Over the last couple weeks I’ve had the opportunity to talk with multiple entrepreneurs that have had nice exits and are thinking about what’s next. After putting thousands of hours into a venture and going through so many low lows and high highs, it makes sense that an entrepreneur would be thoughtful about what’s next. Building a company is incredibly taxing, both mentally and physically. Now, with financial freedom, a good deal of urgency and ambition is often tempered.
When talking to these entrepreneurs, my main point always stays the same: don’t lose your bias towards actions.
Keep moving.
Keep pushing yourself.
Keep exploring.
Keep tinkering.
Many years ago, I was on the other side of the table after we sold Pardot. I was talking to a successful entrepreneur, seeking advice as to what to think about now that it was time for the next chapter in life. He said something that has always stuck with me, “Your skills will immediately start atrophying if you don’t stay in the game.”
Figure out what game you want to play next.
Join/buy an existing business?
Invest in startups?
Do board work?
Do nothing?
Most of the time, the entrepreneurs I talk with want to do something. Rarely do they want to jump in and grind out another startup from scratch. For me, I think of it like the parent vs grandparent analogy.
As a parent, you always have to be on. You have a deep responsibility that’ll likely last a lifetime, but often at least 18+ years. It’s an experience that’s immensely rewording and challenging at the same time.
As a grandparent, you don’t always have to be on. You care deeply but can come and go with no day-to-day responsibility. The highs aren’t as high and the lows aren’t as low, yet the joy is still there.
Entrepreneurs post exit would do well to maintain their bias towards action, figure out what game they want to play, and what level of responsibility they desire. While there’s no right answer, it’s important to be thoughtful and keep moving forward.
David Cummings on Startups 
David, great post as always. I agree with you that you need to keep moving forward, but I also believe the game will always be there even if you take a break from it, for yourself, your family, your health, etc. I often see entrepreneurs and senior leaders jump too quickly into the next thing because they think the game will pass them by or they think they’ll become irrelevant, or lose the there skills. I do think each person is different and will navigate the “next chapter” based on their goals and vision. I just think a lot of folks move to the next thing too quickly because they think they’ll miss out on the game or the game will leave them. As you know I’m a firm believer in taking a break (sabbatical) and re-centering yourself before jumping into the game again. With each chapter you go hard with the lows/highs, I think a lot of folks would benefit from things like sabbaticals before jumping quickly back in the game. With all the temptations and opportunities after an exit, it’s actually harder to switch your brain to a different pace and priority, but I believe it makes you stronger for your next “whatever” when you are ready. By the way, love your analogy of parents vs. grandparents, so true.
Great share, David. Very timely read for me, as I’m in this position right now. I always appreciate your insight.
Great share, David. Very timely read for me, as I’m in this position now. I always appreciate your insight.