Pastry enthusiast Doer of weird stuff
Get to know

Jason

Six last names. $7M+ from weird internet businesses. A pretty unconventional life now lived in a small Portuguese beach town with an awesome wife, daughter, and too many side projects (oops!)

Jason Zook, Portugal, 2023
Jason Zook hi, mom!
will bake for claude credits Scroll ↓
Part I/Present Tense

Still doing weird things, just not quite as weird nowadays.

A few years ago my wife Caroline and I traveled full-time for a year in Europe. We wanted to do a big bucket list trip, but we also wanted to see if the slower European lifestyle was all it was cracked up to be. Well, as you can tell from the headline of the website, it is! I'm currently baking my weekly sourdough from a small beach town in Portugal and still getting used to eating dinner at restaurants at 8pm (which is early by European standards!) You'll find me enjoying pour over coffee at my desk, overlooking fields with 800+ year old buildings scattered on them. It's not where I thought I'd end up, but we couldn't be happier here.

My life is a lot less exciting than it was when I was wearing t-shirts for a living, selling my future, or having the TSA triple-check my ID because my name legally was "Jason Headsetsdotcom" for a year. But if you're here and reading this text, you're probably curious to know more so let's jump back in time…

$1
The price of january 1st, 2009 when my entrepreneurial life changed forever
Jason Sadler wearing an Angry Birds t-shirt, New York Times, 2014
1600+ t-shirts worn for brands big and small around the world. I helped launch the original Angry Birds!
Part II / "The t-shirt guy"

I wore a different company's shirt every single day for five years. Yes, even to a friend's wedding.

On January 1, 2009, a 26-year-old version of me (then Jason Sadler) put on a branded t-shirt, pointed a $150 Flip camera at my face, and uploaded the (super cringey) evidence to YouTube. The shirt cost my sponsor $1. The next day's shirt cost $2. The last sponsor of the year on December 31 paid $365, at which point people couldn't decide if they thought this idea was great or was a 1-year wonder. I called the company IWearYourShirt, and for five years wore a different sponsor's t-shirt every day and created content about them (before "content creator" was even in our lexicon).

I was incredibly inspired by Alex Tew's Million Dollar Homepage, but for years I never had an idea worth pursuing. Until one afternoon standing in my closet when it hit me. The day the IWearYourShirt site launched, I think 8 people visited it. Just a few months later I was on The Today Show and traveling the world to do public speaking gigs about my crazy idea.

At the end of 2009, I'd officially made $83,000 by wearing sponsored t-shirts and had been featured on The New York Times, Forbes, CBS Evening News, CNN, Entrepreneur Magazine, and countless others.

In 2010, IWearYourShirt grew to 2 shirt wearers, then 5 in 2011 and 5 again in 2012. I worked with over 1,600 brands including Starbucks, Nissan, Zappos, Shopify, Kodak, and one of my favorites was helping Pepperidge Farm launch a new cracker! Revenue doubled every year, peaking at $500,000 in 2012. When I officially retired from shirt-wearing in 2013, IWearYourShirt had generated over $1,000,000.

I was, maybe, the first social media influencer (iJustine probably gets that title before me). No one even used the term "influencer" back then either. Oof, I feel old.

Founded
January 1, 2009
Sponsors
1,600
Total Revenue
$1,000,000+
Initial Investment
~$300 on coat hangers

The business model was novel, the daily grind of creating content for five years straight eventually burned me the eff out.

1st?
Before the word existed
Maybe the first social media influencer? Doing the thing before the word existed, for better or for weirder.
Jason Sadler promoting BuyMyLastName.com, 2012
how was the buymylastname.com domain available tho??
how do you follow that up?

By selling your last name to the highest bidder... twice.

In 2012 I got a text from my Mom she wanted to talk (never good). I learned she was getting a divorce, which left me with a last name (Sadler) I no longer needed. So I did what any normal person would do, I decided to sell the rights to my last name!

I created an auction website, started the bidding at $0 to own my last name for a year, and within 24 hours the bidding had climbed to $33,000! I was truly shocked. It ended with a flurry of bids but eventually Headsets.com was the new owner.

A year later, I still didn't have a last name I wanted, so I auctioned it off again and it netted me $50,000 and "Surfrapp" was the name that ended up on the cover of my first book. Not a bad way to make nearly $100k.

Part III/The Name Game

Six last names. Took awhile to find the right one.

Click a name below, you'll get to see me in all my awkward years (which are totally over, btw).

Jason Zook, present era
2015 to present
Jason Zook

My final last name, carrying forward my great-grandfather Roy Zook's name. Easy to say, easy to spell.

$124K
making $1m was cool, ending up in a bunch of business debt was not so cool
Part IV/The Collapse

The business made a million dollars. I was over $100k in debt.

While IWearYourShirt was generating notoriety and revenue, I was too busy putting on daily t-shirts and dancing around my house on camera to realize the business itself was not in good shape. I hired too many shirt wearers, I didn't have the time/knowledge to run the business well, and I became allergic to even logging into my bank account (yikes, never good).

