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You're listening to the Travis Makes Money podcast. What is going on, everybody? Welcome back to the show. On this episode, it's just me, you and the mic and we are talking more about the commonalities of some of the past guests that I've had here on the show. Some pretty amazing people that I've been super blessed to chat with over the years. And this episode is all about obstacles. If you have not read the book the Obstacle Is the Way, highly recommend picking that up. Really anything from, from Ryan Holiday, just because he's essentially repackaging tenets of stoic philosophy into modern day vernacular. So highly recommend checking out his stuff. But this is the topic of today's show because every guest that we had contribute to this particular topic have all come across obstacles in their life, which is, you know, not very atypical. If you're trying to be successful, you're always obviously going to come across a bunch of obstacles. But what's interesting is that for a lot of people, the obstacle becomes the way the, the struggle becomes the story. It's not just something to overcome that exists in the past and something you forget about.
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It literally is the driving force behind
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everything that they do for the rest of their life. Like this thing that they had to overcome that they looked at as a bad thing became the way that they monetized their care, the way that they got their promotions, the way that they built their business or wrote their books or sold their podcast or whatever. Like they have been able to develop an entire life based on this thing that they, when it happened, would have never thought in a million years they'd ever be grateful for it. So it is a pattern that happens over and over and over again. Several guests describe a specific inversion. The thing that caused the most early pain or limitation became with time and intention, of course, the exact asset that made their work extraordinary. This is not reframing it to cope with the problem. Okay. It is a genuine pattern that exists across multiple lives. First one that we're talking about today is from my Buddy. John D. Domenico, he is a comedian and really an impressionist is, I mean, the best way I could say it. But he was the number one earner on all of Cameo for a couple of years running because of his Donald Trump impression. So he, he has been doing impressions for a really long time and even did impressions for Donald Trump before, you know, he was involved in politics. He was doing like, Austin Powers at his birthday party and jumping out of a cake and stuff like that. It's been an entertainer for quite some time, but he really nailed the Trump impression really well. And so when Trump ran back in 2016, got this, like, random burst of business by doing a really, really good Trump impression. And so now he's been on, you know, Howard Stern, the Tonight Show, Jimmy Kimmel. I mean, pretty much every late night show has had him do some sort of a segment, some form of an impression. And he was, like I said, the number one earner on all of Cameo for at least one year. It could have been a couple of years. I don't remember completely. But he was their top earner. He was the most requested person on Cameo. He made six figures on Cameo that year, just doing short videos as Trump for people who paid him on Cameo. So he directly benefited from, from the, you know, polarity of the day. If there's anybody, if there's anybody who walked away winning without much of a loss because of everything that's been happening on politics the last, you know, three election cycles, it's John D. Domenico. He figured out a way to crush it because, you know, whenever Trump is relevant, so was his business, and he makes a lot of money doing it. But anyway, let's get back into the obstacle becomes instrument thing. He said, when I did the impressions, there was no speech impediment. So he's talking about when he was growing up. He had a speech impediment, but when he would do impressions, the speech impediment would go away. So he said, by the time I was six or seven, the speech therapists were basically teaching me how to do more voices. Throat placement, nasal placement, vocal, vocal production, all the things that he uses today. So what, what he was talking about is essentially that he had a speech impediment. He started seeing a speech therapist, and because of the work that he was doing with the speech therapist, they were basically training him on how your voice works and how to get rid of the speech impediment. But for him, it started internalizing and coming out as basically the bare bones, the foundation of what it takes to do.
