by Tim Jahn on July 20, 2010
The way IWearYourShirt.com works is simple: companies pay Jason to wear their t-shirt for one day during the year. During 2009, the first year Jason started this, companies paid $1 for January 1 and $365 for December 31. This year, Jason has a buddy helping him, so the prices are doubled ($2 for January 1 and $730 for December 31). And in 2011, more exciting changes are coming.
But how did Jason come up with this idea? How is he able to be sold out 8 months in advance and have only a handful of days left to sell for this year? Why hasn’t anybody been able to duplicate Jason’s success?
I chatted with Jason recently to discover the answers to these questions and also find out what drives him and his creative business.
You’re definitely the first person I’ve ever heard of that decided to wear a shirt every day and get paid for it.
Well, that’s good, at least I know I’m original.
Absolutely! So, how did IWearYourShirt.com get started?
It wasn’t like I didn’t have a job. I co-owned a web design company at the time in 2008 and watched a lot of the marketing and advertising trends, always reading Adage, AdFreak, and other advertising sites. I saw that a lot of people were cutting back on budgets everywhere, all over the place.
I knew there was an opportunity and I saw all the social media stuff. Twitter was really starting to be talked about, everyone was already on Facebook. Just being able to create a YouTube video with any camera and a tripod, and anybody could do it.
Really, the t-shirt thing was the afterthought. It was really just use social media to promote companies and then what avenue could I do that through.
Oh, so you didn’t even have the t-shirt part of it at first?
No, the t-shirt was kind of the ancillary thing, because it was really like “alright, what can I now fit in, what’s the hook?” What gets everybody in each day and then it’s so easy, because everyone looks at t-shirts, everyone picks t-shirts with brands they like, and sees that stuff.
I imagine at first, when you were telling people about the idea, they might have looked at you kind of funny. Did you have any doubters or people that were thinking that’s never going to work?
Oh yeah! The way that I really kicked IWearYourShirt.com off was I emailed my list of like 500 contacts and just said, “Hey everybody, I’m not pitching you to buy a day, I just thought of this creative idea. I’ve talked to a couple of people about it. They think it’s creative as well, just give me some feedback.”
And it was really kind of 50/50. A lot of my contacts were my friends so they were like “Oh, Jason, that sounds cool, go for it”, not knowing exactly where it would go. And then the other half were people who were like “what?” You want people to pay you to wear a t-shirt? You’re not a model…you may be ok on the eyes but you’re not a beautiful blonde girl, so why would people do this?
So there was a lot of doubt and everything else but I think people realized, especially quickly when it got started, just how hard I was willing to work to promote each company each day. But, the biggest thing was when I hit the front page of Digg for the first time with my New York Times article, which was in December in 2008. It was 153 all negative comments. Like every single comment was negative.
And I think that’s just the Internet audience that has the biggest voice. There are trolls and there’s other people out there. I’m sure you get negative comments on things every once in a while too. People are just more negative in nature then they are positive, so I just had to really realize that I needed a thick skin quickly and that people were definitely going to be jealous of somebody that wears a t-shirt for a living on the Internet.
I was going to say, I’m sure after doubting, jealousy was the next emotion you experienced from others.
Yeah, exactly. I mean, people were very quick to be like “Oh, pssh, I could get paid to do this, if this guy’s just throwing on a t-shirt.” I was like, yeah, go for it. No copy cat has been able to keep up even close.
Why is that? Why can’t someone else just put on a t-shirt or a hat and succeed more than you? What do you have?
It’s funny, I was asked this question a lot last year. I didn’t really have an answer. My answer was just like, “oh well, you know…I don’t know. It’s unique, I was the first.”
It’s my personality. It’s me. It’s my outlook on everything, it’s the way I write the blog posts, it’s the way I put my character into my YouTube videos, it’s entertaining an audience every single day, it’s putting in 14 to 16 hours every single day working on all this stuff.
I don’t sit back and just let it run itself. I know the more I put into it, the more I tweet to people – and not just tweet. If you’re just throwing out tweets, that’s not doing anything. But the more I tweet at people and talk to people about things. Like, today’s shirt is for a cheese company.
I’m just going to search the keywords for cheese on Twitter and I’m going to find some people that are talking about cheddar cheese and ask them about it. Because that’s the way that I know I’m going to get great response for things. I know there was a model who popped up who was wearing t-shirts and I think she did it for 4 months and then gave up because no one was buying anything.
