Bootstrapped a portfolio of internet startups on his own: Nomad List, Remote OK, Hoodmaps, Photo AI, all coded on a laptop.
Starts levels.io and begins writing in public about building businesses and traveling the world.
Publishes "I'm Launching 12 Startups in 12 Months", the challenge that defined his path.
The 12-in-12 challenge is the inflection point: most attempts fail, but two of them become his durable businesses.
Launches Nomad List (later Nomads.com), the community and data project for digital nomads.
Launches Remote OK, a remote-jobs board that spun out of the Nomad List job listings.
Live-codes the first version of Hoodmaps, crowdsourced neighborhood maps, on a Twitch stream in about two hours.
Hoodmaps has been used by hundreds of thousands of people within months of that two-hour build.
On the Indie Hackers podcast, states Nomad List is at roughly a million users a month and $15k to $25k monthly revenue.
His bootstrapping book MAKE passes 10,000 copies sold.
Reports that Remote OK has overtaken Nomad List in revenue, the job board becoming his biggest earner.
Rides the generative-AI wave with Interior AI, which redesigns rooms from a photo.
Interior AI reaches $1k monthly recurring revenue within weeks of launch.
Launches Photo AI, "the first AI photographer", which grows into his flagship AI product.
Appears on the Lex Fridman Podcast.
Launches levels.vc, his own investment fund.
Discloses that Photo AI, running on a single large index.php file, is at $105k monthly revenue and $80k monthly profit.