Uncut with Jay Cutler: Kendall Toole Talks Early Life, Leading Peleton Classes of 20,000 People, and Shares Candid Mental Health Story

by Chris Haney

Uncut with Jay Cutler is back with another brand new episode this week, and we’ve got one of the most popular Peleton instructors around in Kendall Toole joining the show. Peleton is the largest interactive fitness platform in the world that provides live at-home classes for a monthly membership fee. The cycling and fitness brand was founded in 2012, and within ten years it’s built a loyal community of over 6 million members.

As one of the platform’s most popular instructors, Kendall Toole opens up to Jay Cutler about her life and fitness career. Toole talks about her childhood and being homeschooled before attending USC and becoming a cheerleader. She also speaks about discovering boxing and fitness and how it helped her through some tough times in her life.

Toole got candid with our host about her battles with mental health and how she was borderline suicidal for a time. She shares how a career in fitness along with her mother reaching out in her time of need helped save her life. Plus, she explains how she came to work for Peleton, which she didn’t know anything about until she received a direct message from the company on social media. That led to an audition in front of a class of 15,000 people, but she landed the gig even though she knew very little about cycling. Kendall Toole talks about that and much more in this week’s new episode of Uncut with Jay Cutler.

Jay Cutler and Kendall Toole Talk About Her Upbringing and Cheerleading at USC

Previous to finding her calling in fitness, Kendall Toole had a unique upbringing on the West Coast. She was born in Texas and her family then moved to Atlanta for a while. But she calls California home since her family moved to the Golden State when she was around nine years old.

During her conversation with host Jay Cutler, the pair spoke about her growing up right outside of Los Angeles. Like many people in the area, Kendall Toole got into acting at a young age. That led her to quit going to public school as she instead elected to be home-schooled. In fact, she finished high school in only three years as a home-schooled student. That allowed her to take one year off to give acting a real shot, but things didn’t pan out.

Toole would end up accepting admission into the University of Southern California where she became a cheerleader. She amusingly said she tried out on a whim for something to do while in college. As a home-schooled kid growing up, she wanted to do as many normal things as possible during her college experience. Getting to be part of the USC Trojans’ football games were a highlight of her university days as she attended business and film school.

“I was the weird home school kid,” Kendall Toole said to Jay Cutler with a laugh. “So I was like let me try and have all the normal experiences that I missed. Yea, made the cheer team [at USC], that was a blast. Plus running out on that field was so fun. I remember the Stanford-USC game that was completely sold out and that was unbelievable. So that was cool, all those once in a lifetime experiences.”

The Fitness Instructor Chats About Leading Stadium-Sized Peleton Classes

Back when Peleton was still on the rise and only in the U.S., the company had around one million users. Peleton was just starting programs in Canada as the fitness platform headed towards the global behemoth it is now. That’s when Kendall Toole got a DM from the company inquiring about her services as a fitness instructor in 2019.

While Toole is now one of most popular trainers in the company, the instructor fully admits she knew nothing about Peleton at the time. She had never even taught a cycling class, which is the main component of the program. Yet she took a chance and has worked her way up to classes that are filled with thousands of users on the platform. Toole told host Jay Cutler that she’s taught classes with more than 20,000 participants. For reference, that’s the equivalent of NYC’s Madison Square Garden at full capacity. In fact, she’d love to teach a class in a huge stadium like that one day in the future.

“We have 6.6 million users, which is pretty wild. It’s a wild number when you think about it,” Toole explained of Peleton’s enormous member count. “I’ve had classes that are like 20,000 plus and that’s [the equivalent] of Madison Square Garden.”

“Granted I would love the experience of actually getting to do that. So maybe in the future that could happen because I think that energy would be wild. Yea, it’s pretty surreal when you think about it,” she added.

Kendall Toole Opens Up to Jay Cutler About Mental Health

Kendall Toole originally got into fitness through her love of boxing. She fell in love with training and the lessons she learned in the gym. But a few months into that, she hit rock bottom. As she explained it, Toole felt “numb” to the world and it had been building for some time. While boxing was her one respite from the weight of her issues, it wasn’t enough.

“It wasn’t enough because I wasn’t doing the healing I needed to do for myself,” she said to Jay Cutler on the podcast. “Look, movement is incredibly helpful [for mental health]. It’s a piece of [healing]. But quite frankly, I needed therapy, I needed medication, and I needed to balance myself out.”

The popular fitness instructor was very open about her struggles. She even admitted that suicide became a real option that she considered and thought about at length. At one point when things felt helpless, Toole neared a decision to end her life. However, her mother’s numerous messages knowing instinctually that something was wrong with her daughter likely saved her life.

“So I got to a really dark place and was suicidal, and thank god didn’t go through with it,” Toole shared. “I immediately looked at my phone and my mom had called me 15 times. Yea, she knew. That’s really what – before that moment I just had a splash of what would become of my family had I continued with that decision. That pulled me back enough and then I looked at my phone and she’s like, ‘What’s wrong?’ I was like, ‘I need you to come over now.’ She knew, that instinct was so real.”

Kendall Toole speaks further about her fitness career, about the importance of mental health, and much more in this week’s podcast. Make sure to check out her full conversation with Jay Cutler in the video above, or tune in and listen to Uncut with Jay Cutler on Spotify, Apple, or wherever else you listen to your favorite podcasts.