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The Odd Success of I Want To Draw A Cat For You

Updated: Dec 17, 2020


What sparked the idea to turn personalized stick-figure cat drawings into a business?

My brain is a constant fountain of ideas, most of them ridiculous. A while ago I decided to follow through on as many of those ideas as I could, especially when the resources were available. The cat drawing business started as a dare to myself - I wanted to see if I could take a worthless widget, and, through creative marketing, create value. In short - It was a social experiment. How many people could I trick into paying me $9.95 for a stick figure cat?

Was there anything about your experience on Shark Tank that delightfully surprised you?

Getting the offer from Mark Cuban was a delightful surprise! Also, the whole experience of being on the show - interviewing with producers, watching the activity behind-the-scenes - it was very exciting. I've worked in TV and TV production peripherally, and I've always been fascinated by it. It was very cool to be right in the center of it for a few days. Later I'd go on to be a contestant on Who Wants to be a Millionaire? a couple of times, and by comparison I can say that the Shark Tank machine is very well oiled!

What was the biggest lesson you learned from working with Mark Cuban?

I learned a lot of hard lessons from Mark early on. It took a while for me to adjust after making the deal - reality television and reality are bridged by a pretty wide gap. Many of the early lessons reinforced that my deal with Mark was made for television. It was more important that it appeared to be successful than to actually be financially sound.

The biggest lesson I've learned from the whole experience, though, is that really amazing things happen when you live life in pursuit of awesome rejection letters. I've done a couple of TEDx talks about that topic, and it has definitely influenced my life since.

Can you share some of funniest drawing requests you've received? Do you have a favorite?

I was surprised at the number of similar cat drawings I've received - I've now drawn a ton of proposals, weddings, birthdays, anniversaries, etc.

My favorites are the personal ones - the inside jokes that make no sense to anyone but the recipient. I also love all combinations of cats on unicorns, dragons, and rainbows fighting ninjas.

My absolute favorite - every year a woman orders a cat drawing to celebrate another year of sobriety for her husband. I feel great to play a tiny part in that tricky life challenge, and always celebrate when the order comes in.

Where do you turn when you need inspiration, outside of your phone or social media?

I find inspiration in the shower, usually. My favorite ideas happen in solitude, when I don't have any external voices filtering my thoughts! :)

If you could give one piece of advice to creative entrepreneurs, what would it be?

If an idea makes you smile or laugh, cling to it.

Is there a current comedy special, podcast series, or book you're loving right now?

I keep coming back to "I Think You Should Leave with Tim Robinson" on Netflix. Also old episodes of The Rifleman.

What's next for Steve Gadlin?

Thanks for asking!@# I just launched another ridiculous company called OddBox ( It's a monthly subscription box where you get a confusing t-shirt and a bunch of other goofy stuff. Still inching forward, trying to get our commercial in front of as many eyeballs as we can.


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