Sep 9, 2026 · 1h 11m · my-first-million
Tony Hawk inspiring us for 72 minutes straight
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Skateboarding icon and entrepreneur Tony Hawk joins the My First Million podcast to share the lessons behind his legendary athletic career, discussing his relentless mindset, the boom-and-bust economics of action sports, and how he turned his passion into a multi-million-dollar empire and philanthropic legacy.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 30.4% of the talking time here. How this is scored →
The hosts as informed peer 3.5 Guest teaching 1.8 Guest disagreement 0.2 The hosts pushing back 0.1
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:06:25 Tony dismisses Sam's Tompkins Square plan
In a very friendly interview with virtually no true combativeness, Tony humorously shuts down Sam's idea to drop his name and do stretches in front of hardcore skaters at Tompkins Square Park.
Hardest push from the hosts ▶ 1:06:30 Sam claims he'll use Tony's name for street credSam pushes back against conventional skate park etiquette by insisting he will perform Tony's unusual stretch publicly at an intimidating New York skate park.
Biggest teaching moment ▶ 14:15 Tony educates Shaan on early skate economicsTony disabuses Shaan of comparing youth skateboarding to professional sports like the NBA, clarifying that first place at contests paid just $100 and a magazine photo.
The host holds their own ▶ 2:40 Shaan articulates Charity Water's operating innovationShaan demonstrates authoritative business insight by explaining how Charity Water broke standard nonprofit opacity with GPS tracking and flow meters to unlock major donor capital.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Introducing Tony Hawk and Shared Skateboarding Roots | 3 | 1 | 0 | 0 | Sam opens by showing a video of himself skating at Riverside Skate Park, establishing a shared skateboarding bond. Shaan recounts his personal anecdote of traveling with Tony to Ethiopia for Charity Water. The atmosphere is warm, collaborative, and conversational. | |
| Charity Water's Model and The Skatepark Project | 5 | 2 | 0 | 0 | Shaan articulates a detailed analysis of Charity Water's business model and transparency mechanisms. Tony elaborates by explaining how he applied similar tangible impact principles to The Skatepark Project. Both sides contribute domain knowledge without friction. | |
| Early Skateboarding Days and Stacy Peralta's Mentorship | 4 | 2 | 0 | 0 | Shaan inquires whether Tony's exceptional talent was obvious early on, and Sam cites Charlie Munger's framework on taking niche pursuits seriously. Tony explains that his early skating was awkward flailing driven purely by tenacious trick-hunting rather than natural style. | |
| Sponsor Message: Free HubSpot Business Ideas Database | 4 | 1 | 0 | 0 | After a brief HubSpot sponsor mention, Tony discusses his obsession with learning tricks rather than collecting contest trophies. Sam demonstrates skater knowledge by dissecting the culture of measurable incremental progression. | |
| The Price of Greatness in Early Skateboarding | 4 | 3 | 0 | 0 | Shaan draws a parallel to NBA training regimens to explore the price of greatness. Tony educates the hosts on the stark contrast between mainstream sports and 1980s skateboarding, where winning a contest earned only one hundred dollars and gear. | |
| Career Expectations Versus Extraordinary Commercial Reality | 5 | 2 | 0 | 0 | Tony shares that he originally expected to be a high school math teacher before making substantial royalty money at seventeen. Sam draws sharp parallels to early conservative revenue forecasts from Jeff Bezos, David Rubenstein, and Uber's pitch deck. | |
| The 1980s Boom and the 1991 Financial Crash | 2 | 2 | 0 | 0 | Tony narrates the 1980s boom driven by Back to the Future followed by the brutal 1991 industry collapse. He details having his shoe sponsorship dwindle to three hundred dollars and taking odd Hollywood ramp-building gigs to pay his mortgage. | |
| Frank Hawk's Influence and Supportive Fatherhood | 3 | 1 | 0 | 0 | Sam asks about Tony's father Frank Hawk founding the NSA and encouraging him to buy a duplex at age seventeen. Tony reflects on his father's unwavering support and how he applies the same unconditional encouragement to his own children's varied passions. | |
| Navigating Lean Years and Expanding Skill Sets | 4 | 3 | 1 | 0 | Tony recounts learning video editing to survive the slump before Sam brings up freestyle pioneer Rodney Mullen. When Sam mistakenly places Rodney in the Midwest, Tony quickly corrects him that Mullen grew up on a farm in Florida. | |
