CO-HOST | Make Money by Betting on Yourself (Lessons from Tony Hawk's $4M Royalty Deal)

Summary

Travis Makes Money - Episode Summary

Podcast: Travis Makes Money
Host: Travis Chappell
Episode: CO-HOST | Make Money by Betting on Yourself (Lessons from Tony Hawk's $4M Royalty Deal)
Date: May 13, 2026

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Episode Overview

This episode dives into one of the most iconic business decisions in the world of sports and gaming: Tony Hawk’s decision to bet on himself and turn down a substantial upfront buy-out from Activision for his involvement in the Tony Hawk’s Pro Skater video game series. Travis Chappell and co-host Eric dissect not just the numbers behind the deal, but the mindset and financial discipline that allowed Hawk to take such a risk. Drawing lessons for listeners, they connect the dots between managing personal finances, evaluating risk, and creating the freedom to take bets that can pay off in life-changing ways.

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Key Discussion Points & Insights

The Tony Hawk Pro Skater Story

• Jackass, Skating & Tony Hawk’s Pop Culture Impact [00:51-02:43]:

  • Eric jokes about Tony Hawk being a "cast member" of Jackass, segueing into the real topic: Tony Hawk’s legendary video game franchise.
  • Discussion of how skating, and Tony Hawk specifically, was more underground before the video game exploded his fame and made skating mainstream.

• The Deal with Activision [03:54-05:34]:

  • Tony Hawk shares a clip recounting how Activision offered him a $500,000 buyout right before the first game’s launch (1999).
  • Hawk’s mindset: coming from leaner years, “a half million dollars to me, it sounds like a billion gazillion dollars...but I felt like I was in a pretty good place...I thought, I’m going to take a risk because I’m doing okay and I don’t need that money right now.”
    — Tony Hawk, [04:27]

• Financial Outcome [11:15-11:19]:

  • Activision handed Hawk a single royalty check for about $4 million after just the first few games.
  • The franchise has grossed over $1.4 billion to date, with estimates Hawk’s total royalties now sit comfortably in the eight figures.

• ** "You have to assume even if it's only 1%, that's still like 14 [million]."*
  — Travis, [11:24]*

Risk, Reward, and Financial Positioning

• When to Bet on Yourself [12:32-14:32]:

  • The duo discusses the dilemma: Should you take an upfront guaranteed sum, or gamble for long-term royalties?
  • “The same decision for one person could be a really bad decision for another.”
    — Eric, [13:24]
  • Travis highlights the relationship between financial stability and the ability to take risks:
    • “The reason he was able to make that risk is, like, what he was saying on there: he felt pretty comfortable. ...If he were making dumb financial decisions leading up to that time, he might not have had another choice.”
      — Travis, [13:59]
    • The importance of keeping your expenses (lifestyle “burn rate”) manageable so you can stay nimble and “make those bigger bets” comes up repeatedly.

• Lesson for Listeners [14:32-17:26]:

  • “That’s the beauty of making smart financial decisions over a longer period of time: you have the flexibility…you’re not handcuffed to a certain decision because of poor financial mistakes.”
    — Travis, [14:56]
  • Shaquille O’Neal is referenced: living on “20%” of income, saving and controlling expenses to enable risks and big purchases later.

Psychology of Decisions & Regret

• How Do You Decide? [21:17-23:12]:
  • They explore the mental process behind making risky decisions when the outcome is uncertain.
  • “I look at it more like: am I going to at some point regret this decision?...If I can thoroughly answer that question and say no, I will not regret having taken this risk, then I feel like I owe it to myself to do it.”
    — Travis, [22:20]
  • The importance of evaluating downside: “If it crashes and burns, are you still good? ...If the answer is absolutely not, I’ll lose everything, then...you should probably go ahead and take advantage of the opportunity at your fingertips.”
    — Travis, [21:23]

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Notable Quotes & Memorable Moments

• Tony Hawk on risk:

  "For me, having lived through some really lean times, when they say a half million dollars, to me, it sounds like a billion gazillion dollars. ...But I felt like I was in a pretty good place. ...I thought I'm going to take a risk because I'm doing okay and I don't need that money right now."
  — Tony Hawk, [04:08]

