Ryan Sheckler: I Could Have Done More with That Million | Forward Progress

23 Oct 2025 · 8 min · 9 chapters

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In short

Ryan Sheckler reflects on early money, how he used goal-setting to earn big income, and why he regrets spending over $1M on luxury (bottle service, club tables, penthouse suites, private flights). He argues money gave him freedom as a teen, but didn’t bring lasting joy; he wishes he’d invested in assets or a foundation instead. He also discusses his “Sandlot” skate-park mindset, his partnership with Palm Springs Surf Club’s new standstill wave pool (test wave hooked him; bigger pool coming), and interests linking music, sports, and tattoos via Ethica.

Guest

Ryan Sheckler, professional skateboarder/entrepreneur; agent Steve Astefine is credited as “family.”

Key claims

early income shaped freedom; material goals felt empty; planned purchases (with agent and mom) drove savings; agent promised millionaire after 10 years.

Notable examples

first six-figure at ~14–15; goal to buy a Ferrari by 18; “Sandlot” as skate-park culture; Palm Springs wave pool test ride; potential tattoo shop chain.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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First Encounter with Wealth

0:04 to 0:27

Ryan discusses his first experiences with money and independence at a young age.

“It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks.”

First Encounter with Wealth

0:42 to 1:46

Ryan discusses his first experiences with money and independence at a young age.

“First time you're in six figures, you were how old?”

Reflections on Spending

1:46 to 2:52

Ryan reflects on his spending habits and the emptiness of material possessions.

“But even thinking right now, bro, like money didn't really have a grip on me until I was 18.”

Missed Opportunities with Wealth

2:52 to 3:06

He wishes he could have used his wealth to make a more significant impact.

“Because then I could have maybe bought some real estate or like bought assets that like are actually creating revenue and not just, you know, pretty much burning, burning it.”

Goal Setting for Purchases

3:06 to 4:12

Ryan shares how he set goals to save for special items as a youth.

“I would set a goal with my agent and with my mom.”

The Sandlot Analogy

4:12 to 5:11

Ryan compares his skate park experience to the camaraderie in 'The Sandlot'.

Innovative Wave Pool Experience

5:11 to 6:05

Ryan shares his excitement about a new wave pool project in Palm Springs.

“So, new standstill wave pool that's coming in, and super excited to be a partner in it, you know?”

Tattoo Shop Aspirations

6:05 to 7:20

Ryan discusses his interest in creating a chain of tattoo shops.

“There might be the desire at some point on your end in creating a chain of tattoo shops.”

The Role of His Agent

7:20 to 7:58

Ryan credits his agent for guiding him to success in business.

“How much credit do you give to your agent, Steve, for the success you've had on the business end?”
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Transcript

Automatic transcript. May contain errors.

0:01This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required, compatibility and availability varies 18+. As we wrap up the week, we're bringing you one of the many positive messages from our past interviews. Each Thursday, we're sharing stories of our most watched athletes, celebrities, and leaders.

0:36We hope these problem-solving narratives inspire you to tackle obstacles in your own life. This week, Ryan Sheckler.

0:47First time you're in six figures, you were how old? First time I got a six-figure, ooh. Oh,

0:58bro, it must have been early on. First time I made 100 grand, I don't know, 14, 15. Did your parents stop being able to claim you as a dependent when you were like nine, I think? Yeah. Yeah. What do you think you learned about money going through all that? or, you know, having the resource that early in age and now reflecting on it? What I learned about money at a young age was that it was like, it was pretty much kind of a freedom ticket for me, you know? Like if I wanted to go, you know, take my family out to dinner, I could, you know? And like a lot of the times on trips I felt really bad that my brother wasn't with me and that Shane wasn't with me.

1:45And so I would try to, I would try to make up for it with, with gifts, you know, and, and he'd be stoked and it was cool. But even thinking right now, bro, like money didn't really have a grip on me until I was 18. It wasn't important to me until I was getting ready to buy a house, um, until I wanted to buy jewelry. It was all material things, you know, I wanted to have a Ferrari. So like the goal was to like get that by the time I was 18, you know, and so got that. That was a goal. Was I satisfied? No, it wasn't like I kept thinking that all these things that I was buying were going to give me this like sense of joy.

