How Wearing T-Shirts Became a Fun and Profitable Business Model on the Web with Jason Sadler

Jason Sadler joins us for episode #44 of Inbound Now!

Jason runs IWearYourShirt.com and specializes in creating interesting and compelling content for companies who want a different kind of advertising.

In the interview we talk about:

  • How IWearYourShirt.com got started
  • Exactly how Jason keeps his creative juices flowing
  • Tips on Growing a solid social media presence
  • & one of the most important things he wish he knew when starting a web based company

Transcript:

David Wells: Hey, everybody. Welcome to another episode of Inbound Now. I have a very special guest with me here today, Mrs., Mr. Jason Sadler of iwearyourshirt.com

Jason Sadler: I don’t know. Was that a Mrs. or a Mr.? That was like a mix of the two. I’ll take it. That’s fine.

David: I just messed that up so bad. Anyways, Jason runs iwearyourshirt.com. It’s one of the craziest business models I’ve ever seen on the web. It works very well for him. Jason, can you explain what exactly, iwearyourshirt.com is?

Jason: I can. It is a company where I literally get paid to wear t- shirts for a living, and promote companies via social media. It started back in 2009, and I’ve been doing it all the way up until now. We have more shirt wearers now and we’ve had over 1,500 sponsors now or the past couple of years.

That’s it. Put a shirt on, make a video, puts some tweets and some Facebook stuff out there, and just kind of rock out all day.

David: Okay. Got you. Yeah. In the intros to a lot of your videos, it’s you with an angry face, and you’re like, going against billboards and traditional advertising stuff. I think it’s pretty funny. So, with your “shirtvertising,” let’s call it that for right now . . .

Jason: Sounds Good.

David: . . . it’s really more than that, though, right? It’s about creating compelling content around the brand and spreading it out through the social web. So, can you walk us through your creative process, on how you approach each client differently, and make a company that may not be that interesting, work in social media?

Jason: Yeah. This is a really well-timed question for us as a business, because iwearyourshirt.com was me in 2009, two people in 2010, five people last year, and now five people again this year. We’re going through some growing pains, and the fact of social media is obviously changed so much. Right?

When I started this in late 2008, early 2009, there were basically no companies on Twitter, putting their messages out there. So, the only people that were on Twitter were real people, you and me chatting about stuff. So, when I would say, hey check out Pride of Maui, I was one of the few marketing messages that were out there and it was a real person doing it. It had some staying power, whereas, now, obviously it’s a very kludged up system.

The creative process has really changed, because when it first started, I never made a video before. I didn’t have a Twitter account. I had like a hundred friends on Facebook. I didn’t even know who half of them were, because I didn’t set it up. I was just kind of jumping into this, because I thought it would be fun and it seemed like a decent idea, because there were people on billboards, there were radio advertisement hosts, and all that stuff.

I started doing this with the flip cam. I would just turn it on. I didn’t even have a tripod for like the first two weeks. I would just turn it on, and like hold it with my arm out, and just talk to the camera, and say, “Hey, what’s up. I’m Jason.” The videos were horrendous, but it was people seeing into my life, and then also seeing the sponsor attached to that. I didn’t really have to do too much of making a crappy company look cool, or even making a real cool company appeal to other people who may not have know about them. Whereas, the business has evolved to… we kind of became more of a production company, which is good and bad.

I’m starting to realize that there are so many messages that are out there now, that we’re just now another message. Right? It’s Proud of Maui, sponsor of the day, really cool snorkeling and diving tour in Molokini. One, it’s an easy thing to talk about, but maybe people aren’t interested. Maybe they’re not seeing their messages because it just looks like another message. So, what we’re really trying to get back to is pumping some personality into these brands, having it be fun, so it really could almost be any brand because it’s more about us doing fun things, and the shirt just happens to have a name on it. That’s really where we are trying to go.

David: Got you. It’s like, I almost look at it like the evolution product placement. Right? You’re a personality. You and your team have fun, awesome videos, and then it’s like, by the way I’m wearing this shirt. If you want to check them out you can, right?

Jason: And, that’s exactly what I want us to go forward to. We kind of in the past yearish have been more commercial. We made more infomercial style videos, trying to have fun with it, trying to create YouTube videos for people. It’s such a great piece of content. It lives on forever. You can optimize the heck out of it.

There’s a lot of benefits to having a YouTube video, but for our community, which is really the most important part of my business that I’ve grown over the past couple years, I think they’re kind of getting bored with the commercials. They want more of the personality. They want more of the randomness. That’s really what I’m trying to push us toward here, in the next couple months.

