I've come to the conclusion that after their first or second exit, almost every entrepreneur goes through an identical existential crisis and thought process around what to do next with their life. I can confidently say this because I'm going through it right now and as part of my process I've talked to a lot of different entrepreneurs who have experienced something similar.
The process looks something like this:
-After having spent nearly a decade building companies, you finally have the opportunity to lift your head up and see the world at large. There are many different problems that need solving, and a lot of exciting things happening beyond the myopic thing you maniacally focused on for the past ten years. Also, holy shit! While you've been heads down it feels like the world has passed you by. Things have changed! It's time to catch up.
-You begin your journey of reflection and start to recognize a couple different things:
Wow, it would be really great and smart to have a lot more diversification in your portfolio instead of one giant egg. Is there a construct that enables you to do this?
Maybe I should be somewhere between more thoughtful to super thoughtful about the idea I want to pursue next. That will probably produce a better outcome!
Do I really want to commit another decade+ to one single thing again? Do I still have the energy to do this?
-You start to evaluate alternatives to being an entrepreneur. The most obvious one is VC. You're cut out for the job because you've built companies. You also think it might be easier than building a company. You will probably work super hard because you care about being great, but you won't suffer nearly the same stress. Also, you can make a lot of money. And if you're not a shitty person, which you probably don't think you are, you genuinely believe entrepreneurs will like and want to work with you. Maybe you become a VC, but you also want to know if there are other configurations that might work for you.
-Instead of abandoning building things, you come up with the amazing idea that every other entrepreneur has thought of before and decide that instead of building one company at a time you want to build 10 at a time! It's time for a venture studio / incubator! I want to be just like Kevin Ryan and the people at Sutter Hill. If Atomic figured it out so can I! I don't just have to put all my eggs in one basket, I can have many baskets simultaneously!
-Wait! Another alternative to this is just building a Hold Co. Have you seen IAC? Maybe we can buy companies and make them better in addition or as a substitute to just building companies. Have you heard of Tiny? Do you listen to podcasts featuring "business experts" who are building these Hold Cos? OMG have you heard of Constellation Software? Holy shit, LFG!!!!!
-Eh, that was a close call. I almost bought an HVAC company.
-Where do I start? Hunting for ideas feels really icky and disingenuous. When I used to build stuff I did it because I was passionate about the thing. I cared about solving a problem. I didn't just map out markets and analyze companies and say, "There's a gap there! It's time to build!" I want to feel that fervor again. Why don't I feel it? Am I too old? Did I lose my edge?
-I'll just eat some psychedelics and then the answers will come to me. Ugh, no answers yet. Maybe I'll eat some more!
-Okay, I know the Meaning of Life now but I still have no idea WTF to do with mine.
-Now what...
-I guess one day at a time and one foot in front of the other. I believe something will inevitably inescapably call to me and the momentum will snowball. Just need to optimize for luck and serendipity in the interim. Finally at peace. Let's see where it goes...
-Step 3: Profit
And that, my friends, is the cliche, tried and tested journey that insane people embark upon when venturing once again into the unknown.
