Phoenix, AZ. First of what would turn out to be six last names. Same amount of hair as present day.

Name change at age 7. Wildly more hair. Photo definitely taken in a mall near a Sam Goody store.

Umm... can we talk about the style points of this kid rockin' oakleys at the beach? (click the dot)

Should've stuck with it and gone pro. Started zero businesses yet. Just a gangly kid with huge teeth.

Yeah, that's a Bobby's World poster on my wall, be jealous (click the dot).

My first computer. Soon discovered Dragonball Z AOL chat rooms, Dreamweaver, and Geocities. The internet had me from the start.

A last name that became pretty well known. Also, Walgreens photo lab touched up my teeth in this photo lol.

Pierced my ears, had frosted tips, got a back tattoo. Mom wasn't too happy. Sorry mom!

Obviously I don't have a photo of me at the Verizon store, but here's me cooking my first dinner ever. Hah.

The year prior I bricked layups and sat on the bench of my high school basketball team.

Bought obscure phones, resold them for a profit. Definitely my first entrepreneurial venture. Samsung A650 was a hot seller!

My bleached hair phase. This guy goes to college in Jacksonville, Florida to attempt playing college basketball (proceeds to have terrible ankle injury 1 month in).

I worked at one of the first internet coffee companies (Boca Java) photoshopping glare off plastic. Apparently I wasn't good at it.

First real company. Don't think we had any actual clients. But the entrepreneurial itch was officially scratched.

Got paid to photoshop Roger Federer's hair to look amazing. Spent all my salary to own two cars (as a single guy, woof).

BFA with emphasis on marketing and graphic design.

Thank you to my grandparents for the help. Financially though, this didn't end well. #MortgageCrisis

For 13.5 years he was the absolute BEST BOY! A stubborn breed (Staffordshire Bull Terrier), but such a wonderful furkid.

Small design company. Built a social network called "Only Human." Worked with Kanye West (before he went nutso). Clients started noticing I had a mind for marketing, not just design.

Standing in my closet, staring at all the branded shirts I'd paid for: "Wait, why am I paying THEM?" The idea: get paid to wear t-shirts on social media. 12 visitors on day one. Price started at $1/day on Jan 1, scaling to $365 on Dec 31.

$83K revenue in the first year. Featured on The Today Show ("They get paid for that?"), CBS Evening News, and Forbes ("How I Did It"). Before "influencer" was a word.

12 straight movies, one break to jump in a pool, too much bad food, tons of great memories.

Thanks for always supporting all of my crazy ideas, Mom! You're the best!

Evan White joined from LA. Two people, two coasts, same shirt every day.

She DM'd me on Twitter to Skype into an advertising society she was president of. Nearly 20 years later that DM slide paid off for both of us! 👩‍❤️‍💋‍👨

$350K+ revenue but expenses exceeded $370K. The business was scaling but not profitably. Featured in The New York Times and USA Today.

Kinda wish I did lol.

After my IWearYourShirt business failed I let myself go. A 90-day challenge later and I was healthy again.

Auctioned off legal rights to my last name. Headsets.com won for $45,500. Legally became Jason Headsetsdotcom. Headsets.com reported $250K sales increase after.

Spilled my guts and was more vulnerable than I've ever been. A huge thanks to my buddy AJ Leon for this moment in my life (part of why our daughter is named Leon 😉).

On May 6, officially retired from professional t-shirt wearing. IWYS total: $1M+ revenue over 5 years, but ended up $100K in debt (oof). The highs were high and the lows were real. Also grew a gross beard because I was depressed.

SurfrApp won the second auction for $50K. Became Jason SurfrApp. Two name sales, two wild rides.

New website, new social handles. I chose that incredibly savvy domain name because it was the clearest way I could think to describe myself.

A seasonal podcast for entrepreneurs and creatives who aren't confined to literal office hours. Episodes dropped Netflix-style by season. Ran from 2014–2018. Topics ranged from criticism and selling out to vampires and zombies. Monetized with the "bundle of awesome" and show sponsors.

Sold sponsorships on all 200 pages of my self-published book. Earned $75K before writing a single word. The book tells the full IWYS story.

Sold access to my entire life's work, everything I'd created in the past AND future, for $1,000. Made $178,000 and launched this project annually for 3 years netting $500k+.

Sold everything we owned, left Ponte Vedra, FL for San Diego, CA. Lived with Clay Hebert and Julia Roy for a year. Fresh start, west coast style.

Turned the IWYS incremental pricing concept into a SaaS product. A buy button that automatically increases price after each sale. Later sold privately for a five-figure exit. We had a rad "office" set up!

Adopted my great-grandfather Roy Zook's surname. Last name #6. The last one. For real this time.

Reopened at $1,500. Continued growing the community. Had a short doc made about me, neat!

Two SaaS products I built with Paul Jarvis. ofCourseBooks: saveable workbooks for online courses. YourPack: simple community directories. Both had five-figure exits.

Website analytics dashboard that combined traffic, email subscribers, and revenue in one place. Built as a 60-day challenge. Later sold privately for a five-figure exit.

The proposal I gave in the back of an Uber? Not great. Getting married on a cliff with donuts and tequila and zero stress? Pretty epic! Thanks for being my life partner, Carol. 💖

I convinced Caroline to join the antics in BuyMyFuture and give an insane deal on everything she creates/created too!

Continuing my streak of talking Caroline into things, it took 6 months of beach walks, but she finally agreed we should combine her Made Vibrant + my JasonDoesStuff + our BuyOurFuture into one entity to rule them all!

My second book, published by Running Press. A guide to finding happiness by embracing what makes you different.

Our furkid crossed the rainbow bridge. One week before Covid shut everything down. Wowzers. Miss you, buddy.

Like many people, the pandemic led me to sourdough bread baking. Unlike most people, I started out with a "turd loaf" but have kept baking every week since.

Getting ready for full-time travel life. If you've done it once, doing it a second time is slightly less terrifying.

Visited 9 countries, slept in 51 beds, took 17 flights, and only lost one Kindle and one dopp kit the entire time. Shout out Peak Travel Backpack!

Some of the best food and sunsets we've ever had in our lives.

Decided to try living abroad. Landed in Lourinhã, Portugal on a D7 visa and never looked back. New chapter.

Adjusting to life in Portugal, baking weekly, and enjoying working more than 1-2 hours per day between flights, Airbnbs, and passport checks.

This was an amazing few weeks of my life. Just fully dove in. One of the best games I've ever played, important enough for this history page 😂

Baking isn't her thing, but every once in awhile she does and it's always a great memory!

Celebrated WAIM crossing over $2.5m in total revenue!

My first child. Born August 30, 2025. The tiniest co-founder.

She had no clue what was going on, but we soaked every moment in we could.

Just two non-technical founders 👩🏻‍🦰👨🏻‍🦲 building real products with AI. vibecoding.to

After an 8-year hiatus, my personal slice of the internet is back! Still doing stuff, just, you know, juggling a 👶 and too many ideas while doing it.