| Landing the Historic 900 at the 1999 X Games | 2 | 2 | 0 | 0 | Sam asks Tony about his intense mental lock-in state prior to landing the 900 at the 1999 X Games. Tony describes eliminating fear and thoughts of catastrophic injury, knowing he would either make the trick or leave in an ambulance. | |
| Deconstructing the 900 and Generational Trick Progression | 3 | 3 | 0 | 0 | Shaan admits his shock that Tony had never landed the 900 in practice. Tony walks through the technical mechanics of the varial 720 and explains how the pristine X Games halfpipe allowed him to commit repeatedly until completion. | |
| The Genesis of Tony Hawk's Pro Skater | 2 | 2 | 0 | 0 | Tony details the genesis of Tony Hawk's Pro Skater, from humiliating early pitch meetings with dismissive publishers to testing an early prototype at Activision featuring Bruce Willis on a skateboard. | |
| Authenticity, Beta Testing, and Rejecting the Royalty Buyout | 4 | 2 | 0 | 0 | Sam cites specific nostalgic game details like real-world spots and the punk soundtrack. Tony explains demanding creative approval rights, secretly distributing burned beta discs to real skaters for feedback, and turning down a half-million-dollar buyout. | |
| The $4.5 Million Royalty Check and Global Fame | 4 | 1 | 0 | 0 | Tony recounts receiving a single 4.5 million dollar royalty check when four THPS titles dominated the top ten sales charts. Sam places Tony on the Mount Rushmore of culturally defining athletes alongside Jordan and Gretzky. | |
| Overcoming Injury and 'Finding Your Kickflip' | 3 | 2 | 0 | 0 | Shaan praises Tony's perseverance after shattering his femur and his message to 'find your kickflip'. Tony lists components of his business empire including Birdhouse, 900 Films, speaking, and angel investments like Nest and DocuSign. | |
| The Economics and Legacy of Birdhouse Skateboards | 4 | 2 | 1 | 0 | Sam notes the brutal unit economics of skateboard decks remaining flat at sixty dollars for decades. Tony recounts how integrating Birdhouse decks into THPS despite his partner's objections saved the brand and catalyzed its golden era. | |
| Maintaining the Love for Skating Amid Fame | 4 | 1 | 0 | 0 | Sam discusses early pre-internet skate culture, video magazines like 411, and DIY zines. Tony physically displays an original zine he produced in 1982 at Del Mar Skate Ranch and describes meeting tech figures like Kevin Rose through skating. | |
| Keynote Speaking, Lifelong Goals, and Grandparenthood | 3 | 2 | 1 | 1 | Tony discusses aging, keynote talks, and his grandson. When Sam laments how long it takes his hips to warm up, Tony demonstrates a physical pre-skate stretch on camera, playfully mocking Sam's idea to use his name for cred at Tompkins Square. | |
| Street Skating, Police Encounters, and a Georgia Shakedown | 3 | 1 | 0 | 0 | Sam brings up the youthful thrill of running from police while street skating. Tony shares a story of being detained in a rural Georgia holding cell until an ATM cash payment resolved the situation. The hosts close with glowing praise for Tony. |
Statements from this episode (27)
Shaan Puri: Donor transparency drove Charity: Water's outsized nonprofit success
“And I just think that that was such a unlock for him and why charity, one of the reasons charity water was able to do so well as a nonprofit compared to the kind of standard operating procedures of nonprofits.”
Tony Hawk: Foundation has contributed to nearly 1,000 skate parks
“It's getting close to a thousand that we have contributed to.”
Hawk required sponsors to donate 10% to 20% to his foundation
“Any contracts that I entered into in terms of endorsements at the time, I made sure that 10 to 20% went straight to the foundation or that they were able to give even more.”
Tony Hawk: Skaters often lose motivation after reaching milestone accolades
“There's a mindset, especially in skateboarding, where you want to make it, right? You want to get on the cover of Thrasher, or you want to have a good video part, or you want to win a contest, and if you get to that goal, you might lose your incentives.”
Hawk: Early skateboarding competition first prize was only $100
“To reach the top of skateboarding at the time I did it meant that you got your picture in a magazine. That was it. I mean, truly, like, first place for a competition was a hundred dollars.”
Hawk: Skate royalties exceeded his math teacher's salary by age 17
“And then once I was 16, money started to come in through royalties and suddenly realized that I was, I live making more than my math teacher. At age, 17.”
