Steve Gadlin is an entrepreneurial weirdo.
In 2010, Gadlin’s improv-comedy game show, "Don’t Spit The Water," was made into a TV pilot that aired on WCIU-Channel 26.
“I aim to delight and confuse,” he said. “I’m going for comedy experiences that make you scratch your head and wonder what you just saw.”
You might remember Gadlin from reality TV success. He’s the guy who dared to believe there was money to be made selling personalized stick-figure cat cartoons on the Internet.
And to think, it all started as another one of Gadlin’s silly ideas.
“It was a social experiment that asked the question, “Can I make stick-figure cats, the ultimate widgets, and create a market for them on an ecommerce site?” Gadlin said.
The custom cat cartoon business had minor success when Gadlin put out a Groupon deal that scored 1,000 orders.
Then, he answered a "Shark Tank" casting call with a short email that read, “I draw stick figure cats, let me at 'em.”
“When I got on the show, I expected to get torn apart,” Gadlin said. “And I was looking forward to that."
Instead, Cuban offered to invest $25,000 — more than double Gadlin’s $10,000 wish — for a 33 percent stake in the company.
Gadlin’s first thought, “He did the math wrong. … I better grab the money and hightail it out of there.”
That’s what he did. In fact, Gadlin has neither seen nor spoken to Cuban since. They discuss the bizarre business venture exclusively via email.
“Steve is crazy enough to be crazy good,” Cuban said in an email. “I couldn’t think of a better cat-drawing partner.”
When it comes to drawing cats, though, it’s a lopsided partnership. Cuban agreed on air to draw one cat for every 1,000 orders.
But since the show aired last year, Gadlin has inked 12,233 stick-figure cats — which sell for $9.95 a pop plus shipping. Cuban, the eccentric Dallas Mavericks owner, has drawn exactly two cartoon felines for a thousand bucks each.
“So, you could say Cuban owes me 10 cats,” Gadlin said.
The 37-year-old Web guru at Weigel Broadcasting in the West Loop isn’t pressing his billionaire partner to make good on his promise to draw cats.
“You know, I started with such low expectations, and now it’s a slightly legitimate business. I’m not going to pretend that I’m at all disappointed where this has taken me in the last year and a half,” Gadlin said. “Orders are steady. I draw 25 to 50 cats a day. Sometimes to keep up with demand, I draw 100 a day.”
And it gets better.
Last month, Gadlin started negotiating with American Greetings to turn his stick-figure cat drawings into a line of silly greeting cards that are expected to get market-tested in a few stores.
But Gadlin isn’t giving up his day job just yet.
“Realistically, I thought this would hit a peak, then a valley and eventually die off. But I’m hoping that we don’t hit a peak, and we can take this project even further,” he said. “For me, the whole goal has always been to do these stupid projects and see how much stupid attention I can get out of them. And I Want To Draw A Cat For You, well, it’s the big one.”