MicroConf - The day I sold Drip

The day we closed the Drip sale, it was a summer Friday. I was at my kids’ cello and violin camp in Oregon.

I was sitting there signing the sale documents on my phone (which isn’t really what you want to be doing) and the instructor was glaring at me because, you know, I was supposed to be listening to my kids. 😬

And then my technical co-founder, Derrick, texted me a screenshot of the bank wire. He said, “That’s a lot of zeroes, sir. Congratulations.”

It was such a virtual high-five moment.

Sometimes people leave comments on my YouTube videos telling me to get a haircut, so I send them that bank transfer screenshot. (Just kidding. But can you imagine?)

The thing is that when I tell this story, I usually leave out the much less appealing stories of the 13 months preceding that moment:

The story of crying in my car because I was so stressed out.
The story of my short temper, which I took out on my wife and kids more than I’d like to admit.
The story of the very real stress of exiting, which no one talks about — and which I found myself unprepared to deal with.

I was living in this post-agreement, pre-check purgatory. Everything was up in the air. Everything mattered SO MUCH. And most of it was out of my control.

(Also, no one really wants to hear how stressed you are about your potentially life-changing exit. Which I get. It feels like hearing “Oh no, I’m about to be rich and successful, wah!”) So I had no one to talk to.

Probably your reaction reading this right now.

Since that exit, I’ve grown MicroConf, started TinySeed with Einar Vollset, and invested in a number of businesses.

Meanwhile, my wife, Dr. Sherry Walling, has worked 1-on-1 with founders in her private psychology practice, helping them navigate big decisions and transitions.

We realized we were both seeing the same story play out over and over.

Founders and SaaS entrepreneurs were thinking about exiting. Or they were midway through the process. Or they’d just come through the other side. And all of their excitement and joy was getting completely subsumed by dread, anxiety, and paralysis.

Selling your business is a good thing, right? So why does it sometimes FEEL so bad?

Sherry and I looked around for resources that spoke not only to the complex financial and legal logistics of selling your business — but to the mental and emotional toll of the process. We couldn’t find any.

So we wrote our new book, Exit Strategy: The Emotional and Financial Guide to Selling Your Business Without Regret.

Exit Strategy is for human entrepreneurs. You built (or bought) a business, yes. But YOU’RE still a human. And sometimes being human gets messy.

This book is your step-by-step guide to preparing for the mess and navigating your own well-being and your relationships. So that ultimately, you can feel calm and confident about your next steps.

Check out the Kickstarter to back the book (or read the first chapter for free).

Rob

P.S. A few friends were kind enough to read Exit Strategy in advance. Here’s what they said:

“My exit was a psychological rollercoaster unlike anything I had experienced before, as I struggled to separate my identity from the business. In this book, Rob and Sherry cover both the business and psychological aspects that founders face when selling their companies.”
- Ben Chestnut, Co-founder, Mailchimp

“Nailing your exit isn't just about the deal—it's also about not losing yourself in the process. Because what’s the point of a successful exit if you’re too burned out to enjoy it? This book helps you to consider not only the business but also the life you’ll lead after the sale.”
- Dan Martell, Wall Street Journal bestselling author of Buy Back Your Time

Even if you have zero plans to exit your business, I’d love for you to check out Exit Strategy.

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