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!

I've spent the past several months decompressing and occasionally thinking about what to do next, or more accurately, thinking about how to think about what to do next. One of the things I keep coming back to is a conversation I had with Nigel Morris (one of the kindest, sharpest, and most affable entrepreneurs out there) last year. He shared a framework that really resonated for me: Spend the first third of your professional life/career (ie ~15 years) building a network and becoming an expert in something. Use the middle third for capitalizing on and leveraging the knowledge and skills you've accumulated. And the final chapter can be spent paying it forward.

I like this because it's a simple way to think about things and also provides a framework for asking some important questions: What are you actually good at? What does a career or profession mean to you? For the middle third, to what end(s) do you wish to capitalize or leverage the foundation you've built? It's a tough series of questions to answer, and they usually beget more questions than answers, but it's been a fun and insightful journey for me to try to tackle them.

One of the things I'm grappling with is that I dislike the word career. Perhaps the concept is offensive to me because I don't like thinking about a strong dichotomy between "work" and "personal" life. It's also challenging to think about what else you can do with a history of entrepreneurship other than build more companies or do some form of venture to help other entrepreneurs. Regardless, this way of breaking things down into three ~15-year intervals (or The Rule of 45) is a forcing function to ask some of the right questions when reflecting on the past and evaluating the future.

Watching the world of technology evolve at its fastest rate ever due to AI hitting its stride is absolutely nerve wracking. As an entrepreneur focused on software, I feel like I'm experiencing an existential crisis. I imagine most founders are going through something similar. It's anxiety inducing. We are grappling with unanswerable questions right now: What is the future of software? Will what I'm working on be made obsolete by AI over the next 12 months? 24 months? 5 years? What does it mean if the rate of progress and change continues to accelerate? What The Fuck?

Most people building things have been living in a relatively safe world. Tyler Cowen hits the nail on the head when he proclaims, "Virtually all of us have been living in a bubble 'outside of history.'" Technology entrepreneurs have certainly experienced a lot of change in the past two decades with the transition to cloud and mobile, but those moments felt much more understandable. Sure, there were plenty of surprises and disruption, but nothing even remotely comparable to the seemingly inevitable radical AI upending that is upon us.

It's a moment in time where we experience equal parts excitement about what is possible and absolute dread at the thought that everything we know how to do and excel at feels like its growing increasingly irrelevant by the day. I am immensely grateful that Fundera was acquired two years ago and I'm a free agent that gets to soak this all in and think deeply (although it's unclear what good the deep thinking will actually do). I do not envy founders who are many years into company building and need to grapple with the existential questions this moment in time requires. I have a great deal of empathy for you.

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!

I've spent the past several months decompressing and occasionally thinking about what to do next, or more accurately, thinking about how to think about what to do next. One of the things I keep coming back to is a conversation I had with Nigel Morris (one of the kindest, sharpest, and most affable entrepreneurs out there) last year. He shared a framework that really resonated for me: Spend the first third of your professional life/career (ie ~15 years) building a network and becoming an expert in something. Use the middle third for capitalizing on and leveraging the knowledge and skills you've accumulated. And the final chapter can be spent paying it forward.

I like this because it's a simple way to think about things and also provides a framework for asking some important questions: What are you actually good at? What does a career or profession mean to you? For the middle third, to what end(s) do you wish to capitalize or leverage the foundation you've built? It's a tough series of questions to answer, and they usually beget more questions than answers, but it's been a fun and insightful journey for me to try to tackle them.

One of the things I'm grappling with is that I dislike the word career. Perhaps the concept is offensive to me because I don't like thinking about a strong dichotomy between "work" and "personal" life. It's also challenging to think about what else you can do with a history of entrepreneurship other than build more companies or do some form of venture to help other entrepreneurs. Regardless, this way of breaking things down into three ~15-year intervals (or The Rule of 45) is a forcing function to ask some of the right questions when reflecting on the past and evaluating the future.

Watching the world of technology evolve at its fastest rate ever due to AI hitting its stride is absolutely nerve wracking. As an entrepreneur focused on software, I feel like I'm experiencing an existential crisis. I imagine most founders are going through something similar. It's anxiety inducing. We are grappling with unanswerable questions right now: What is the future of software? Will what I'm working on be made obsolete by AI over the next 12 months? 24 months? 5 years? What does it mean if the rate of progress and change continues to accelerate? What The Fuck?

Most people building things have been living in a relatively safe world. Tyler Cowen hits the nail on the head when he proclaims, "Virtually all of us have been living in a bubble 'outside of history.'" Technology entrepreneurs have certainly experienced a lot of change in the past two decades with the transition to cloud and mobile, but those moments felt much more understandable. Sure, there were plenty of surprises and disruption, but nothing even remotely comparable to the seemingly inevitable radical AI upending that is upon us.

It's a moment in time where we experience equal parts excitement about what is possible and absolute dread at the thought that everything we know how to do and excel at feels like its growing increasingly irrelevant by the day. I am immensely grateful that Fundera was acquired two years ago and I'm a free agent that gets to soak this all in and think deeply (although it's unclear what good the deep thinking will actually do). I do not envy founders who are many years into company building and need to grapple with the existential questions this moment in time requires. I have a great deal of empathy for you.