The Accidental Entrepreneur Who Built a Brand on Joy
What happens when you follow fun, not fear
“I really don't think I'm creative or skilled enough to pursue a truly creative career. I know whatever comes next will require a radical leap, and I need to convince myself to take it.” —Ray Baker’s journal, one year ago
After we had chai lattes at Kolkata Chai Tea, Ray Baker, sporting hot pink hair and paint-smattered overalls, led me into her new work habitat: a (also) hot pink Williamsburg screen print studio.
After teaching me how to use the screen printer, she said, “When I worked a corporate job, I had this fear: I was too creative to enjoy a corporate job, but not creative enough to make it as an artist. I knew I wasn’t unique in this, but figured anyone who shares this existence is doomed and destined to feel this way.”
Today, instead of having the worst of two worlds, she’s found the best, as the Founder, Owner, and Designer of Sweet Baby Ray's Tees.
Ray insists that the company happened through luck, starting with her friend gifting her an art class of her choosing. Depressed and hating her corporate job, she chose a course in a medium she’d never tried before, screen printing. She printed her first t-shirt and, as she saw it come out the other side of the machine, “Holy shit. This is about to be my whole personality.”
And it became that and much more.
After the first studio visit, she found joy selling screen-printed t-shirts on a SoHo street corner, never imagining where it would take her.
But the girls, the gays, and, apparently, a surprising number of Australian and British straight white men, flocked.
“I can't claim that I had the courage or wherewithal to quit my job and do this. I was laid off. I started doing this as a hobby. And then it just happened to turn into this,” she says.
And by “this,” she means: 5,700 of her t-shirts have sold in eighteen stores in twelve cities across New York, Pennsylvania, Florida, California, Texas, South Dakota, North Dakota, North Carolina, and Georgia and five markets, including Artists & Fleas, Chelsea Market & Williamsburg Market, Renegade Craft, Women's Market at Moxy Hotels, and Hot Girl Market. Ray has grown a social media audience from zero to 5,200 engaged followers, shipped online orders to 32 states, directed 2 photoshoots, recorded a podcast, and convinced her grandparents that cunt is an empowering term (although she doesn’t recommend trying this at home).
When I ask her how she’s succeeded as a creative, she says, “It’s all…I’m just lucky.” She pauses and prints another t-shirt before continuing, “Though I think the takeaway is I never stopped cultivating my creative hobbies outside of work. What I will take credit for is that I could have been laid off and been like… I need another corporate job asap, even if I don’t love this career. But I chose this.”
To an outsider, Sweet Baby Ray’s looks like everything but luck. Each step of her life points to her one day starting this company. As a kid, she did art classes and art camps. Each year of high school, she chose art as her elective. When she graduated from Duke University, she worked in marketing at a children’s clothing brand, Primary, and then at Bodily, a clothing brand designed for new mothers. And while working her 9-5 jobs, she never stopped nurturing her creative side. She started a freelance design company, Sunday & Co, in her free time.
“I never had the balls to go to art school or something like that. In school, I had the ‘gifted,’ type A vibe, but the older I get, the more I’ve been able to let go of that. If anything, those are my worst qualities that hold me back. It’s been a slow evolution as I get older. But art and creativity have always been there,” she says.
When I asked her about the inspiration for her most popular t-shirts, she says, “Anything from early-aughts heroines to reclaimed slurs used against women, such as the word, ‘cunt.’”
“The idea for the CUNT t-shirt came from a subway ad for CUNY—the Y curved just enough that it looked like it said cunt instead,” she says laughing.
On Sweet Baby Ray’s anniversary, Ray posted on LinkedIn reflecting on the year’s successes including convincing her grandparents that the word cunt is empowering. When I told her that some of my older readers will struggle with the word too, she said, “I convinced my grandparents that cunt is an empowering word the same way I do when older women stop me on the street. I tell them that it’s reclaiming a word used against us. Like, how queer used to be an offensive term and now queer people call each other queer…it also helps that I have very liberal grandparents.”
Speaking with Ray about her career evolution, I couldn’t help but notice a pattern in her life: a talent for paying attention to the present, drawing artistic inspiration from that material, and having the fearlessness to put it out into the world. I thought about all the tech CEOs I’d interviewed with for Chief of Staff roles. I asked each one during interviews what drives them to build their companies, and the answer was, “an industry is broken and needs to be disrupted,” or “we’re trying to make this a generational company.” Something about those answers made me turn down the offers.
Watching Ray print another t-shirt in her hot pink studio, I wondered what drove her.
When I asked, she said, “I guess joy drives me. This is my hobby… And I especially love returning to my start and selling shirts on the street in SoHo. I just want to do what I love for as long as possible.”
For years, Ray doubted her creativity. She didn’t believe she had enough talent, bravery, or whatever it was to succeed. But as it turns out, she didn’t need someone to confirm her talent. What mattered was that she showed up, created, and let herself follow joy.
Today, the shirts, the followers, the storefronts, the markets, the word “cunt,” are all proof of what happens when you stop waiting to feel ready, following prescribed rules, and start honoring the joy that already lives inside you.
Ray didn’t find her way forward by being certain or taking radical leaps. She found it by just starting it anyway.
Gotta start somewhere, right?
