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Are you spending time with wealth-generating people?

Dropbox’s founder shares his roadmap to becoming a dollar billionaire.

CAMBRIDGE, MASSACHUSETTS – We’re all the average of the five people we spend the most time with. So who are you spending your time with, and are they the types that can help lead you to billions?

It’s all about where you are and whom you know, 30-year-old Drew Houston told graduates at the Massachusetts Institute of Technology in Cambridge recently. Houston has seen the figures in his bank account accelerate from $60 to $600-million in the eight years since he graduated from MIT and started file hosting service Dropbox.

He told the graduating class of ’13 of the importance of poker, tennis balls and obsession, as well as, persistent reading, the magic of five, the necessity of impatience, never getting comfortable, and moving to where the action is.

He and a friend started their first business, an educational course, at the age of 21 while working as restaurant waiters. It did well, but not brilliantly. Then he designed a computer gaming course for poker.

“A couple years later, things started going downhill. I felt like I had to paddle harder and harder to make progress, and at some point I just snapped and couldn’t deal with any more… I felt guilty for being so unproductive. I was thinking: well, maybe I don’t have what it takes after all. So I took a little break.” And that’s when he started paying attention to what he needed to do for success.

This is his road map to become a dollar billionaire:

Read every business book you can, especially about marketing, sales, and management.

Be obsessive. “The happiest and most successful people I know don’t just love what they do, they’re obsessed with solving an important problem, something that matters to them. They remind me of a dog chasing a tennis ball: their eyes go a little crazy, the leash snaps and they go bounding off, plowing through anything that gets in the way. I have some other friends who also work hard and get paid well in their jobs, but they complain… a lot of people never find their tennis ball.”

Sometimes the sideline is the main event. Pay attention. “Dropbox started out as [a] distraction. That little voice in my head was telling me where to go, and the whole time I was telling it to shut up so I could get back to work. Sometimes that little voice knows best….The hardest-working people don’t work hard because they’re disciplined. They work hard because working on an exciting problem is fun. Keep listening for that little voice.”

The importance of exceptional networks. “They say that you’re the average of the five people you spend the most time with. Who would be in your circle of five? If I hadn’t come [to MIT], there would be no Dropbox. Surrounding yourself with inspiring people is just as important as being talented or working hard. Your circle pushes you to be better.

Are you in the best place? For whatever you’re doing, there’s usually only one place where the top people go. You should go there… One of the biggest mistakes you can make is to settle for the number-two location.”

Your heroes are part of your circle too – follow them. If the real action is happening somewhere else, move.

Stop planning. You’re ready. Do it. Now. “If you have a dream, be careful that you don’t let reading about it or writing papers about it get in the way of doing it. The best learning is doing. Otherwise, if you spend all your time checking boxes and ‘getting ready’ to follow your dream, chances are you’ll end up working for the people who just went out and did it. What you should be doing is not getting ready but getting started.” (See his first application for funding for Dropbox).

Don’t stop to count the money. “I remember the day our first investors said yes and asked us where to send the money. For a 24-year-old, this is Christmas and opening your present is hitting refresh over and over on bankofamerica.com and watching your company’s checking account go from 60 dollars to 1.2 million dollars. At first I was ecstatic … but then I was sick to my stomach … [thinking] someday these guys are going to want this back, what the hell have I gotten myself into?

[But] building [Dropbox] has been the most exciting, interesting and satisfying experience of my life… It’s also been the most humiliating, frustrating and painful experience, and I can’t even count the number of things that have gone wrong.

Don’t aim for perfection, take risks, and learn from the mistakes. “In the real world, if you’re not swerving around and hitting the guard rails every now and then, you’re not going fast enough.”

Your biggest risk isn’t failing; it’s being too comfortable. “Bill Gates’ first company made software for traffic lights. Steve Jobs’ first company made plastic whistles that let you make free phone calls. Both failed.”

Failure doesn’t matter: you only have to be right once.”

Stop worrying. Be adventurous. “I used to worry about everything, but I can remember the moment when I stopped and got over it. I read something online that said ‘There are 30 000 days in your life.’ On a whim I [calculated] 24 times 365 and [thought] … I’m almost 9 000 days down. What the hell have I been doing?

That night, I realised there are no warm-ups, no practice rounds, no reset buttons. Every day we’re writing a few more words of a story. From then on, I stopped trying to make my life perfect, and tried to make it interesting. I wanted my story to be an adventure. And that’s made all the difference.”

Excelsior! “My grandmother is here today, and next week we’ll celebrate her 95th birthday… She always ends our phone calls with one word: ‘Excelsior,’ which means ‘ever upward’.”

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