A lot has changed lately. I've moved to Argentina, took a full-time job, and we are settling into a sense of stability that feels earned rather than inherited.
As I settle into this new chapter, I felt the need to look back and make sense of the path that brought me here. This is a bit of a long memoir: it's a look at the 20 years of traveling, tech, and trial-and-error that shaped how I see the world today.
I used no AI at all to write this (only proofread).
I hope you enjoy the read.
The Wild West of the Web
I grew up in the Southern California suburbs in the late 90s/early 2000s.
My dad got our first Macintosh around 1995 and I went online for the first time to find cheat codes for N64 games. I wasn't allowed to have video games but all my friends had them—but few of them had the internet like me.
My parents bought me Macromedia Flash 4 for my 12thh birthday. Before elementary school was out, I was making Pokemon websites with Angelfire and Maxpages. I'll never forget my dad asking me how the hell it was possible that I had a music video of blink-182 running around naked on my computer.
"It's called Napster, dad."
"How'd you hear about this?"
"I met this person on AIM through my Pokemon site, they told me about it."
"What's their name?"
"I don't know. His username is UpYours2000"
I hosted my first podcast RSS feed on a free VPS in 2004. My co-host and I were sophomores in high school and we started the feed on episode 25 to make it look like we were experienced podcasters before moving over to iTunes.
I started a YouTube channel when I graduated in 2006 to host the videos I'd made for my high school news program. I was much more into video creation than website building by that time. I wanted to go to film school.
The Bohemian Wanderer
Instead, despite my youth on the cutting edge of tech culture, I ended up spending my university years trying to shed my skin of all technological fancy. On a slow conversion to Kerouac-inspired bohemianism, wine, and weed, I left the bubble of my youth to study abroad in France, Mexico, and Costa Rica and study language, literature, and the flames of historical revolution.
When I graduated college, I quit my cushy job at one of the biggest post-production sound houses in Hollywood because I couldn't imagine getting roped into the 40-hour week grind for the rest of my life. I'd rather be broke, I told myself, then become a slave to the paycheck. Little did I realize how much cumulative stress that would create for me over the next 15 years. I was making a huge sacrifice but it wasn't the sacrifice I thought it was.
Meanwhile, I'd also been witnessing the rise of the corporate internet. Something about it felt wrong. It had been cool and fun to build in the late 90s/early 2000s. The culture had been exploratory and human. But by 2010, it was all SEO and marketing, social networks and algorithmic feeds, keeping up with the next big thing. It didn't feel cool or fun to me, it felt like work with too many rules. And I didn't like rules.
So I bade a bittersweet farewell to the hobby I'd always loved and "fucked off."
I traveled in & out of Europe for 2 years as a writer of fantasy & science fiction inspired by the existentialism I studied for my BA in French Lit. I was halfway communist because I thought the world was so fucked up from the U.S. Empire yet my Bachelors Degree hadn't required me to read any Solzhenitsyn. I'd read Confessions of an Economic Hitman, believed 9/11 had to have been an inside job because no one was doing anything about the obvious facts, and saw Obama as a very obvious continuation of Bush. I stopped watching movies that came out of corporate USA and only listened to the obscure electronica I found on invite-only torrent sites.
In my rebellious anger at the world I didn't want to be part of, I soon ran out of money and decided I would give in—my way. I moved to Bangkok to become a full-time English teacher. It was fun and I enjoyed working with kids when I wasn't hungover. But despite the foreign culture and debauchery (I wrote a book about it), the lifestyle once again had me running after my contract was over.
That would be my last real job for almost 15 years.
From 2012 onwards, I leaned into a lifestyle of high human connection and low overhead, subsisting just a couple steps above pure charity. I did everything I could to not have to dedicate my life to the capitalist lifestyle of what I considered selling my soul. My parents couldn't understand how I did it–but I never went to jail and I never asked for money despite frequent financial stress, so they didn't complain. They were smart not to, though parts of me wish they had.
During that era, I traveled over 50 countries on a shoestring budget, focusing on people & culture (and girls) over sights & comfort. To save money, I was an avid Couchsurfer and even became an ambassador for Couchsurfing.com before Airbnb took over the world. Hitchhiking was my preferred mode of transportation and I often traveled with a musical instrument. This is how I learned the guitar, accordion, and trumpet. It also helped me make money and friends on the streets. I had a pact with myself and the universe to always accept anything people offered me—food, lodging, rides, even love. While pure of heart, this intention also lead to many hard knock lessons being learned.
