From the Archive: Tony Hawk: Mastery, Failure, and the Trick That Changed Skateboarding

The James Altucher Show

James Altucher

Education, Business

4.6 • 2.7K Ratings

🗓️ 7 March 2026

⏱️ 50 minutes

🔗️ Recording | iTunes | RSS

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Summary

A Note from James:

Tony Hawk is one of the greatest athletes of all time—but what fascinates me most isn’t just the tricks.

It’s the mindset.

Tony didn’t just become the best skateboarder in the world. He built an entire ecosystem around what he loved: competitions, companies, tours, sponsorships, and one of the most successful video game franchises ever created.

What’s interesting is that none of it was planned that way. It came from constant experimentation, falling—literally—and getting back up again.

In this episode, Tony talks about the path to excellence, how he handled criticism and failure, the moment he finally landed the legendary 900 trick, and how skateboarding evolved from an underground subculture into a global industry.

Episode Description:

Tony Hawk didn’t just change skateboarding—he helped transform it into a global cultural phenomenon.

In this archival conversation, Tony shares the real story behind his career: learning to master fear, surviving the ups and downs of a niche sport, and eventually building a massive business empire around skateboarding.

He explains how passion drove him through the lean years when skateboarding almost disappeared, why constant experimentation helped him stay at the top, and how a combination of timing, risk-taking, and creative control led to the success of the Tony Hawk’s Pro Skater video game franchise.

The conversation also explores the legendary moment when he landed the first successful 900, the importance of protecting your brand, and why mastery often comes from relentless curiosity rather than natural talent.

What You’ll Learn:

Why pursuing passion—even during downturns—can create long-term success
How failure and repetition build elite skill in any discipline
Why protecting your brand and intellectual control matters in business
How the 900 trick became one of the most iconic moments in sports history
Why continuous learning and experimentation are essential for staying relevant

Timestamped Chapters:

[00:02:00] The Physics of Skateboarding & Learning Through Failure
[00:03:12] Introduction
[00:03:38] Developing Air Awareness in Skateboarding
[00:04:10] The First Time Going Airborne in a Pool
[00:05:05] Learning How to Fall Safely
[00:06:19] Aging, Risk & Walking Away from Mega Ramps
[00:07:17] Skateboarding’s Rebellious Origins
[00:08:00] Creativity and Individual Style in Skate Culture
[00:09:00] Advice for Pursuing Excellence
[00:10:00] Learning Every Aspect of an Industry
[00:11:35] Skateboarding’s Collapse in the Early ’90s
[00:12:33] Becoming a Professional Skater
[00:14:02] Mentorship from Stacy Peralta
[00:15:13] Going Broke During Skateboarding’s Down Years
[00:16:29] Skating Parking Lot Shows for $100 a Day
[00:17:31] The X Games and Skateboarding’s Comeback
[00:18:45] The Video Game That Changed Everything
[00:19:31] When Tony Hawk’s Pro Skater Became “The Game”
[00:20:24] Lessons from Skateboarding Applied to Business
[00:21:17] A Failed High-End Denim Business
[00:22:43] Being Called a Sellout
[00:24:00] Protecting Your Brand and Reputation
[00:25:13] Creating Tony Hawk’s Pro Skater
[00:26:20] Designing the Game Mechanics
[00:27:20] The Long Road to the 900
[00:29:35] Landing the 900 at the X Games
[00:31:08] Becoming Tony Hawk Inc.
[00:32:21] The Importance of Total Immersion
[00:33:29] Designing the Downward Spiral Ramp
[00:35:24] Advice for Raising a Passionate Kid
[00:38:12] Business Advice from Tony Hawk’s Sister
[00:40:29] Working with Family
[00:43:04] Why Some Athletes Fade After Success
[00:44:28] Clearing Up the 900 Controversy
[00:48:00] The Hoverboard Prank

Additional Resources:

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Transcript

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0:00.0	This isn't your average business podcast, and he's not your average host.
0:06.7	This is the James Altasier Show.
0:12.6	Presenting the archive.
0:14.7	Classic episodes that remain timeless.
0:16.7	The raw, unfiltered conversations from the early days in which people shared their failures
0:21.8	and showed us exactly how they rebuilt everything from the ground up.
0:27.2	And so everything you do is amplified in terms of your speed, your height, and so it's almost
0:34.9	two to three times your usual height. And one wrong move on that,
0:42.3	you know, just one small adjustment the wrong way is tragic. And I just don't have the youth
0:47.4	that I can survive those kind of falls. I get paid more money than I ever imagined to go ride
0:53.4	my skateboard, which still seems absurd to me.
0:56.0	It's funny, it was a totally different industry then.
0:58.0	So the way I turned pro was I had reached the top of the amateur ranks,
1:03.0	and I'm filling out the entry form to the next event,
1:05.0	and there's a checkbox that says amateur, and there's a checkbox that says pro,
1:09.0	and so I checked the pro box and then that was it and I said
1:16.1	Riley I know you're good at those things but you're exceptional at skateboarding you're already
1:23.1	way better than most kids your age and I know you know it's hard to go from beneath my shadow,
1:30.0	but you do have your own style, you have your own direction,
1:32.7	and you know, you don't have to follow my footsteps necessarily,
1:36.5	but you do have an opportunity here.
1:49.0	So I have to admit, I have to ask totally stupid, naive questions first.
	...

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