I’ve made millions, should I sell my company and move on?

How do you know when it’s time to seek new challenges?

Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So, throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

– Mark Twain

Truer words have never been spoken. In every startup’s life, founders are more confident in taking risks, because they don’t have much value in their companies yet to lose. To grow beyond initial stages, you have to take chances. This could be building software applications, products, services, or research. This is particularly true in industries where the market opportunity is large enough for you to take risks in the early stages. In the early days of Google and Facebook, this approach generated alot of innovation that today would be impossible due to their size and stage. You can’t just write software at Google or Facebook anymore….or even Microsoft. The plethora of hoops to jump through is reflective of their size and stage.

As a founder, the value of your startup grows as the company grows. With this growth, owners become more conservative fearing greater damage than when it was a smaller business. Through the journey, you may have earned a good income, made other investments and built a stable financial ecosystem for yourself and your family.

Many Founders are never quite done. It’s not unusual for Founders to have more than one endeavor at the same time. Growth and entrepreneurial maturity also brings into focus a need to pursue interests beyond your primary one. Perhaps it’s sailing, travel, new ideas, new industries….there will always be that call to the frontier. The question now is, should you sell and move on?

It’s more fun to ride a horse than a camel! When days of excitement turn into days focused on bureaucratic continuity, perhaps it’s a sign for inward introspection and a gaze over the frontier.



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Alani Kuye

Alani Kuye

Technocrat, Pragmatist, Geek trying to un-geek myself! Founder/CEO