How it Feels to Sell Your Startup

It’s every startup founder’s dream: to exit. To hand somebody the keys to the kingdom, turn around and do a little heel-click while walking off (or sprinting away) into the sunset. To be done. To move on. To throw your life-ruining iPhone 40 feet in the air and watch it crash into a million little pieces — one piece for every painful email that you endured. To hear the words “Wires have been sent.” To be able to look your spouse in the eye and say, “We did it. Thanks for sticking it out with me all these years. I can start helping with the laundry now.”

I’m pretty sure I don’t believe in the messiah, but, like every startup founder, I used to pray for the day when the clouds would split and an angel from heaven would descend unto the earth to announce: “You did good, kid; we’d like to buy you.”

And then, about a month ago, it happened (the acquisition, not the Clint Eastwood-like Acquisition Angel).

But there were no trumpets. No parades. No I-told-you-so’s. No glamorous vacations or funny out of office notifications. Exhausted and worn from the years of constant blood, sweat and tears, I didn’t even take toll (at least, emotionally) of our accomplishment before receiving my new email address and being told to show up to the acquirer’s New Hire Orientation.

It felt like just another day, with all the ups and downs to which I’d grown so numb.

Earlier this week, I went back to our old offices to clean them out. It was my first time ever being there alone. The walls were covered with Post-Its and diagrams drawn in dry-erase ink. Desktops were ornamented with little self-motivating notes and reminders. Everywhere I looked there were artifacts of life, of team-work, of excitement. And maybe I’m the first person to ever become sentimental about 30-somethings doodling stick-figure diagrams explaining how to properly flush the toilet, but for the first time, I realized that I actually miss the playful startup days — the days when every idea could lead to a world of possibilities.

The acquisition process, by comparison, is a startup’s puberty phase. It’s scary, it’s permanent and, to a first-time entrepreneur, it’s unlike anything you’ve dealt with while growing your startup.

1. The process is clinical.

An acquisition involves many people. Your management team. Your lawyers. Your accountants. Your board. Your shareholders. The acquirer’s management team. Its analysts, and lawyers, and accountants, and consultants. And while you’d like to believe that everyone cared about all the great things you’d done, the truth is, once the Term Sheet is signed, momentum does the rest of the work. Things just happen and no one has time to invest personally in the outcome. Except you, of course. You’ll be an emotional wreck — thinking and re-thinking the deal while everybody else involved is just trying to do his/her job.

2. The process will threaten the health of everything you’ve built.

Unless you’re a large company that simply wears the “startup” tag, the acquisition process will severely overwhelm your resources. It will feel like things are falling apart as you begin to necessarily drop the ball on day-to-day items. The culture you’ve built will begin to crack as employees begin to internalize their own fears. There’s no surviving a failed acquisition. So the CEO’s job, once acquisition discussions have begun, is to finish the job.

3. The money matters, and then it doesn’t.

As a founder or CEO, the day an acquisition closes should be a pretty good day, financially. But I’ve been surprised how little the money matters, post-close. If anything, it’s an empty feeling because you’re no longer thinking about future potential; instead, you’re just left wondering if you would do it all again. And the answer is: Yes. You would. Because you don’t start a startup to be rich. You do it because it’s an avenue for a normal person like yourself to take a turn at being wildly creative. Money is good, but it’s not the reason to do anything.

The only job of a startup CEO, is to steer the ship through a successful voyage and back into port safely. Which is not to say that getting acquired is anti-climactic — it’s just different than first-time entrepreneurs expect it to be. Merely surviving doesn’t sound exciting, but where else does one have the freedom to do anything necessary to survive? That’s living! And I already miss it all. The camaraderie, the stress, the creative output. The tiny, rare victories, which outweigh thousands of losses. The pace, dis-order and chaos of it all. It was fun.

As I finished cleaning out the office, I thought about lingering for a while. Maybe I’d just sit down on the floor and try to inhale a bit more of the life seeping out through the walls. But it was all gone. The people, the notes, the drawings — all of it gone, having matured beyond this exciting mini world we created for ourselves.

And maybe that’s the lesson: Enjoy it. It’s better to live the startup experience than it is to look back on it. And who knows if you’ll ever have a chance to experience those playful days again.

Instead, now I’m stuck helping with the laundry.