Bootstrapped Founder #64: The Grief and Loss of Selling a Business

Dear founder,

If you prefer listening over reading, you can listen to this episode of The Bootstrapped Founder on my podcast.

This week, my partner, co-founder, and love-of-my-life Danielle Simpson appeared on the Software Social Podcast hosted by Michele Hansen and Colleen Schnettler. In a remarkably open and honest conversation, Danielle touched upon many different topics regarding our journey with FeedbackPanda, but one thing stood out to me: her story of how she dealt with the aftermath of selling the business.

Now, I have talked about this before on several podcasts myself, but listening to Danielle share her perspective made me think. I highly recommend listening to her account because it provides some context and contrast to what I am talking about here today.

We sold our business back in mid-2019. I was on the brink of burnout from being the sole technical person in a company with thousands of customers. I was anxious, stressed, and glad to have the opportunity to step back from the day-to-day work. Also, the chance of becoming financially secure with the sale was very alluring. Still, I knew from having listened to many episodes of the Indie Hackers podcast and John Warrillows Built to Sell Radio that selling your business isn't exclusively a positive experience. I read about it, I knew about it, I thought I was prepared.

But I wasn't. When we handed over the reins to our company, it only took the people at SureSwift Capital a few days to completely replace us. That wasn't surprising, as we had consciously built a sellable business and made ourselves easily replaceable. What did surprise me was how empty my days felt right after that. I knew that life would slow down a bit, but I wasn't aware of how much that would confuse me.

Originally, my plan for this time after selling the business was to take a mini-retirement. I had it all planned out in my head. This involved a whole lot of playing World of Warcraft, cooking, reading, and relaxing. In fact, this had been my dream for decades for when I would finally retire.

I enjoyed this for exactly three days.

By day four, I felt horribly empty. Here I was, doing what I thought I always wanted to do instead of working. Within less than a week, I knew that this was something that would never bring me the joy that it might have brought a decade ago.

I have since understood why this felt so unfulfilling: I didn't only sell a business. I gave away my catalyst for passion.

Building a business with Danielle has been the most satisfying thing I had ever done up to that point. No matter how fondly I remembered my Warcraft raid-leading days back in 2008, they were totally eclipsed by building a software product that helped notoriously underappreciated teachers create a better life. I had just experienced a baseline shift.

The social impact of FeedbackPanda was the new baseline for what I could accomplish. And I had just given away all of that.

Danielle talks about this moment on the podcast. We both fell into a lull, a void. We had worked so hard to build this business that didn't only pay our bills but also gave us a constant stream of appreciation: every day, a customer would thank us in some form or another. They'd shoot us an email, shout us out on Facebook, or just let us know through Intercom. It was awesome, and it gave us the fuel to keep going. Once we handed over the company, all of that stopped. No more appreciation. No more motivation.

This is the part where my experience diverges from the one that Danielle had. I believe that she was identifying with the business much more than I was. She was the visionary, the teacher-turned-entrepreneur, who built something for herself and other teachers. I was the tech co-founder, the facilitator, the developer who built the thing and learned how to create a business around it. My connection to the teachers we served was very real, too, but it came from a different place. I knew that this business wasn't an extension of myself but a product of sorts. For Danielle, it was much closer to her heart, as were the teachers that we served.

I also had something else queued up — at least somewhere in the back of my mind. During FeedbackPanda, I always felt the need to write but never found the time. I was so caught up in the development and customer service work that I didn't carve out an hour or two to take my thoughts and put them to paper. It was only when I was already extremely burnt out from the day-to-day work that I actually started writing. In a blog post that I never published, I laid out all the ways I was struggling with the business and how I had tried to solve those issues with automated systems. It was a cathartic experience, and it showed me two things: writing helps me make sense of my problems, and I really enjoy the process. This last-resort attempt at dealing with the stressful life of running a business with over 5.000 customers with just two founders and no employees laid the foundation for what was about to follow.

After we sold and fell into that void, I quickly started planning for the next phase of my life. With gaming and passively consuming being out of the picture because they promptly had lost their appeal, I found my joy of writing to be an internal motivator. Consequently, I began to start writing for a yet-to-be-created blog, which turned into a newsletter, a podcast, and finally, a book.

At the same time, I started building an audience on Twitter, sharing my work and helping other founders with their businesses. I quickly found the appreciation that I had lost had re-appeared tenfold within the founder and indie hacker community, who embraced me with their support and encouragement.

I found my passion in writing. I found my people in the founder community. So I threw myself into this work, mere months after we had sold. We had transitioned FeedbackPanda within a month or two after selling in June 2019, and by November, I was already working on my tenth blog post. I wouldn't call myself a workaholic — I like napping too much for that to be true — but I definitely went into a new occupation fast.

Sometimes I wonder if I should have grieved and reflected on the loss of such a monumental business for longer. I occasionally remember a particular exchange with a customer and the joy they expressed when we helped them solve their problems. The immediacy of that feedback is something I miss. It is much more delayed: people who read my book take a few months to actually see the results of applying the concepts and learnings I shared with them.

Well. The fact that I get to share these thoughts with you today shows me that I've moved on. There are losses and grief in selling a business, and there is an opportunity to start something new. In Danielle's episode of the Software Social podcast, this in-between phase is called Sitting in Your Discomfort, and it's an interesting experience. It's hard to feel good about feeling confused and disoriented, but it's a natural part of the post-sale process. I've seen entrepreneurs stay in this stage for years, and others almost skip it.

If you ever plan to sell your business, consider these experiences. Talk to founders who have been there. Consider where your passion and encouragement will come from after the sale. You don't need to have all the answers, considering the questions will be enough.

Thank you for reading this week's edition of The Bootstrapped Founder. If you like what I wrote about, please forward the newsletter to anyone you think would enjoy it too.

You can find my book Zero to Sold at zerotosoldbook.com. It is being sold on Amazon and Gumroad.

If you want to help me share my thoughts and ideas with the world, please share this episode of the newsletter on Twitter or wherever you like, or reach out on Twitter at @arvidkahl.

See you next week!

Warm Regards from Berlin,

Arvid