Be a Startup Superstar

Chapter 2Pick the Right Start‐Up for You

Don't worry about failure. You only have to be right once.

—Drew Houston, co‐founder and CEO of Dropbox

Are you chomping at the bit, ready to bolt from a corporate desk to the start‐up track? I was, too, when, soon after graduating, I signed up at my first start‐up. I rushed into the first opportunity that presented itself. This was a mistake. I knew next to nothing about the company—I didn't know about its funding, growth plans, or marketing plans. I didn't even really know what we sold. I knew the name, of course, but the product was some sort of specialized technology and I only had a fuzzy idea of what it actually did.

Ultimately, the company was successful. It had smart people at the helm, a strong product, and a compelling story. In many ways, it's the luckiest I've been in my career. Because in my haste, I made every possible mistake I could have made. And even though the company ended up being a success, we experienced long periods of struggle where we had to lay off swaths of the sales team, and it looked like the whole thing might fold. Which happens far too often.

At a dinner party a few years ago, I met a man who told me he worked an eight‐to‐five job for a big company in Austin. I asked him if he liked what he did, and he shrugged and said, “It's a job.” He volunteered to me that years earlier, he had gotten in on the ground floor of a start‐up and loved it, but it tanked after two years, and he never tried to work for ...