David: Got you. How did you go about selecting your other team members?

Jason: Yeah. So, the first year it was obviously, just me, so I just picked myself, which is an easy one. When the first year sold out in six months, I had been talking to a guy by the name of Evan White. He had been helping me get some PR, and just kind of brainstorming. We were chatting. I was like, listen, I know I want another shirt wearer. I’d like to find a girl because it would be a good back and forth for a guy and girl in a shirt, but I just didn’t know anybody. I didn’t even know where to look to find a professional t-shirt wearer, someone who could do this full-time. It’s a lot of work. It’s every single day of the year. So, we were on the phone on day. I was like, “Listen, man. How about you just do it, because you kind of have the same schedule as I do. You know how this works.” He was like, “All right.” So, that was literally how I found my second shirt wearer.

Then, at the end of 2010, we did a YouTube video hiring process. Basically, someone would film a three to five minute video. They had three requirements. You had to wear a shirt. You had to be awesome. You had to say why you were better than somebody else. I mean, that was it. I didn’t care about where you worked before. I don’t care about where you live. None of that mattered to me. I just wanted to see if you could be on camera. So, that was the process.

We picked people, and we did that again for the shirt wearers that you see this year. Deandre Upshaw has been our only return shirt wearer. He was here last year, and he’s here this year. That’s how we find people. I think that’s the only way we could, because it’s such a weird job.

David: Right. That’s awesome. Yeah. Your team is kind of diverse, spread across… is it just in the U.S., or is it worldwide?

Jason: Yeah. It’s just in the U.S. We got Sara Biel in California, Beminy (sp) in New York City, Deandre in Texas, and Shawn Ely was actually in Detroit, Michigan, but he was tired of the cold weather so he moved, actually, here to Jacksonville. He came down and visited twice. He was like, “I wanted to move anyway, and this place looks awesome, so?” He lives like six minutes down the street, and we’re always filming videos together.

David: Nice. I love the concept for the company. It seems like it’s so simple, yet you’re kind of the first to do it, right?

Jason: Yeah.

David: You’ve got a ton and ton of traction from the press. You’ve been mentioned in the New York Times, Fast Company, Wall Street Journal, Mesh (sp) Mobile, the list goes on and on. What is the key for getting those big press mentions?

Jason: Luck? I wish I had a formula that I could give people, but it’s so funny. I didn’t know anybody in the press world, so when the New York Times thing hit, that was through my buddy Evan. He had known somebody and that came through, but then, after that, everything was really just organic.

I distinctly remember getting the email in 2009 from Reuters. A guy said, “Hey, I want to profile you for a week, and just know what you do. This job looks ridiculous.” I was like, “All right.” I guess his editor got word, he found what I was doing, and he was like, “Let’s fly him up to New York City, and let’s walk around with him, and see what he does.”

So, I did this whole piece on Reuters, and from there that was kind of where everything kind of took off. Getting into all these other outlets, it’s really just been continuing to do what I do, just trying to keep it fun, trying to keep it different. Even now, I’ve got a reporter for CNBC, who always contacts me, looking for new stuff. I write for entreprenuer.com, actually youngentreprenuer.com. It usually goes through entreprenuer.com. I just try to keep things as fresh and interesting and new as possible to keep the press wanting to talk about ireadyourshirt.com.

David: Got you, So, they’re also talking to you a lot about this stuff you guys are doing in social media. Right?

Jason: Yeah. I think that that kind of comes along with it, because my business is built on social media. If Facebook crashes tomorrow and it’s down for a day, I’m screwed. Not really, but for the most part, there goes a lot of my audience. If Twitter is having the fail whale, I have a terrible day. I’m pulling what little hair I have out.

So, really we kind of put all our eggs in social media because I believe in it. I think it’s awesome. I think a lot of companies are obviously seeing the potential. Now, it’s just a matter of rising to the top, above the rest of the marketing jargon and nonsense.

David: Got you. Yeah. Iwearyourshirt.com, and you as well, have a pretty large social media presence, a pretty large community. What’s your secret sauce there? How did you really foster that?

Jason: I’ll steal a line from Gary Vaynerchuk. It really… a lot of inspiration from him when I first got started. That was just to care. I wanted to know something about every single person who ever tweeted at me. I wanted to know something about anybody who ever became my friend on Facebook. I still do a live show every single day, although, we’re kind of phasing it out in the month. I’ve been on live video for almost three years straight, every single day.

