Today I talk with “Shark Tank” alum and quirky creative comedian guy, Steve Gadlin. We discuss keeping one’s energy up after over a decade of making artsy stuff, the logistics and finances of running a stage show in Chicago, and chasing down very exciting rejection letters.

Elizabeth: I only kind of know you, Steve. You worked with my husband at WBEZ. I was on Don’t Spit the Water once. I watched you on Shark Tank. I’m sorry to ask you this because I hate this question, but can you tell me about yourself?
Steve: Of course, my name is Steve Gadlin. I guess I’m a comedian, but I don’t really do comedy. I create comedy things, be they stage shows, or television shows, or weird eCommerce experiences.

I started in Chicago’s improv scene and produced some of my own shows. Eventually I morphed my creative projects to fit my lifestyle. For example, when I moved out to Evanston, I started to do creative projects that didn’t require me to leave my home. After I got married and had kids, I started looking at creative projects that required much less of my time. Now I have single days the require a lot of work, and then several weeks of not having to do anything.

I’m still finding, figuring out what other things I do.

You also have a full time job, is that right?
I do. I build websites. I manage a web team for Shure Incorporated, which makes microphones, headphones, and various other audio equipment.

I have a mic right here, in fact. Let’s see is it Shure? Yup, Shure, I think it’s an SM48. There we go. Right there on my desk. Sorry, I digress. Family and kids … you have three kids right?
I do, I have three kids.

How on earth do you balance three kids, a job, and doing other stuff creatively?
I get that question all the time. I try to tell people, I don’t. I don’t balance those things, at least not in a healthy way. It’s very stressful, and I give myself permission to suck at at least one of those things any given day. I try not to let that be parenting most days, but some days, it’s parenting …

I also work with a lot of great people. Even the projects that have my name on them, like Steve Gadlin’s Star Makers, are really worked on by a squad of people. I’m not as busy as that makes me sound.

Okay. Well, I’m still impressed. 

You’ve been at it with comedy about as long as I have with music, fifteen years or so. I watch you on Facebook, and you always have a lot of enthusiasm, excitement, and energy. Personally, I find it hard to keep my energy up after all these years. For you … ?
Oh definitely. My latest passion, this television show. If anything has zapped my energy in the creative world, it’s trying to pitch a television show. We’ve done it  all. We pitched Comedy Central, Nickelodeon, TruTV, and then several local television stations. I’ve pitched TV shows on all scales, in all places. I lose all energy when I am trying to figure out how to work the business side of the creative world versus just getting out there and making creative things.

It’s really hard to stay positive amid constant rejection. Especially when you believe in something so strongly, and you just can’t get the curators to get on the same page as you.

Did you know that TV would be that difficult before you started?
At first I thought TV was this inaccessible impossibility that only magical people have access to. As some of my close friends started to have success, it began to seem more possible. Our show had some early success — people were reaching out to us instead of us reaching out to them. But so much of it just never really went anywhere. I guess I’m back to thinking that it’s just this impossibility that requires this 24/7 hustle that I don’t have in me.

You’ve done so many different kinds projects. When you start a project, do you have any sense of how the money is going to work or how you’re going to fund it?
I never used to. When I was doing stage shows, it was money out of my pocket. It was never that expensive to produce a show at The Playground, or at Comedysportz. It started to shock me though when I saw the level of effort you put into something has no bearing on the return.

We would do an eight week season of our talent competition Impress These Apes at Comedysportz, and that’s eight weeks of everyone working really hard. We would have sold-out houses for the whole run, and at the end we’d collect … $1,000. It just seemed impossible to me. I realized, “Well, no one must doing this for business, this must all just be for kicks.” If I had gone into it trying do a show where I could make money, I just never would have mounted one. It never would have happened.

It might be that I just don’t know the business side of it, but I also just think it’s a pretty strange path to profit.

What about the logistics of putting together a show?
I knew nothing at all. Don’t Spit the Water was the first show. I booked the stage with the idea that I’d put together a sketch show. Two weeks before the date, I hadn’t written any sketches. I tried to get out of my contract, but The Playground wouldn’t let me. I just took out a sketch pad and mapped out Don’t Spit the Water, called a bunch of people, and we got the sketch together real fast. Then it stuck around for four years.

I really learned a ton. The way that show grew, it grew at just the right speed for me to figure it out what the hell I was doing. I’ll tell you that’s another one that never was profitable. We were selling out constantly. I put so much money in that show and the promotion, and the materials, and the costumes, set photography. None of it ever came back. We tried to pay talent; that was a wash real quick too. All of that really taught me the basics of producing a show. I know how to make rain around a silly little idea, but the logistics are all very made up on the spot as I go along.

