This is an interview with Jason from iwearyourshirt.com. Jason came up with a fun and interesting idea for marketing businesses by wearing a paid-for shirt everyday for one whole year. For Jason to wear a shirt, businesses or people paid by the day starting at $1 January 1st and $365 for December 31st. He still has some days left and is more than willing to wear and promote your shirt for any number of days.

What inspired you to start iwearyourshirt.com?

I’ve always been an out of the box thinker and lover of creative and interesting marketing/advertising ideas. I wear shirts on a daily basis, don’t typically care what the shirts say and knew that a lot of companies make shirts to promote their stuff. I put 2 and 2 together, started my pricing structure extremely low and exploited a bunch of free social media tools on the web to help me out.

What has the overall perception been with your idea of wearing a new shirt everyday?

When I first started the project back in October of ’08 there was a mix of positive and negative feedback. My friends/family obviously supported me 100%, but like me, they didn’t think it would take off as well as it has. I just gave my first ever presentation at a Refresh Event in Toronto and not one person clapped when my name was announced to speak because they had never heard of me. 7 minutes later my presentation was done and people were clapping and lining up to ask me questions. Moments like that are very rare and really awesome.

When do you think all of the day slots will be sold off?

A couple times this year I guessed and was wrong. I am not worried about the last remaining days selling out, but I hope it happens sooner than later!

What do you plan on doing after the end of the year?

Wearing more shirts obviously… Ha. The project will continue in some shape or form, I just haven’t figured out exactly what that is yet. I love meeting all these new great companies/people and wouldn’t mind having my wardrobe picked out for me again. Maybe start next year at $2? Can we lock you in for a day Josh?

Josh Here: I would absolutely love to book days next year if you were to do it again. Especially if I get first dibs.

What are some of the different venues you plan on visiting while wearing others shirts?

No planned venue visiting. I’ve told people from the start, I am living my life.. You didn’t spend $67 and get to tell me what to do all day. You spent that money to have me be your advertising for a day, get your name out there to a new audience and see me in your shirt. As far as planned events I will be attending, I have a few weddings coming up, a trip over the summer at some point to somewhere tropical and that’s it.

Have you had any strange encounters while wearing other people’s shirts?

Not too many strange encounters. I always get really funny looks when I explain the idea to a complete stranger, a stranger who is typically not internet savvy. I have had a couple ‘celebrity sighting’ moments. I had someone DM me on Twitter saying they were sitting behind me in a movie theater and I had a guy come up to me in the Washington DC airport and ask if I was “the iwearyourshirt guy”? That stuff is pretty neat.

How would you measure the success of your shirt wearing venture with nearly four months behind you?

I would say it has been very successful. 334 days have been sold at this point, I haven’t gone a month without a monthly sponsor and I am still receiving media attention. I really enjoy meeting new people and encourage anyone to reach out to me. My e-mail address is iwearyourshirt@gmail.com and my Twitter name is @iwearyourshirt. I’m easy to find and happy to chat. Obviously when I am sitting on Oprah’s couch I know I’ve made it… haha, kidding, maybe.

How much time a day are you spending on the adventure?

Typically between 6-10 hours depending on the day. I spend a lot of time interacting with people on E-mail, Twitter and Facebook throughout the day, along with all the content creation that goes on (daily photos, video and live video show). The more time I spend, the more results I see. I could spend 3 hours a day and be done, but I know I wouldn’t be in the position I am right now.