Every person that comes through, I talk to them. I’m not just hosting a show and doing something, and there’s no interaction. I want to know who Sandra Diana is, who’s there. Who the other people who are showing up. I want to know something about them. To me, I think that’s what has been really great for the community

We do a lot of giveaways and promos and stuff with our sponsors. We try to make that fun as well, not just a, sign up for the newsletter, to actually do something that people feel interested in or good about.

David: Got you. So, speaking of contests, you just recently ran a contest on your site for a MacBook Pro, which I entered and lost, cough, cough. You had over 37,000 entries. It seemed like it did very, very well.

So, when you’re running these social media contests, are there anything that people or companies should keep in mind to make sure it does as well as it could do?

Jason: Yeah. I think you really… number one, have to have a compelling prize, right? Everyone’s giving away and iPod or an iPad. At some point you have to realize, Okay, what do I want to get from this, and what am I willing to get out of it?

The Tracky Team actually contacted me, and they’re like, “What do you want to give away? What would you want to win?” I said, “Listen, we do iPads, not left and right, but once a month here, it seems, on iwearyourshirt.com. Let’s do something bigger. There’s a new MacBook Pro that’s probably going to come out.” Luckily, it did, because I don’t know what we would have done if it wouldn’t have. Let’s do that. That’s what we focused on. Luckily, having a service like Raflocopter, I know you saw how simple that was.

David: Yeah.

Jason: It’s unbelievably simple to manage a contest. I mean I did nothing but respond to tweets, respond to comments, see people liking stuff and try to interact with it. That’s part of it, too. If you just set something up, and sit back, and go, “All right. Let’s wait for the entries to come in,” it’s not going to happen. You have to try to get people interested. You have to talk to people. I did a good bit of that. Thank you to Sara Evans on the Tracky Team for also helping spread that out.

David: Got you. Yeah, Raflocopter is pretty awesome. Actually, I’m running it with a client right now, and it’s from when I saw it on your site. I was like; this is ridiculously easy to use. It makes people tweet about it, once a day if they want to. It just gets the word out there, like crazy. I wish I actually invented Raflocopter.

Jason: You and me both, especially for as much contesting stuff that I used to do, I should have done that.

David: Got you. Right now are there any copycats out there, people who have tried to emulate what you do?

Jason: There were a lot more in the beginning. I think, I don’t know if they all just started talking to each other, and realizing that, I’m crazy, and obviously, I work every single day and film a video every single day and answer all these emails and put all these tweets out, and do all this stuff. A lot of people want days and time off, and I don’t necessarily need that, because I love what I do. I’m entrenched in social media. I love t-shirts. I don’t like wearing other pieces of clothing, so for me that works.

There were tons of copy cats in 2009, especially after the first year sold out. There always seems like there’s four or five each year. They’ll go and email my previous clients. My clients will forward me the emails, “Hey, there’s another copycat.” That loyalty that I’ve built with these clients is nothing more than me trying to be as transparent and honest as possible with them. I think that’s really been my staying power

Like you said, I was the first on to do this. I’ve built the audience. I’ve built the following. I’m sure someone, if they had a good marketing mind, could come and do this, as well, and create some competition. I would be fine with that, but I haven’t seen anybody do it full on, and I’m okay with that right now.

David: Interesting. I was thinking about pivoting Inbound Now into iwearyourunderwear.com.

Jason: There you go. I’ll be glad to introduce you to Jockey. They were my underwear sponsor for two years. They’re great people, so you can start with your pitches, right there.

David: I need some models, though. I don’t think anybody want to see that, but, yeah. So, we have a question from Twitter. I tweeted earlier today, if anybody had any questions for you. Riseupandgo on Twitter asked, “How much would it cost for Jason not to wear a shirt for a day?”

Jason: That’s fun. So, I have a couple ways to answer this question. The first one is, Josh Spear, from Under Current, I’m not sure if you’re familiar with him, but he was kind of one of the first tastemakers online, finding cool gadgets, luggage, and travel stuff. He actually paid for a day in 2009, and didn’t send me a shirt, on purpose. He was like, “I want to see what you do”. I was like, “Did you just pay me to not wear a shirt?” He was like, “I’m not going to say one way or another.”

So, I remember I wore no shirt that day. I went through Chick- fil-A drive through that day. I went about my day without a shirt on. I didn’t go to the grocery store or anything, but I did that. It was fun.

I had a couple days in 2010, and before, where I didn’t get the shirt. It didn’t show on time, so I just embraced it. I was like, “Well, I didn’t get a shirt. This is part of the job, so let’s do this.” Nowadays it’s more focused on the team, so I don’t want the team to run around and feel like they have to be topless.

