Question: Do you still love the company you built?
I have loved companies. I have also hung on too long when that love waned because I am human like you and in that humanness we are all flawed.
I restored a wonderful Ferrari in 1999. It was truly a labor of love, although waking at 4 AM to call around Europe looking for a flywheel truly sucked. After the restoration was finished, I drove it all of 200 miles. The end result was satisfying and I resolved to never part with the car – a very low serial number 328 GTS – the last year of a wonderful model.
That feeling changed in early 2001 when I took my future wife on our first date. Late that evening I took the tarp off the car in the garage and (gasp) let her drive it. The relationship was nascent but I had no fear. She handled throttle, clutch and shift points as I reached over and grabbed the wheel. Yep – she let me steer from the other side. We achieved a remarkable level of trust as speeds hit triple digits in the hills of Sepulveda Boulevard just North of UCLA.
That would be the last time anyone drove the car prior to me placing an ad in the renown Ferrari Market Letter.
Why sell? Well, how the hell can you top it? A first date with that kind of adrenaline? It’s an un-effing-repeatable pinnacle.
Back to my original question: Do you still love the company you built?
If you cannot answer yes with conviction, then its time to either:
(A) Become Chairman and hire a CEO
(B) Take steps to optimize things and sell it
If you no longer have passion and it has become a grind, then it’s time to sell. Set aside all the seemingly logical inner-dialogue (read: arguments) about price, value, investment and reading the effing tea leaves about market prices in a year or two. Your satisfaction is much more valuable. And, your time is 10X more valuable than that.
Get over it. Sell it. Find the next dream.