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You Won't Believe What Your Favorite Peloton Instructors Used to Do for a Living

Before becoming legends of the leaderboards, Tunde Oyeneyin, Matty Maggiacomo and Jess Sims were spinning their wheels at other gigs. They share their inspiring journeys with E! News.

By Holly Passalaqua, Sarah Grossbart Jan 09, 2021 8:00 AMTags

Are we all still doing the whole how it started vs. how it's going challenge in 2021? Because, if so, the Peloton crew has some submissions. 

And we don't just mean the affect hours of riding, running and tree posing can have on a body. Because before they were the instructors who had you clipping in day after day, committing to at-home workouts long before the coronavirus made them mandatory, the fitness crew's most famous faces were spinning their wheels at other gigs. 

Inspirational spin instructor Tunde Oyeneyin? Once an in-demand makeup artist. Tread guru Adrian Williams, he of the "negativity makes me nauseous" declaration, an aspiring pediatric nurse. And Olivia Amato was a Wall Streeter who would cry each Sunday about having to return to her finance job. 

Now, of course, they're legends of the leaderboard. They're the faces some 3.5 million devotees—including Kate HudsonCiara and Ayesha Curry—have seen, perhaps, most regularly across the past 10 months. But how it started? Well they have got some stories to pedal...uh, peddle. Eight fan favorites relive the ride with E! News. 

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Peloton Trainers' Favorite Workout Moves
Tunde Oyeneyin

You gotta appreciate the former beauty guru's glow up. Because, frankly, she already thought she was living the life as a Los Angeles-based makeup artist when she felt the urge to clip in at an indoor cycling studio while in New York for a gig. Shelling out $40, "I'm resenting the class before the class has even begun," she admitted of the experience. "Then 45 minutes later, I leave in a state of euphoria. I literally skipped back to my hotel room."

It was then that she experienced what she called a premonition: "I felt this blue wave of light rush over my body, and I knew I would be cycling for the rest of my life. I knew I would be teaching." Back home in L.A., as she informed her friends she'd be wiping away her makeup career to become a fitness instructor, she was surprised when "they said it sounded like the best thing I could do for myself."

They weren't wrong. The notoriously positive Houston native, the daughter of Nigerian immigrants, said she misses "nothing" about her old life. "Everything that my career in makeup gave me—which was the ability to gift people with a feeling, confidence—I get that at Peloton in a mass and grand way," she insisted. 

Which is basically what she said back in that initial interview with Peloton VP Robin Arzón. "I told her, 'If I get this job, I know that part of my life's work will be to allow other people to know that anything is possible.' If this can happen for me—a child of immigrant parents, a child who struggled with her weight for her entire life, a child who suffered with her own self confidence—if this can happen for me, it can happen for anyone."

Olivia Amato

Hard to believe someone as confident as the New York native having a weekly breakdown, but such was the Wall Street vet's experience in finance. Landing her job in sales and trading right out of college, it never felt like exactly the right fit despite her love of numbers. "I grew up playing team sports and that was such a big part of my life, so I thought training people could potentially be a bigger passion of mine," she explained, "but my parents sort of shrugged that off."

So she resigned herself to a life of crying every Sunday night, anticipating her return to the trading room floor the next morning. "I was good at my job, but I didn't like my job," she noted. "And I thought to myself, 'I can't live the rest of my life like this.'" 

Writing down a list of activities that sparked joy, she narrowed in on the happiness she felt when bringing clients to workouts and a post-sweat green juice and stocks chat rather than meeting out for drinks. "I started to look at the instructors of the classes I was taking and thought, 'Why can't I be doing that?'" she recalled. Auditioning at a studio, "I was definitely nervous," she said. "I mean, I was leaving a secure job in finance and had no idea what my next move was going to be." But now the bike, tread and strength instructor is so grateful she pushed past her fears of letting those around her down. 

"Honestly, I have no regrets about the choices I've made that have led me to where I am today," she said. "I certainly appreciate what I learned while I was working on the trading floor, and I carry those experiences with me still today, but I don't miss it. And I wouldn't trade where I am now for anything else."

Adrian Williams

Floundering a bit when it came to choosing a career path, the aspiring pediatric nurse got a much-needed shot in the arm from a close pal. "A good friend of mine suggested that fitness could be a way I pursued helping people while still doing something I love," he recalled. "Naturally, after attaining my first client I was hooked and decided it was something I wanted to pursue full time."

Taking his first steps with the brand this past summer, the tread instructor had some anxiety. "I launched with Peloton during quarantine, but also during the Black Lives Matter movement," he shared. "The idea that my launch was important at that time was hard to digest because all I could think about was how much we needed to come together and heal as a nation. I took that idea and brought it with me on stage. If I could be a source for healing for our members, then there was nothing to be nervous about." 

Real talk: Seemingly overnight he had amassed a following of more than 73,000 on Instagram, a fact he constantly has to remind himself because "I'm just a person doing what I love."

Which is why he remains grateful for that dose of real talk he received from his friend. "For so long I worried about taking all the right steps that I never actually moved out of fear," he explained. "I'm a firm believer now, looking back at my path, that mistakes are one of our best teachers. It took the right and wrong paths to get me to Peloton, but I'm here! Listen to your heart, put in the work. You will get there eventually."

Jess Sims

Years into her teaching career, the college basketball star received a big lesson courtesy of her then-boyfriend. Despite that fact that she "loved teaching—I loved the kids, I loved the families and I loved my coworkers," Sims felt unfulfilled.

Realizing that her favorite moments "were all when I was teaching kids about health, wellness and movement," whether coaching basketball or leading gym class, she knew it was time for a change. But "I kept saying, 'I got my masters in education! I worked so hard to get to be a school leader! How could I leave it all?'"

