by Barry Chudakov on July 31st, 2011

Interview: Professional Shirt Wearer, DeAndre Upshaw

“Professional Shirt Wearer” DeAndre Upshaw wears his hair in Rasta braids that fall in beaded lines around his wide smile. A self-proclaimed “Social Media Ninja” who grew up forcing his friends and family to perform in short films he wrote, directed, and produced, DeAndre has spent the majority of his professional career helping people connect to others via social media. He performs for (‘works for’ doesn’t seem accurate), a company that embodies multidimensional storytelling.


DeAndre Upshaw of whose mission is to wear shirts that engage people and promote companies.


When clients buy a day on IWYS (all 365 days of 2011 are for sale and you can buy multiple days at a time), that day IWYS pros wear a t-shirt with the client’s name on it. Founded by Jason Sadler, IWYS pricing started at $5 a day and goes up $5 each day from the day the company went live. The t-shirt is just a convenient vehicle, a badge cum booster rocket for the bigger idea. Once you buy your day, that day becomes an event to be watched, an event you effectively both sponsor and engage to build content for. The five key people of IWYS create content on your day, content that is unique to each client. Five “unique/fun/creative” YouTube videos, five live video shows on Ustream (3 hours of streaming), five to fifteen photos. All content is shared to each of the five individuals’ Facebook and Twitter profiles.

The storytelling twist here is that clients like Starbucks, Jockey, GoToMeeting and Smarties pay to engage the IWYS network. “You are buying social media content creation and the content being shared with a far-reaching community.” Like a billboard wrapped around a VW bug that drives through the neighborhood, the storytellers of IWYS move through digital neighborhoods with a different message updated regularly. (“Live video in 20 minutes! You ready?”)

Behind the well-designed website and the monogrammed webcam pitches that make local Toyota dealership spots look timid, IWYS is transmedia storytelling gone Monty Python. Note it is not called or The I in iwearyourshirt is someone real, someone with real connections, a media personality with a growing, evolving audience. Here we are witnessing the morphing of a cultural artifact, the 30-second commercial, into a social media TED-like mashup where technology, entertainment and design come together in a pitch to the burgeoning and ever more networked digerati.



Having connected on Twitter, I caught up with DeAndre earlier this week to talk about iwearyourshirt, storytelling and what sort of life, or Metalife, he lives when he’s online telling stories for the clients whose shirts he wears. We started our discussion with something at the heart of IWYS, the power of storytelling.


METALIFE: What makes a good story?

UPSHAW: I think that every brand and every company has a story to tell. So when a company comes to iwearyour shirt and buys a day, the first thing I do is try to figure out what their story is. What is the best way I can get their message out to a wide audience using the skills that I have to tell their story? So I think that one of the important things when you’re looking at marketing via social media, when you’re thinking about posting things on Facebook or sending out a few messages on Twitter, is you have to ask how does this play into your company’s story? Because everything that you put out into the world, everything that you put out into the atmosphere is a part of your story. So when people come to iwearyourshirt, they’re looking for us to enhance their story using multimedia, become a part of their story.

METALIFE: Well, that blows your hair back if you think about it for a moment. Most clients still want to tell customers their story, not invite customers to become part of it. Which brings us to our first Metalife question: to what extent are you real for your customers and how do you make yourself real for your customers, when you’re just wearing a shirt with their name on it?



