Pro Skateboarder Leo Baker’s Newest Trick: Sticking To Business

If you’re scrolling through the Netflix browsing menu for something excitingly different, boldly unique and ultimately empowering and inspiring, catch Stay on Board: The Leo Baker Story. It’s new to Netflix, starting tonight, Aug. 11, and it’s unlike any film you’ve ever seen.

Maybe that’s because Leo Baker is unlike any man who’s turned sports fame into a business fortune.

His passion for skateboarding since he was a toddler led him to start his own company, Glue, with Stephen Ostrowski. He’s following in his rock star father’s footsteps by going into music, with his first song on Spotify. His goofy-foot expertise is something even gamers who can’t grind can emulate from their couch, by playing Baker in an official Tony Hawk videogame. Nike even created a Leo Baker shoe and plastered his image on huge billboards all over his hometown of New York City.

And now he’s on Netflix in a documentary, directed by Nicola Marsh and Giovanni Reda. They tell the life story of the celebrated skateboarder, known all over the world since he was a sidewalk surfing teenager from Covina, California. He went by another name then, and sported long blonde locks for the longest time, until he started to present in a more masculine way.

One of the ways Baker said he did that, like a lot of trans boys, is to wear a binder or chest compression undershirt under his tops.

“Appearing to be flat-chested gave me confidence in a way that I never felt before, which overrode the discomfort of physically having to wear it,” he said. “I wouldn’t leave the fucking house because if I would have to put it on ice and feel like it. So there was a lot of just like a lot of just like little like minutia that or like nuance, like mundane things in my life, but, like, that were affected by just that alone and. Even if I was wearing, like, baggy enough clothes and you couldn’t, like. Like, outwardly, you don’t really see what’s happening there. I could still feel that there’s something there. it takes me out of it. Always took me out of the space I was in.

Throughout the film, Baker talks about how fame changed, and interrupted, what he wanted out of life.

“Leo’s story is one about the courage to be yourself and jump a misaligned life path to pursue a truer one,” the film’s executive producer, Alex Schmider, told me. “That’s a universally compelling journey I hope people can, if not directly relate to, feel inspired by. Whatever the stakes or expectations, no matter how high or set, Leo shows it’s never too late to be yourself and define the terms for your life. What an empowering example not only for LGBTQ people to see, but everyone.”

In 2020, Baker abandoned a chance at Olympic gold to start his business and be the man he always knew he should be. Baker told Time magazine last year why he resigned from the first-ever U.S. women’s Olympic skateboarding team and changed his name from Lacey, to Leo.

“It was a big fear that I was going to lose everything that I’ve worked literally my whole life for,” Baker said, revealing he had believed himself to be a boy since he was young, and finally realized he was transgender at the age of 19.

“I know a lot of trans people go through that: Will I lose my family? Will I lose my friends? Will I lose my job? Will I lose my life? It’s a scary thing to embark on,” Baker told Time.

Early in the film, co-director Reda asked Baker about his fear of coming out, and the potential for backlash. I won’t spoil the dramatic scene with his response, but in a Zoom conversation earlier this week, I asked Baker about his emotional reaction to that very question.

“That was at the very beginning of the process of making the documentary. That was the first interview,” Baker told me. “It just was overwhelming to think about, the possibility of backlash, because that’s all I could imagine there being. And I didn’t want to go through a feeling of losing everything, or it mirroring when I first started becoming more masculine, how my career shifted, and things were just different for me after that. I was like, ‘Well, if that is enough for me to lose everything once, then this will be enough for me to lose everything again, after having rebuilt it from that place,’ you know? It’s like, I am who I am, and people are either going to respect it or not, but I’m not going to change. It just felt like a repeat of that. And I just didn’t really know what the fuck I was going to do.”

Baker, 30, and the filmmakers documenting the twists, turns and tricks of his life,

“In my circle of family and close friends, everyone has always been supportive. So I decided that whatever happens, I’d just take the loss. The compromise was not worth it. I couldn’t keep putting myself on hold.”

“Appearing to be flat chested gave me confidence in a way that I never felt before, which overrode the discomfort of physically having to wear it. Got it? Yeah. At the beginning, that was like enough. But after like 6 to 7 years of that, I was like, okay, I can’t do this anymore. Like, I won’t like, I wouldn’t, like, leave the fucking house because if I, I would have to put it on ice and feel like it. So there was a lot of just like a lot of just like little like minutia that or like nuance, like mundane things in my life, but, like, that were affected by just that alone and. Even if I was wearing, like, baggy enough clothes and you couldn’t, like. Like, outwardly, you don’t really see what’s happening there. I could still feel that there’s something there. it takes me out of it. Always took me out of the space I was in. And just, like, I’m just too, like, aware of what’s going on in my body and it’s feeling wrong. It’s more just like there was a presence of. Discomfort for a long time. And now there’s like an absence of that. So there’s just like space to, like, experience new things in ways that I just wasn’t able to before, like, I could imagine. But, like, there’s nothing like actually having the feeling of it. I’m very centered, like spiritually and emotionally, mentally, in ways that I just never was before, because I was there’s always this, like, constant wondering how I’m being perceived and like how I perceive myself and how I’m feeling in my body and like. And then just like having so much of that building up all the time and trying to cope with it, it’s like I’m in a constant state of coping with being uncomfortable instead of just, like, living my fucking life. Just now, like very recently in my life, I have like I feel a sense of like. It’s more just like an ego death kind of a thing, because I don’t I’m not thinking about my body and what I look like. I just feel okay. And I’m just, like, doing the stuff I care about. I’m not like. Thinking about how I look. I just feel good.”