A $20,000 Watch That Tells More Than Time

After struggling for years, an entrepreneur finally splurged -- and it pushed her to work harder.
A $20,000 Watch That Tells More Than Time
Image credit: Courtesy of Rolex & Panerai
Magazine Contributor
Deputy Editor
3 min read

This story appears in the May 2018 issue of Entrepreneur. Subscribe »

Ashley Longshore is very familiar with the meaning of starving artist. “I have price-shopped for tortilla chips at Walmart, OK?” says the New Orleans-­based pop artist. Today Longshore’s work -- think Abe Lincoln with a sparkly turquoise beard and a bedazzled blazer -- is beloved by the art world and celebrities alike. (She counts Salma Hayek, Blake Lively and Eli Manning as clients.) But it took her a long time to get here. 

Related: 8 Proven Habits for Ultimate Success

“I’ve been doing this for 24 years, and in my 20s, I was broke as hell,” she says. “I hated [selling paintings through] galleries. Giving up 50 percent of a sale sucked.” So instead, she started networking, hustling to make connections through friends and professional contacts, slowly building a clientele that purchased directly through her. “A great friend in Antwerp offered to have a show for me, so I started building this network of art-buying people all over the world. The pieces started coming together.” 

Four years ago, Longshore finally felt financially secure. She had consistent sales, and she knew her weekly averages and what she could -- and should -- be charging for a painting. After years of coveting expensive items that seemed out of reach, she walked into a jewelry store, dropped $20,000 and walked out with a Rolex for herself and a Panerai for her “main man.” 

Related: The 12 Covenants of Success

“I started thinking about tangible items in terms of paintings,” she says. “These two watches are two small paintings. I sell six or seven of those a week. Ashley, buy the damn watch. Buy the fucking watch with a wad of cash, and then go to the studio and paint four paintings to make it up. And damn it, I did.” 

The purchase wasn’t just about bling. “As an entrepreneur, there’s always a fear of, I never want to be broke again,” she says. “Spending that money triggers a little fear mechanism. It sparks a fire that’s got gasoline all over it. It’s an incentive for me to work harder.” 

Related: 7 Mindsets That Guarantee Enduring Success

It’s also a reminder of what she’s capable of. “I fucking earned this,” she says. “This is the real American dream, and that’s why I want that Rolex on my wrist. I want to keep track of my time. My productivity: That’s the most valuable thing I’ve got.” 


More from Entrepreneur

Get heaping discounts to books you love delivered straight to your inbox. We’ll feature a different book each week and share exclusive deals you won’t find anywhere else.
Jumpstart Your Business. Entrepreneur Insider is your all-access pass to the skills, experts, and network you need to get your business off the ground—or take it to the next level.
Let us help you take the NEXT step. Whether you have one-time projects, recurring work, or part-time contractors, we can assemble the experts you need to grow your company.

Latest on Entrepreneur