It only lasts so long when someone’s just sitting there and looking pretty. It’s like “oh this is great!” but at the end of the day, it doesn’t do anything, it’s not ever going to go anywhere.
I think that’s really been it – my personality and my drive to keep this thing going.
I feel like, especially people that come out of school and have the entrepreneurial spirit, they think about starting something right away. But, I think there’s something to be said for, and I want to get your opinion on this, for joining a nine to five or getting a typical office job to figure out what you don’t want.
Is that how it worked out for you?
I didn’t know this at the time, but I look back and I’m so happy that I spent the amount of time that I spent at my 9 to 5. Maybe I could have spent a year less or something, but you learn so much more from the mistakes that you make and from the bad experiences that you have than you do from good experiences.
You never learn from the “oh, this is fantastic! What did I learn from this?” Nothing. It was good.
But when you have a terrible boss, when you have a terrible group that you have to work with, when you have crazy deadlines for projects that shouldn’t need crazy deadlines, when you’re working the day after Christmas in a 9 to 5 job, those are miserable things.
And you’re just like “how can I make sure that I never have these things happen to me again?” Or at least learn how to deal with these things better.
I think that’s why customer service has been such a huge thing for me because I was treated like crap for quite awhile at that job. And I think that a lot of people are treated like crap that are watching this interview or that read Beyond The Pedway or that check out IWearYourShirt.com.
You don’t have to be treated like crap. Especially if you can work really hard and have a creative idea, or at least a creative outlook on things. You don’t have to be treated like crap at a 9 to 5 job.
Check out all our interviews with entrepreneurs!
- 37signals - Jason Fried
- A Space Apart - Jason & Gretchen Goodrich
- Airbnb - Nathan Blecharczyk
- AirRun - Rob Matthews
- Alexis Grant
- Allie Osmar Siarto (2010)
- Allie Osmar Siarto (2011)
- Annie Sorensen
- Apply in the Sky - Emily Chiu and Chiara Piccinotti
- Arment Dietrich - Gini Dietrich
- ArtistData (2009) - Brenden Mulligan
- ArtistData (2010) - Brenden Mulligan
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- BatchBlue Software - Michelle Riggen-Ransom
- Behance - Scott Belsky
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- Bite Size PR - Ryan Evans
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- BlogDash - David Spinks
- Bonsai Interactive Marketing - Danny Brown
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- Brazen Careerist - Ryan Paugh
- Buffer - Joel Gascoigne
- Buzz Referrals - Jordan Linville
- Carol Roth
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- Chris Bennett
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- Fathead Design
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- Firebelly Design - Dawn Hancock
- Firespring - Jay Wilkinson
- Flowtown - Dan Martell
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- Foodie Registry - Ben Reid (2010)
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- FoodTree - Derek Shanahan
- Foursquare - Dennis Crowley
- Freckle - Amy Hoy
- FusionCharts - Pallav Nadhani
- Giftiki - Bryan Jowers
- Github - Chris Wanstrath
- GiveForward - Desiree Vargas Wrigley
- Goshi - Jack Eisenberg
- Grasshopper - David Hauser
- Groupon - Andrew Mason
- GrubHub.com - Mike Evans & Matt Maloney
- Grubwithus - Eddy Lu (2010)
- Grubwithus - Eddy Lu (2011)
- gtrot - Brittany Laughlin
- Hello There - Shane Mac
- Hudl - John Wirtz
- Ideal Project Group - Andrew Wicklander
- Inkling Markets - Adam Siegel
- Instant Technology - Rona Borre
- ItStartsWith.Us - Nate St. Pierre
- IwearYourShirt.com - Jason Sadler
- IWearYourShirt.com - Jason Sadler (2011)
- Jun Loayza
- Junto - Marcy Capron
- Life After College - Jenny Blake
- Life In Perpetual Beta - Melissa Pierce
- Lifesta.com - Eran Davidov
- Little Independent - Lesley Tweedie
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- MCC Recycling - Michael Mills
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- MightyNest - Chris Conn
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- Milk Products Media - Todd Tue
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- Mineful - Jaime Brugueras
- Ms Career Girl - Nicole Crimaldi
- MyZeus - Patrick Algrim and Brandon Weiss
- NextStep Test Prep - John Rood
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- One Day One Job - Willy Franzen
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- POP! Social Media - Jill Felska & Jenn Krenn
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- Short List - Jason Goodrich
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- Threadless (2009)
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