How to Succeed as an Artist and Entrepreneur with Ashley Longshore

Ashley Longshore is self-proclaimed “artpreneur” based in New Orleans, whose pop art celebrates American consumerism. She’s breaking the mold in her field as a self-represented artist. With write-ups in Forbes, Vogue, ELLE, she’s been called a “one-woman entrepreneur” and touted as a modern day “Andrea Warhol”. Her clients include many of Wall Street’s elite, and art lovers in cities including New York, Miami, Houston, and LA. This past year she’s been hard at work on her next collaboration in Japan. Some of her most notable clients include the likes of Salma Hayek, Penélope Cruz and Blake Lively, to name a few. With commissioned pieces starting at $30,000, Longshore earned her first million dollars in revenue this past year.

She’s been in the game for twenty plus years, so she knows a thing or two about hustling. We sat down with Longshore in her stunning studio in uptown New Orleans where she dished advice on what it’s really like to be an entrepreneur, no holds barred.

What’s one piece of advice you’d give to your 25-year-old self?

Get my ass in a spin class. There needed to be more balance back then. Youth, Dignity, Virginity are three things you never realize you lose until they’re gone. I have no regrets about my work ethic and how much I’ve pushed myself. And I don’t regret my wildness at all either.

What sucks the most about being an entrepreneur?

I think that you just want to succeed in everything that you do. Entrepreneurs have so many ideas. One thing that really sucks is that there’s never enough time for all of the ideas–especially as an artist and entrepreneur. I’m fully aware of the fact that if I live to be 110, there’s still not enough time for everything that I want to make, see and do in this life.

What’s it really like to grow a business?

A: You’re planting a garden. This is what I tell young artists, any entrepreneur if you’re young, you’re starting out. I’m going to find good soil, and plant some seeds. Now am I going to come back the next day and is there going to be a big fucking apple tree? HELL NO!

I gotta pull the weeds out. I gotta make sure the little rabbits don’t get in my seedlings. I gotta make sure it gets sunlight. I gotta make sure it gets rain. I gotta make sure it doesn’t get flooded. I gotta make sure the bugs don’t get to it. I gotta PROTECT this thing and watch it grow.

And then we have a fruit tree. Then once you have a fruit tree, you got people trying to take your fruit. You got your low fruit and your high fruit. You have to keep the monkeys off your fucking tree. That’s a whole other cycle. It’s a garden. This whole thing is a garden.

How do you keep the crazy calm?

If I feel like I’m about to lose my shit, I work. I get out there and I work. I’m proactive. If I have a huge commission list and I’ve got clients waiting and I get emails from designers checking on that painting, what do I do? Do I sit around and fucking worry about it? No. I do something. I fucking get in there and I work. That is how I stay calm. I work. Because I love that what I do, it makes me feel good. Happy clients make me feel calm. And my reward is money. And there’s an infinite amount to be made in the world. You just have to figure out how to do it.

What’s your biggest fear as an “artpreneur”?

I think my biggest fear as an artist is not being understood, which means people not buying my artwork. My biggest fear, and of any entrepreneur, I think, is being broke. I’ve been there before. I don’t want to go back there. But I’m in control of those fears.

What was the highest point of your career, as of today? The point when you were like, fuck yeah, I’m doing it!

Every time I sell a painting, I feel that way. It’s the best high ever, even if it’s a little painting or a big one. It’s like winning, yes! Fuck yes! It’s like the validation. It’s this whole love thing that somebody buys my painting and they live with it, and it’s hanging on the wall and they love me enough to spend their fucking money on it, and now I’ve got that money, and now I can go buy more canvas, and turn that into art, and turn this into more money. This is fucking magic! It’s the greatest fucking feeling in the world! I think that’s what fuels entrepreneurs. It’s the biggest fucking high.

You posted a quote on Instagram by Deepak Chopra, “You must find the place inside of you where nothing is impossible,” which I love so much.

Me too.

Can you tell me more about that?

I had so much work to do, and I found that quote and I posted it for myself. A lot of times people think “I’m like Yeaah, I’m already there!” No, I’m on this journey too, man. I’m posting this because it’s what I need right now for my soul. You can see that on my feed when I’m crazy and wild and other times when I’m posting these inspirational things because I’m talking to myself out loud so the world can hear it. I’m like, Ashley, you can do this. You’ve got all this work to do. You’ve got clients to do, and other clients coming in. You’ve got a Japanese collaboration right now. You can do this.

“Just do it. Find that spot and just fucking focus and do it. Find it. Find it because you have to. Because you don’t have a choice. That’s my thing. I don’t have a choice. This is it. Today is the youngest I’m ever going to be. Right fucking now in this moment. Now.”

That’s the other thing when you’re a successful entrepreneur. You have obstacles and you have a list of things to do and you just are PROactive. You don’t sit around and talk about doing it, you do it. You don’t sit around and talk about why something isn’t going to work or why it won’t work. You just make it work. You have to figure out how to channel your energy in the right way. (whispers) How do you get to the top of Mt. Everest? You fucking climb it. You think that shit is easy?

Do you ever have moments of self-doubt?

Of course. Every day. Self-doubt keeps us humble and human.

If you don’t have self-doubt, then you’re probably going to lose relatability. I think the main thing about entrepreneurs, most of them that I’ve met, is that they’re humble, cool individuals that understand themselves very well, which is why they’re successful. And I think a lot of that comes from fear and self-doubt and overcoming that.

And that is a part of every day. What if I paint a painting and nobody likes it? What if I post something on Instagram, and nobody likes it? What if nobody buys this? What if I’ve moved into this new, space and all of a sudden my career is over? What if this is the best time that I’ll ever have? What if I never get good press again? What if I’m not relevant anymore? What if I’m old and nobody likes the things that I’m offering anymore? What if I get to be old and I can’t afford the things that I like anymore, if nobody likes me as an artist? These are just very real things that I think honest people will admit that they feel everyday.

“That’s another thing about being an entrepreneur. You fail just as much as you succeed, if not more. So, you have self-doubt, but you learn how to overcome it 100%.”

Any last piece of advice for entrepreneurs out there reading this?

A: Just remember, it’s the good and the bad, baby. You gotta dig deep and be an explorer for that spot that makes you fearless and stay there. Stay there. Stay there, but stayyyyy humble. The most successful people I know are the most humble. It’s all a journey that will lead you to your destination. You just gotta roll with the good shit and the bad shit.