Hawk says Back to the Future sparked a 1986-1990 skate boom
“When Back to the Future came out in 85, kids wanted skateboards. I mean, Marty McFly invented the skateboard, and a lot of kids, that was their first glimpse of what's possible. So there was this sort of wave of popularity that happened, like, 86 to ninety-ish”
Tony Hawk: Peak annual earnings during the 1980s skate boom were around $100,000
“I would say probably in, in my best year was, In the 100,000 ish, you know, in the late eight, mid eighties, late eighties, that was like lawyer salaries sort of thing.”
Tony Hawk: Airwalk cut his monthly sponsorship pay from $1,500 to $300 within one year
“I was making about 1500 dollars a month from my shoe sponsor Airwalk. They would call me every month or so and say, oh, you know, we really got to cut you down a little bit. So then that went to a thousand and then two months later that went to 500 and eventua…”
Tony Hawk edited an NEC TurboGrafx commercial during the 1990s downturn
“I actually, ironically, edited a commercial for NEC TurboGrafx, which was a video game system at the time, because my friend worked for them and said, hey, Tony could do this for a 10th of the cost that you're gonna pay, and I did it.”
Tony Hawk: Great skaters show fierce intensity rather than joy
“There's a, they can't quench their desire, and they do some of the craziest stuff. They do some of the hardest things, and they just have this look of intensity, not joy, It doesn't look joyous. That's what it is.”
Tony Hawk: Rodney Mullen invented the kickflip, 360 flip, and flatground ollie
“You know, Rodney, like, he created the flat ground ollie. He created the kickflip, the three 60 flip, the impossible, and he did it, and he was on to the next one.”
Tony Hawk: No skateboarder had landed a 900 before 1999
“No one had made it completely and ridden away.”
Hawk: Modern skaters land back-to-back 900s and kickflip varial 900s
“They do 900. They do back to back 900. One kid did a kick flip body barrel 900. You know, so he's got a kickflip in the middle of the 900.”
Hawk: 14 years passed between the first 720 and 900
“The era that I grew up in, a three 60 was the most you could spin, and then Mike McGill did the five 40, and then I did a seven 20, And then, 14 years passed, and between that and a 900.”
Hawk: First million dollars came from Tony Hawk's Pro Skater
“Well, I mean, you're talking about My First Million, that, that's where it came from. Without question.”
Hawk says Nintendo rejected his early 3D skateboarding game pitch in 1997
“So I went with him to meetings. We met Nintendo. We met a few software publishers and just no takers.”
Hawk: Early THPS prototype featured Bruce Willis skateboarding with a gun
“And the first version of what became THPS that I got to play was Bruce Willis on a skateboard with a gun strapped to his back. Doing all eyes and kickflips across the desert.”
Hawk modified friends' PlayStations to beta-test Pro Skater with real skaters
“I burned copies of it from my friends while we were developing it, so like a few of my friends have beta versions of THPS, and I actually modified their PlayStation so they could play it, because I wanted honest feedback from real skaters.”
Hawk says declining Activision's $500,000 royalty buyout led to his first million
“Right before the release, they called me and said, we want to offer you a buyout of future royalties. I said, what does that mean? They said, we want to offer you half a million dollars, and then you won't get royalties going forward. At that time in my life, …”
Tony Hawk: Activision gave him a $4.5M check for Pro Skater
“When the fourth game was released, if I have this right, I had lunch with my connection at Activision. I actually went up to LA. He's like, I really want to talk to you about the game and the future of it. And fourth game just got released. It got to be in the…”
Tony Hawk: Hitting an imperfect milestone unlocks future progress after setbacks
“Find Your kickflip , it doesn't have to be perfect. It doesn't have to be the dream that you have set for yourself, but get to that stage, because then there's more to offer. There's more to get to after that.”
Hawk discloses angel investments in Nest, Blue Bottle, and Liquid Death
“Nest, Blue Bottle well, Liquid Death, but they're, You know, they're still trying to figure out what they're doing. Events.com I think is about to go public. And a bunch of others that I'm still holding on to.”
Hawk predicts portfolio company Events.com is about to go public
“Events.com I think is about to go public.”
Parr: Skateboard deck retail prices have remained at $60 for 20 years
“Decks have been like, 60 dollars for like, 20 years. Like the price has always been the same. They're still 60 bucks. When I was 14, they were 60 dollars.”
Tony Hawk: Birdhouse Skateboards is not profitable, but he doesn't care
“Yes, Rob's right, it is not a profitable business but I don't care.”
Hawk: Kevin Rose introduced him to his Blue Bottle Coffee investment
“Kevin Rose. Cause he was a hardcore skater when he was doing dig and he actually got me to go to my first comic con cause he wanted to do an interview with me. And it's funny cause I live in San Diego and I avoided comic con like the plague because of all the …”