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The fastest growing businesses aren't doing more, they're delegating smarter. Upwork helps you bring in expert freelance help f so you can delegate and keep on moving. Upwork is a one stop platform to find, hire and pay expert freelancers across web and software development, data and analytics, marketing, business operations and more. It helps grow your business by giving you fast access to specialized talent across over 125 different categories so you can fill skill gaps, launch projects faster and scale support up or down without committing to full time headcount. You can browse profiles, review past work and get help scoping the role so you can hire with confidence and get started quickly with business. Plus, you can access the top top 1% of talent on Upwork. And with AI powered shortlisting, you'll get matched to the right freelancer in under six hours. No endless searching required. Upwork also cuts down operational hassle by handling things like contracts and payments in one place so you can spend more time running the business. Thousands of growing businesses already trust upwork to hire flexible, high quality freelance talent for everything from one off projects to ongoing support, including my own. We've used Upwork I don't even know how many times in the last almost, I don't know, decade that we've been in business. We use Upwork constantly to help fill in gaps and hire contractors and get projects done. It's completely free to sign up and posting a job is easy. Visit Upwork.com right now and post your job for free. That is Upwork.com to connect with top talent ready to help your business grow. That's up w O R K.com Upwork.com this episode of the show is brought to you by Whatnot. So I was scrolling on Whatnot because I really, I just wanted to see what it was about. And I started experiencing what I can only describe as like a social media shopping channel. But it's live shopping. You got to go try it out, okay? Because it's not just for the buyers, it's also for the sellers. Whatnot is the largest dedicated live shopping platform. Whether it's beauty, collectibles, electronics, luxury, fashion, even cookies, sellers are building real thriving businesses. Anybody can sell. Whether your business is big, small, or yet to exist, people selling on whatnot sell 10 times more than on other major marketplaces. 10 times more. That's because you're not just listing products, you're building real connections with actual buyers. Across Whatnot, the number of sellers making over $1 million a year has doubled. Consistency pays Off. It's not just a side hustle. It's a real path to building something that lasts whatnot. Buyers spend more than an hour a day in the app, which is crazy. They're not just browsing and searching for content. They're engaged, they're buying and they're coming back. You go live, show off products in real time and then turn what you love into real income.
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I went on there the other day
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just shopping around looking for some stuff tuned into a live stream. Ended up with a couple of shirts and I love them. And you get sort of live demonstration and you get to ask questions about the product and how does it feel and what's the fit and all those types of things. You can get answered live so you can make sure that you're making a better decision even as a buyer. So search whatnot wh in the app store, download it and you can start selling right away.
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Good impression. And, and, and by the way, one of one of my most viral like short. Not. It's not a short, it's an actual clip, like a three minute clip on, on you my clips YouTube channel. I think it's sitting around a million views or something like that. But it's basically the step one, step two, step three of how to do a Trump impression. And, and he talks about all this stuff, talks about, well, where is the person that you're trying to do an impression? Where are they from? What's the cadence of how they talk? What's the tonality of how they talk? Is it at the top of your mouth or the front of your mouth or the, is it in, is it nasal? Is it not nasal? And he walks you through how to do an impression and then he does one about Bill Clinton and, and Christopher Walken and all these. But it's cool to see that. Like I would not have, I would not have this career if I didn't have this, this hindrance, this obstacle when I was a kid where I had this speech impediment and then went to speech therapy, figured out that I could do all these other voices with the stuff I was learning here and started getting people to laugh when he was a little kid and fell in love with it and then built an entire career in the, in the comedy entertainment industry. So that one's directly like, here's the obstacle. Here's what I ended up doing with the rest of my life. Would not have done this if I didn't have this obstacle. Pretty cool story. Next was artist Gilmore. He said basketball is the fur. Furthest thing from any of us. It was just about survival at the time, just to find food for such a large family. So Artis was a professional basketball player back before the ABA NBA merger. So this is quite some time ago. And then he played in the NBA after the merger with the aba. And we talked a little bit about, like, race relations at that time, because, you know, you were turning back the clock. This was stuff that he was dealing with. Very, very, like, unavoidably dealing with this type of stuff. And so his. In his mind, like, he wasn't thinking about basketball for a long time because he was just thinking about how do we put food on the family? Or how do we put food on the table for the family? Food on the family. And then essentially started realizing that basketball was this vehicle, like the thing that he was not able to do for a really long time because he didn't play until later in life. The thing that he wasn't able to do for a really long time because of all the other external circumstances sort of became the thing that enabled him to step into this new version of himself, away from some of the vitriol that existed at that time toward black people in the country. And he was able to earn the respect of the fans and the owners and the managers, and then started getting paid well to play a sport. And then by doing that, he was able to put food on his family for a really long time. Food on his. I keep saying that. Food on his family. He was able to provide food for his family for a very long time through the thing that he wasn't able to do for a long time because there was no food on the table for his family. So basketball became that vehicle, even though it evaded him for a really long time. Next comes from Garrett White, who's an online entrepreneur. He's generated tens of millions of dollars online teaching men, businessmen really a lot.