• On maintaining flexibility:

  "That’s the beauty of making smart financial decisions over a longer period of time: you have the flexibility…you’re not handcuffed to a certain decision because of poor financial mistakes."
  — Travis, [14:56]

• On the danger of overextending yourself:

  "If he were making dumb financial decisions leading up to that time, he might not have had another choice."
  — Travis, [13:59]

• Regret and risk:

  "I look at it more like: am I going to at some point regret this decision?...If I can thoroughly answer that question and say no, I will not regret having taken this risk, then I feel like I owe it to myself to do it."
  — Travis, [22:20]

• On big wins and big losses:

  "The same decision for one person could be a really bad decision for another."
  — Eric, [13:24]

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Key Timestamps

• 00:54 — Introduction & Jackass/Tony Hawk Pop Culture Banter
• 03:54 — Tony Hawk details the initial Activision royalty buyout offer
• 11:15 — The $4 million check and the scale of Tony Hawk’s eventual earnings
• 12:32 — Deep dive: When do you bet on yourself versus take a guaranteed payout?
• 14:56 — Financial freedom as a root of strategic risk
• 21:17 — How to make tough calls and live without regret
• 22:20 — Travis’ philosophy on risk, regret, and making big moves

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Tone & Style Highlights

• Friendly, conversational banter between Travis and Eric, peppered with pop culture references and personal anecdotes.
• Practical, encouraging tone; rather than shaming mistakes, the discussion empowers listeners to make better financial decisions.
• Blend of humor (“Travis and Eric learn to skate”—[10:15]), self-awareness, and insightful breakdowns of life-changing decisions.

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Summary Takeaway

The episode uses Tony Hawk’s extraordinary royalty deal as a lens through which to examine risk, reward, and financial discipline. The key message: Betting on yourself can pay off spectacularly, but only if you’re in a financial position to have that option. The most actionable advice is to live within your means, control your expenses, and keep financial flexibility, so that when those rare opportunities arise, you’re ready to take the leap—and possibly change your life.

Transcript

[A]

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[B]

Hey, Travis. A new Jackass movie's coming out soon.

[A]

Finally.

[B]

I know. I tell you every time I see you. Yeah, you give me the idea. That's the most important thing of the year. Today I want to talk about one of the Jackass cast members, Tony Hawk.

[A]

Is he a cast member?

[B]

No, but he was in some of them. I was making a joke because everyone knows him as the skateboarder. I was just.

[A]

But you know him from Jackass.

[B]

No, I know him from the games.

[A]

You know, from Tony Hawk Pro Skater.

[B]

Yeah, it was a weak intro. I'm going to be honest. I don't like it. No, I thought it'd be funny to be like, you know Tony Hawk, the guy from Jackass.

[A]

Yeah, good one.

[B]

And it gives me an excuse to show you a clip of him getting hurt real quick from Jackass. But I do want to talk to you about Tony Hawk and his video games, which. God, I wish there was a video game about me that was as successful as his skating game was.

[A]

Don't we all?

[B]

I don't know if that's crazy, but I wish that was the case. Well, here's a little stunt gone wrong. This'll play really poorly for the audio experience. This will play really well for the visual audience here on Social. But here's this cool stunt real quick.

[A]

Alan strikes me. I'm like, oh, I just killed Hawk.

[B]

I've never seen you slam stupid. Ooh.

[A]

Yeah. That was my.

[B]

I mean, he has. It's a weird thing how I always thought that, too. Like, he was just like, better than us and he would get out of it.

[A]

But then, like, watching his documentary and

[B]

I was like, oh, he didn't get out of Tunis. Like, he got destroyed of times in the most, like, terrifying ways, like hitting your.

[A]

Like breaking your arm is like, man.

[C]

I've actually since. I've since then gotten hurt worse. And I'm surprised I got away with just what the injuries I did there.

[B]

So that's a pretty gnarly fall, huh?

[A]

Yeah, no kidding.

[B]

Well, that may have really hurt, but you know what doesn't hurt? The royalties from Tony Hawk Pro Skater.

