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.

Advice is a tricky thing. We get it all the time. We give it all the time. And we seldom know if what we are giving or getting is actually any good until we evaluate it in hindsight. As an entrepreneur, I've spent a lot of time speaking with mentors, advisors, peers, and friends asking for advice, listening to their stories about what they've done over course of their careers and how they've handled certain situations. As an investor, I spend a lot of time sharing my own stories and advice with other entrepreneurs.

Whenever giving advice, I like to provide a disclaimer that whatever I'm saying is strictly informed by my own set of unique experiences, and that the context in which I learned whatever I'm sharing is important. When receiving advice, I think this is a crucial thing to internalize: not everything you hear, even if it's from a person you genuinely admire and trust, may be relevant to your situation. Understanding the context in which they learned a lesson is key in applying that knowledge to your own set of circumstances.

When receiving advice, it's important to be very wary of people who declaratively state, "You MUST do this!" Unless someone is sharing something that is objectively true, like 2 + 2 = 4, then you must push to understand the context of their experience. The other exception is when someone's advice is an oft cited cliche. I've found that most advice-oriented cliches are usually truisms - they're tropes that have been learned and repeated over and over again (e.g. "Hire slow, fire fast").

I like to think of advice as little kernels of knowledge I accumulate over time that I can draw on whenever I feel it's applicable to a certain situation. Collecting these data points and refining how to apply them over time is a unique skill in and of itself. But, as the cliche goes, context is key.

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.

Advice is a tricky thing. We get it all the time. We give it all the time. And we seldom know if what we are giving or getting is actually any good until we evaluate it in hindsight. As an entrepreneur, I've spent a lot of time speaking with mentors, advisors, peers, and friends asking for advice, listening to their stories about what they've done over course of their careers and how they've handled certain situations. As an investor, I spend a lot of time sharing my own stories and advice with other entrepreneurs.

Whenever giving advice, I like to provide a disclaimer that whatever I'm saying is strictly informed by my own set of unique experiences, and that the context in which I learned whatever I'm sharing is important. When receiving advice, I think this is a crucial thing to internalize: not everything you hear, even if it's from a person you genuinely admire and trust, may be relevant to your situation. Understanding the context in which they learned a lesson is key in applying that knowledge to your own set of circumstances.

When receiving advice, it's important to be very wary of people who declaratively state, "You MUST do this!" Unless someone is sharing something that is objectively true, like 2 + 2 = 4, then you must push to understand the context of their experience. The other exception is when someone's advice is an oft cited cliche. I've found that most advice-oriented cliches are usually truisms - they're tropes that have been learned and repeated over and over again (e.g. "Hire slow, fire fast").

I like to think of advice as little kernels of knowledge I accumulate over time that I can draw on whenever I feel it's applicable to a certain situation. Collecting these data points and refining how to apply them over time is a unique skill in and of itself. But, as the cliche goes, context is key.