Download The Podcast MP3

Episode 286:  Advice from Dropbox’s COO

Dennis Woodside left Google, for DropBox. Everyone thought he was crazy.

DropBox was this little tiny company.

What was he thinking?

“So you ask why I would go from Google to Dropbox. Just play the movie forward. Where’s it going to be in ten years? It’s logical to me that the company that pioneered this notion of putting your files in the cloud is going to have all kind of opportunities and going to solve problems for everybody in the world. A lot of people don’t think that way. They think very linearly. That’s how we’re taught as kids. That’s how you’re taught in college.

(And that’s how Dennis was taught to think in law school. But he got out of that rut. More on that later…)

“You have to rewire your brain a bit,” he said.

You have to ask yourself, “What trends do I understand to be true?”

And “If I extrapolate that trend to its logical conclusion, what does the world look like?”

That’s what Dennis did. And that’s how he found Google. And later, Dropbox.

He said Google was tiny when he first joined.

“What year?”


There were only a thousand employees.

“When I joined Google everybody thought I was crazy because it was a little tiny company,” he said, “but I felt one of the most exciting things you can do with a career in Silicon Valley is to help grow a company. And be there early… There’s a lot of uncertainty. And competition is really hard. You have to figure everything out. That’s the hardest part, but the most rewarding.”

Dennis is now the COO of DropBox. How did he go from lost lawyer to a leader in Silicon Valley?

I wanted to know.

“Ultimately, I realized I wasn’t going to be a great lawyer,” Dennis said.

This is where his career path changed from one end of the spectrum to the other. He reinvented. He learned a whole new set of skills. And he adapted to an ever changing digital world.

Most people are thinking about the next ten days, Dennis is thinking about the next ten years.

He saw DropBox as a pioneer. And is vision paid off. DropBox is one of the fastest growing companies maybe ever. And there are billions of people who are signing up every month.

I wanted to learn how to cultivate that same skill. The one that lets you have a vision. And believe in it.

Also Mentioned: