How I knew I was done with my company

I thought I would never sell my company. When National Public Radio did a story about me in 2004, I said I’d stick it out until the end, and I meant it.

In 2007 I did a ground-up rewrite of the website software from scratch. And man, it was beautiful code. The proudest achievement of my life at that time was that software. Wonderfully organized, extensible, and efficient: the culmination of everything I’d learned about programming in ten years.

After a successful relaunch and Christmas rush, I was looking at my plan for 2008 and beyond. All my plans needed a huge effort for little reward, but were required for future growth. I had broken it into about 20 projects, each taking 2 to 12 weeks.

But I wasn’t excited about any of them.

I’d taken it far beyond my goals, and realized I had no big vision for it being much else.

The next week, I got calls from three companies, each asking if I’d be interested in selling. I said no, as usual, since I’d been giving the same answer for ten years.

But just to be open-minded, that weekend I opened my diary and started answering the question, “What if I sold?”

I had done this a few times in previous years, but the answer had always been, “No way! There’s so much more I want to do! This is my baby. There’s no way I could let go.”

This time it was different. I thought how nice it’d be to not have 85 employees and all that responsibility. I wrote about how nice it’d be to get outside a bit and feel free from all that. I got excited about all the cool new projects I could do instead.

I realized the bigger learning and growing challenge for me was letting go, not staying on.

Surprised by this, I asked Seth Godin’s advice. All he said was, “If you care, sell.”

I think his point was that my lack of enthusiastic vision was doing a disservice to my clients. It’d be better for everyone if I put the company in more motivated hands that could help them all grow.

I called a friend and asked him to grill me upside down about this big decision. “What other ways can you achieve the freedom you want, without selling?” After an hour of questions like this, we both came to the conclusion that I was really done.

As with any breakup, graduation, or move, you emotionally disconnect, and it all feels as if it were in the distant past.

I felt like I was already on the highway with a little box of stuff, moving cross-country, with my old home long gone, never to be seen again.

By the end of that day, I was no longer derek@cdbaby.com.

Unfortunately, like a divorce, the paperwork took another seven months. I let two companies bid, and ended up choosing the one with the lower bid, but that I felt understood my clients better.

But it was never about the money. The decision was done in that one introspective day of writing in my diary and talking with friends. I was completely unconflicted, and knew it was the right decision.

I went to bed that night (January 18, 2008) and slept longer than I had in months. Then I woke up full of detailed ideas for my next company, but that’s a different story.

The reason I’m telling all this is because I’ve been asked the question a few times by other entrepreneurs, “How do you know when it’s time to sell?”.

My answer is, “You’ll know”, but I hope this detailed story helps illustrate that feeling.