Jason SurfrApp

Jason SurfrApp is kind of a marketing genius. I thought about how to start this post out for quite some time, because I didn’t know how to touch on everything quirky Jason does in  just an opening paragraph. So, I decided, I’m not going to. There’s many facets to Jason SurfrApp, so I’m going to just go through them one by one. I’m not going to lure you in with an opening statement because his name does the luring all on its own. Meet Jason SurfrApp.


I heard about Jason about 5 years ago in an awkward classroom. I heard about this guy starting up a business by wearing companies’ shirts. I’m sorry, what? I Wear Your Shirt is how people most commonly know Jason SurfrApp, formerly Jason HeadsetsDotCom, formerly Jason Sadler. The idea started one night in 2008, and launched in the beginning of 2009. Basically the idea is each day Jason would wear a different companies shirt, a “walking advertisement,” let’s say. Along with wearing the shirt, Jason would share this business among the mass social media outlets he had. I did say genius, right? What started out as just him formed into multiple people being a part of this shirt-wearing plan. I Wear Your Shirt was represented in various places among the fifty states. Let’s imagine what Jason’s closet looked like; wearing a different shirt every day for 5 years straight, I had to ask about laundry. Must be nice only washing clothes once a month. However, you may know him from I Wear Your Shirt but Jason retired from IWYS earlier in 2013. I Wear Your Shirt is still in existence and Jason is still the founder and CEO but you will find him choosing his own shirts now.

One of the first questions I had for Jason was asking him if he knew there was a Wikipedia page about him. I felt a little nervous going into the interview because of how many times I found his name on webpages and in news interviews. Until I landed on one of his personal blog posts. If you’ve seen any video of Jason, you know he’s a pretty funny guy, but this post was something that let me walk into the interview with enough comfortability to talk to him. I didn’t know a lot of the questions that I wanted to ask him before hand, but one I did know was about his humble attitude. I know from watching others and learning myself that being humble doesn’t always come natural. Jason talked about how he came to a point where he felt awesome for making a profit off on his idea, but then had a realization that he hadn’t helped anyone along the way other then promoting a business in trade for a revenue. He then began to look at other entrepreneurs because that’s what he would have wanted. “I don’t know everything and I’m not someone you should follow in the footsteps of, but here is what I’ve learned,” he told me, as I downed my favorite chai in Jax. ”I used to not want to share where I fell short, but now I’m happy to embrace the failure and share.” Which, to me, personally, is something I want to hear. It’s relatable when you’re able to be real, especially with so many followers. Jason constantly strives to be an open book on any outlet you can find him – especially on his blog. To look at someone who has been in many media publications in the past 5 years and see that they still don’t have it figured out, it’s encouraging.

There’s a lot to share about Jason and one of them is his last name, SurfrApp. There’s a story behind it as you would have guessed. He’s a creative and marketing genius, I said that already, right? In 2012 he had a brilliant idea to auction off his last name to any business for the whole year of 2013. Why? Jason already had a quite the social media following and entrepreneurs looked to him constantly. This would be a way for a business to partner with Jason and get a unique form of advertisement. For 2013 his last name ended up being Headsetsdotcom. This year he sold his name to a company called SurfrApp for $50,000. So who is SurfrApp? Well let’s put the purpose of changing his last name to practice, check it out here.

Want to learn from Jason? Well you’re in luck, he’s currently working on a book. And of course, he’s doing it in true SadlerHeadsetsdotcom, er SurfrApp, er Jason fashion. He’s been wanting to write a book about the ups and downs of entrepreneurship for the past couple of years. I believe this book is one-of-a-kind as it will be a crowd funded book. He won’t be using any sort of major publisher, so you’ll actually be able to see who funded the book through each page. Currently, there are still pages left to be purchased, so if you have a business that you’d love to feature, or if you want to join the community of this book, be sure to find out how to. Oh, geesh, name of the book? Creativity for Sale. As it will be just that, Jason really does have a passion for entrepreneurs, and this book will give how-tos and life lessons for the creatives. He desires to see people step out of that 9-to-5 and live off of a passion they have inside of them.

So we had to ask, being pretty well known and not from Jacksonville, why did he choose to stay here? “I love this town,” he came here over 14 years ago to go to college and has watched this town grow up. “I love the different parts of the city and the possibilities for it.” We talked about how Jacksonville is a little bit slower compared to other cities which makes it prime for growth because if you have an idea, you have time to build it up. Does he have a favorite place? Of course, with no hesitation he gave a big shout out to TacoLu. I had to agree, those chips and salsa deserve a shout out. Maybe one day it will be Jason TacoLu?

I mentioned it already, but Jason is very sincere and truly a humble guy. Which is why I’m going to tell you, if you are an entrepreneur, send him a message, email, tweet, or carrier pigeon. I was so impressed that he actually responded back to an interview with us, “I never want to be the guy who reaches whatever success means to you, I want to always respond back because that’s what I would want.” There’s so many parts that make up Jason SurfrApp that we didn’t even touch on, so please reach out to him or just stay up to date with his personal blog.

Amanda Gibson

Photography by Morgan Burden