051: How To Make A Living Wearing T-Shirts (Jason SurfrApp)

Jason SurfrApp

Have you ever had an unconventional idea for a business? Or experienced massive resistance to getting started? If  you said yes to either of those questions you’ll want to listen to today’s guest, Jason SurfrApp.

I’m sure you’re thinking his last name is unusual and it is! His birth name is Jason Sadler and he has also legally changed his name to Jason HeadsetsDotCom in the past.

In this episode you’ll hear the stories behind that name change as well as how Jason became Jason SurfrApp for 2014, and his unconventional marketing tactics that built a million-dollar social media marketing company in its first few years. Join us as we talk about all of this and more on the 51st edition of How’d You Get Into That?.


Jason grew up in a family that moved around a lot, with a single mom who was always trying to find a better situation for them. Because of their numerous moves, he became accustomed to constant change very early on in his life.

Also early on in his life Jason had dreams of becoming a zoologist. At least he did until the age of 14 when his mom got a computer. He started tinkering with building websites and soon taught himself graphic design.  From there he started selling websites until it was time to go to college. He began at a school in New Jersey, but ended up in sunny Florida where he graduated with a degree in graphic design and a minor in psychology.

Like so many of us by the time Jason began doing graphic design for a living, he realized he didn’t enjoy it although it was easy for him and it paid the bills. He eventually got a job doing graphic design for the Association of Tennis Professionals (ATP), a  job which helped him see that a traditional corporate environment was not for him. He enjoyed the people, but not the work or the environment. He started to slowly shift from wanting a stable secure paycheck every week to embracing his independent, entrepreneurial drive.

One day, over burgers and fries, a friend suggested they start their own graphic design company. They created a 6 month launch plan and that’s when Jason would quit his job and go full-time with their new agency. They started landing clients, and sure enough, within six months, he gave his 2 weeks notice at ATP.


  • How to know when let go and move on to the next project.
  • The power of working a plan.
  • How to face your fears and overcome your resistance to failure.
  • Why taking action is the key to your success.
  • How Jason dealt with being called a sellout.
  • And so much more!

As great as it was owning his own agency, Jason started feeling like there was something more out there for him. In 2005 a lot of their clients were asking about how to leverage social media. Jason started researching and saw huge opportunities to facilitate connections between real people and great companies.

Then one day an idea hit him: why not get paid to wear a shirt with a company’s logo on it and talk about it on social media, as a unique advertising idea for companies? So he started IWearYourShirt. Every day he represented a different company online using social media sites like Facebook, Twitter, and YouTube. Major news outlets picked up his story and that’s when things really exploded for him.

Shortly after that his mom told him she was getting a divorce. Jason told her that if she wasn’t going to have that last name anymore, than neither was he. That’s when he had the idea to sell his last name to a company! He says his last name has never really defined him so he bought buymylastname.com, created an auction to buy his last name, and launched the site. At the end of the 30 day auction his last name sold for $45,500 to headsets.com.

After completing the auction he legally changed his name to Jason HeadsetsDotCom. The company saw a massive spike in sales as the media buzz began to take effect. In 2014 he sold his last name again to SurfrApp, a Yelp-like app for surfers.

Jason believes that anyone who feels trapped and wants out of their current situation can do it, without a doubt. Everyone has fears and everyone experiences resistance. The more you take action, the more you will be unafraid to fail and the more you will learn from the process. Taking some action is better than taking no action and clearly the actions he has taken have worked out well for him.

Please join me in thanking Jason for sharing his amazing stories, his ingenuity and his creative entrepreneurial spirit with us! Thanks for being here and we’ll see you next time.

Tweetable: “You don’t get what you don’t ask for.” Jason SurfrApp


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