Despite my nomadic ability to slip through the cracks of an increasingly corporate world, I still worked hard. As a digital native, the Golden 2010s, as I refer to them now, was a beautiful time to come of age in the world—especially if you weren't tuned into what was happening in tech, politics, and society. I learned to produce music and released albums on Soundcloud (this link has only newer-ish tracks).
Work trading in hostels, I also wrote a few weird books that I never put out but my friends & family always read. All I wanted was to do the thing; not hustle to earn anything from it. I would exercise my digital creativity for 6-10 hour days before finding a cheap beer buzz with new friends every night. I was one of the first generation of Tinder users and it slowly replaced Couchsurfing as my means of meeting friends, lovers, and even hosts all over the world.
I had a knack for picking up enough of the local language to get by, or at least entertain the locals. This was a large contributor to my unorthodox, happy-go-lucky success on the road in this transitionary moment in history. If you could find a translator app that worked, you still needed Wifi—I didn't travel with a data plan. I still speak 3 languages fluently; though apart from speaking English and Spanish daily today, my French is a little rusty.
During that period, connections from my past would occasionally hit me up to make them a website or edit a video and pay me a few hundred dollars. I never had much more than that to my name, and I fell into credit card debt early on, preferring the bottle and pen over a job and paycheck. Bukowski-inspired, I told myself one day I'd be rich from a book I wrote. I also abhorred SEO and marketing; so any online endeavor I began was destined to fail before it began. All the work I did for people was always with the limited stack I was familiar with back in the early 2010s (Wordpress and Photoshop)—but clients never understood that.
The Cost of Freedom
In 2014, I sucked up my pride, bit the bullet and charged a GoPro and forehead strap to a credit card, and started a YouTube channel to take seriously. I'd heard of creators making money from ad revenue and thought "hey, I could do that!" It wouldn't conflict with my values if I made the content my way. In those days before thumbnails, my "third-eye travel" channel did gain traction and even made me a few thousand bucks over the course of a few years (especially when I went viral in Nepal's 2015 earthquake); but the audience ultimately tended to be more into my legal cannabis dispensary video tours than my travel and psychedelic consciousness sondering (which I would have preferred being known for).
Driven by a new desire to do more than just "exist," I bought an actual DSLR camera and shifted gears. I started a 501(c)3 non-profit for creating "smiling media" for charities, NGOs, orphanages, local communities, and any other low-budget organizations that had a story to tell but no means to tell it. I hosted an IndieGoGo campaign to kickstart the project. I occasionally attracted large donations to expense my well-intentioned travels—but ultimately, everywhere I went I traded my extended video documentarian labor for room and sometimes board. But I was still always strapped for cash, racking up credit card debt slowly but surely—and stressed.
Between 2015-2020, this lifestyle created opportunities for me I could never have planned with all the money in the world. I spent time exotic places like Cote d'Ivoire, South Africa, Ethiopia, Jamaica, Colombia, Argentina, Nepal, India, Bali, Hawaii, Vietnam (and more), tagging along with actual locals living their lives. To this day, my various YouTube channels still act as a post-mortem portfolio of the hundreds of videos of people I met and documented on my travels. I had to admit, too, that in running the 501(c)3 it was also fun to manage a website again, create styleguides and letterheads, and try to generate attention on social media.
The digital world I'd been trying so hard to avoid was once again capturing my attention, but the social entrepeneurship was just the beginning. After hearing Andreas Antonopolous on the Joe Rogan Experience in 2013, Bitcoin was put on my radar—later I even asked folks in West Africa about it—but despite sounding cool, to my economically-ignorant brain, it still sounded like more bad capitalistic financialization stuff. Regardless, I was still swallowed up by the crypto explosion in 2016 when I put $150 into the DAO launch as an exercise in learning how to use the Ethereum network.
And then the DAO got hacked and made global headlines. I made my first foray into participating in a global conversation with a VLOG about it: to me, the most fascinating part of the hack was how the community came together to decide to reverse the hacked coins. While I've since come to disagree with that decision, I still agree with my thought process at the time: "What a cool technology, that people can pool together funds without the need for any banks or bureacratic middlemen and make decisions that are best for the community."
That reversal changed my life, however, because then came the windfall. Caught in the crossfire of the DAO hack and the reversed coins, that $150 worth of ETH would transform into almost $20,000 about 18 months later in early 2018—more money than I'd ever had or imagined having. I sold before it hit that peak, but it was still enough to pay off all my debts. I was a financial idiot, but suddenly the red ink vanished. For the first time since college, I was back in the black and the show could go on.