UPSHAW: When you’re a person presenting yourself every single day, it’s impossible to some extent not to be real. It’s impossible not to show who you really are. There are people who have been in my chat who have seen me every single day since January 1st. So my life is intertwined with the companies that I work with. However, it’s sort of like being ‘on’ all the time. It’s an amplified version of myself. What you see when you’re watching a video of me—say the company is quick weight loss pills, a fictional company—obviously I am not taking quick weight loss pills every single day of my life. Because they’re one day, they have paid me for one day to promote their products. The line blurs between I am promoting this company and I am using these pills; but I’m saying: “to the best of my knowledge, they’re a pretty cool organization, they’re a pretty good company.” So the fictionalized version of myself, a singer, a dancer, someone who does goofy things is just an exaggerated version of myself. Obviously I don’t spend a good deal of my life singing randomly. What you see when you look at IWYS is a group of people who are making videos and using themselves to push a product. So when people look at me or Jason, or Angela, Neal or Amber, you’re really seeing for the most part who we are—just an exaggerated persona. Of course, sometimes I’m jumping out of buildings—obviously that doesn’t happen to me in real life but as far as our personas and what we present to the world, that’s all us.

METALIFE: And to some extent the ‘realness’ of you is what you’re selling, isn’t it?

UPSHAW: Right. We’re selling ourselves because the thing about IWYS is that community is one of the most important aspects of it. Because I am just one person out of millions who makes videos on YouTube. And the thing that takes a video of mine, a video selling something that otherwise people would not care about—quick diet weight loss pills—is that the community around IWYS knows who I am and they know that my personality traits are coming through in the video. So they’ll watch the video for me, they don’t watch the video because of quick diet weight loss pills; they watch because they think that I am interesting digitally or comedically. They know that I will deliver something that will make them smile or make them laugh. And then they’ll move on with their lives.



METALIFE: How did you find and build that community?

UPSHAW: I came into IWYS this year, 2011. Jason had done a lot of the legwork in terms of building it up. We came in and there were people who were utterly devoted to the community. They would show up every day, every single day at the same time, watch five shows, leave comments on videos, and when I say every single day I’m not exaggerating. There are people I have been communicating with every single day since January 1st. Saturday, Sunday, whatever holidays have been since then. So the community that was in place was already a good community. What I’ve been working on this year is building my own community, and through doing that building up IWYS. I’m reaching out to people who at this point haven’t been touched by the IWYS launch, and that starts with my own community, people that I know, people I’ve grown up with, people I’ve gone to college with, people I’ve worked with; I introduce them to iwearyourshirt and by doing that I grow the community.

METALIFE: You were a filmmaker, you were in drama. What brought you to the point where you wanted to be a YouTube star, a YouTube personality?

UPSHAW: I have a degree in journalism and public relations with a concentration in broadcasting and a minor in film and digital media which is a fancy way of saying I can write things and I can film things. When I was a senior in college, I actually won a job competition, becoming the spokesperson of a credit union. A marketing firm that only works with credit unions was trying to raise credit union awareness for young people. And so they did this big search in Texas to find the person who could represent credit unions in Texas. The job entailed doing a YouTube video every week, posting things, going to events. I got a car with a fancy wrap around it, a whole bunch of logos and things on it, and from there it launched my professional career working in video. About 2009 I started making videos for them: it was a one-year contract. Then when I graduated from college I started working with the marketing firms that ran the competition. I did some stuff with them for a year and that’s when I made my first foray into live video. And interestingly enough, the way I found out about IWYS is that the company I worked for purchased a day on iwearyourshirt. Then Jason announced a public search for people to work with them, and I thought it might be kind of cool to branch out.



METALIFE: If I consider what you guys do, it seems to me you take your personal integrity and personal connections—your reputation and network—and loan them to a company for a day. Is that accurate?

UPSHAW: I would say that is accurate. Nobody wants to listen to or watch someone daily who is not interesting. When people look at me, I am someone they want to spend time with or hang out with or get to know better, if that makes sense.

METALIFE: Makes perfect sense.

UPSHAW: So when people look at the people of IWYS, we’re all people you could see yourself having lunch with, or hanging out with. And, yes, the lines between my personal life and professional life online have always been very blurred because my entire professional life I have worked in social media. And so the people who work for iwearyourshirt are indistinguishable from their personal lives, if that makes any sense.

