Post Entrepreneurial Exit —Bias Towards Action #BusinessTips - The Entrepreneurial Way with A.I.


Saturday, March 12, 2022

Post Entrepreneurial Exit —Bias Towards Action #BusinessTips


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, Khareem Sudlow