However, I don’t do a lot of things with my shirt off, mainly because, I don’t know about you, but as an entrepreneur, as a business owner, I have totally lost track of my fitness, my diet, all this stuff. I don’t feel great about taking my shirt off. I am starting a 90-day challenge. I actually haven’t put it out publicly, so this is the first place anybody’s heard of it. On my personal blog, actually, after this interview goes up, I’ve got it post written and I’m 20 days in. I wasn’t going to tell the public, but in 70 days from today, I will hopefully look like a bronze statue, either that or I’m a complete failure.

So, we’ll see. You’ll have to check back in August. Then, I will not have been paid to take my shirt off, but hopefully it will make me feel good about, getting in shape and staying back where I was.

David: Got you. Cool. You mentioned that you have done live video for the past three years, but you’re phasing that out. Why are you phasing that out? Was live video, kind of like a trend that was hot, and is kind of dying down, or is the audience not there? What’s the reasoning behind that?

Jason: I don’t know the direct answer to that. I think for me, there wasn’t enough change in the show that I did. The show was always, me on that couch, behind me, talking about whatever, stuff that was going on in the news, some sponsor related things, and just trying to have fun. I think that as with any TV show that gets old if you don’t change it.

For me, it was an hour commitment every single day. It wasn’t me giving enough value to the community that I could be giving in an hour and I wasn’t getting enough back from the community either. That’s no fault of theirs, because like I said, there wasn’t anything that was drastically different.

So, I just kind of sat back, and looked at, all right, how much time am I spending doing this? What’s my return on it? It was nothing. I’d rather spend an hour tweeting with as many people as I possibly can and having all those conversations than if 20 people show up to a live show, or five, or ten, whatever it may be. I think live video is great, but I think it’s very difficult if you don’t have a full production and plans, and like your own Tonight Show, basically. It’s not going to keep people interested.

David: Got you. So, I agree with what you’re saying. If it’s just a show and the audience isn’t getting value, it seems like it’s not worth doing. On that point, though, you do a video every single day. One of the things that I’ve struggled with doing video, if I was going to do something every single day, I feel like I’ve almost run out of ideas or my idea wouldn’t be good enough. How do you jump that hurdle, and really come up with something new and creative, every single day?

Jason: Luckily, I think, two things. Number one, my brain is wired in a very weird way, so I get these companies and all the sudden I just think of something random. I think that’s helpful. The other thing is that every company is different. Today is Pride of Maui. Yesterday was a surveillance camera company called, QC. You see the difference in those companies. There’s no way those videos would be anywhere similar. Right? It would be completely different, just because they’re different companies. That helps a lot.

When I look at these companies, and a lot of them now, we look at what their goals are in video because we want them to be able to reuse this video, or put in on their Facebook page, like Pride of Maui did today. I think that that’s important to me. I know what they want, and I can serve that forward.

Going forward here, what I really want to do is create more content that’s just fun, inspiring, spontaneous and look to Twitter and look to Facebook, and look to my community, and say, “What do you guys want to see in video? What really interests you? Do you want to see me do a bunch of trick shots, like a random video trick shot. Okay. I’ll go do that.”

I think it would be fun to really let the community drive the content that’s being made. That makes them feel like they’re getting something out of it, and it makes me not have to do so much thinking, because I’m like, “All right. That’s a good idea. I’m going to go do that.”

David: Right. Got you. So, you mentioned the video you did today, is now on the Pride of Maui Facebook fan page. Do you think a lot of your success with iwearyourshirt.com comes from that? You’re promoting that company. They’re also in turn, promoting you because they’re sharing that content out through all of their different channels?

Jason: Absolutely. I think that in continuing to build this community, as we get sponsors that come forward, we tell them, it’s only going to be as much as what you make of it. How often do you pay people to wear t-shirts for you? It’s not very often. Right? So, if you’re spending the money, if you’re doing something interesting, share it.

Share the crap out of it, because people are not going to be like, “Oh, this is stupid. Why did you pay these people to wear a t-shirt?” They’re going to be like, “What in the world is this?” Whether the video is dumb or not, the idea of it makes companies look like they’re thinking out of the box and doing something interesting, which has definitely helped us.

We’ve had a lot of community overlap with some of our sponsors, where we see people come from different pages and hang around for a while, because they are interested. They do see something fun and different. I think that’s really cool and that’s fun.