The financial pressure was relieved for now, but within that newfound breathing room the nature of my travels and lifestyle began to shift. I was moving away from the solitary 'me' of the nomad years–a person defined by how little he needed or wanted–and toward a version of myself that had the stability to handle the weight of deep & consistent connection (both with others and myself).
This transition manifested as a long, beautiful but emotionally-taxing roadtrip with a girlfriend through Australia. In trying to build a serious relationship together, this adventure acted as a period of seasoning I needed to complete my transformation from solo wanderer to man capable of building a shared reality. It was there, amidst the dusty miles of the Nullarbor where we decided I'd take a bus the rest of the way, that I no longer wanted to navigate the world as an individual moving through space & time, but as a partner. This would prove a necessary prelude to the whirlwind that was about to follow.
Despite the dramatic break-up, that seasoning proved essential. If my wandering years were the slow, activating heat of the charcoal, then my 2019 landing in Argentina (after my first ayahuasca ceremonies in Colombia) was the perfect moment for the meat to finally hit the grill. I was there to work on a travel film with a motorcycle adventuring entrepreneur I'd met in India years prior, but the real heat was internal. I was beginning to feel the burnout of the nomadic life. I craved substance and wished to feel worth more than just videography, and the physical reality of being a man in his early 30s with more back pain than he cared to admit.
And then, in the heart of Buenos Aires, the flavor of my life changed entirely when I met someone whose trajectory would synthesize perfectly with my own, sparking an unexpected—but appreciated—next chapter for us both.
The Return to the Machine
Over the next 2 years (after the 2020 lockdowns, of course) we sought out a home base for the sudden family we were starting. Sojourns in Peru, Argentina, and California eventually lead us back to the most magical place I'd ever come to know in my travels: the Big Island of Hawai'i.
I'd always dreamed of building my own off-grid home and growing my own food, and so that's what we set out to do. We sold all the Bitcoin we'd managed to scrounge together before the run up to $69k to build this life for my wife and two young children. Having a self-sustainable life was much more important than savings, I told myself.
But alas, not all that glitters is gold. Or digital gold.
The stress of living in a rustic tiny home with a baby and a toddler, no money or consistent electricity in a cash-impoverished location had negative effects on both of us. (We made videos about it but I've since taken them down for privacy reasons.) I buckled up to start learning how to market myself and create a personal brand, to monetize an audience, and to provide value; anything required to provide for my family... but becoming a revenue-generating entrepreneur is a slow-going process to anyone who'd avoided the hard work for over a decade.
Within 2 years of building the home, we threw in the towel. Under the weight of our financial hardship, the very nature and natural living we'd invested in enjoying was feeling impossible to appreciate. We rented out our tiny house and, at the behest of an opportunity that came my way, decided to move to El Salvador to build a life as entrepreneurs in Bitcoin Country.
In ES, I helped found Sovereignty Studios and the Build in El Salvador project over the course of 2024-2025. We hosted retreats, made media, and hosted a podcast connecting the Bitcoiner community of El Salvador. For the first time I felt part of a movement bigger than myself. More important than myself. What better place to grow roots for my children than in a place with such a bright future? Bitcoin is largely still the only hope I see in the world.
But it didn't take long to feel like the country's progress was more of a marketing campaign than reality. The grassroots community was for real, but the government-driven "Bitcoin" projects... well, something felt off about it all. Plus I'd already done my time in third world countries as a traveler—why was I choosing to live in one now, with all that it entailed, when I still didn't have any financial or professional stability to keep us going? What was better for my kids, an uncertain present or an uncertain future? The dream was over just as soon as it began.
Not to mention I was hardly making enough money to live. As my entrepreneurial projects crumbled with my outlook on a long-term future in ES, a bright side appeared amidst everything: I was becoming a competent solopreneur, a full-stack creator. After a decade of running from the structure that would grant me economic harmony, things were now starting to come together.
To this end, in early 2025 I started over—again—and decided to master agentic AI. This was a fresh topic because models were only recently becoming capable of accomplishing agentic tasks—but it big. Huge.
And more importantly: this was me. For the first time since the mid-2000s, it felt OK to nerd out on technology again because it was just so cool, unique, and difficult to compare to all the other nonsense I'd witness happen to the internet since my childhood (Thank God). For the first time in my life I felt like I could do anything online. All the things I once needed a budget and a freelance developer to accomplish, I could now do by telling a machine. I began feeling like my deepest creativity could finally explore itself.
