Profile Complete!

Before we drop you off in your brand spanking new member dashboard, would you like to take the grand tour?

Learn More About IWearYourShirt and How I Made $1,000,000

IWearYourShirt logo

Who am I? My name is Jason Zook (formerly Jason Sadler, Jason Headsetsdotcom, and Jason Surfrapp) and I am/was the founder of IWearYourShirt. During the recession of 2008 I decided I wanted to get paid to wear t-shirts for a living. Just a few years later I’d generated over $1,000,000 in revenue.

IWearYourShirt is no longer active and is not hiring.

It ran from January 1, 2009 to May 6, 2013.

iwearyourshirt jason zook t-shirt guy

For over five years IWearYourShirt (IWYS) worked with 1,600+ small businesses, Fortune 500s, authors, non-profit organizations, food retailers, service companies, and many more.

The Today Show visited and spent time in my closet. I was featured in a segment called “They get paid for that?” After the first year of IWYS sold out, CBS Evening News spent hours in my closet talking about the unique business I’d created in that same closet. I was asked by Forbes Magazine to share the story of IWYS in my own words as a part of a segment titled “How I Did It.”

During those five shirt-wearing years, I, and the multiple shirt wearers that worked for me, created thousands of videos (3,312 to be exact), photos (over 12,000!), posts on social media, and had countless media outlets talk about IWYS.

In 2013 I decided IWYS had grabbed its moment in Internet history and I moved on to new projects.

Get the full IWearYourShirt story

If you want to read the tell-all book about IWYS and the first few years of my entrepreneurial journey, grab a copy of my first book Creativity For Sale.

Creativity For Sale by Jason Zook

In the book, I share all the mistakes I made building IWYS, the small victories I enjoyed, and all the whacky adventures that happen when you get paid to wear t-shirts for a living!

You can also watch a short documentary that was done about me in a series called The Remarkable Ones:


What Am I Up To Now?

Wearing and owning a lot less t-shirts, that’s for sure!

These days I work on projects related to the site you’re currently reading (Wandering Aimfully) with my wife Caroline. We focus on a couple of fun things:

  • We send a weekly email newsletter focused on living an intentional life.
  • We offer a paid monthly membership community where creative folks can reach their goals together.
  • I keep trying to find new and interesting ways to make money while having fun doing it.
  • Check out my /now page to see the most up-to-date list!

My previous website to this one was called JasonDoesStuff, which is where I transitioned all my social media handles away from IWearYourShirt to @jasondoesstuff. In fact, I’ve transitioned almost completely away from social media altogether. That’s for another story that you can read here (30-day social media detox) and here (why I quit Facebook).

Will I ever bring IWearYourShirt back?

I get asked this question fairly often and the answer is: No.

IWYS had its moment in time. It was quite the rollercoaster! It made me the person I am today, but I’ve moved on and I’m extremely excited about all the fun stuff I get to work on these days with my wife.

Want to get a weekly email* that shares our thoughts and fun new projects? Scroll down and enter your email get “Wandering Weekly” every Monday.

*(Please do not subscribe and ask me for a job. IWearYourShirt is NOT an active business any longer.)