[A]

Are we doing a guessing game or are you.

[B]

No, no, I just want to. I just want to show this clip because before we get into the royalties, which I do have, I know you're going to say, what did he make from that? He turned down a deal with Activision early on that led to him making a lot of money.

[A]

Oh, interesting.

[B]

But it was a. It was a significant amount of money at the time to be offered. So for those of you that don't know, I don't know if you know this. When did the first Tony Hawk Pro Skater game come out? Because I was surprised because I played how. When I was a youngster, I was gonna say. And that was like, 2004.

[A]

Yeah, I was gonna say Tony Hawk Pro Skater 1. I do remember playing this on my N64.

[B]

You probably remember when it came out when I was old. Head unk7.

[A]

I'm gonna put it like 2000. 2001.

[B]

No.

[A]

1998.

[B]

No.

[A]

Okay.

[B]

Higher.

[A]

I don't know, 99.

[B]

Yeah.

[A]

Okay.

[B]

That's when Phantom Menace came out, too.

[A]

Oh, yeah.

[B]

How about that? All right, so here's a clip of him talking about Activision, the game developer.

[C]

When they were close to launch of the game, they started to sense that there was buzz about it. It was already getting good reviews from. From previews of the game publishers. I mean, not the magazine publishers. So they knew they had a good game overall, and they felt this. This surge of interest. And so they offered me a buyout of future royalties right before the game launched, which at the time it was. They offered me a half million dollars. And they said, you know, actually, what does that mean? They said, well, that. That's. You get that right now. And then no money going forward. And for me, having lived through some really lean times, when they say a half million dollars, to me, it sounds like a billion gazillion dollars. I mean, it would. No one had ever spoken those types of numbers to me before, but I felt like I was in a pretty good place. I was. I was doing well in other ways. I was, I was still skating a lot. I was doing events. I was, I had good endorsements. I was, I was doing, we had. Birdhouse was starting to actually be profitable. My skate. I had just bought a new house with a, with not, you know, I, I had a loan, but my loan was manageable. And I thought I'm going to take a risk because I'm doing okay and I, I don't need that money right now. And even the timing of that, like, if it had been just a few months before that when I was looking at houses, maybe I would have taken that. But I, I didn't. That was definitely the best financial decision of my life.

[A]

Yeah, no kidding. I assume he goes on to say how much he made from royalties.

[B]

No, but I found it elsewhere.

[A]

Oh, okay.

[B]

He's never fully disclosed the total amount,

[A]

but people are estimating because the franchise has made over a billion dollars.

[B]

I think it has.

[A]

Yeah.

[B]

How'd you know that?

[A]

Tony Hawk.

[B]

How'd you know that?

[A]

I just know things.

[B]

Yeah. The Tony Hawk's pro skater franchise has generated more than $1.4 billion in sales over its lifetime. I feel like skating used to be like during the early 2000s was so huge.

[A]

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[D]

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[E]

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[A]

like pre Tony Hawk era, it was so it was like wild Underground. Yeah, it really was the name of

[B]

one of his games, who it is.

[A]

But. But it really was, though, like, it wasn't like. It's funny now to be looking back on it because, like, oh, it's Tony Hawk. Of course. He's a legend, but like, at the time, he wasn't Tony Hawk yet. You know, he was Tony Hawk within the skater world, but nobody outside of the skater world, like, not a lot of people knew who he was.

[B]

Yeah.

[A]

And. And skating itself was still like, relatively new, you know what I mean, at that time. So for. For him to be offered half a million dollars to. To do something that he was already going to do, I'm sure that had to be like a. Let me take a couple days on this one. But then obviously he ended up making the absolutely correct decision.

[B]

I was, I was doing my walk the other day and I passed a skate park and I thought, I should try that. And then I thought, nope, too old. I kept walking.

[A]

That's a bad decision.

[B]

That would be fun. We should do a video. Travis and Eric learned to skate.

[A]

Yeah.

[B]

And we just started a skate park.

[A]

I don't think that video would end well for either one of us.

[B]

Yeah. No, skating. Skating was huge.