Thankfully, that's when her boyfriend chimed in and "said to me, 'Yes, you are supposed to be a teacher, but maybe you're just in the wrong setting.' And that right there was my biggest a-ha moment! I wasn't 'throwing away' all of the experiences that I had, I was taking what I've learned from my six-plus years in education and applying those transferable skills to a new place."

And though she misses her kids (one even took her class!) little else feels different. "Literally everything translates to my work as an instructor," she explained. "From coming up with quick, actionable and memorable cues to help people understand how to do a deadlift correctly to reminding everyone that they're not alone—they're part of a team—it's all the same. Adults are just taller kids. They still need explicit instructions, engaging programs, fun music, an understanding of 'why' we are doing something, and a sense of community and togetherness."

Matty Maggiacomo

The tread and strength instructor's long-held dream of being an on-air broadcaster ground to a halt with one assignment. Freelancing for a local station, he was tapped to cover an incident on a Long Island, N.Y. expressway that left a teenage pedestrian dead. 

"My directive from the news desk was to go and knock on the door of the child's home—and speak to her parents on camera," he recalled. "I was numb. There are amazing journalists out there who can do that job—but in this case, it wasn't me. I couldn't drag myself to go. I believe I told my executive producer that we had the wrong address and I couldn't find the parents. It was in that moment that I felt I was doing more 'harm' than 'good.' Who in their right mind would have wanted to speak to me in the lowest moment of their life, after losing a child? I was done."

A few weeks later, he turned down the offer for a full-time reporting position. Already training clients on the side to make ends meet, he dove into teaching at a studio before landing his role as tread and strength instructor. And while he wishes he still got inside news scoop, the performer in him feels incredibly fulfilled. "Peloton doesn't even blink an eye when I ask to teach a class in full makeup and a costume," he said, adding the job "allows me to flex my creative muscles to reach through to an audience who yearns to be entertained while they exercise."

Hannah Frankson

Admittedly, it wasn't a huge leap from the UK resident's former life to her job motivating Peloton riders. A runner and competitive triple jumper, she worked out pretty much every day alongside Jamaican world champion Trecia Smith and Cuban-British world champion Yamilé Aldama "mixing weight training, sprint training, plyometric and technique sessions together." 

Consistently "around the top five triple jumpers in the country," Frankson recalled, she put her all into training for the 2012 London Olympics: "I believed it wasn't an impossible dream and although it didn't work out for me, I am pleased I can look back knowing I did everything I could have at that time to try and make it." Retired from professional athletics, she tried her hand at a more standard 9-to-5 "but sitting down was just not for me," she admitted, "and I realized that I would be happiest spreading my love for fitness and exercise."

Though she sometimes feels pangs for the excitement of competition, the rush she gets from her riders more than makes up for it. "I was surprised by how far it reached. I get messages from people all over the world and parts of America I've never heard of," she shared. And she certainly prefers the camaraderie over constantly trying to edge out her cohorts. "One of my track friends told me that there are more important things in life than running round in circles," she said, "and I've loved the journey of learning that to be true."

Dr. Chelsea Jackson Roberts

After earning her Ph.D. in educational studies from Atlanta's Emory University, the public school teacher looked deep into her heart's center and confessed to her now-husband that rather than seek out a tenure-track position, she wanted to lean into yoga. Inspired by Yoga, Literature, & Art Camp for Teen Girls at Spelman College she'd founded while finishing her dissertation, Jackson Roberts said she "knew that it was an impactful way to reach youth, their families, and communities."

Still, she had some trepidation "because I didn't know what this detour would mean," she noted. "I remember wondering if people would judge my decision because I spent five years in a Ph.D. program where most people look to be professors after finishing." 

Her leap of faith paid off in the form of Red Clay Yoga, the expansive nonprofit she cofounded with her husband in 2015, and her role at Peloton that sees her fielding "hundreds of letters from members, photos from parents who have young Black daughters who were excited because they saw their reflection and possibilities in me," she shared. "I can't tell you how many times I have received tags from members who say I am 'their bestie' in their heads. Or, parents who say their children have named their dolls after Dr. Chelsea Jackson Roberts. It is really sweet. I will never get tired of it!"

Aditi Shah

Sometimes mom truly does know best. Because it was, in fact, the finance grad's mother who first suggested she explore a life as an instructor while she was staying with her parents in Bangalore, India after college. But though she was filling much of her days with classes and training, "I felt that yoga was just for me." 

Eager to follow her dreams of modeling and acting, she packed up everything to meet with an agency in Mumbai some 600 miles away and, on a whim, the agent brought her to a Garnier casting "and somehow I booked it." Suddenly, she was an in-demand face traveling the world as a model: "I loved every moment of it." 

Still, the idea of one day opening a yoga studio remained at the back of her mind and when she committed to a summer in New York City studying acting, she decided to enroll in a basic 200-hour yoga training. "Somehow my whole world changed," she recalled of the sudden realization that she wouldn't be returning to Mumbai or her model life. With only half a suitcase worth of clothes, she found an apartment and pieced together a living with freelance marketing gigs, acting jobs and, of course, yoga. 

"I started my own business to help bring yoga and meditation to companies in NYC and co-founded a pop up meditation event called Mindful Morning," she shared. "I've taught retreats in Italy, Haiti, and for thousands of people in Times Square."

Which is when Peloton came calling or, rather, slid into her DMs—a chance message leading to her joining the team in charge of launching the brand's yoga and meditation content. Her path has included more than a few twists and she embraces each one. "We write out our futures at such a young age," she explained. "It's your story; you're allowed to change it. Reinvent yourself as many times as you want to."

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