The Itinerant has been an ongoing experiment to develop a repeatable personal content curation, consumption, and creation process. That sounds overly formal. Truth be told, it’s me pulling on the seemingly inexhaustible number of intellectually stimulating threads and doing it publicly. The ultimate vision is to do it together, in a community, with other like-minded individuals. In the process, I’ve also unexpectedly learned a lot about new media.

To recap the experiment so far:

• Iteration 1 (2021): newsletter, long(er) form content, focused on areas of personal investment interest. I explored niche thematic areas (i.e., the Colombian real estate market, quantum computing, digitizing real-world assets, etc.) and several potential personal investment opportunities. I learned that the process of researching and writing something I felt confident sharing in public took too long to do as a hobby outside my day job.

• Iteration 2 (2022): newsletter, shorter form curation of articles with my summary voice-over and take on ‘why interesting.’ Similar focus areas to Iteration 1, it was a test at greater efficiency without sacrificing quality. Turns out – it still took too much time, and now I was doing more consuming and curating than thinking and creating.

• Iteration 3 (2023): newsletter, even shorter form: bulleted links to articles organized by topic, with a target of 1x/quarter longer form pieces. I now got down to the most efficient method for consistently writing each week, except it wasn’t writing. It was curated based on my consumption. So I did have more time to reflect and write quarterly pieces, but I found this approach of sharing these links to take longer than it was worth still.

• Iteration 4 (2024 - current state): no more weekly newsletters. If people want to follow the content I am curating and consuming, they can now do so here. I’ll only be sharing long-form content as I have time to write it. Less self-imposed pressure = more organic, creative output and greater enjoyment. I’m also beginning to experiment with other forms of media, including live streams and podcasting.

Coming into the 2023 year, I set the goal of 50 weekly ‘quick hit’ newsletters of curated articles, 4 long-form deep dive research pieces, and ad hoc double clicks into personal investment opportunities I was considering. I’d give myself a “C” for a performance last year, passing, but barely (25 weekly pieces, 6 long-form pieces, 1 personal investment write-up).

You could make the case that after three years and multiple pivots in approach, I should recognize the reality of what it takes to produce high-quality content consistently and that I don’t have the time to do it.

This would be a fair conclusion, but it misses the point: I’m doing this for an audience of 1:  me. The process is more important than the outcome, and the benefits have been tangible. Allow me to explain.

1. Reading, thinking, and learning about a wide range of topics outside my immediate field has always been a joy-giving activity for me. It's not work; It’s how I’m hardwired. I like to explore. This entire effort started when I realized I should start making public the reading, research, exploration, and thinking I was doing already. So many good things have materialized throughout my career and life simply because I put myself out there.

2. Putting ideas on paper and connecting the dots across disparate threads and topics helps crystallize my thinking and conviction. It highlights the limitations of my understanding of the topics and forces me to wrestle with the nuances in a way I wouldn’t if I weren’t writing about them.

3. It forces me to continuously practice new methods and mediums of communicating ideas. It provides a more tangible and durable entry point into the discussions at the very frontiers of technology, innovation, science, history, business, and life.

4. It allows me to hold myself accountable and to back-test prior assumptions I’ve made about technologies, markets, investments, or ideas writ large. I could still write and not make it public – but that would be a missed opportunity. While there is certainly a professional risk in publishing partially formed ideas, the benefits outweigh the risks. That may change with time and is something I consider carefully.

5. It’s also worth highlighting that my evening/weekend adventures in real estate investing and then later into web3/crypto emerged directly from the practice of research, exploration, and writing. It is not intellectually dishonest of me to attribute the financial success I’ve experienced thus far in those areas directly back to this experiment.

No year-end self-reflection can be complete without asking the hard questions. So here we go.

• Q: Is what I’m publishing a good representation of who I am and what my professional maturity and capabilities are? The reality is I’m writing for myself. Chances are slim that anyone will find it, let alone judge my competency against it harshly. A good example is to look back at the early pieces published by Joe Rogan, Gary Vee, or Fred Wilson. I don't aspire to what they’ve become, but it’s a good reminder that starting and focusing on consistent improvement is infinitely more productive than not starting at all.

• Q: Could I be using this time more productively by working nights/weekends on things directly related to my day job? Perhaps – for a while, but I would burn out. The Itinerant is life and energy-giving. It’s not work. It’s play. Playing regularly allows me to be authentically myself and more present in my work and the lives of those who matter most to me. It also doesn’t hurt that many of the rabbit holes I find myself going down are relevant to my day job. There was a time early on in my career when I tried to ‘just stay focused’ and would use nights and weekends to work rather than explore additional intellectual pursuits. There is a time and a place for everything, and I see the value in that during certain seasons. Staying hyper-focused on one vertical and not pulling the threads of other intellectual interests stifled my excitement about that day job and ultimately did more harm than good. While the focus is essential to accomplishing goals, the nuanced reality is you need to know how to balance hyper-focus with intentional creative exploration and permit yourself to be intrinsically motivated. When I allow myself to engage in my many other intellectual pursuits, I find it allows me to be even more present in my day job and helps me look at problems through multiple lenses.

• Q: What is a good example of how this has benefited my work in healthcare venture capital? Candidly, I’m still working towards a strong concrete example. But I am confident that it will materialize. Less concrete examples are abundant: (1) Personal deep dives into the technicalities of deep tech, such as quantum, blockchain, and artificial intelligence, let me probe more thoughtfully into healthcare-specific applications. (2) The simple process of undertaking this experiment has shown me how challenging new media is to do consistently well. It helps me empathize with founders seeking product engagement and exploring digital marketing avenues.

So with that, here’s to 2024, filled with more public intellectual exploration and contemplation. Hopefully, someone might find value in it; I know I will enjoy and benefit from it.

Thank you to ChatGPT for copyediting support.