[A]

So, yeah, I had a six month stint in like high school where me and my friends got into skateboarding.

[B]

Yeah.

[A]

And that was the only time of my life.

[B]

It's not too late.

[A]

Immediately jumped out of it. So. Yeah.

[B]

The franchise has generated more than $1.4 billion in sales. Licensing deal for his name and likeness reportedly ran for about 16 years, so from 1999 up to 2015. But there was also a 2020 remaster, which I would assume there was some new deal structured with that. But the one thing that we do know is that he said on a podcast that after the first few games, first like three games, Activision handed him a single royalty check for about $4 million, which covered his earnings up to that point.

[E]

Jeez.

[B]

So did pretty well. And people estimate it's probably in the eight figure range at this point. Like how much?

[A]

You have to assume even if it's only 1%, that's still like 14.

[B]

Well, the remaster, I think I have it here. The remaster was one of the best selling games. Yeah. The 2020 remaster, Tony Hawk's Pro Skater 1 and 2 became the fastest selling title in the series, hitting 1 million units sold faster than any previous, which would have added more royalties if his deal still applied.

[A]

The video game industry is just so huge, dude. It's so massive.

[B]

Do you know, Mark, did you find this out with me. I don't know. Do you know what the largest demographic of gamers is?

[A]

No.

[B]

It's like 30 to 40 year old women.

[A]

Is that true?

[B]

Because they log the most time, they're playing Angry Birds, Candy Crush. There was somebody, I swear that was on your show. That's crazy. We talked to someone who said that. But yeah, because they were like, who's the biggest demographic? I was like, oh, 16 to 21 year old guys. Right. And they're like, no, it's actually the most games, the most money spent on games. The most time game gaming is like mobile gaming.

[A]

Changed it for a lot of that demographic.

[B]

Right, right.

[A]

Made it more accessible.

[B]

But yeah. So when it comes to the actual deal itself, I thought it was a good thing to bring up a conversation about like, when do you take the gamble on yourself versus take. Cause like the thing that it's like what we're saying about marriage, it's like you have the survivor story of like, well, mine worked out well. Everybody else that did the exact same thing is divorced 10 years later.

[A]

And that's definitely the scenario that's taken place in this type of a world for sure.

[B]

I have to imagine a lot of people that sign a TV show or movie or business deal, book, whatever, and they go, I'm going to bet on myself, I'm going to turn down your half a million dollars and I'll take the royal. And then it doesn't sell at all, or the game is a flop or whatever, it doesn't have the longevity. And then they go, damn, I should have took the deal. He's saying that's the smartest financial decision in my career. So the same decision for one person could be a really bad decision for another. If you're sitting there, you're Tony Hawk, you're getting offered that. How are you determining whether I take this immediate bump or I'm gonna wait it out and see what happens.

[A]

Yeah, it's so tough to say what I would have done in that scenario. I would like to think I would have made the same decision if I was his friend.

[B]

I'd be like, dude, it's not. It probably just assume it's not gonna work out.

[A]

But that's also one of those things. What we're talking about on a previous episode about how like why it's important to keep your living expenses low and to like keep your lifestyle burn low is like if he, if he were making dumb financial decisions during like leading up to that time, he might not have had another choice. Like he might have been presented that offer and been like, I have to do this. I'm $200,000 in debt and I. I can't afford my car payment anymore. My. My house is going to get foreclosed on, my cars are going to be repossessed. Like, I need the cash. But he was able to make the decision to take a little bit of a risk there. I mean, a big risk there to set himself up to be in a position now where he literally never has to work again just from royalties on video game.

[B]

Yeah.