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It's.
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It's not just business. It's. He touches on a lot of different things. He said, it wasn't about pursuing prosperity. I was running away from poverty. I was so tired of being broke, tired of not understanding money, tired of being this guy, all this personality and nothing to back it up. And I think there's something really powerful in this realization that he's talking about that. He said, I wasn't pursuing prosperity. I was running from poverty. We, as human beings, really, we have two internal motivation factors. It's either we are running to something or running away from something. It's a move toward pleasure, or it's a move away from pain. And what they've found over the years is that the move away from pain is much more motivating than the move toward pleasure. So it begs the question, how can you engineer a version of struggle or pain that requires you to go get after it for some period of time? Like, if you find yourself feeling comfortable, you know, like, you're. You're not. You're not making a ton of money, you're not able to save that much, you're not really investing that much, but you make enough to live a good life, and you're just finding yourself comfortable. And even though in your mind you're like, of course I want more, you're not doing the work to go get more because you're currently satisfied and comfortable with what you have. And by the way, if you're completely content with what you have and you have no desire to do this, then so be it. But if odds are, if you're listening to this show, it's because you want to go get some more money or because you have a version of your life that you want to live that you're not currently living. And so if you find yourself sort of in this position, the way that I recommend to people to, like, stir up that motivation is to go deprive themselves of the thing that they feel comfortable with. So take the money that you have, the safety net, and go do something with that money. Not. Not something stupid. Okay? Just throw in a hopefully obvious caveat. I don't mean, like, go buy your BMW. Now, that's not exactly what I mean, but get it out of your bank account. And this is one of the things I picked up from my conversation with Grant Cardone. And by the way, I've seen this happen with a ton of different entrepreneurs. Now, this was just, like, one of the first ones that I had a conversation around this, and it was back in, like, 2018, so, like, eight years ago. And he talked about how when he was, like, actively trying to build up his wealth, it was be. It was. He had this. This philosophy where he was working on his sales ability. I think he was in car sales. He's working on his sales ability basically all day, every day. He was obsessed with becoming the best salesman he could be and then started making some good money for the first time in his life. But he kept his lifestyle really, really low, and he started banking money. Banking money. Banking money, banking money. And then what he would do is he lived by this philosophy of, if I was putting money in my bank account, I didn't want to feel comfortable and relaxed and look at my bank account and see like of this big balance. So I started shopping real estate, real estate deals so that I could take the money that I was earning and go put it somewhere else where I can't get it. Like I don't have access to this thing. And he learned a lot about real estate, to be fair at that time. And it wasn't just like a willy nilly decision. So he went out, learned, learned it, studied it, walked properties, finally found a property, put all of his money into that property and then the, like, the bottom line was that he, I think he said something like in order to become wealthy you have to live like you're broke even if you have money. So that's the, the, that's the struggle area. That's sort of the, the, the lonely chapter, the dark chapter, whatever you want to call it is, is where you, you're, you're doing all the work and you're getting some results, but you make an active decision to not increase your lifestyle creep just because you're having results at this time. And the, the lack of the money in his bank account kept him motivated to go out and get more money because when he put that money in the real estate deal, the money was gone. Like you, you know, it's not like, it's not like your Robin Hood account where you could just go connect your bank account and transfer account super easily. You know, once you put the money in that deal, the money's in the deal and you're sort of left up to the markets a little bit. Now of course there's ways to get money out of that deal, but it's not very easy. And if there's some sort of correction in the market, you know, you're at least holding onto that property for quite, for at least a couple of years. Even if, even if the market's appreciating, if the property's appreciating because if you sold it, you have to pay all these closing costs and you have to pay, you know, real estate commissions and all this other stuff. So you have to at least wait until the, the, the appreciation of the equity covers the cost to get rid of the property. So it just wasn't liquid, it was, it was in an asset now, in an asset that was performing well and that in the future would perform extremely well. So he lived by this philosophy of like, okay, even if I am being prosperous and abundant and I'm making all this money, I'm going to