With a new breath of confidence, I started my fifth serious YouTube channel to share what I was learning with the world. Relative to anything else I'd ever started since my Pokemon days, it blew up right away. I made free little micro-courses to collect email addresses, and started selling low-ticket products. Created a handful of courses and a community in which to sell them. Attention was flowing my way doing something I absolutely loved: exploring a fun new technology and making videos about it, connecting with people (albeit digitally) along the way. This is also when I started making content on the side with Venice, the coolest and most aligned-with-me (crypto-meets-AI) company I'd ever come across. More on that in a moment.
On the home front, we were devastated by our loss of time and funds in El Salvador. We ended up back in Hawai'i only to re-live the same problems we'd experienced before. We tried renting out a new, bigger, on-grid place and while it did made life easier, we got kicked out when the house was sold to an Airbnb investor. For the first time ever, I wasn't stressed financially but domestically. We still weren't accomplishing the stability we knew we needed.
There was nowhere else for rent in our little preferred pocket of the island, and my joke to my wife soon became a legitimate fork in the road: "I'd rather live in Argentina than anywhere else on this island." Ha.
We packed up a small container of everything we had owned and accumulated in Hawaii and shipped it to Argentina. After a quick stop-off in South Dakota to become nomad residents (yes, that's a thing), and a week in Las Vegas to speak at Bitcoin 2026 (I was invited to come speak about AI and solopreneurship), we headed down to Argentina to my wife's hometown with 12 suitcases. I was making money for once, yet I was back in debt again.
By this time Venice had offered me a full-time job. I knew it would be smart to take it, but something about working for someone else was hard to swallow after so many years on my own. Processing all the ego involved in deciding to work for someone else again, as well as having to say goodbye to the hints of success I was finally tasting in my very own revenue-generating business (for the first time ever), it took over 4 months for me to finally sign the contract.
But I signed it, and now here I am. Recently arrived in Argentina in a house in a peaceful area that's big enough for all of us. It might also go up for sale before we're done renting it, and we might even be able to buy it if we play our cards right. The plan is to be here at least until I get my citizenship, which will take a minimum of two years. Hopefully we'll want to stay after that, too.
After 15 years with no stable employment, I can't deny that it feels good to have some income security. Especially as the kids get older and the requirements of providing for a family increase in cost. It also feels good to know we have committed to 2 years with no significant travels. I have not experienced a period of quiet like that in over 20 years, since I was 18 living with my parents.
But perhaps even better than that feeling of stability is what I get to do at this full-time job—like I'm a kid again, I get to mess around with fun new technology and then make videos about it. This helps the company make money. What I'm appreciated for, what I was hired to do has much less to do with the hustle than it does with contributing my part to a business machine that makes money. (It helps that I'm fully aligned philosophically with the company's ethos.)
While I'm glad I learned it and I know I must teach my kids it, the "serious entrepreneur" phase seems to have been a passing moment to give me the confidence to put myself out there as I became the man that could provide for his family, as blind as to what may come as the hitchhiker unknowing where tonight's highway may lead him. For me, this stepping into the unknown lead to a very aligned and lucrative job opportunity. The same shit I was doing as a tween I'm now doing professionally.
And for all I know, assuming I don't get fired, this might be the last era of my life where I'll really need to work for money. In the crazy times we live in, this is a blessing for which I am incredibly grateful. At the end of the day, there's a lot more money to be made participating in a corporate industry like this than being a creator-educator forever. The irony is not lost on me.
But while I will probably always love building, creating, and providing value to others in the game of making money online, I have this fantasy where it's summer in central Europe, the sun is strong, and I'm once again on the shoulder of a rural highway with my thumb out.
There's an accordion slung over my shoulder, some bread and cheese in my backpack, and I've got no idea where I'll sleep tonight. I have no plan as to where I'm actually headed. More importantly: I don't care about these things. I don't need to, because I am content in the moment. I know my wife is happy in the nice house I was able to buy her, and my kids are grown, healthy, intelligent, and successful in their own adventures of learning about themselves. My parents are proud.
I'm rich, or I'm broke, and it doesn't matter either way. I have been intimately acquainted with either economic state and I know peace in both. I've accomplished my purpose in the digital realm that this lifetime has invited me to traverse, and it's lead me to great riches in the physical.
A car pulls over to ask (probably in French) where I'm headed. I hop in and we drive off. The driver's camaraderie is the highest and purest form of abundance I can ever know. I'm back in the real world again, connecting with real life people again, able to explore with an open heart again.
But this time, and for the first time ever, I am finally free.
