Hello friends on my blog, this is a note i sent out with some liquor filled chocolates to friends and colleagues a month back, it’s about where I’ve been and where i’m going! Enjoy!
Happy sometime in April, and weÂÂlcome to draft #50! Initially, I wanted to write a New Year's letter about my travels & work with startups. Ironically, though, my travels and work with startups kept me too busy to finish the letter and send it out. Between January 7th and April 1st, I drove across America and backpacked in Costa Rica, and it was each morning that I found myself writing and re-writing this draft in cities across Northern and Central America. So let it stand that this is either the latest New Year's letter of all time or a perfectly timed spring note - and with that, here we are, with a box of hard liquor chocolates (Macallan 12) and hopefully the first of many written correspondences. My aim is to share where the past year has taken me—through my work with startups, my physical travels, and the books that have helped shape me. Through these three modalities, I've gone on a journey to embrace uncertainty. And if this letter ever gets boring, feels like it's dragging on, just eat 8 of those chocolates real quick, sit back, and then read on.
Early in the year (March 2024?) I left my role at a New York-based Venture Capital Fund, where I was investing in machine learning infrastructure. All was going well, but I got the itch, the type of itch that just can't be scratched by Zoom meetings or another deal, only by movement, the movement that takes you further into your connection with the people and places around you. There was no advance planning, grand strategy, or future job waiting, just a sense that life had much more to offer me and I ought to go get after it before it passed me by.
Every morning, as I dressed, I listened to Marty Robbins, Waylon Jennings, Jim Croce, Willie Nelson, or Hank Williams, feeling drawn to the ballads, songs, and stories of an unpredictable life on the road. As old country filled my apartment, I began to dive deeper into the journeys of those who had lived the life on the road before me, reading nearly 100 books, almost all of them memoirs & biographies about musicians, hikers, backpackers, those who struck out on their own to see what laid outside of the well-worn path. But there was just one quote from the many pages I read that stuck with me daily and it was by my favorite travel writer, Rolf Potts, who wrote,
"Sadly, the traffic lights of life will never all be green at the same time. Conditions are never perfect. "Someday" ("someday I'll do this, someday I'll do that") is a disease that will take your dreams to the grave with you" - Rolf Potts, Vagabonding
With the disease of "someday" in mind, I undertook three massive journeys this year through the startups I worked with, the miles I covered, and the books that shaped me. While each endeavor looked separate, they were deeply intertwined. My reading fueled my desire to travel, my work with ML startups drove me to crisscross the country, and my desire to not let "someday" define my life pushed me to explore deeper into relationships, places, and sectors of work I'd never truly explored. In preparation for my physical travels, I read, and each author seemed to throw me a bone, teaching their own "rule of the life on the road."
After I left my job in New York, my pace of reading picked up, with many of my favorites came from Jack Kerouac, Chuck Palahniuk, Hunter S. Thompson, Tom Wolfe, Bill Walton, Charles R Cross (Jimi Hendrix Biography), as well as Gary Tillery (George Harrison Biography). After reading about the journeys many of these authors described, I had one question, what would my life look like if 'someday' were today?
Knowing I needed to find out, I gave my notice, bought a beat-up 2010 Acura MDX with 100K miles on it, crisscrossed the country, covering roughly 20,000-25,000 miles, and formally struck out on my own professionally. Frequently, I just got in the car and started driving, calling friends 400-800 miles away, asking if they were home and if I could crash on the couch in 2-36 hours.