So do feel like you know more now? Now you can tell in advance, like “oh that’s going to be a good idea” or “that’s not going to be worth it”?
Well, I liked it better when I didn’t care about the money side of it. Now with Star Makers, it costs me about $26,000 to produce 26 episodes of a show. If you compare that to any other show that’s on TV of course it’s really inexpensive.

But I’ve hit this wall where, at the end of a season we’ve made enough money to cover that season, but not enough to produce future shows. Unless we find a network to invest, or that crazy person who who thinks they can help us, I have to magically come up with all this cash or it doesn’t get to happen again. That was never the case for projects that were much smaller in scale. It was easier to lose a bunch of money on something and not worry about it.

So Shark Tank. I’m a big fan — how did you end up on the show?
I started IWantToDrawACatForYou.com just as another one of my projects. I was like, “Well, now that I’m married, have kids, and live far away from the city, what can I do that just requires me to sit in my basement and not leave the house?” I started making these cat drawings and applied to Shark Tank as a joke. They put me on the show. I went assuming I’d be comic relief, but then Mark Cuban invested in my cat drawing company.

For a couple of years it consumed my life. It was a second full time job. It generated a lot of money, but the money all went back into my other creative projects. It looks great on paper, but the real effect of it is not anywhere as impressive as it seems like it should be. Part of that’s because I don’t know how to run a business. The other part is because none of my other creative projects are profitable. So any money put into those just sort of disappears.

It was a crazy experience. I wouldn’t trade if for anything, but it definitely disrupted family and financial life, with everything in chaos for a couple of years.

Was Mark, or Mark’s people, very involved?  Or hardly involved at all?
He was involved early on — he’d email every week. He was very friendly with me. Then at a certain point when he saw that I wasn’t as profitable as I could be because of the way I was running it, because of the way I funneled out money to what he would call, “frivolous creative projects,” he wrote it off as a joke. He said “this is a WTF company,” I think is what he called it. From that point forward there was no real collaboration. Except for him asking for tax papers every year. It never turned around and became more profitable. It was a little disappointing how it all turned out.

Did they offer help running the business side of things?
No, it was on me. The participation was really limit to weekly emails. His investment was more for other things that we could do. He wasn’t expecting to turn a profit on cat drawing. The ideas he proposed to me didn’t really match the types of things I wanted to be doing. It seemed more like he was just trying to use me for free technical help for his other businesses. I wanted to be in the creative world not in the help people with their websites world. We just did not sync up.

I think both of us had weird expectations. On my end you come out thinking you just won the lottery. That you’re going to be a bazillionaire. It doesn’t really materialize in most cases.

Is there an informal club of Shark Tank alums who talk about their experiences?
I do keep in touch with several other people from the show. It’s a roller coaster. It’s nothing anyone expects it to be when they go into it. We were third season, so it was scary, still pretty new. I’d say people on it now have a much better support group going into it, with people who know what to expect and can help them thought the process. There does seem to be a group of them that are already very successful in business. Who get on the show and help each other out. My business was not really a great fit into any of that.

When you say you’re not very good at business it’s funny because I think of you as better than than average bear when it comes to business. Is that a phrase? “Better than the average bear?”
No. Well maybe. Yeah I think that’s … smarter than the average bear.

Smarter than the average bear. Yeah.
I am smarter than bears, I am better than bears. I think what I’m good at is hustle, making deals, pitching things, making things happen, finding opportunity where other people wouldn’t look for opportunity. I’m not good at keeping books or being conservative with funds. My thing is always to make the deal, make the thing happen, then just sort of wing it.

Do you know what’s next? Will you keep doing Star Makers?
That’s the hope. I’ve got a couple of calls scheduled to pitch to other stations locally. I’m really trying to just give away the season we have as a proof of concept and to demonstrate interest. It really is a personal passion, but for me, I haven’t even gotten those nearest to me on board, but it’s something I can’t give up on yet. I have this vision about where it can be down the line. I have to chase that.

Have you thought about advice you would give your kids or other kids interested in doing creative stuff?
It’s important to just do things even if you cannot figure out how you could possibly do things. When I give talks about the Shark Tank experience, I talk about chasing down very exciting rejection letters. If you chase those rejection letters, occasionally really interesting things happen. It’s way cooler to chase the no than it is to chase the yes. If you just try to do things that are so out there, you’ll have a lot more success than if you try to follow along with how things are done.