Introduction

My phone buzzed. It was an incoming email.

I never have email notifications turned on, except for two weeks in late June of 2016. The startup I had launched two and a half years prior had grown into one of the top 10 companies in our space and was in the final throes of being acquired.

Some acquisitions are scary. All of them are stressful.

This one was going to be life-changing, which made it even worse. If it didn’t go through, I’d be back in the startup grind. Restless sleep. Loads of stress. Financial uncertainty.

For something I had dreamed about for decades, running a fast-growing bootstrapped startup was more of a mixed experience than I’d anticipated. There was absolutely fun to be had (“These are the good old days,” I used to remind the team), but the struggle was real. And it was taking a toll on me.

My mind flashed to the day we crossed $1 million in annual revenue. The day we hired our eighth employee. The day we finally moved into a real office with huge windows overlooking a busy downtown street. In each of these moments, I felt like I’d made it.

I then flashed to my “lost” six months in 2014 when I thought of nothing else except how I was going to make payroll. The moment I broke down sobbing in my parked car because of the stress of the acquisition. Or the moments I yelled at my wife or kids for things that were far more my fault than theirs.

And yet there I sat, in a college classroom outside of Portland, Oregon, in late June 2016. I was at my oldest son’s cello camp. He was practicing with a group of other musicians. And I had a new email notification on my phone.

“This is insanity,” I thought. “I can’t believe this has come together.”

To the chagrin of the cello instructor, I motioned that I needed to step out of the room for a moment. I opened the email, signed the final documents that would be life-changing in many ways using my index finger on an iPhone screen, and clicked “confirm.”

It was done. The result I had dreamed of for decades and been “all in” on for 15 years was over. I could take a deep breath and relax. At least, that’s what I kept telling myself.

I opened my mobile banking app and logged into our company bank account. “That’s a lot of zeros.” By far the most money I had ever seen in one place. At that moment, life felt different.

A text message arrived from Derrick, my cofounder, with whom I’d spent the past three and a half years building Drip. He’d sent me a screenshot of the company bank balance.

He followed up with a bitmoji of him in a green suit with dollar bills falling around him, which was quite out of character for my typically reserved cofounder.

I exhaled slowly. The stress wasn’t going away. I hoped it would soon.