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.

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!

Today is my official last day at Fundera / Nerdwallet.

For the first time in my life, I have absolutely no clue what will come next. This is a new experience for me and it fills me with anxiety. But I am eager to learn how to explore and embrace the uncertainty.

When I was a teenager I played tennis competitively. I was a nutcase and would regularly throw tantrums and break rackets when I lost. I saw a sports psychologist and he told me about an ancient Chinese phrase called wu wei which he described as meaning "go with the flow." While it's a minor perversion of this Taoist concept, Westerners have adopted it to represent an orientation of "effortless action," "non-doing," or "action through inaction." I love it and it has served me well.

As a Type-A-Control-Freak-INTJ, wu wei doesn't always come naturally, but when it does it's beautiful. I am ready to go with the flow.