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Skateboarding Legend Tom Schaar on How to Fall 999 Times and Still Win

What does it take to become the youngest skater to ever land a 1080? Grit, resilience, and the courage to fall—again and again. In this electrifying episode, pro skater and Olympian Tom Schaar joins John R. Miles to share his incredible journey from backyard ramps to global podiums.

But this isn’t just about tricks and trophies—Tom opens up about battling fear, redefining success, and learning to rise after every fall. Whether you’re chasing a dream or stuck in a setback, this conversation will remind you that falling is part of the climb.

At just 12 years old, Tom Schaar landed a trick no one thought was possible: the world’s first 1080 on a skateboard. It didn’t just change the sport—it made history. But what most people didn’t see were the hundreds of failed attempts, the bruises, the setbacks, and the mental battle it took to get there.

In this episode of Passion Struck, Tom joins John R. Miles to discuss what it really means to push past fear, master your mindset, and get back up 999 times so the 1,000th try changes your life. From Olympic glory to personal resilience, Tom shares the deeper story behind the fame—and how the same principles apply far beyond the skatepark.

Want to learn the 12 philosophies that the most successful people use to create a limitless life? Order John R. Miles’s new book, Passion StruckTwelve Powerful Principles to Unlock Your Purpose and Ignite Your Most Intentional Life.

Like this show? Please leave us a review here – even one sentence helps! Please post a screenshot of you listening on Instagram & tag us to thank you personally!

Introducing The Ignition Room

Last week, we officially introduced The Listening Room—a dedicated community platform for Passion Struck listeners and supporters. It’s designed to deepen audience engagement around the podcast and provide a space for more meaningful interaction beyond the episodes.

The Listening Room will feature:

  • Direct community access to episode discussions
  • Bonus and behind-the-scenes content
  • Exclusive giveaways and early announcements
  • A space to build a deeper connection with our growing audience

We’ll also be using it as a touchpoint for future content drops, book releases, and live events.

Click here to learn more and enter our giveaway from a Passion Struck pack – Welcome to the Ignition Room.

“Fear is part of it. If you’re not scared, you’re probably not doing anything that really matters to you.”

tom schaar

In case you didn’t already know it, John R. Miles (@John_R_Miles) takes your comments and questions for Momentum Friday right here every week! If you want him to answer your question, register your feedback, or tell your story on one of our upcoming weekly Momentum Friday episodes, drop us a line at [email protected]. Now, let’s dive in!

Hear the secrets and philosophy of the World’s GREATEST high achievers every Tuesday and Thursday, and tune in each week for an inspirational Momentum Friday solo message.

Listen to the episode on Apple PodcastsSpotifyPodcast AddictPocket CastsStitcherCastboxGoogle PodcastsListen NotesAmazon Music, or on your favorite podcast platform. You can watch the interview on YouTube below.

The Skater Who Outgrew the Podium: Tom Schaar on Purpose, Pressure, and Life Beyond the Olympics

What happens after you become a legend before you can drive? In this revealing episode, Tom Schaar sits down with John R. Miles to unpack the often overlooked reality of early success: what it gives you—and what it takes away. Beyond the medals and viral tricks, Tom opens up about the mental toll of fame at a young age, the pressure of staying on top, and why stepping away from skateboarding has helped him rediscover joy.

He reflects on the transition from Olympic-level training to carving out a more intentional, authentic path that includes snowboarding, filmmaking, and just being a kid again. The episode also explores the powerful role of mentors, the emotional rollercoaster of performing on the world’s biggest stage, and the freedom that comes with letting go of perfection.

What You’ll Learn in This Episode With Tom Schaar:

  • How Tom built mental toughness to deal with fear, pressure, and expectation at an early age.
  • Why Olympic glory isn’t the endgame—and what truly matters after the lights fade.
  • How snowboarding changed his perspective and helped him fall back in love with movement.
  • The truth about burnout—even when you’re “living the dream.”
  • Why letting go of structure and returning to play brought back his creative edge.
  • The surprising impact of meeting Snoop Dogg on his post-Olympic mindset.

WHY IS THIS EPISODE WITH TOM SCHAAR A MUST-LISTEN?

Because behind every highlight reel is a human story—and Tom Schaar’s is one of transformation. This episode goes deeper than the skatepark and into the heart of what it means to grow up in the spotlight, learn who you really are, and redefine success on your own terms. If you’ve ever hit a wall after reaching your goals or struggled to find purpose beyond performance, this conversation will leave you thinking, reflecting, and inspired to shift your own path.

Thank You, BIOptimizers, For Sponsoring

This November, BIOptimizers is offering an exclusive Black Friday BLOWOUT! Get discounts on all their amazing products—including Magnesium Breakthrough—plus up to $100 in free gifts. Don’t miss out! Visit https://bioptimizers.com/passion to shop now

Thank You, Hims, For Sponsoring

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Thank You, Mint Mobile, For Sponsoring

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Thank You, Rosetta Stone, For Sponsoring

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Thank You, Prolon, For Sponsoring

Reset your health with 15% off at “ProlonLife.com/passionstruck.”

STARTER PACKS

Motivational quote said by Tom Schaar for the Passion Struck Podcast with John R. Miles episode 603 on How to Fall 999 Times and Still Win

Are you new to the show? These Starter Packs are collections of our most popular episodes grouped by topic, and we now have them on Spotify.

