We caught up with the brilliant and insightful Eric Grady a few weeks ago and have shared our conversation below.

Hi Eric, thanks for joining us today. Earning a full time living from one’s creative career can be incredibly difficult. Have you been able to do so and if so, can you share some of the key parts of your journey and any important advice or lessons that might help creatives who haven’t been able to yet?

Absolutely. My name is Eric Grady. I’m a caricature artist, a stand up comedian, a business owner and entrepreneur. I recently moved to Orlando, Florida, from Myrtle Beach, SC, to start a new caricature company. I have been drawing caricatures since 1989, and I opened my first caricature company in 1992. Then, in 1996, I started performing stand up comedy. I travel when I can, around the country, and abroad, performing stand up. But mostly, I’m in Orlando, running my caricature company. I also have some other businesses in the works.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

Absolutely. My name is Eric Grady. I’m a caricature artist, a stand up comedian, a business owner and entrepreneur. I recently moved to Orlando, Florida, from Myrtle Beach, SC, to start a new caricature company. I have been drawing caricatures since 1989, and I opened my first caricature company in 1992. Then, in 1996, I started performing stand up comedy. I travel when I can, around the country, and abroad, performing stand up. But mostly, I’m in Orlando, running my caricature company. I also have some other businesses in the works.

Is there something you think non-creatives will struggle to understand about your journey as a creative?

I think most non-creatives would have a hard time believing that I could make a living, drawing caricatures. But I can. And I do. And the people who work for me do. None of us are rich from it. But we make a living. Some more than others. Of course you have a lot of people who do it for a while, and then give it up. But I know a lot of caricature artists who make a living, drawing caricatures. I’ve also noticed that many artists end up finding other art forms that they’re interested in, and pursue that as well. For me, it’s stand up comedy. For others, it’s painting, or acting, or any number of things. I’ve known a couple of caricature artists who tried their hand at stand up. But I think we’re (creatives) the kind of people who find a passion, or passions, and pursue them, and hope that they make money, as opposed to (noon-creatives) having a plan to make money, and hope that a passion reveals itself.