In May of 2013 when I officially announced my retirement from t-shirt wearing, I had accumulated $124,000 in debt and was in pretty negative funk. The burnout was pretty public. My motivation to work was almost non-existent. Thankfully, I had family to help me out financially and I had Caroline to get me through it emotionally.

What got me out of that funk? A lunch with a friend where I (shamefully) asked if he could pay for my $9 burrito because I legit couldn't afford it. At the end of that lunch I left with an idea to write a book about my story, a fun way to generate revenue I'd never seen anyone try, and a vigor to share my journey of turning my life around.

Jason Zook, portrait
Portrait of a man who now understands the difference between revenue and profit. Took a while.

Looking back, 2013 was probably one of the hardest years of my life. But, it was also one of the best because it taught me so many lessons I now carry forward in everything I do.

3yrs
we turned our debt into a game
Caroline and I hunkered down, worked with financial advisors, worked our butts off, and in less than 3 years we'd pay off all $124,000 in debt. The final credit card payment was GLORIOUS!
Part V / The Rebuild

It started with a DM on Twitter, it ended* in marriage on a cliff.

The initial DM was a request to be a speaker at the UF Advertising Society where Caroline (then Winegeart) was the President. She talked me down from my normal virtual speaking fee and a year later she talked me into hiring her to help keep IWearYourShirt running smoothly.

Since then, I feel like I've been the one talking her into weird things. She's my partner in life but also my partner in business. Caroline has world-class design/branding skills, is super smart when it comes to strategy, and brings a level head to all my crazy ideas.

In 2013, I got to watch Caroline start her own business (Made Vibrant) which went on to generate 6-figures a year and eventually land her a book deal of her own with Chronicle books. It was super fun watching her go from hand-lettering wedding invitations to doing design work for New York Times' bestselling authors and speaking on stage at a TEDx event.

We've had quite a journey together since 2010 and I'm excited to see where we take things these next 15+ years (and beyond!) *Ended feels like we died on the cliff, we didn't. It just felt poetic to write the headline that way.

Jason and Caroline on their wedding day, 2017
married, on a cliff in san diego, we had tequila and donuts after this photo

When we clawed our way out of debt we heavily shifted our thinking into the idea of "enough" and running "calm businesses." These simple principles are crucial to every decision we make these days.

enough is enough

I spent my 20s chasing more. My 40s are about enough.

Everyone has a different number. Everyone has a different lifestyle. The most important lesson I've learned around money is if you're chasing after other people's dreams and not the ones you define for yourself, you'll never be happy and you'll never stop chasing.

Part VI/The Books

Two books. One self-published, one traditionally published. Both weird.

Creativity For Sale cover, 2014
Book One·2014

Creativity For Sale.

I sold every page before I wrote a single word.

At the start of 2013, I had $9 in my bank account and was $99,991 in debt. Over lunch, my friend Dave asked why I hadn't written a book about the whole IWearYourShirt mess. I told him I felt like a failure. He said, "not every book needs a happy ending." On the drive home, I came up with the idea.

I'd sell a 140-character sponsor message on every single page of a book I hadn't written yet. 200 pages. Page one priced at $600, each page $3 cheaper than the last, down to $3 on page 200. Front cover, back cover, and both inside flaps sold separately. I called the project SponsorMyBook, because subtlety has never been my thing.

Day one: over 100 page sponsorships sold and more than $10,000 in the Shopify account by afternoon. Five months and roughly 2,000 emails later, I'd locked in 204 sponsors and $75,000 for a book that didn't technically exist. My trust circle talked me out of traditional publishers, so I self-published it.

Creativity For Sale has gone on to sell over 20,000 copies. It didn't top any lists. But I still get emails from readers saying my little sponsored book changed how they think about their own creativity, which beats a bestseller list any day.

Jason Zook holding Own Your Weird, 2019
Book Two·2019

Own Your Weird.

I wrote the book. I meant the title.

In 2018, I launched a project called Dear Book Publisher where I tried to flip the model of finding a book publisher on its head. I set a 30-day timeline, had an open invite, and eventually found a great book agent who got me a deal with Hachette's Running Press.

One year later, Own Your Weird hit the proverbial shelves. It didn't launch on any bestseller lists, but that was never the goal. I simply wanted to pick up where I left off with Creativity For Sale and continue sharing my entrepreneurial journey. I wanted to give readers the permission slip to embrace their weirdness (aka what makes them unique).

I think I have one or two more books in me. Just going to continue to collect experiences, stories, mistakes, and cobble them together when the time feels right.

Part VII/The Other Experiments

Every product was an experiment. Some of them stuck around.

After IWearYourShirt wound down in 2013, I did a "floaty dance through life." Tons of different experiments, some worked, some didn't, a ton of lessons learned along the way. Teachery started completely by accident in late 2013. I made my first online course, but didn't like any of the available platforms. So, I did what all intrepid entrepreneurs do and I opened up Photoshop! A few hours later, I had a design I wanted and I shared it with friends to see if they liked the course idea. They all asked what platform the course was on. Light bulb moment! 13 years later, Teachery has generated over $1m in revenue as a complete side project.