David: Got you. Yeah, I see a huge opportunity for a lot of businesses out there. They kind of just do their own thing, live in their own silo. I think if there was a lot more collaboration, especially with content, and video content, I think there’s miles and miles of leverage there. Yeah. Do you agree?

Jason: Yeah. I mean, definitely. The live video thing is a great example. You get so stuck in your ways of doing the same thing that you do, and you’re comfortable with. Even if that’s pay-per- click or banner advertisements, whatever you do, think about, what can spice this up? What can really put resurgence into the brand? Yeah, it may be worth selling, at the rate we sell it, but could we do something that could take that up a whole notch.

You look at Dollar Shave Club, I’m pretty sure they didn’t expect the result that they had after that video, but it didn’t cost them a whole crap load of money to make that video. It didn’t cost them a whole bunch of time. They just made it, put it out there, and it was completely different than anything they’ve done before. That’s why it worked so well. So, I think creativity is key in getting outside of your silo, like you said.

David: Okay. Got you. So, let’s shift gears a little bit to the actual business model of iwearyourshirt.com. So, it’s a primarily online business, right?

Jason: Yep.

David: What’s one thing that you wish you knew, or wish someone told you in starting a business that’s primarily on the web? What’s one thing you wished you knew starting out?

Jason: Hire an accountant. The $500 that you are going to spend on an accountant as a business owner for having a full online business, will save you so much of a headache. The first two years of this, I don’t know why, I just was like, I don’t want to spend $500. It’s the best money that you can spend. It’s ridiculous. When I think back now, I’m like, “Wow.” That not would have saved me a ton of money, but the headache of all this stuff that I have to do.

I think the other thing too is when businesses are getting started online, think about the domain name that you are going to buy. Think about the Twitter handle that you want. These things are where the people are. So, if you’re thinking about a company name, and you don’t check to see if these things are available, or somebody might already have them, you’re going to shoot yourself in the foot. I think that’s a good one.

The other thing too, is pick a platform and run with it. If you don’t have time to do Twitter and Facebook full-time, pick one. It’s not going to hurt you if you just stick to one or the other. Maybe you will build up the time and the audience that you can move to another one. Really focus on what will do well for you.

David: Got you. Did you choose a platform, starting out, and then transitioned to the array?

Jason: I picked all of them. So, that was one of my mistakes from the beginning. I wanted to be on every platform. I used TubeMogul, and pushed my videos out to like 30 different video platforms, and all this stuff. The time I was spending to do that versus the return was negligible. It wasn’t worthwhile.

I finally had someone come to me, I don’t even remember who it was, I think it was a sponsor. They were like, “Why are you doing this? You’re getting like three views here and there. You’re getting all this stuff. Is it really worth the effort?” I looked at him, and I was like, “No, it’s not.” I’d rather focus on YouTube, where I have over 8 million views now, just on YouStream was the live video platform before over a million views, just on Twitter, just on Facebook

I kind of came back, and think about email marketing. I didn’t even think about having an email list. That’s a very important thing that I just didn’t think about. It’s just continuing to think about the basics, pick the ones that really work, and run with it.

David: Got you. Cool. So, Jason, where can people find you online?

Jason: Iwearyourshirt.com. I’m on Twitter @iwearyourshirt. We’ve got a fan page, which is facebook.com/iwearyourshirt. I also have a personal page because I outgrew the regular 5,000 wall on Facebook, which stinks, but you have to do it.

Actually, I’m really excited about; we’ve got some changes coming up in the next couple of weeks. We’re focusing on video production right now, but we’re starting to do weekly sponsors, which I think are going to be really exciting. It’s going to be a lot more community focused. If you’ve ever been a part of the ireadyourshirt.com community, and you’re watching this, or you a potential to become part of it, we’re going to have a fun little setup, where you can pretty much dictate what we do, for our weekly sponsors. You can have a voice for those sponsors. I’m really excited for the upcoming changes. I just want to keep growing and changing and evolving this brand.

David: Got you. Yeah. I appreciate your time. I’ve definitely been keeping an eye on iwearyourshirt.com. I first heard about you guys, it was on the Rise to the Top Show.

Jason: Oh, yeah, with David Siteman Garland.

David: Yeah. I was like, “Are you kidding me. This guy wears t-shirts for a living?” I was amazed.

Jason: Awesome.

David: Keep up the good work, man. I appreciate your time.

Jason: I appreciate it. Please keep watching so that I can keep my torso clothed.

David: All right. Will do.

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About the Author

David is Founder of Inbound Now and a Fanatical WordPress Designer & Developer. He believes that the internet is a magical place where wonderful things can happen. Say hi to him @DavidWells

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