The collection
20 years of weird ideas, internet experiments, and businesses most people said wouldn't work. Some didn't. Most of them made money anyway.
Husband-and-wife building apps with AI. Community votes on what we build.
Voice memo to vertical video. Ditch complex video editing for good!
Online course platform with a lifetime deal. Simple, no transaction fees.
Un-boring business coaching. $2M+ revenue over 6+ years. All the tools and support you need.
This site! Revived in 2026 after an 8-year hiatus. Still doing stuff.
Turned the IWYS incremental pricing concept into a SaaS product. A buy button that automatically increases price after each sale. Sold privately.
A curated bundle of digital products sold together at a massive discount.
Pay $1,000 once, get access to everything I'd ever create. Made $178K in the first round.
Auctioned my legal last name. Headsets.com won for $45,500. I legally became Jason Headsetsdotcom.
The couples edition. Pay once, get everything Caroline and I ever make. $520K+ combined.
Loved the Sunrise calendar. When it shut down I tried to build a replacement. Couldn't get early support.
An open letter to publishers and agents to land a deal for my second book. And it worked!
Partnered with Omar Zenhom to create a no-brainer online course creation course.
Paul Jarvis and I built a daily emoji story by email in 24 hours. Quickly shut down but fun!
Teamed up with Paul Jarvis to help nonfiction authors finally finish their damn books.
College "design agency" with roommate Travis. Zero real clients. Peak delusion.
A short-lived but fiery project challenging the status quo of online business advice.
My first online course! Using years of IWYS experience to teach landing sponsorships.
The course I wish I'd had when I started writing.
A podcast with Paul Jarvis about running online businesses, ups and downs, and everything in between.
Got paid to wear a different company's t-shirt every day. 1,600+ businesses, Today Show, CBS, Forbes. Then ended up $100K in debt.
After retiring IWYS, I needed a new identity. My digital man-cave from 2013–2018.
A podcast about doing things that actually move the needle in your business and life.
Saveable workbooks for online courses. Built with Paul Jarvis and Zack Gilbert. Sold privately.
A 7-step, 7-day guide that uncovers hidden profits in your existing business.
Set out to get 1,000,000 t-shirts donated. Unfortunately, I didn't know anything about NGOs.
My very first "startup." A social network to share stories and lessons learned. Worked with Kanye West (before he went nutso).
Teamed up with Paul Jarvis, Kathleen Shannon, and Emily Thompson to teach podcasting.
Nathan Barry, Paul Jarvis, and I stripped away the nonsense about building and selling your first digital product.
Wouldn't it be fun to see corgis wearing little saddles?! This business won't ever exist... or will it??
What's it like when you work for your spouse? Short podcast answering those questions.
Sold sponsorships on every page of a book before writing a single word. $75K in pre-sales.
Second sponsorship course focused solely on podcasting.
Website analytics dashboard combining traffic, email subscribers, and revenue in one place. Built as a 60-day challenge with Matt Giovanisci. Sold privately.
Won my second last name auction for $50K. I was legally "Jason SurfrApp" for a year.
Caroline's hand-lettered motivating t-shirts. Low margins. Oh well!
An online store that ONLY sold unicorn or pizza themed products. Surprised this failed?
Public-facing live view of my writing document. Zero privacy. Maximum accountability.
Simple community directories. Built with Paul Jarvis. Sold privately.
Self-published, 2014. The full IWearYourShirt story — every page was sponsored before I wrote a word.
Published by Running Press, 2019. Own your unique traits and live a more congruent life.
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