When you’re raised without TV and video games while attending a typical public school in the early 2000s, you’re bound to face a bit of cultural friction. But the best ideas often come when we so desperately need a solution.
This was the exact environment that award-winning artist and creative director Ivan Cash found himself in. Like most great artists, he was an outsider. He had different ideas. He was ‘weird’. And, he was bullied for it.

But like many great artists, this level of ‘other-ing’ led to a very important moment: that of self-actualization.
As part of our Makers Podcast series, we sat down with Ivan to hear about his story of going from outsider to artistic director, why the best work has a real message, and how he once got thrown in jail for a t-shirt he made. You can listen to the full episode on iTunes here.
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Being OK with being a bit weird
“I think it was just getting more comfortable with myself and the fact that I was a little weird and I did have a different way of looking at things. And I think it was just accepting that and realizing that I could still connect and relate to other people even if we didn’t have the same exact common ground culturally.”
Charged with this acceptance of who he was, Ivan set off to college in search of a medium to channel this sense of connection. But he didn’t find it in a lecture hall or studio, he found it in a masked vigilante with a spray can halfway across the world.
In the early 2000s, Banksy had moved from relative obscurity in London’s East End to a worldwide cultural phenomenon with his signature pieces depicting class struggles and current issues popping up in New York and beyond. It was Banksy’s ability to comment on real issues and in public that really stuck with Ivan.
“I was probably one of the only people that knew who he was in my whole college and it was very exciting and very fresh, this idea of culture jamming and having a voice and a message and infusing that without needing permission. It satiated my need to feel a connection.”
At the time, Ivan was taking a screen printing course and decided to make the t shirt his own medium for cultural commentary. A huge Knicks fan, Ivan set his sights on their head coach at the time, Isiah Thomas—a 12-time NBA All-Star who couldn’t quite translate his success on the court to success as a coach.
“So I chose this idea from ‘Don’t hate the player. Hate the game.’ And I changed it to ‘Don’t hate the player or the game. Hate the coach‘.”
He started producing a small run of these bright orange t-shirts with his slogan and Thomas’s face on it.
Ivan threw together a website and a few orders trickled in. Nothing big. But then a blog wrote about him. And then another. And soon he was getting orders and people asking if he sold his shirts outside the Garden where the Knicks played. He didn’t. But he decided he should.
“The challenge for any creative person is in not falling victim to a certain idea of how things have to be or of how a reputation needs to be maintained, and really being dedicated to taking risks.”
He found a vendor that he could partner with off Craigslist and they met outside the stadium and he started selling the shirts as fans walked into the stadium.
“This was a magical moment. I think it was one of the first times that I saw a direct connection between something I created and people that felt inspired or just excited to come in contact with that creation. And so it was just this magical experience and every game I went to I sold more shirts and I started getting news coverage because this coach was making so many bad decisions that it became this mockery.”
And just like that Ivan had gone from TV-less household to the 6 o’clock news, selling his message. But the moment wouldn’t last because right before the 4th game as he’s heading in…

“Three police officers were waiting for me outside Madison Square Garden and apprehended me as soon as I walked over. Before I was even set up or selling shirts. They put me in handcuffs and took me to a holding cell in Midtown South precinct.”
They held him for just over three hours. Just long enough for the Knicks to lose the game.
“I immediately called a couple newspapers who I had been in touch with just from selling the shirts earlier and the story ran on the first page, big color photo, ‘Student arrested for ‘Fire Isiah’ tees’ and I guess that’s what started it all.”
From observing the world to actively participating
“It was thrilling. You know, when you’re younger you’re coming into the world as an observer, not necessarily as a participant. And so to me it felt like a rite of passage. Like, I’m really participating. I have a voice and people are receptive to it.”
“I don’t think that using my voice to talk about sports is my calling, but it is definitely what gave me the epiphany of how even a broke college student can create a piece of content that can be seen by the masses. And that was a really powerful lesson to learn at such a young age.”
Ivan finished college and went on this journey to figure out what his next step would be. He travelled from New York to San Francisco. He picked up some jobs at advertising agencies and eventually landed at Wieden+Kennedy in Amsterdam—one of the top advertising agencies in the world.
And while this was an extremely prestigious position, his story doesn’t end there.

Building a career out of side projects
After just 5 months at Weiden+Kennedy, Ivan faced one of the toughest decisions of his adult life.
Like so many of us who achieve that ‘dream job’, once the honeymoon period is over, we realize it’s not for us. So despite facing a ton of debt, no steady income, and the thought of living in a foreign country halfway across the world, Ivan quits.
This is when he starts to think about the kind of work he actually wants to do—the work that will bring him personal satisfaction and happiness. It was this shift in thinking and perspective that brought him to his first side project—Snail Mail My Email.
“At my job, I was sending a shit ton of emails. Everyone’s sending a ton of emails. And I’d be surprised if I met someone who wanted more emails. It’s overwhelming. And I’ve always had a recognition that handwritten letters are deeply personal and meaningful. They’re a way of letting someone know you really care about them.”
And while many of us live in the reality of never being able to hit Inbox Zero, Ivan wanted to take this frustration and this emotion and turn it into something that would be meaningful to humanity as a whole.
“And so my idea was to invite strangers to email me a message and a recipients address and I would handwrite that message and send it to the recipient of their choosing, free of charge. They could also request a custom option like a doodle or a flower petal or a lipstick kiss just to play up the tangible nature of letter writing.”
He sent the idea to friends and family and a few requests started to trickle in, and then on the fourth day (just like the fourth day of his t-shirt sales) a couple of blogs picked up the project and boom! Just like that 1000 letter requests roll in.
“At this point more and more blogs and media outlets were picking up this story and I started getting messages from people all over the world offering to help out as letter artists. So essentially I started to outsource the project and include many more participants than just me to interpret and write these strangers’ requests.”
“And it was one of those magical things that I think could only happen to someone that’s heartbroken and has just transitioned in their location and their vocation. And yeah, this amazing community of people came together and we ended up sending over 10,000 letters all across the world. Over 200 volunteers helped write these letters and that was over a 30-day period. It was the most magical thing in the world. It was very, very profound for me.”
“I feel like the curse of success is that you have a reputation and people expect certain things.”
And more than just another validation of his artistic vision, this project became a way for Ivan to share his social commentary on the state of technology and its role in our life.
A message that you’ll find in almost everything he does, from the ‘Last Photo‘ project, where he travels to different cities and asks people to show him the last photo they’d taken on their photo, to putting up ‘No-Tech Zone‘ signs around public parks in San Francisco as a statement of how we spend our time and what our society has become.

“I think that I’m really good at making simple concepts come to life. I think it’s a really clear call to action. I try to have every one of my projects be something you can describe in a sentence. And even if there are more questions that follow, I’d hope that one sentence gives you enough information that you can understand what that project is in full.”
And with so many open, outward facing, and personal projects under his belt, the last thing we needed to know was just how Ivan gets over the fear of putting his work out there and being seen. Because unlike his original inspiration, he doesn’t hide behind a spray can and a pseudonym.
“At the beginning of my career, I felt that I had less to lose. I just felt that it can’t hurt. I’m just going to put a bunch of stuff out there and see what sticks. And now I feel like the curse of success is that you have reputation and people expect certain things.
“I think that the challenge for any creative person, whatever they’re doing, is in not falling victim to a certain identity of how things have to be or of how a reputation needs to be maintained, and really being dedicated to taking risks and experimenting. Because a very inherent part of experimentation is failure, and I think that failure is a necessary part of pushing creative boundaries.”
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