I saw the Badlands in South Dakota, the deserts of Arizona, the crisp mountains of Colorado, and the flat high plains of the central US; I lived on 4 hours of sleep in New York City, biked to have beers with my friends in DC, I gained Portuguese Citizenship and spent time in surf hostels on the Portuguese Coast. I lived down in Costa Rica in a hostel for a month with some friends, bought a motorbike, then realized I had no idea how to drive a manual, saw the eclipse in PA, ate my way through Mexico City, and meandered around Lima. I traveled throughout England, staying with friends, and tried to convince the University of Cambridge to let me mentor students in their startup program while spending my nights sleeping in the back of a Chinese restaurant and later above a pub. Hustling from place to place, I lived out of a small hiking backpack most of the year, praying for a washing machine and a dorm bunk with no bedbugs. I experienced a father-son road trip where my dad joined me for 3,042.5 miles on the road from DC to AZ; I went to Sturgis, the largest Motorcycle rally in the world (in a car), witnessed frightening gun violence in a city I've long loved, Washington DC, and attended my first 4-day silent meditation retreat in West Virginia. And it was between rest stops, hostels, friends' couches, and calls from my mother, curious as to which country or state I was in, that I worked.
I used to invest in early-stage ML startups. Now, I invest in the people behind them—and work alongside them. For most of the year, I buried my head in academic journals and continued to become well-versed in the underlying algorithms and architectures that make up modern AI/ML models. Then I decided that my strength was at the intersection of operating and investing, so I took some time to work at my portfolio company, Brev Dev, and did whatever needed to be done, jumping in to run the complicated strategic and operational hurdles of our successful acquisition by NVIDIA alongside co-founders Alec Fong & Nader Khalil.
As the year went on, I continued to spend time at the intersection of investing and operating. I played a tiny role as an existing investor, focused on owning narratives for Arcee AI, contributing to their successful $24M Series A led by Emergence. I then invested in a few fantastic AI/ML startups, such as Odyssey Systems, BBB (Biological Black Box), a Stealth ML company, and Roboflow. For Roboflow, I was able and happy to connect a friend at GV (Google Ventures), which resulted in a fantastic and well-deserved $40M Series B. I also funded a stealth brain-computer interface company and became an advisor on narrative + strategy. As 2025 has gone on, I've taken roles at breakout portfolio companies Vellum & Biological Black Box.
Outside of investing and lending a hand to portfolio companies, I worked with a friend at an influencer marketing agency on GTM, shot a short documentary on Drag Racing & Paleontology alongside a college buddy, recorded the first three episodes of my podcast, built community through dinners ranging from 4-50 people on both coasts, operated on the partnerships team at Telly (portco), helped Wally Health (Portco) setup an organic marketing campaign in New York, volunteered with Bradley Tusk's fantastic Mobile Voting initiative and informally guided many founders on how to get the most out of their YC experience.
I've been fortunate to have people I backed financially bet on me back personally, oftentimes hiring me to run strategy and interview them for many hours, then draft memos about how their products and companies fit into the larger world; this has worked especially well for highly complex deep learning companies. These companies have complex products; where merely explaining the product and how it works is a substantial undertaking. My daily work spanned Tel Aviv hours in the early mornings, New York mid-day, then LA and SF deep into the evenings. There was never a moment where I did not feel immensely grateful to be trusted with such high-impact matters by folks who have worked their entire lives to get to where they are now. It is precisely why I push myself, not for returns but because I owe it to the people who put their faith in me to help tell their companies' stories.
Story, strategy, and narrative are where I spend most of my time now while actively investing in startups simultaneously; assuming a few I's get dotted and T's crossed, I will have worked at roughly 70%+ of my direct AI/ML investment portfolio, something I never expected. Still, when trust, technical knowledge of the products, and longstanding relationships come together, often the natural thing to do is work together a bit closer. I could not be more grateful to the CEOs & friends who have allowed me into their worlds to work alongside them; my work can't exist without theirs. All that to say, I'm working, I'm traveling, and making sizable investments in my relationships. In a move that's been a long time coming, I have moved out of my apartment and into my 45-liter backpack, becoming fully nomadic for now. 2025 will be a year where I continue to prioritize my relationships from a personal and professional perspective. I hope you can be part of that, so shoot me a text, call, or send a note back! One of the CEOs I worked with this year invited me to his wedding; that's the kind of connection I want more of in 2025—where work and life intertwine. So keep in touch, make "someday" today, and let me know if I can crash on your couch!
Happy New Year and Happy April – John