“When I was around 19 or 20, it felt like I was waking up and didn’t recognize my own life,” says Real magazine founder Ocean Pleasant who has since sunset her company moved to Hawaii.
Ocean Pleasant
The TikTok astrologer—known as Witchy Kid—reflects on finding herself after sunsetting the magazine that she dropped out of high school to start. This is the first in the Forbes Under 30 Mental Health series.
Ocean Pleasant never liked wearing blazers. Yet, in spring of 2017, the 16-year-old founder and editor of Real, a social activism-focused teen glossy wore a tweed one to present her company to the executives at Hearst in their midtown Manhattan boardroom. The Texas native had dropped out of high school, secured a Thiel Fellowship (which pays young founders to leave school and pursue entrepreneurship), and moved to New York City one-and-a-half years ago with the goal of building America’s next great teen media company—without even a driver’s license. But that day, in that boardroom, Pleasant looked around—gazing upon the top industry minds who were interested in elevating her—and realized she did not want to become any one of them. About six month later, with offers to expand Real’s distribution into new nationwide retailers (including Target), she sunset the company.
“I skipped the developmental period as a teenager where you’re figuring out what you want to do, who you are and what your interests are,” she says. “Ultimately, I didn’t know if I wanted to be defined by how much money I’m raising, what lists I’m on or the contacts in my phone.”
Pleasant started Real in 2014—before the age of TikTok and woke culture. Her mission: to bring social activism to fellow teens in the pages of the magazine she started at age 15. And she succeeded: Real had 150,000 monthly subscribers with circulation at 40 nationwide U.S. retailers, including Whole Foods Market by 2016 when Pleasant landed on the Forbes 30 Under 30 Media list. The 120-page magazine included deep interviews with adult celebrities like Richard Branson and Alicia Keys who talked about grownup things like sex trafficking and ocean conservation—a far cry from Disney star gossip and quizzes to determine crush compatibility of Real’s newsstand neighbors. Most importantly, Pleasant did it all with no full-time employees. Rather, she worked 12-plus hour days, ate only takeout (mostly hot dogs) and had no personal relationships outside of Real.
“When my peers were shopping for prom dresses, I was scaling a national business,” says Pleasant. “It seemed normal at the time because when you’re in an incubator or program for young entrepreneurs it’s such an echo chamber.”
She came to realize the Thiel Fellow, Forbes 30 Under 30 and founder identity she cultivated had destroyed Ocean Pleasant, a kid allowed to make mistakes without facing the wrath of venture capitalists. “There was a lot of fear and anxiety because my identity at that point was so tied into who I was, what I made the [Forbes] list for and what I built. I was the magazine girl,” she recalls. “Every facet of my life was defined by being an entrepreneur. Walking away from that meant walking away from everything.”
Ultimately, she bought a one-way ticket to Los Angeles and shut down Real’s entire operation. In LA, she had no plan other than to pursue music in some capacity because, in music, she had found joy. In 2015, she performed as an acoustic singer-songwriter opener for reggae band Soja on a nationwide tour, including a stop at Bonnaroo at 17. “I realized there was this whole other part of me that I wasn’t exploring because startup culture took everything I had to give.” And to her surprise, friends, family and investors were supportive of her decision to reroute her life.
She did just that—writing songs about the changes that happened after leaving her first serious relationship and starting over in every capacity—with her acoustic guitar. She found a therapist, life coach and dedicated daily moments to journaling and meditation, learning to show up for herself. A year into Los Angeles living, she delved into her passion for astrology—enrolling at Debra Silverman Astrology to understand cosmic destiny. And two years after sunsetting Real, she started up again in 2019: This time as Witchy Kid, an astrologist-for-hire, marketing herself by releasing TikTok videos about how the stars determine behavior and life patterns.
“Did I see it becoming a full-time career? No. It was a cool side hustle,” she remembers with a laugh. “Then it was like: I’m doing two-to-three sessions per day. I was asked to go back and teach at the school.”
In the spring of 2020, then 23-year-old Pleasant downloaded TikTok. Eight months later, she had 100,000 followers who watched her videos to understand how to understand relationships, work and family from a cosmic vantage. With this following, she’s now able to charge $150 per 50-minute client session, fund her music career, and has relocated to Hawaii with a childhood crush who has since transformed into her life partner.
This year, Target launched Witchy Kid’s collection of astrologically sound personal care products. In July, Pleasant debuted Witchy Kid Collective, to foster community around her teachings. “The beauty of starting a company this time around is that I let it be what it needed to be. There was no external pressure for scaling or timing. It was whatever I had interest and bandwidth for,” she says. “It feels really healthy and inspired in a way I don’t think I had before.” Though she’s still a solo founder, she believes she had to do it wrong once to do it right forever.
She thanks her therapist, life coach, journaling and meditation. But mostly, she thanks herself for leaving a life of venture capital-backed singularity to build comfort in self-grown plurality.
“I think of fertilizer—when your plants stop growing because there’s no nutrients in the soil—that’s how some founders feel at the end of their ride; there’s just no nutrients left,” she sighs. “The two-year reset of honoring my physical and mental needs, pressing reset, reconnecting with my passions and my real interests—that was fertilizing my spirits and my career.”