METALIFE: Absolutely. You’re describing Metalife blur. The blur of our personal, online and professional lives is something I write about regularly on Metalifestream. So, yes, you’ve just touched a nerve here. Given that, where do you end and where does IWYS begin? Do you ever wonder about who is who?

UPSHAW: I don’t. I spend a good deal of my life working. As you can imagine, pushing out content every day is not something that you can just brush aside. I don’t have problems like having alter-egos or anything like that. Obviously I am not ‘on’ 24/7. When the camera’s on or when my show is happening, I’m filming, or I’m recording a track to sing, I’d say it’s an exaggerated version of me, which is a true version of me because I don’t change radically for the camera, I just take what I got and amp it up.



METALIFE: Finally, where is storytelling video going? What do you think is working now, what is going to work or what isn’t going to work in the future? Give us your predictions on storytelling and video and how you see them coming together.

UPSHAW: When I sit down to decide to make a video or do something for a client, I try to figure out what the story is. A few days ago we did a big campaign for Jockey, the underwear company. And they just said, ‘Go out on the street …” They have a new line of products and they want people to test them. They wanted us to go out into the street and get feedback from people. And when I got out there we filmed for an hour and a half, we interviewed people, I tried to pick up as much B-roll as possible, and when I came home I crafted a story around that. If you watch the video, it has a beginning, a middle and an end. And I think that there’s a reason that traditional and conventional storytelling has held up for the past thousands of years: stories should begin, they should have some sort of conflict, and then they should end. And I think when people watch video on YouTube or Hulu or they watch on Funny or Die, this process is so ingrained in people’s heads, in order for videos to be successful, aside from your little flash in the pan—people falling down or LOL cats, aside from those videos that go by because people like to see bad things happen to other people—videos that are successful have a beginning, a middle, and an end. Even viral campaigns, things that seem to just pop up out of nowhere, have a beginning, a middle and an end. So when they’re watching a video, people want it to follow a format they’re familiar with. There are things on YouTube that I would gladly watch if they were a series. As the legitimacy of YouTube as an outlet for creativity grows, you’ll see it more and more receptive to real stories and real people.

METALIFE: Well, that raises a question about backstory. You are DeAndre Upshaw of IWYS; you’re DeAndre every day and you’re also a new product everyday. As discussed, you’re infusing that product with your authenticity. And to some extent lending the product your backstory, right?

UPSHAW: I would never look at myself as DeAndre In the twenty-first century, in 2011 right now I am DeAndre who works at And everything I do at IWYS is a part of my story, but it is not my whole story. And I think when a company is setting out to make their mark in social media or make their mark on the world at large, their employees, the people who work for them, need to keep the personal touch. I mean there is no one person who says I am Best Buy, or I am Phillip Morris or I am Johnson and Johnson. When you allow your employees, when you allow the people you work with and allow yourself not to let work strictly define you, things work better. Instead via social media you can say I am this person and this is what I do. I believe people respect you more for that. People respond to people, they don’t respond to organizations. And I know that when I shoot a tweet to Southwest Airlines, Southwest the business is not responding to me. I know there’s not some person named Southwest sitting in a little room responding to me: I know that it’s a person. And so there’s a difference between having a Twitter handle that’s just Southwest and a Twitter handle that’s Becky at Southwest. Because Becky is a person and Becky can respond to the way that I feel and Becky is a human. Becky is a person. People respond to people and that’s the trend of where I think social media is going.

METALIFE: And that’s the really unique thing about you, isn’t it? You’ve given corporate messaging a real face, a live entity; this message is coming from a personality, a person who has something to say. Isn’t that headed towards a new thing?

UPSHAW: There’s a lot of transparency in what we’re doing. Because people who go to and people who have been watching my videos know that I don’t work for Quick Diet Weight Loss Pills. They don’t pay my bills all the time. They know when I make a video for them that I am the person who is representing them. That’s my backstory and I’m sticking to it.


DeAndre wearing a shirt for Survival Straps.


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