I started drawing caricatures in art school. I taught myself to draw them… but wait. I guess it really all started when I was 4 or 5 years old. I grew up in Charlotte, NC. I liked to draw. But what 5 year old doesn’t? One year, my mom took me and my siblings to an arts and crafts fair / show called the Southern Christmas Show. While we were there, we saw what I thought to be, an older gentleman (aged in what I think would be his 60s), wearing a white smock type jacket, a beret, glasses, and a goatee. He was drawing caricatures in profile. I remember he was drawing a blonde lady, (mid to late 20s) with a hairstyle like Sammantha, from Bewitched (this would have been around 1970,, ‘71)., and he drew her playing tennis. My mom looked at me and said “oh look Steven. You could do that.” Which I thought was an odd thing for her to say to me, because my name Eric. Kidding. But that evening, after we got home, I tried it, and couldn’t, in any way, do that. But years later, after years of art classes in school, and I guess some raw talent, I went to art school at the Art Institute Of Atlanta. While I was there, a mall called Underground Atlanta opened. I went with some friends to see the place. And there they were! Caricature artists! Back at school, after a little bit of encouragement from one of my instructors, Donna Perdue (she drew caricatures when she was younger), I was able to teach myself to draw caricatures. They were nothing like what I can do now, but they were pretty good, at the time. I was able to get some gigs here and there, drawing caricatures at events. Usually directed to me by the school. After a short while, I was the go to student for caricatures. After I graduated, I went to work as a color separator at a screen printing shop, until I got a job at an amusement park called Carrowinds, in Charlotte, NC, drawing caricatures. I worked there one summer, and realized I was the top money maker. So the next summer, with a loan from my father, I opened my own caricature stand in Myrtle Beach, SC, where I ran, and expanded a caricature company, from 1992, through the summer of 2013. The problem was that it was seasonal. So we had to make as much as we could over the summer, and live off of that during the winter. Along the way, I took up stand up comedy. I got pretty good. And comedy seemed to help me at the caricature stands, or maybe the caricatures helped my comedy. It’s hard to say. But I spent a couple winters in New York City (summers in Myrtle Beach), doing somewhere around 45 comedy shows per week. One summer, after a couple fun winters in NYC, one of my workers at my caricature company persuaded me to make him a manager, and he’d cover the caricature stands, and I should go out to Los Angeles to do stand up. A year later, 3 of the 4 caricature stands were permanently closed, and I was fed up. I gave up the remaining shop that I had, and went to work as a caricature artist, for a friend of mine, who owned several caricature locations at Disney World. Here’s where it gets really interesting (about time, right?). About 6 months after arriving to Orlando, I get a call from a magician that I knew from Myrtle Beach. He tells me that there’s a group of entrepreneurs that wants to hire a comedy magician. But he doesn’t do comedy magic. Just magic. So he wants to sell them on a magician and a comedian, and he wants me to be the comedian. I agree. And he gets us the gig. I talked to the guys who were hiring us, and we had an idea, which we ended up doing, to pretend I’m a new member of the group, I “infiltrate” the group, and then on the last night, at the banquet, I roast them. Yes, and yes, they said. I do the gig. While I’m there, these guys had speaker after speaker. They constantly talked about their businesses. I couldn’t write down notes fast enough. They were all rich. Some more than others. Some WAY more than others. But I noticed they all seemed to have 3 things in common. And I had 2 of those things, but not the other. The things they had in common were that none of them felt they could work for someone else. I total identified with that. Two: They all opened a business that failed. So far, I’m two for two. And the third thing they all had in common?.. they all learned from their mistakes, and reopened their business, or opened another business. Mind. Blown! When I got back to Orlando, I immediately started planning my reopening, and/or opening a new business. As soon as I was able to return to Myrtle Beach, I reopened the one remaining caricature location that I had, I found a second and third location, and hired a staff. And my business had the best years that I ever had. Now, I embrace failure. Failure has taught me so many things. And it continues to teach me. That’s something people never seem to tell you. Lucky for me, those guys told me. Then, in 2020, Covid hits. We had to shut down like everybody else did. It was tough. Luckily, South Carolina was pretty lax on the Covid restrictions, after they said we could go back out. So in Myrtle Beach, the people came out in droves. The problem is that Myrtle Beach, being such a poor state, it gets some unsavory characters there for a cheap vacation. And there were some instances where myself and my artists were actually in danger. But luckily, none of my people were ever hurt. Also, along the way, I had to close down one location, and then another. Not because I wanted to but because the landlords were going to make changes to their buildings that would drastically and negatively, affect my business. Side note: Back in 2013, when I worked at Disney World, there was a mall that I wanted to open my own caricature location in, called the Orlando Vineland Premium Outlets. I even went so far as to try to rent from them. But they were full, and wouldn’t rent to me. But when Covid happened, a lot of businesses weren’t able to survive. So I approached them again. This time, they had room for me, and were happy to rent to me. Later, they asked me to expand, which I did. And it’s been great being there. It’s also a year round business. Not seasonal, like Myrtle Beach. Looking back, I am so incredibly thankful to those entrepreneurs who taught me that it’s not only ok to fail. It’s good. If it weren’t for all of their failures, I wouldn’t be here today. I’d be miserable, at a job I hate, with my only sanctuary being the occasional stand up gig. But instead, I’m running my own locations, having a blast doing it, and doing the occasional stand up gig. Before I graduated high school, an admissions agent (or whatever she was called, came to my art class from the Art Institute Of Atlanta, and later, another one from Parsons School Of Design, to talk to us about going to their school after high school. I really wanted to go to the Art Institute. My father was totally against it. He wanted me to go to a “real” college. I remember his exact words were “if you want to go to Art school, then go to a real college first. After you graduate college, if you still want to go to art school, I’ll send you to art school.” So I went to college. I failed out after one semester. Later, I was able to get into another college. After one semester, I failed out of that, too. So I went to community college. It took a little longer, but I stopped going there, too. Finally, my dad was fed up. So he reluctantly sent me to Art school. Bear in mind, I wasn’t dumb. But I was definitely unmotivated. I didn’t want to be there. If there was one place I wanted to be, it was “somewhere else”. I never even partially applied myself to my “studies” (I put that in quotes because I did not study). While I was in art school is where I learned about caricature. My dad was a businessman. He wanted me to learn business. But I wanted to draw. He wanted me to get a “real” job, too. But I wanted to draw caricatures. Eventually, I made it work. I’ve made a living doing caricatures for a long time. If I’m being honest with myself, he was better at business than I was. Probably because he went to a real college. But I succeeded, doing what I loved. What’s more, I’ve owned my business longer than he owned his. My favorite quotes and speeches come from people who talk about doing what you love. And that’s what I’ve done. So whenever people ask me for advice, I always ask them first, what do they love to do. If your bills would always be paid, and you’d never be hungry, what would you do? And you can’t say go on vacation for the rest of your life. You’d eventually get bored off that. What do you LOVE to do? And then find a way to make a living doing that thing. For me, it was caricatures… until I found stand up comedy. And now, I’d do stand up for free if I had all the money I’d ever need. But it’s because I love those things. I think most creatives think that way. Possibly even unconsciously.

