Featured Entrepreneur – iwearyourshirt.com

Today’s featured entrepreneur is Jason, of iwearyourshirt.com.  Iwearyourshirt.com is an innovative and fun approach to marketing and advertising. How’s it work?  Every day in 2009 Jason will be wearing a different shirt, your shirt, for promotion.  As Jason says, 

“In this up and down economy I’m outsourcing my wardrobe (namely shirts) to corporate America and you! I’m going to wear a different shirt for 365 days straight in 2009, take multiple pictures throughout my day and blog about it. Days are sold at “face value” so January 1 is $1 and December 31 is $365.”

The possibilities around this kind of marketing are limitless, and the buzz factor is sure to be high with such an original take on marketing a product or service.  Jason has already sold 115 of 365 days in 2009, so it appears word is spreading fast! 

We were lucky enough to make contact with Jason through Twitter, and he was not only kind enough to grant an interview, he also went above and beyond by offering a day of his services to one lucky Small Biz Bee reader! 

That’s right, one lucky Small Biz Bee reader will get a day of Jason wearing your shirt to promote just about anything you can think of.  

What do you have to do to win a day at iwearyourshirt.com?

All you have to do to win is sign up for Small Biz Bee’s newsletter.  That’s it!  Just sign up for our newsletter between December 8th and December 22nd and you are eligible. The winner will be drawn at random on December 23, 2008.  

Use your free day to advertise:

Jason explains below exactly what you get by having him wear your shirt for a day, and you’re really only limited by your own imagination. Use your day to promote:

  • Yourself
  • An event
  • Your company
  • Your product
  • Personal message (Happy Birthday Mom?)
  • Your website/blog
  • The possibilities are endless

    A special thanks to Jason for making this happen!  Below Jason shares what it took to get his project started, some challenges he faced, and what he thinks the future holds for iwearyourshirt.com.




    When did you start the business?


    iwearyourshirt.com (IWYS) was conceived on September 24. That was the night/early morning I was laying in bed and had a light-bulb moment. After a month of tweaking the idea, talking it over with friends/family and having the Thought & Theory team build the site, I was finally able to launch on October 21.


    How did you get the idea?


    I am always amazed at interesting little marketing ideas that work, the “Million Dollar Homepage” was a big inspiration for me. I wanted to think of something I was in complete control of, but was still easy and inexpensive enough for people to get value from.


    What sources did you use to fund your biz?


    Everything is self funded with some design/development time donated from the company I co-own, Thought & Theory.


    What was the biggest startup challenges?


    The biggest challenge was trying to get things up and running fast enough. There are a lot of moving parts behind the scenes and I really wanted people to have a simple and flawless experience. No matter how hard you try, there will always be bugs and errors that pop-up. Another challenge is adoption. Trying to reach an audience of people who understand the value and like to have a little fun with marketing/advertising.


    How did you overcome those challenges?


    You really have to be patient. I can’t sit here and try to tell you that you will find every problem before it happens, that just isn’t realistic. When I was doing bug testing I wanted everything fixed immediately, but it can’t be done that way and you have to take care of what is most important first. Knock out the things you think are critical to a person’s experience on your website and worry about the nit-picky items later. As far as overcoming the issue of adoption, I still haven’t found the perfect answer. Sites like Twitter and Facebook are a big help, but it also helps to have a solid network of contacts. I wouldn’t be where I am today without some great people I knew prior to this project lending a helping hand. 


    What has been the response/reaction to iwearyourshirt.com?


    The response has been overwhelmingly positive, within a week of launching the IWYS Calender, January, February and March sold out! I’ve had a bunch of people come to me and tell me they love the idea, they wish they had thought of it and can’t wait to watch me in 2009. It’s definitely not easy putting yourself out there, whether you are wearing 365 shirts or launching your own startup


    Best advice you can give to a new startup?


    Be confident in the product you are selling, don’t give up at the first sign of trouble and nothing is an overnight success


    Biggest lesson you’ve learned from all of this?


    Launch your project. Sometimes you might think you need every bell and whistle, but starting with a solid foundation is more important then launching a feature-intensive project. 


    Why do you think Small Biz Bee readers would benefit from buying a day on iwearyourshirt.com?


    Getting your name out there is tough these days. Banner advertising isn’t worth the money, especially not compared to the cost of IWYS. I really feel like this is a great opportunity for people to learn about different brands, companies or products. Not only are you engaging an Internet audience, I am going to out there everyday, trying my hardest to get the shirts seen.


    If someone buys a day, what can they expect you to do on that day?


    This has a question that has been asked a lot and I want to make it very clear, I am not just wearing the shirts for a photo and video on that day. I am wearing the shirts from the time I get up in the morning until I go to sleep at night. What if I have an important meeting or an occasion that requires nice clothing? That’s what sports coats are for.. nothing on my schedule or in my life is too serious for a t-shirt and sports coat. But as far as exposure is concerned, IWYS will be featured on the homepage of Ustream.tv for a daily 20 minute show. The same show and other video clips will be spread across YouTube, AOL Video, MySpace Video and multiple other video sharing sites. IWYS is a member of the FuelMyBlog network which is connected to 20,000+ other blogs and bloggers and will also be spread to an audience of 10,000+ Facebook and Twitter users. Daily photos and blog posts will be featured on Flickr and the IWYS Official Blog to round out every day.


    What’s the future look like for iwearyourshirt.com?


    Hopefully a bunch of great Small Biz Bee readers will join IWYS and buy a day or two, because I already have big plans for 2010. I really want to create a sustainable medium for advertising that reaches an audience that cares. 



    I’m a 26 year old business-creative currently living in Jacksonvile, FL. I’ve used the Internet and design for business pursuits for the last 10 years, both professionally and personally. After working a few design focused jobs, it became clear that the marketing and business end of things were much more interesting and rewarding. In 2006 I co-founded Thought & Theory, a company that specializes in creating, designing, talking about and developing simple and beautiful web applications. I’ve worked with large advertising companies, social networks, professional sports leagues, along with other various new media and Internet related work. Outside of the web and computers, I’m a sports fanatic, both watching and participating in, a movie buff and an automotive enthusiast.



    All Small Biz Bee readers have a chance to win a day of Jason’s services. All you have to do to be eligible is sign up for our newsletter between December 8th and the 22nd. One winner will be drawn at random on December 23, 2008.  

    Use iwearyourshirt.com to promote:

    • Yourself
    • An event
    • Your compnay
    • Your product
    • Personal message (Happy Birthday Mom?)
    • Your website/blog

    Post a comment

    You may use the following HTML:
    <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>

    CommentLuv Enabled