BuyMyFuture was a pretty wild swing. By 2015, I had created multiple courses, a few small products, and packaged it all up with a community for $1,000. The first launch had 178 buyers. I was… shocked. I launched BuyMyFuture a few more times, then my wife and I combined forces to create BuyOurFuture. Over $500,000 generated and no one has complained that I haven't built that flying jet ski I promised.

Wandering Aimfully was the natural move after we sold our futures. Combine our businesses into something with more of a purpose and a vision. Just the term "wandering aimfully" felt like it described us well by 2018. It had a bumpy start as we tried to figure out what the business model was, but by late 2019 we'd shifted it into a lifetime business coaching program, and by summer of 2025 when we did our last enrollment we'd netted $2.5m.

If you want to read about EVERY business I've ever started (the good, the bad, the weird) head to the projects page and enjoy.

Teachery (13yrs)
$1,000,000+
BuyMyFuture + BuyOurFuture
$500,000+
Wandering Aimfully (2018 to 2025)
$2,500,000
All the other nonsense
~$3,000,000
Career total
$7,000,000+
Part VIII/Favorite Things

The stuff I keep bringing up without being asked.

One of the easier ways to get to know me is to catalogue what I keep mentioning in newsletters, on podcasts, and to Caroline for the 47th time this week. In no particular order. No claim that this list makes me interesting.

No. 01 / Baking
Weekly sourdough
Almost every week since 2020. Yep, caught the sourdough bug during covid and now I can't stop. I still never named my starter tho.
No. 02 / Coffee
V60 pour-over, single origin
I didn't drink coffee until I was 30 years old. A few years later I discovered what "good" coffee was and I've been a pour over addict ever since. Favorite beans? The fruitier and weirder the better.
No. 03 / Puzzles
Puzzle time with Caroline
How'd you like that sick rhyme?? We enjoy a great puzzle and Magic Puzzle Company has changed puzzles for us forever. Seriously, try them, they're worth every penny.
No. 04 / The Beach
Daily family walks
Every day at 5pm, non-negotiable. We used to do these with our fur-kid Plaxico, now we do them with a real kid Leon. Less poop to pick up is a small bonus!
No. 05 / Plaxico
Almost 14 years. He was there before the t-shirts, the name auctions, the debt, and every dumb idea in between. Still miss him every single day.
No. 06 / No Alarms
Waking up without one
I'm sure this will change when Leon has a school schedule, but I haven't woken up with an alarm in 15 years and want to try not to for as long as I can.
No. 07 / Caroline
Partner, co-founder, co-parent
Going on 16 years together. Lots of business ventures. Tons of amazing memories. Here's to another 16 (at least!) years, Carol. ;)
No. 08 / Guilty pleasure
Cinnamon rolls
This is probably one of the things I miss most about the U.S. I make my own cinnamon rolls (this recipe), but I miss getting these at coffee shops.
where i got my start

My first corporate job was Photoshopping Roger Federer's hair.

In 2004, I worked at the Association of Tennis Professionals as a junior graphic designer. A big part of the daily task was opening Getty Images and cloning tennis-player hair back into place where the wind had blown it sideways. Federer, Nadal, Djokovic. All of them. Professional athletes, it turns out, have really demanding bangs.

Part IX/A calm life in portugal

These days, I'm less "online." But ideas are always flowing.

I wrote all the copy on this website from a small Portuguese beach town we call home now. The town is so small, in fact, that I met the mayor at a random dinner event and I see him once or twice a month and we say hello. Never thought I'd know a mayor in Portugal!

Caroline and I are working hard on vibecoding.to, our newest venture together where we're basically starting over from scratch again (why not leave behind a business in Wandering Aimfully that was making $30k/month… oof). But, after 8 years of business coaching, we just had to do something else and AI has opened up a ton of doors for us. We also send a weekly email called Growing Steady that tracks our progress along the way.

I'm working more on Teachery than I ever have before, also thanks to AI (mostly Claude Code). There's an entire new version of Teachery coming soon. Built entirely from the ground up. My goal is to have it be the fastest, easiest, and most fun way to create a course or digital product in a matter of minutes.

Jason with daughter Leon, 2025
new dad, august 2025. a whole new reason to not check email before noon.

And then of course, I'm embracing being a Dad. We waited longer than most to have a kid (mostly at my request). But, I think we made the perfect decision because we ended up with an awesome little girl and are in a life position that affords us help and tons of flexibility to enjoy all the precious moments with her.

Hope you enjoyed learning more about me. If you read this far, I applaud your attention span!

Growing Steady/The newsletter

We made $2.5M as business coaches. Now we're starting over from scratch.

We're Caroline and Jason. For almost a decade we built courses and coaching programs. Then AI showed up and changed the whole game. Instead of stressing about it, we got curious. We taught ourselves Lovable and Claude Code, and decided to go all in this year on vibe coding. Now we're documenting the whole messy, exciting process of pivoting in public.

    We send one email a week. What we built, what broke, what we'd do differently.

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