Have you ever had to pivot?

I love this question. Because I love this story. One summer, after a couple fun winters, doing stand up in NYC, one of my workers at my caricature company persuaded me to make him a manager, and he’d cover the caricature stands, and I should go out to Los Angeles to really pursue stand up. A year later, 3 of the 4 caricature stands were permanently closed, I came back to Myrtle Beach, and I was fed up. I gave up the remaining shop that I had, and went to work as a caricature artist, for a friend of mine, who owned several caricature locations at Disney World. Here’s where it gets really interesting (about time, right?). About 6 months after arriving to Orlando, I get a call from a magician that I knew from Myrtle Beach. He tells me that there’s a group of entrepreneurs that wants to hire a comedy magician. But he doesn’t do comedy magic. Just magic. So he wants to sell them on a magician and a comedian, and he wants me to be the comedian. I agree. And he gets us the gig. I talked to the guys who were hiring us, and we had an idea, which we ended up doing, to pretend I’m a new member of the group, I “infiltrate” the group, and then on the last night, at the banquet, I roast them. Yes, and yes, they said. I do the gig. While I’m there, these guys had speaker after speaker who spoke on entrepreneurship. They constantly talked about their businesses. I couldn’t write down notes fast enough. They were all rich. Some more than others. Some WAY more than others. But I noticed they all seemed to have 3 things in common. And I had 2 of those things, but not the other. The things they had in common were that none of them felt they could work for someone else. I total identified with that. Two: They all opened a business that failed. So far, I’m two for two. And the third thing they all had in common?.. they all learned from their mistakes, and reopened their business, or opened another business. Mind. Blown! They made me realize that failure can be a really great thing. If you embrace it, you can learn from it. Now, I embrace failure. Failure has taught me so many things. And it continues to teach me. That’s something people never seem to tell you. Lucky for me, those guys told me. So when I got back to Orlando, I immediately started planning my reopening, and/or opening a new business. One day, while I was still at Disney, the owner of the caricature company at Disney World, posted an article, on the company Facebook page that he had found online. It was about an artist who took photos of people’s faces, while blowing a leaf blower toward their face. I thought they were hysterical. You can find them online. Do a search for leaf blower portraits. I thought to myself, “this needs to be a business. But instead of just copying this guy’s art, I should put a green screen behind the person and in front of them, from the neck down. Then photoshop their body, to make them look like they’re traveling at an incredible rate of speed. I could make them look like they’re skydiving, or riding on a motorcycle, or rollercoaster, or whatever.” My arm was aching from all the patting myself on the back for how GENIUS of an idea this was. I spent thousands of dollars opening the business. After being open for 3 days, I made a combined total of $58. At that rate, I wasn’t going to make the first rent payment. After that third day in business, I was laying in bed that night, tossing and turning, worrying about what I was gonna do. How was I gonna pay the rent? It’s due in 5 days. Then I remembered that failure is a good thing. I decided in a matter of minutes, that I could open a caricature shop in that location, and I could do it in 3 days. The next morning, I went to the landlord and pitched him. He reluctantly agreed. And I got it open in 4 days. Rent was 2 days late. But I made it. That location ended up being the best location I had ever had at that point. That was my favorite pivot.

Contact Info:

• Website: Crookedeasel.com
• Instagram: @crookedeasel
• Facebook: https://www.facebook.com/Crooked-Easel-108669715271399/
• Twitter: @crookedeaseI
• Youtube: https://youtube.com/channel/UCcr-YLUNvJabr5hXppdxctQ
• Other: You can also do a google search for the worlds tallest comedian to find my comedy