You can also browse starter packs for existing listeners to find your old favorites. Every week, John interviews everyday heroes from all walks of life. Learn how to subscribe to the show and never miss a new episode and topic.

Like this? Please subscribe and join me on my new YouTube platform for peak performance, life coaching, and personal mastery.

Inside Tom Schaar’s Olympic Rollercoaster: Pressure, Performance, and Meeting Snoop Dogg

When Tom Schaar talks about the Olympics, he doesn’t romanticize it—and that’s what makes his story so real and refreshing. In the episode, Tom gives an honest, behind-the-scenes look at what it’s like to compete on skateboarding’s biggest stage… and it’s not all gold medals and glory.

First off, Tom didn’t even expect to qualify. He tells John that he entered the Olympic qualifiers more as a fun challenge than a serious career move. But one thing led to another, and suddenly he was headed to Tokyo, repping Team USA in the first-ever Olympic park skateboarding event.

Tom opens up about the sheer pressure that came with it—representing not just himself, but his country, in front of the world. He shares how the vibe at the Games was intense in a way that even the X Games or Dew Tour couldn’t compare to. Unlike those other events that felt more laid-back and community-driven, the Olympics were tight, super structured, and full of expectation. And because COVID restrictions were in place, there wasn’t much of an outlet—no crowds, no cheering fans, just this weird bubble where athletes were kind of isolated from the world.

That pressure wasn’t just physical, it was mental. Tom talks about how hard it was to stay in the right headspace. Even though he’s been competing since he was 11, he says this felt completely different. There was this weight of proving yourself, not just as a skater, but as an Olympian.

He even admits that he didn’t have his best day in the final. He fell on his runs, which was tough to swallow, especially with everything leading up to it. Instead of letting it break him, Tom reflects on it as a moment of growth. “It made me realize I was ready for a break,” he says in the episode. That Olympic experience became a turning point where he started thinking about what else he wanted from life beyond constant competition.

Oh—and yes, he did meet Snoop Dogg. Tom laughs as he tells how Snoop was just casually chilling in the Olympic village, and how surreal it was to chat with him. As wild as it sounds, that moment became one of the few lighthearted memories from a high-stakes event.

So yeah, the Olympics weren’t just about skating for Tom—they were about realizing what he wanted next. He doesn’t sugarcoat it. It was amazing, stressful, eye-opening, and ultimately the start of a new chapter.

THANKS, Tom Schaar

If you enjoyed this interview with Tom Schaar, let him know by clicking on the link below and sending him a quick shout on Instagram

Click here to show Tom Schaar your thoughts about today’s episode on Instagram.

Click here to let John R. Miles know about your number one takeaway from this episode!

If you want us to answer your questions or you want John to discuss a topic on one of our upcoming Momentum Friday episodes, drop us a line at [email protected].

RESOURCES FROM THE SHOW WITH TOM SCHARR

Please note that some of the links on this page (books, movies, music, etc.) lead to affiliate programs for which The Passion Struck podcast receives compensation. It’s just one of the ways we keep the lights on around here. Thank you so much for being so supportive!

  1. Tom Schaar’s Website
  2. Tom Schaar’s Instagram
  3. Passion Struck Core Value System: https://passionstruck.com/the-passion-struck-core-belief-system/
  4. Listen to Passion Struck’s interviews with New York Times bestselling authors Gretchen Rubin and Seth Godin.
  5. Check out Passion Struck’s Episode Starter Packs on Spotify or Passion Struck starter packs to get started with the podcast.

My solo episode on The Mattering Mindset in Love – Choose the Love You Deserve

Can’t miss my episode with Jennifer B. Wallace on the Consequences of Prioritizing Achievements Over Mattering

My episode with The Art of Listening: How to Make People Feel Like They Matter

Catch my interview with Laurie Santos on How to Matter in a Busy World

Listen to my solo episode on Fading into Insignificance: The Impact of Un-Mattering in Our Interconnected Era

About Today’s Guest, Tom Schaar

Tom Schaar is a professional skateboarder and history-making athlete best known for landing the world’s first 1080 on a skateboard at just 12 years old. By the time he was 16, Tom had already racked up gold medals at the X Games, Dew Tour, and Vans Park Series, becoming one of the youngest and most consistent forces in competitive skating.

In 2021, he represented Team USA at the Tokyo Olympics during skateboarding’s historic Olympic debut. Known for his calm focus, relentless drive, and down-to-earth personality, Tom is not only a pioneer in the sport but also a role model for young athletes chasing bold dreams. Today, he’s exploring life beyond the podium while staying rooted in the skate culture that shaped him.

Follow John R. Miles On Social

* Twitter: https://twitter.com/Milesjohnr

* Facebook: https://www.facebook.com/johnrmiles.c0m

* Medium: https://medium.com/@JohnRMiles​

* Instagram: https://www.instagram.com/john_r_milesacks for existing listeners to find your old favorites. Every week, John interviews everyday heroes from all walks of life. Learn how to subscribe to the show and never miss a new episode and topic.

* Gear: https://www.zazzle.com/store/passion_struck/

Learn more about me: https://johnrmiles.com.

Passion Struck aspires to speak to the humanity of people in a way that makes them want to better, live better, and impact the world.

Passion Struck’s mission is to unlock the power of intentionality for the benefit of us all. To create a world where we live better, be better, and impact the world through our unique and powerful content.

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