[A]

Using his name, image, likeness. But the reason I like my opinion on that is to say that the reason that he was able to make that risk is like, what he was saying on there is like, he felt pretty comfortable. It's like, oh, I have this deal going on. My company's doing pretty well, you know, doing some appearance. I have a manageable payment. But again, all of those things could have easily been the constraints in his life that would have made him take that massive payday over. Just saying, you know what, I'm just going to see how this thing works out. So it's less like, what would I do in that scenario? And more just like, for people listening. This is a massive reason why it's really important just to keep your lifestyle creep as low as you can and keep your burn rate as low as you can and make it manageable because you have the ability. That's the beauty of making smart financial decisions over a longer period of time, is that you have the flexibility, you can stay nimble, you can make the decision to take this job in a different state that moves you across the country. And yeah, it's a risk. And I don't know exactly how it's going to work out, but I'm doing okay right now. And I'm not in a position where I have to. I'm not. I'm not handcuffed to a certain decision because of my poor financial mistakes. And obviously it ended up working out really well for him. But I think that's more of my takeaway for most people is that when you're looking at a decision of whether or not to bet big on yourself or to, you know, take this mountain of cash that's being offered up front, the decision is going to come down to how much pain am I currently in? And if the answer is not a lot, then you can make those bigger bets and take the bigger risks. But. And that's true of any risk, whether it's somebody offering you a bunch of money for something or it's you looking at spending a bunch of money on a business idea that you know is going to cost a lot of money to be able to whatever iterate on the product or to put together a big marketing campaign or you know, order your first bank of inventory. You know, it's like, well, that's going to be a big financial risk to do these things. But I'm doing it for the potential outsized reward. But I would not be able to take these risks if I did not do all these other smart financial decisions in the meantime to set myself up to be in a position where I can take those risks for something that's actually meaningful and important to me. So that, that's more my, my takeaway is just, it's another reason to just be frugal and financially responsible in the meantime until you get like at this point now he can take a bunch of different risks, you know what I'm saying? Like once the game hit, now he can do, make, make more quote unquote dumb financial decisions because they're no longer dumb. You know, like when we had, when we had Shaq on, he was talking about like, oh, I live on like 20% of what that 20%. I know how to spend money, you know what I mean? And I loved and I like to spend money. I like to buy nice things, like to go, I like to do crazy stuff with the money that I have. But the money. But that's no longer a dumb decision because it's the money. It's his play money and he can do all that, right?

[B]

Well, I hope the Jackass cast got their money up front for the Jackass tie in game in 2007 because that did not fare so well.

[A]

I didn't even know they made a game.

[B]

Nobody.

[A]

Now that seems pretty crazy. That didn't do well. That seems like almost like a Grand Theft Auto style.

[B]

You like how I brought that full circle back to Jaga?

[A]

Did you play the game?

[B]

No.

[A]

Well, and you're a massive fan, so.

[B]

Yeah, it sold 280,000 copies when it came out in 2007.

[A]

Just didn't do very well.

[B]

It looks very bad though. I've watched playthrough videos where people talk about how bad it is.

[A]

Really?

[B]

Yeah. That's the weirdest. Okay, wait, can I ask you this? Can I ask you a question? Let me raise my hand. Do you have anything that you watch a lot of content about that you don't do?

[A]

What do you mean?

[B]

So like for example, I often find myself going down rabbit holes like when you're just like watching YouTube videos and it'll be like gameplay videos where people are playing a game and they're giving commentary or reviewing a video game. I don't own a video game console and so sometimes I'll be like, why am I watching? But I like watching. Here's a playthrough of this 2008 video game and they're giving commentary. A lot of my viewing is that. Do you have anything like that where you're like, oh, this guy makes birdhouses. Well, you make a lot of birdhouses. So something that's not that.

[A]

Not necessarily. I think the closest I would get to that would be TV and film. Like the how to behind it. Watching them create special effects things.

[B]

Doing that shit now, buddy. What, you're making the shows now, buddy?

[E]

Oh, yeah, yeah.

[A]

Well, yeah, we're doing that a little bit. Yeah. But that would be probably the closest thing that I could think of would be like, I like seeing how those projects come together and geeking out on that a little bit. But that's not necessarily the same thing. I definitely don't watch like video game walkthrough videos.

[B]

Don't say like that. No, I always like, the other day I watched. It was like the. I was watching a bunch of YouTube videos about 007 licensed tie in video and I started the third video. I was like, what am I doing? But they were so good and there's so many good creators in that space that, that it's like, it's almost like it saves.

[D]

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[B]

Me playing the game because it's like, oh, it's so interesting. The way he described it. Interesting. I don't know.

