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!


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.

When in Roam

Every once in a while I interact with a new product and have an epiphany: “Ah! This is it. This is the future and how the world will work.”

Over the summer I caught up with one of my favorite entrepreneurs, Howard Lerman, and he said he had something to show me. It was a new product he and a bunch of colleagues from the various companies he had previously founded were building. He gave me a high-level overview of what they were doing, but showing always beats telling. And when Howard demoed, I knew that I was witnessing what the future of work looked like for companies that operate out of an office, remotely, or a combination of the two. There has already been a lot of good coverage of Roam and I encourage you the check it out: Howard’s remarks, CNBC, TechCrunch, Squawk Box, and IVP.

Many companies are trying to find ways for people to work better together remotely by creating some version of a browser-based HQ. We’ve seen everything from Meta’s futuristic avatar-based version of the workplace metaverse to various permutations of gamified work experiences. Most of them come across cartoonish and impractical. But Roam actually feels like a HQ, but in the cloud. It’s a viable virtual office.

I fell in love with it for several personal reasons. First and foremost, it mimics a physical office. I can see who is present, who they’re meeting with, “knock” on their “doors,” and have spontaneous conversations. It’s the only thing I’ve seen that comes close to the in person experience. It’s intentionally skeuomorphic, or as Howard describes, a “breakthrough office graphical interface,” the same way Apple designed for the iPhone when they were acclimating the world to transitioning from desktop to mobile.

I need to be around people in order to feel energized, productive, and happy. If I ever were to build another company, I’d want to work from home 1-2 days per week and be in an office surrounded by people 3-4 days per week. Roam is the tool that creates a seamless experience transitioning through these modalities, ensuring nobody loses out on the magic of collaboration. It also eliminates roughly 50% of Zoom meeting time by making quick hallway conversations practical – the average meeting time in Roam is ~8 minutes!

The shift to distributed teams, remote work, and an asynchronous cadence has been confusing and hard for most founders and leaders. There’s always a creeping suspicion in the back of your mind that people are phoning it in and that you’re losing the magical moments that make building things so special and rewarding. And for those who value a performance based culture, the transition to remote or hybrid is a steep learning curve with few best practices. Roam is a happy equilibrium. It’s the solution we’ve been waiting for that needs to exist. It’s not that Roam enables managers to surveil, it’s that it creates a work setting that enables people to flourish regardless of where they are. Some people and roles will always be able to operate asynchronously and that’s great. But that’s the exception, not the rule. And Roam empowers different configurations to embrace best practices and develop new ones for a rapidly changing work world.

I believe that Roam will be the platform that enables more magic moments between colleagues and helps us to do even better work together. I’m lucky to be an investor backing Howard and the incredible Roam team. Sign your company up here.