Like many artists, Matthew Cortellesi had a problem: He was great at making art — but terrible at selling it.
Then he made three basic changes to his business, and sales picked up. “I’ve gotten so many orders,” Cortellesi said recently.
What changed? It’s a simple formula that any artist can follow: First, create a headquarters. Next, package your work. And finally, build relationships.
In this article, you’ll see how each part of the formula Cortellesi’s business — and how it can impact you too.
Meet the coach that helped Cortellesi
Entrepreneur had an idea: What if we picked one talented artist who struggles to make a living from their art, and paired them with a coach who specializes in turning artists into entrepreneurs?
Cortellesi fit the bill: He’s a New York-based photographer who’s been at it for 30 years, capturing unique images of the urban environment (like the one at the top of this article). When we connected, he had an active Instagram account but almost no sales strategy. People would DM him to ask about buying prints, and he was selling about 40 a year for $375 each.
Entrepreneur paired him with Carolyn Edlund, founder of Artsy Shark. She teaches online courses and works directly with artists, to help them make a living off their art.
Cortellesi and Edlund met for two coaching sessions. You can hear their full conversation on Entrepreneur’s Problem Solvers podcast, either by clicking here or by listening in the player below.
Underneath, we’ll break down the three main lessons that Edlund taught Cortellesi — and how it can help your art business too.
Rule 1: Create a headquarters
Cortellesi had about 10,000 followers on Instagram, which Edlund said was great — but it was also a problem:
“Instagram’s algorithm is keeping your work from being seen by the very fans who are following you,” she told Cortellesi.
Many artists rely upon Instagram or other social platforms, because it’s a great way to showcase their work. Edlund agrees that it can be valuable — but artists should also remember that they don’t own their social media audiences. They have no way to directly contact all their followers, and each post they make will only be seen by a fraction of users.
That’s why, according to Edlund, every artist needs “a headquarters” — an online hub that they drive all their visitors to. Cortellesi had a website, but it was barely functional.
“Your website is your headquarters,” she told him, “and I am going to encourage you to really build that out as a place where you want people to go.”
Then she asked him: “How many newsletter subscribers do you have?”
“I have no idea,” he replied.
It’s time to prioritize the newsletter, she said. Newsletters are the most direct way to reach your consumer, because unlike Instagram, there’s no algorithm standing in between you and your subscribers.
Edlund recommended a funnel: Cortellesi should use his Instagram feed to drive newsletter subscribers, and then use the newsletter to consistently drive people to a revamped version of his website.
And what would be on that website? That’s the second lesson.
Image credit: Photo by Matthew Cortellesi
Rule #2: Package your work
Cortellesi is a prolific photographer. He’s always shooting new material and then posting it to his Instagram.
That’s great for his creative process, Edlund says — but that prolificness was also bleeding out into his sales offerings. When people were inquiring to buy his photos on Instagram, they were seeing a huge range of offerings: too many photos, and too many ways to print them.
“If you have 495 images and they all come on 13 different substrates with 12 different finishes and 15 different frames, people are going to get analysis paralysis, and they’re going to just freeze up and leave,” she told him.
Instead, Edlund recommended that he narrow his offerings. Instagram can be a showcase where he posts everything, but his website should have a more straightforward and limited buying experience.
“Choose what you feel are the best to offer, and then offer them in maybe three sizes,” she says. “So they get maybe nine choices.”
When an artist does this, they’re making life easier for the customer. It’s as if the artist is saying, “Here’s the best work to choose from.”
Cortellesi said this was a challenge — how do you narrow down years’ worth of work? Then he realized that Instagram could be his friend: By looking at which images drove the most likes and comments, he had a sense of which images would be most sellable.
Rule #3: Build relationships
Why do people buy art?
“People aren’t just buying artwork,” Edlund said. “They’re buying the story, and they’re buying the artist.”
Artists often forget this, she says. They’re so focused on their art that they forget to sell themselves too. She encouraged Cortellesi to share the stories behind his photos, as well as to be open about his own story as an artist.
Then, she says, find every possible way to share those insights, and to build personal connections with his audience.
She offered a couple ways to do this:
Live events: He could display his work in galleries, art festivals, or anywhere else that people are. “When someone has seen your work in person, they will remember the in-person experience,” she says.
Special deals: Artists should offer ways to support and fund their work, like a GoFundMe. Then, Edlund says, the artist can foster relationships with their supporters with ongoing deals and gifts. “Maybe you give them 25% off,” she said — and include a hand-written note to thank them for their support.
Online messages: Personal interactions matter, both online and in person, and sometimes a simple DM can turn an onlooker into a customer. For example, she says, Cortellesi should DM people who leave comments under his posts and say, “Hey, I’ve just launched a new site and I have a special offer going on. I’d love for you to see my work.” When you directly offer people a special deal, you can convert casual followers into paying customers.
What Cortellesi did next
After speaking with Edlund, Cortellesi spent months building a new website. Just as Edlund recommended, it offered a limited amount of his photography — and he explains the story behind each photo.
He also created a logo, and then printed cards that featured the logo and his website address. He’s going to start going to restaurants, cafes, and anywhere that displays art, to speak to the owners and inquire about hanging his photos on the way.
In short, he said, he’s feeling emboldened — because he finally realizes that his art won’t just sell itself. He has to be the one to sell it.
“You are ready,” Edlund told him, “and you’ll be marketing forever. You don’t have everything at once, and that’s fine. Do one thing at a time, learn from your mistakes, and you’ll see what to avoid in the future. You are set up for success.”
It’s simple, really: Artists thrive when they think like entrepreneurs. And sales is its own kind of art.