[A]

But it also ties into your love of 007, though.

[B]

I also do. That is the other thing I've always thought about doing is doing like a channel where I review like movie tie in games. But I don't wanna do that. I'm busy. In conclusion, literally everything this year I'm just like, I'm too busy. But that would be fun someday. Hey, maybe sometime I'LL come over, we'll crack some beers and watch some movie tie in. Video game channel videos. How about that?

[A]

Sounds like exactly how I'd like to spend.

[B]

We could invite Tony Hawk over.

[A]

Well, I'm down for that. Do you have his number?

[B]

No.

[A]

Okay.

[B]

But I have his game.

[A]

Weird to offer.

[B]

I have the disc somewhere.

[A]

We can't make that happen anyway.

[B]

No.

[A]

I'd be so upset with you if this whole time you knew Tony Hawk.

[B]

Imagine I've just been holding it till I feel like you're worthy. Like one day I just randomly go, travis, you've earned this. And I just give you Tony Hawk's number.

[A]

Yeah, that'd be nice.

[B]

What would? Nevermind. All right. Anyway, no, I thought that was a really interesting clip just because of the whole, like, every time I hear. Every time I hear any story of like, an athlete passing on a deal or a musician being like, I kept the rights to my music even though. And I'm just like, there's so many people. That would be the worst decision ever.

[A]

Yeah.

[B]

And I don't feel like I'm ever closer to being like, what's the metric by which to make that decision?

[A]

Yeah, Well, I think it. I think it's that. I think it's. If it does not go well for you, then what? If it crashes and burns, are you still good? And if the answer is absolutely not, I'll lose everything, then it's like, well, you should probably go ahead and take advantage of the opportunity at your fingertips right now. But if it's like, yeah, like, it might be a little tight for a while, or, you know, I might have to cut back on a little, A little bit of this, a little bit of that. It's like, yeah, that's fine. But like, I look at it more like, am I going to at some point regret this decision? And if I can thoroughly answer that question and say like, no, I will not regret having taken this risk, then I feel like I owe it myself. I owe it to myself to do it and just take the risk. But that makes me okay with the outcome, if that makes sense. Like, even on this dinner party thing, it's like, I've thought about that a lot. Was like, there's so many other places where I could put this money where I know for sure there would be a really good return. But. But will I regret not having take advantage taking it, not having taken advantage of this opportunity in the future? I do believe I would regret that. And I played out all the worst case scenarios in my mind. Over and over again to the point where I was like, look, if the worst case scenario does happen, I still think that I'm going to view this as like a good decision. And I made the decision that I thought was best to make at the time with the information that I had at the time. And that's like, that's all you can do. Or else you're going to drive yourself crazy thinking about everything single decision you've ever made and being like, I wish I would have made a different decision, which is only going to cause you to have more indecision in the future. And then you're never going to pull the trigger on anything that has any sort of risk to it. So there's, there's not, there's not a, there's not a way to win that game. Sure. You just have to make the best possible decision you can make at that time and, and then move forward and accept the results regardless of what they may be.

[B]

Right. Right.

[A]

But.

[B]

Well, we have a game to play, so we better go. We got Tony Hawk. We got a Tostino's pizza in the oven. We got Tony Hawk on deck. My Mountain Dew is poured.

[A]

It sounds fire.

[B]

We're gonna go so good. Actually, not right now because I'm in my fitness journey in my health era.

[A]

Quest Pizza and diet Mountain Dew, dude. Protein pizza, Diet Mountain Dew.

[B]

Coke Zero, man. Yeah, Coke Zero is the Bam Diet Baja Blast. All right, well, God bless.

[A]

Anyway, that's it for this episode of the show. Remember, money only solves your money problems, but it's easier to solve the rest of your problems. Money in the bank. So let's start there. Here on the Trav Makes Money podcast. Thanks for tuning in. Catch you guys next time.

[B]

Peace.

[D]

Some follow the noise. Bloomberg follows the money. Whether it's the funds fueling AI or Crypto's trillion dollar swings, there's a money side to every story. Get the money side of the story. Subscribe [e-mail].