What Are Founder Retreats?

After I left Drip, I took six months off to decide what to do next. I wasn’t sure I was going to start another company.

I wanted to do something fun. I love tabletop games, so I considered getting into the tabletop game space—maybe manufacturing them, publishing them, or building a tabletop gaming site.

I was actually in talks with a major tabletop review site and was starting to look at a hard pivot. What would it look like to sell the podcast? To sell MicroConf? Maybe it was time for me to get out of the startup game and sail off into the sunset to game until I got bored of that and moved on as well.

I was on the verge of making a life-changing decision, and I needed some perspective. I decided to go on a retreat.

The two biggest things that have helped me in my journey as a founder are masterminds and founder retreats. Without those, I sincerely don’t think I would be as successful as I have been.

My wife Sherry has a PhD in psychology. She started going on annual retreats after we had kids, where she got away for 48 or 72 hours without podcasts, movies, or books—just herself, a notebook, and silent reflection.

When she first started taking retreats, it didn’t sound like my thing. I’m always listening to a podcast or an audiobook. I’m constantly working on the next project. But after seeing her come back from these retreats energized and focused, I decided to give it a try.

I booked myself a hotel on the coast and drove out for the weekend with no radio, no project, no kids, and no distractions.

Over the course of that two-and-a-half-hour drive, things began to settle. I started feeling everything I hadn’t had time to feel for the past year. In the silence, I had sudden realizations because I was finally giving them quiet time to emerge.

During that retreat, it became obvious that my whole life had been about entrepreneurship. Ever since I was a kid, I have wanted to start a business. I’ve always been enamored with being an entrepreneur and the excitement of startups.

I realized that I was coming to this decision of what to do next because of the idea of wanting to get away from the thing that had caused me to feel bad—as though startups were at fault rather than the decisions I made.

At that time, my podcast had more than 400 episodes, which had been recorded over eight years. That wasn’t an accident. It existed because I loved doing it. I showed up every week even though it didn’t generate any revenue.

During my retreat, I realized that being involved in the startup space is my life’s work. The podcast, my books and essays, MicroConf—all were part of my legacy. Instead of selling it off and striking out in a new direction, I decided to double down.

Within a couple months, I launched TinySeed. Then I leaned into the next stage for MicroConf, where we transitioned from a community built around in-person events to an online and in-person community, plus mastermind matching, virtual events, funding, and mentorship.

I also began working on this book.

As a founder, it’s important to know yourself. Even if you started out with firm self-knowledge, the fast pace and pressure of bootstrapping a business—not to mention the pressures of the rest of your life—can make it difficult to see your path. A founder retreat is a way to reacquaint yourself with yourself every so often.

After my first founder retreat nearly a decade ago, I started going on a retreat every six months. Now I do one a year, and it’s one of the most important things I do for myself, my business, and my family.

If you’re considering a retreat, several years ago Sherry wrote an ebook called The Zen Founder Guide to Founder Retreats that explains exactly what questions to ask yourself, the four steps to ensuring you have a successful retreat, the list of tools she recommends bringing along, and how to translate your insights into action for the next year.