2:24And they did for a little bit, you know, but like it was empty. It was very empty. And, you know, I've wasted I've wasted over a million dollars for bottle service and, you know, tables at clubs and penthouse suites and, you know, flying private. And whatever it may be, all these like material things that I look back on now and it's like, man, I kind of wish I would have saved that, you know, million dollars. Because then I could have maybe bought some real estate or like bought assets that like are actually creating revenue and not just, you know, pretty much burning, burning it. or you know could have done more with that million could have really put the million dollars just into the foundation and gone out and helped and and actually been able to do more than what we're doing obviously I talk about going back but I wouldn't change anything that my life has been because it's sat me right here right now clear-headed and motivated before you made it big what was the most creative way you went about saving money to get something special for yourself or someone else?

3:33We would say I would set a goal. I would set a goal with my agent and with my mom. And, you know, if I wanted a new car or a new watch or something like that, it would be. I'm going to win this contest or if I at the end of this year and the state championship or win the championship of this, then I'm going to then I'm going to splurge. And so for me, it's always been goal setting I've always been a goal setter so it wouldn't really be like walk outside and I'm gonna go get a car today you know even though on the show it made it look like we just went out one day and bought an escalator it was like no that that was planned you know we planned to do that but the magic of television made it look like I just woke up and decided to go spend 70 grand on a car business today uh sandlot times yeah tell me about how that came about sandlot of times is representative of my skate park my friends um derived from the sandlot the movie which is like one i get the chills it's random i love that movie because of the the fellowship that these guys have you know they stick together they ride together they all show up at the same park and they just have fun they lose track of time completely and they're just hanging out and playing and as an adult my skate park is the sandlot that's pretty much the new you know life of Ryan let's put it that way you know our Sheckler sessions that I used to do with Red Bull but it's mine you know it's mine we own the content what's to say here about Palm Springs wave company Yeah, Palm Springs Surf Club.

5:17So, new standstill wave pool that's coming in, and super excited to be a partner in it, you know? It's pretty awesome to be able to go out to Palm Springs, golf around, and then show up at the wave pool and surf for four hours and just get barreled. I got to, I luckily got to ride the test wave, the sample wave. And just from the sample wave, the ride on it hooked me, dude. And to think that it's going to be three times bigger, like wider pool, longer rides, bigger wave, left and right, maybe even split peak. There's an air section. It's just like, it's a playground. It's actually a playground for surfing.

6:05There might be the desire at some point on your end in creating a chain of tattoo shops. It would be cool. For me, it's like I think that music and sports and tattoos kind of all go together these days, you know. And a goal of mine, you know, with one of the companies that I'm a part owner in, Ethica, you know, that's kind of a branch where we're going down right now is the music side, you know. and I think with the studio that they've created and kind of the atmosphere that is going on with the brand that a tattoo company or tattoo setup goes right in with it. And that's funny you know about that.

7:01It's interesting that you know about that. That's like really right now at the beginning of even conversations of doing it. But yes, ideally, I've spent a lot of time at the tattoo shop. I hadn't noticed. Yeah, a lot of time at the tattoo shop. I love, obviously, getting tattoos. I have to slow down a little bit. I don't have much room left. So it's, you know, it's a fun world. It's a painful world, but it's fun. How much credit do you give to your agent, Steve, for the success you've had on the business end? Steve Astefine, bro, is like family. He absolutely is family to me. I remember our first meeting.

7:41He said, Ryan, if you promise me 10 years of hard work, I will make you a millionaire. And we'll get you to a point where you never have to work again. And I promised him. I said, yeah, absolutely. And that was like, that was 13 to 23. And those were some of the gnarliest, hardest working years of my absolute life. That's it for now. But if you're hungry for more In-Depth with Graham Benzinger interviews, Head over to youtube.com slash Graham Bensinger. You can dive into our deep library, which includes more than 2 ,000 clips spanning 12 plus years. Thanks again for listening.

From the publisher

Skateboarding and reality TV star Ryan Sheckler reflects on his evolving relationship with money, including earning his first $100K before he could drive and “wasting” more than $1M with material things like bottle service, penthouse suites and private jet flights. Sheckler also talks of current business interests, including Sandlot Times, Palm Springs Surf Club and a potential deal involving a chain of tattoo shops.


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