The Rule of 45

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.

It’s difficult to make predictions in times like these. It seems as if even the best builders will be subject to significantly more volatility and randomness when it comes to their success. And the bar was already dauntingly high. One thing I believe to be true is that this new world will put a premium on people who deeply focus on problem-solving instead of opportunism. The past decade has been riddled with people searching for arbitrages in software, and I think AI will likely drive the returns of that approach close to zero. Dedication to solving a problem (even if it’s coupled with opportunism) will pay dividends. Primarily because it gives you a more profound reason to wake up motivated in the morning and the willpower to battle through what will certainly be the most insanely volatile decade in technology in history.

Advice and Context

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.

The Disaggregation of Search

For the first time in decades, the way we search for things on the internet is being disrupted. Google, which by every measure is the world’s leader in search, has built a remarkable business surfacing information when we have questions. But a series of new innovations, namely ChatGPT and LLMs, coupled with new frontiers in search UI (e.g. chat-based search), are going to rapidly transform how we get the information, and hopefully knowledge, we seek over the coming decade.

I once read that the history (and future) of business is just an endless cycle of aggregation and disaggregation. I went to Google to figure out where this theory came from and the results I got back were not helpful. So I went to ChatGPT and found exactly what I was looking for:

Before Google the way we found information on the internet was by combing through verticalized directories that were compiled by humans working for companies like Yahoo and MSN. Google, through an innovative approach to programmatically and algorithmically indexing the web that yielded results far superior to any other search engine, aggregated the entirety of search such that we only had to go to one place to get the information we needed. Goodbye, directories. Hello, one search bar to rule them all. We’ve seen its evolution over the past two decades and it has had a profoundly positive impact on the world.

Today, it is hyperbolic to say that search is broken. But it is an understatement to say that it could be better. The amount of information available on the internet has grown by many orders of magnitude since Google’s inception, and the way in which we interact with information (i.e. through web and mobile applications) has changed dramatically. It has become impossible for a single search aggregator to answer all of our questions in a systematically excellent and satisfying way.

Over the past several months, a new suite of tools (e.g. ChatGPT and LLMs) and experiences (e.g. chat-based search) have been introduced to hundreds of millions of people across the globe. These are the beginnings of the infrastructure that will power the disaggregation of search. Jim Barksdale once famously stated:  “there are only two ways to make money in business: One is to bundle; the other is unbundle.” It is my belief that search is going to be unbundled over the upcoming decade (and then ultimately re-bundled when AGI can satisfy all of our search desires in a uniquely personalized way, but that’s for another (several?) decades). And it’s going to happen by entrepreneurs building on the aforementioned tools to target underserved and overlooked customer segments that Google cannot prioritize satisfying.

The defining characteristics of these search dis-aggregators are that they will be differentiated from conventional search in UX (e.g. chat-based and other novel approaches), vertical or use-case specific to improve the thoroughness of answers, and powered by LLMs that uniquely improve as usage grows. The tools are finally here to create search and information-finding experiences that are 10x better than what Google can do across a wide variety of verticals. We are beginning to see it with companies like Consensus and Phind and several more highlighted in these good pieces by Connie Chan and Justine Moore at a16z and Talia Goldberg at Bessemer.

I have spent the better part of the past decade building businesses that used Google and SEO as their primary customer acquisition channel. If I were to build something new I’d focus on creating a 10x better experience than Google can for a specific vertical or use case and relentlessly work to establish it as the most trusted brand for providing the right information in a compelling way within our area of expertise. It’s an exciting time to unbundle your bit of search.

2023 Goals

Last year I publicly shared my goals for 2022. I like having a public record of this. Diving in, here’s how I stacked up against my goals from last year. I am really happy with my achievement rate. If these were OKRs I’d consider it a successful year.

I like a tops-down approach for personal goal setting, beginning with answering the question: “If I were 80 years old, what would I regret / not regret having done over the course of my life?” From there I like to list out my ten-year goals at a very high-level, and then dig into annual goals.

This year I have updated my regret minimization framework:

By the time I’m 80 years old, I won’t regret having spent an abundance of quality time with my family, having read and retained the learnings of terrific books and being knowledgeable about the world (both the way things work and why they work that way), knowing myself and what makes me truly happy, having traveled and explored the world to my heart’s liking, spending time in nature, feeling like I’ve made people’s lives better and contributed to civilizational progress through my professional endeavors, and investing in the relationships that matter most with friends and family.

I’ve also updated my long-term (10 year time horizon) goals. I really like how these are simple and more about the way I will feel in ten years instead of objective numerical measures of success.

And finally, I modified my goals for 2023. These aren’t a major departure from 2022, they’re really more of a continuation of what has been. I think it’s good that these are iterative and evolutionary – it makes them feel doable and realistic and hopefully will enable the progress to compound over a ten year period.

Here’s to a fun and meaningful 2023!