Most of tech company founders that are in the Hall of Fame and that we all look at started as technologists and learned the business side on the job. There’s very few examples of going the other way. It’s just part of the game. That gave me some comfort later on, and I wish I heard that at the beginning.”