'Your job as a CEO changes every 12 to 18 months': Dropbox founder on what it's like to run a company that grew to $10 billion

Drew Houston started Dropbox when he was 24.

About 10 years later, the file-sharing service has more than 500 million users and generates $US1 billion-plus in annualized revenue.

On an episode of Business Insider’s podcast “Success! How I Did It, Business Insider US editor in chief Alyson Shontell asked Houston what it’s like to go from running a small, fast-growing startup to running a company that was valued at about $US10 billion in 2014. 

“I think at first you have to be systematic about training yourself, and what you really want to solve for as a founder is making sure that your growth curve stays ahead of the company’s growth curve,” Houston told Shontell.

He continued:

“And so that means figuring out what you don’t know and learning it, and no one is going to do that for you. The challenge, especially as a company is scaling, is that your job as a CEO changes every 12 to 18 months — it’s just that no one taps you on the shoulder and tells you that. Furthermore, you might not get a lot of partial credit for the stuff you’ve done well. You’re judged by a completely new scorecard.

“So, for example, in the beginning, you’re just spending time building a prototype, and it’s all about creating the product. But then once you have a product, you need users. How do you get distribution, how do you grow — that’s a whole different challenge. And then the scorecard changes again once you have distribution, then you need revenue, and then you need a working business model.

“Then you get competitors, and then it’s not just revenue, but it’s actual cash flow or profit. And so, as in real life, the scorecard changes at these different break points and different points of adolescence or maturity in the company. That’s probably the most bewildering part of the job is that your job changes so much. Just when you think you’re getting good at the old job, you have a new one that is totally unfamiliar.”

However, he said, “It does level off, and you do learn all the different parts of the job, so it becomes less daunting over time.”

Personally he focuses on, “‘What’s our pipeline of product?’ Some stuff is still the same,” he said.

He went on:

“It’s just: ‘How do I make sure that we have the absolute best people on the team, how do we make sure they’re working well together?’ And fortunately, if you bring on great people, you divide and conquer on this problem. So we’ve brought in great leaders from all the great companies, which helps a lot.”

Listen to the full interview on “Success! How I Did It”:

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