PROLOGUE

“If you join this startup, I guarantee you’ll leave richer.”

I say that to nervous job candidates. Then I pause, because what comes next is the part that matters: “Just not necessarily financially.”

That idea is one of the central truths of my career, and it is where this story begins.

In a large company, a job often comes with boundaries; that may be comfortable, but it is also a limitation. In a startup, the boundaries are blurry because there are never enough people to do all the work that needs to be done. Something important is always waiting for an owner because everyone is already drinking from a firehose. The people who thrive are often the ones who notice the gap, step into it, and say later, “I saw this needed to be handled, so I started handling it.”

That is startup life at its best: messy, urgent, exhausting, generous, and educational.

At its worst, it is the roller coaster from hell.

On Monday, you come in and get some news that convinces you that you’re about to change the world. A customer finally gets it. The demo works. A key hire says yes. An investor seems ready to write a check. You get past the bug you thought was a roadblock, proving that it was only a speed bump. You are at the top of the hill, convinced the entire future is opening before you.

On Tuesday, you come in, and things are falling apart around you. The customer puts the brakes on. The demo crashes in a new way. An employee quits. The investor doesn’t return your calls. Suddenly, your cart is careening toward the bottom.

On Wednesday, you come in expecting to pack your desk, and your phone rings. The customer has found a way forward. The demo problem was only a hiccup. The investor calls back. The cart has not flown off the track. Its momentum carries it up the next hill. The ride is not over.

If you can handle the ride, I guarantee you will leave richer. If you join a startup and you hate it, that is one of the richest things you may learn. Startups aren’t for you. If that is the case, get the hell out of there as quickly as you can.

However, if the ride does not scare you — and you discover that you thrive on the adrenaline — you will see an entire company unfold around you. You will be in the meetings, part of the decisions, and close to the action. That is access you would rarely get at a large company.

You will wear a dozen hats you might never have worn there, and you will learn faster. You will not merely watch other departments struggle; you will reach over and help them solve their problems.

Most of all, and scariest of all, you will see how far the track stretches — or how soon it ends. That is the runway: the number of months before the company runs out of money. During that time, the company must keep laying track ahead of itself through additional funding, increased revenue, or both. The hope is that the rails remain ahead of the cart long enough for the company to reach solid ground: profitability, an acquisition, or an IPO. The alternative is flying off the end of the track into bankruptcy.

I opened by promising that you would leave richer. Here is the last part of that promise, and the most important. If you learn to love the climbs and throw your hands in the air during the drops, be careful: the ride can become addictive.