Every weird
Twenty years of internet experiments and businesses most people said wouldn't work. Some didn't. Most of them made money anyway. A few exited. A couple became books. All of them are here.
The full inventory.
My wife and I have completely pivoted in 2026 and we're building multiple apps this year starting from scratch!
A simpler way to edit vertical videos, no video timelines, quickly match b-roll to audio.
Creating content consistently is HARD. AI makes it easier, but still kinda sucks. This project aims to fix that.
Growing up I dreamed of being a Pixar animator. This YouTube channel is making that dream a reality and is for my daughter Leon.
A course platform I started by accident in 2013. It's made $1M+ in revenue as a side project, trying to focus more time on it.
Lifetime business coaching membership Caroline and I built. $2.5M netted over six years. Last new enrollment was summer 2025.
We're SO BACK BABY! I'm doing lots of stuff and needed a home for it.
Incremental pricing app, where you set an initial price and a "bump" in price after each purchase. What I used to start IWearYourShirt.
I curated a bundle of digital products from creators I liked. Sold them together with my buddy Paul Jarvis.
I sold lifetime access to everything I'd ever make for $1,000. 178 buyers in the first round. $178K, kind of shocked.
Sold my last name... twice. First auction won by Headsets.com for $45,500, the next year SurfrApp bought it for $50k.
The couples edition. Pay once, get everything Caroline and I would ever make. $520K+ combined across the rounds.
Loved the Sunrise calendar. When it shut down I tried to build a replacement. Couldn't get early support.
I wrote an open letter to publishers and agents to land a book deal. Running Press published my second book 'Own Your Weird.'
Omar Zenhom and I made a course about making courses. Very meta. People bought it anyway.
Paul Jarvis and I built a daily emoji story by email in 24 hours. Quickly shut down but fun.
Paul Jarvis and I teamed up to help nonfiction authors finally finish their damn books. The name was the whole pitch.
College "design agency" with roommate Travis. Zero real clients. Peak delusion.
Paul Jarvis and I made a course about building a personal brand that sounded like you and wasn't afraid of it.
My first online course. Five years of IWYS sponsorship lessons, packaged up for people who wanted to land sponsors of their own.
The course I wish I'd had when I started writing.
Paul Jarvis and I recorded this for two years. Online businesses, the ups, the downs, the broke parts. Mostly the broke parts.
I got paid to wear a different company's t-shirt every day for five years. 1,600+ brands, Today Show, CBS Evening News, Forbes. $1M+ in revenue. $100K in debt at the end (oof).
The original version was on Tumblr. Lol. My digital home for a few years while I figured stuff out.
A podcast with my buddy Greg Hartle, talking business and shooting the shit.
Paul Jarvis, Zack Gilbert, and I built saveable workbooks for online courses. Sold it privately.
A 7-day course I made on finding hidden profits in a business you already have. Step-by-step, no fluff.
I set out to get 1,000,000 t-shirts donated. Unfortunately, I didn't know anything about NGOs. Educational experience, for sure.
My very first "startup." A social network for stories and lessons. We even worked with Kanye West (before he went nutso). Did not become Facebook.
Paul Jarvis, Kathleen Shannon, Emily Thompson, and I made a course on starting a podcast. The 2015 internet was a different place.
Nathan Barry, Paul Jarvis, and I stripped the nonsense out of building and selling your first digital product. One sitting, no fluff.
Just really thought I had a great idea here. Wouldn't it be so fun to see them in little saddles??
What's it like working for your spouse? Caroline and I made a short podcast about it. Spoiler: we're still married.
I sold sponsorships on every page of a book before I wrote a single word. $75K in pre-sales, then I had to actually write the thing.
My second sponsorship course, this one just for podcasts.
Matt Giovanisci and I built an analytics dashboard in 60 days as a challenge. Traffic, email subs, revenue, all in one place. Sold privately.
I auctioned my last name a second time. SurfrApp won for $50K. I was legally Jason SurfrApp for a year.
Caroline hand-lettered motivating t-shirts and we sold them for a year. Margins were brutal. Oh well.
My first attempt at a Shopify store back in 2015. You could buy plush unicorns or pizza. Never got off the ground.
I wrote the first draft of my second book completely in public over the course of 2 weeks. Was pretty fun!
Paul Jarvis and I built simple directories for online communities. Sold privately.
I self-published this in 2014. The full IWYS story, with every page sponsored before I wrote a word. 200 pages, 204 sponsors.
My second book, published by a traditional publisher (Running Press) and was well received.
An autonomous blog post generator I built for Teachery. Learns from SEO/GEO data. 100+ articles published. Traffic has barely moved. Will report back.
Reels and carousels for @teacheryco, made entirely by Claude Code. Not fully autonomous yet, but I'm getting close.
Trying to see if I can make a Faceless YouTube channel with lofi vibes get any traction as a small side project.
An autonomous blog that writes articles about the "zero human company" movement. Just a way to keep me up to date on new stories.
My failed attempt at getting an OpenClaw going. Loved the concept, she fired off 40 cold outreach emails without consent. Oops.
Very early on this, training AI to learn my writing voice and create responses in the form of tweets and email newsletters. So far, pretty terrible.
A simple 1-page site built entirely by Claude, before Claude Code existed. Doing absolutely nothing with it.
Trying something absolutely wild, only 15 minutes per night, letting AI agents fully build this. It's kind of working? Will share eventually.
A Wordle-inspired word game I had Lovable build in late 2024. Need to pick it back up, it was a fun one.
Want to see the next round of experiments before anyone else does?
Growing Steady is our newsletter about pivoting in public. Caroline and I made $2.5M as business coaches, and now we're teaching ourselves Lovable and Claude Code to build real software as two non-developers. Subscribers get real revenue updates, voting access on what we build next, and early access to every app we ship.
