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Jason Headsetsdotcom Gives New Meaning to Selling Books

10/15/2013 12:05 pm ET | Updated Jan 23, 2014

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Jason Headsetsdotcom (formerly Jason Sadler) is the Founder and CEO of
IWearYourShirt, where he wears sponsored t-shirts for a living. He
even sold his last name for $45,500. Jason's current project is
selling sponsorships for his upcoming book, "Creativity For Sale," the
shop for which is an entrant in the Build A Business Competition.

We caught up with Jason to learn what it's like to be a human advertisement.

How did the idea to use yourself as an advertising vessel
first come to you?

Back in 2008, I co-owned a web design company and a lot of our clients
asked us about social media. We weren't using them, but we kept
getting asked so I knew there was an opportunity there. I figured I
could use all those free social channels, try to grow an audience by
sharing interesting companies, and create a new medium for
advertising. The t-shirt part of it happened because I loathed picking
what shirt I wore each morning and knew most businesses had t-shirts
printed at one time or another. The rest fell in place from there.

When did you realize you were on to something?

During the course of IWearYourShirt, thousands of people came to the
website every single day to consume advertising. That is unheard of.
But they did it because what I offered was entertainment and novelty.
Try to tell me that exposing businesses to an actively engaged
community of people raising their hands to watch ads isn't valuable to
a business. You can't. I may be "the guy that just wears shirts" to
some people or "the guy who has the easiest job in the world" (I saw
many headlines implying just that over the course of my almost five
years), and that's okay. Because I believe in the services I provide
and the value I create.

Do ever feel that you've lost a piece of your personal
identity by branding yourself?

Not at all. This is my identity. I like being the guy who put himself
out there and made a name for himself doing something that had never
been done before. I like doing things differently and proving people
wrong. To me, if you're not challenging yourself and doing what you
love, that's a negative effect on your personal identity. Just because
I work closely with brands and integrate them into my life, doesn't
mean they dictate what I do or who I am as a person.

How does your family feel about you shedding your last name?

My Mom got a divorce and I didn't want to keep that last name anymore.
After being able to sell what t-shirt I wore for nearly four years, I
think my family believed I could sell anything. They were a bit
apprehensive that I'd end up with a controversial name, but that's why
I set the terms and conditions of the auction and had first right of
refusal. Plus, my family has always known me as "Jason" and that's
never going to change.

What do you hope to achieve with SponsorMyBook?

I understand why at first glance people might say that I'm just
slapping ads on the bottom of book pages, but my intention is so much
greater than that. The mission of this book is to help people
understand the value of their own gifts and talents and to help them
understand how to make money doing what they love. The companies that
sign on to sponsor the book (and essentially help pay for its
publication) are those that are effectively saying I support the
mission of this book. And because the book project itself will be
featured in detail within the pages, they are as much a part of the
story as they are ads beside the story. By attaching themselves to
something that is different, something that pushes the envelope, I
believe they are gaining much more value than a simple banner ad or
billboard can provide.

What's been the most rewarding part of your experience as an
entrepreneur?

I don't hate Mondays. Sounds silly, but it's absolutely true. I love
doing what I do. I love having the freedom I have. The harder I work
the more results I see. I can't imagine myself working in a standard
corporate job ever again.

To sign up for Shopify's Build a Business competition click here:

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