A few years ago I started a silly social experiment – IWantToDrawACatForYou.com. I wanted to see how many people would pay me $10 to draw stick figure cat for them. After a successful Groupon and an accidental deal with Mark Cuban on ABC’s Shark Tank, I got a bit more than I bargained for, and my life became one big Sharpie high. Just yesterday I drew my last cat drawing. 18,794 stick figure cat drawings later, I’m bringing the strangest chapter of my life to a close.
My proof: http://iwanttodrawacatforyou.com/AMA.jpg
What I’m up to now: http://sgstarmakers.com
How much money have you received from this endeavor, the $10 per drawing or a different figure?
The answer to that is complicated.
I suppose I’ve probably grossed over $300k on stick figure cat drawings. But when things were really busy, I was renting office space and paying several employees to help with fulfillment. I was also spending freely on other creative projects, none of which really took off.
I’ve been creating things for a long time – often at the expense of other creatives who volunteer their time and energy. This gave me an opportunity to pay these people for things. So I had more logos designed, songs created, etc. in an attempt to give back to folks who had supported my projects.
This project helped me purchase a mini-van when my third child was born, and also made it easier for my family to move into our first house.
I’m no good at math – but that’s how I measure the success of this venture.
Did you seriously make 187 k off this project?
Also I cant believe you got a deal with Mark Cuban. Do you have an opportunity or is there an opportunity to work with him in the future?
When things were humming, my overhead increased significantly. I don’t have much business savvy, and wasn’t prepared for the volume that Shark Tank generated. Also, Mark’s investment was earmarked for other creative projects. Long story short, no, I didn’t make 187k off this project.
That is one of my big regrets. Someone with more business sense could have had a more life changing financial gain from this business. Me? I’m kind of a fuck-up.
I’m not sure about further opportunities with Mark. My own assessment is that I have burned this bridge through sheer naivete and the inability to communicate effectively with a billionaire.
How was Mark Cuban to work with?
I can’t complain. He invested in my project and gave me the time of day. He had much larger investments to worry about, yet responded to my questions and said nice things about me in the press.
Since you are moving away from the cat-drawing project, is Mark Cuban still involved in your new project(s)?
No, Mark is sadly not interested in my other projects.
So, what you are saying is “count me-owt”?
What was your specific background prior to beginning this career?
By day I build websites. By night I create comedy to delight and confuse by way of stage shows in Chicago, and a couple of TV projects.
Drawing cats for money was nothing more than a social experiment – a belch of artistic expression.
Why are you no longer going to draw cats?
As much as I have loved this 3-year ride, treating cat drawings as a company is draining and time consuming. I have a full time job, three kids, and other creative projects all clamoring for my time.
It’s a scary thing to give up the one creative project you’re actually known for. But I feel it’s necessary for me to move on to other things if I want to stay happy and sane.
After drawing 18,794 cats, were there any that were particularity noteworthy or memorable to you?
Sometimes, while drawing, I’d forget what the LAST cat I drew was. There were so many requests they’ve all blended together.
Except for one.
My favorite cat drawing request was from a guy who had just tricked his brother into smoking his pubes. He wanted me to draw a cat for the big reveal.
From one social Puck to another, I was happy to play a part in his little prank.
How in the world did you pitch, “I’m gonna draw mediocre cats for money” to the people on Shark Tank? Also, what did Cuban see in the company at the time?
No disrespect taken!
My pitch consisted of a rap and a dance, which was the last thing anyone expected to see. Cuban said in the press that he considered this an acqui-hire… a way to tap into my creativity and tech know-how, which he saw as a rare combination.
These 60-seconds will explain much:
What do you mean by accidental deal with Cuban?
I just mean that I approached the show as if I was there for comic relief. I was just some wacky dude with a silly dance and a company that peddled stick figure cat art. I walked in there with nothing to lose, looking forward to being completely eviscerated by their panel of bazillionaires.
Instead, Mark Cuban offered me money, and we became business partners.
Would you do it again? If you were to relive your life 3 years ago, would you do it?
I would definitely do it again. But I would approach it a lot differently. I have all sorts of regret to work through with this. When you make a deal on Shark Tank, you’re handed an incredible opportunity… I spent three years trying so hard not to blow it.
Did I blow it? Who’s to say? But it’s a question I’ll ask myself every single day.
Did you scan all your drawings?
I did! They are all online (and still posting) at . That’d be one heavy book!
How many “pussy” drawing requests did you entertain, on an average -per day?
It depended on how close I was to a Shark Tank re-run. On the busiest days, I’d get over 300 orders. But on average, about 20 per day.
When things were humming I would try to fulfill 25-50 orders per day, though that number would balloon during the holiday season.
What’s your favorite color? Cat or Dog Person?
Green is my favorite color. I don’t like cats or dogs. I’m not a pet person. Also, any plant I keep dies.
What’s your next plan? What was it like seeing people actually buying your product?
Having people buy my product was incredibly gratifying. This was an experience I will never forget… such a lucky, awesome thing that came into my life. I’m still growing from it to this day.
Did you ever distracted by Barbara Corcoran’s teeth while you were taping Shark Tank?
Not that I can recall. But hey, it was all such a blur. So maybe?
Mark Cuban seems like he’s actually a nice guy, probably the best person to get a deal with. Would you agree with that?
I’d say Mark is way more accessible than you’d expect him to be for a guy with so many businesses and responsibilities. I can’t really speak for the off-camera attitudes of the other Sharks, so it wouldn’t be fair to speculate.
But he’s also all business in his communication. I suppose he has to be. The show paints the relationships as more of a mentorship through its update segments, and I’m not sure that’s ever really the case. These are investors, and they want a return on their bucks.
You’ve kind of skirted around the topic, but you said you burned that bridge. Could you elaborate just a tad on that?
I think Mark and I are from different planets, and made all sorts of assumptions about each other going into this. I just like to do creative things and get attention for them. He expected me to be a bit more business-minded, and after seeing the first annual report from my accountant remarked “You just turned this from an awesome business into a WTF business.”
It was sort of down hill from there..
Did you ever draw a cat peeing on/kicking/choking/killing a dog?
And I do think I have drawn cats beating up dogs and other cats. And I’ve definitely drawn cats peeing on things. The most violent drawings always centered around sports rivalries.
How many markers do you think you’ve gone through?
I would estimate I’ve gone through thousands of markers, Sharpies, color Bics, etc.
How will everything you’ve learned from this success help you with shaping your next endeavors?
The best lesson I took from this was that the ridiculous ideas in my brain can actually find success when presented in the right context – and if I execute them with confidence and sincerity. And that’s my plan for http://sgstarmakers.com, my latest passion project.
Anyone tell you that you look like Joe Scarborough?
Nope, you’re the first!
How’d you learn to build websites?
I’m self taught. I found that building websites was a useful skill in promoting my various creative projects. I took it on as a hobby, and it soon became my full time job. Now I run a 7-person web department at a broadcasting company in Chicago.
Do you own any cats?
I am very allergic to cats. I tried adopting one a few months ago, but we had to return the cat to the rescue one week into it. Much to the chagrin of my three kids, who enjoy cats of the non-stick-figure variety.
Did you start this AMA with the intention of personally responding to every single question?
I did! Is that wrong?
After 18k plus drawings, are you a less terrible artist than when you started?
I am! You should see cat drawing #1 compared to the more recent ones. One of the unexpected byproducts of this experiment was I actually became pretty freaking decent at drawing cats for people.