pretend like I'M broke in the meantime, and I'm just going to store this money away, put it in an account that I can't see, that I can't touch, so that when I do pull up my bank account, I look at it and I go, damn, I need to get back to work. I gotta, I gotta go back and work and make sure that I, you know, can feed my family this month. So at first he focused on like, I'm being rich on paper instead of being rich in his bank account. And it gave him this healthy fear to move away from the pain of potentially not being able to provide his family. And that's what kept him going for all those years. And I've seen this happen. You know, people like Alex Hermosi was the same way. Slept on the, the floor of his gyms just to keep his living expenses low while he was building the gyms. Both of them, I think both of them drove Camrys for the entire time. And there's a story where Alex talks about where he pulled up to an event, he was speaking at the event and he was, you know, starting to do really well at the business. And he had had seven figures liquid in his bank account. And he pulls up and the, some guy that saw him get out of the car, knew that he was speaking and goes like, you're driving a Camry. He's like, I thought you're supposed to be rich. And then Alex just kind of like looked at him and goes like, well, you should see my bank account. And then walked inside and it was like this external pressure that makes you feel like, oh, well, you're rich, you should be driving a Lamborghini. And it's like, no, no, not necessarily like the people who drive. I won't say this is a blanket statement because it's not always true, but a lot of times the people who drive the Lamborghini are the people who can barely afford to drive the Lamborghini and they put all their money into the Lamborghini and then the Lambo becomes like their identity, right? They're the, it's, they're a Lambro where that's basically their entire identity is drawn from the car that they drive. And they probably actually can't really afford it.
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The fastest growing businesses aren't doing more, they're delegating. Smarter Upwork helps you bring in expert freelance help fast so you can delegate and keep on moving. Upwork is a one stop platform to find, hire and pay expert freelancers across web and software development, data and analytics, marketing, business Operations and more. It helps grow your business by giving you fast access to specialized talent across over 125 different categories. So you can fill skill gaps, launch projects faster and scale support up or down without committing to full time headcount. You can browse profiles, review past work and get help scoping the role so you can hire with confidence and get started quickly with business. Plus, you can access the top 1% of talent on Upwork. And with AI powered shortlisting, you'll get matched to the right freelancer in under six hours. No endless searching required. Upwork also cuts down operational hassle by handling things like contracts and payments in one place so you can spend more time running the business. Thousands of growing businesses already trust upwork to hire flexible, high quality freelance talent for everything from one off projects to ongoing support, including my own. We've used upwork I don't even know how many times in the last, last, almost, I don't know, decade that we've been in business. We use upwork constantly to help fill in gaps and hire contractors and get projects done. It's completely free to sign up and posting a job is easy. Visit Upwork.com right now and post your job for free. That is Upwork.com to connect with top talent ready to help your business grow. That's up. W-O-R-K.com Upwork.com this episode of the show is brought to you by Whatnot. So I was scrolling on Whatnot because I really, I just wanted to see what it was about. And I started experiencing what I can only describe as like, like a social media shopping channel. But it's live shopping. You gotta go try it out, okay? Because it's not just for the buyers, it's also for the sellers. Whatnot is the largest dedicated live shopping platform. Whether it's beauty, collectibles, electronics, luxury, fashion, even cookies, sellers are building real thriving businesses. Anybody can sell. Whether your business is big, small, or yet to exist, people selling on whatnot sell 10 times more than on other major marketplaces. 10 times more. That's because you're not just listing products, you're building real connections with actual buyers. Across whatnot. The number of sellers making over $1 million a year has doubled. Consistency pays off. It's not just a side hustle. It's a real path to building something that lasts. Whatnot. Buyers spend more than an hour a day in the app, which is crazy. They're not just browsing and searching for content. They're engaged. They're buying. And they're coming back, you go live, show off products in real time and then turn what you love into real income.
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I went on there the other day
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just shopping around looking for some stuff tuned into a live stream. Ended up with a couple of shirts and I love them. And you get this sort of live demonstration and you get to ask questions about the product and how does it feel and what's the fit and all those types of things. You can get answered live so you can make sure that you're making a better decision even as a buyer. So search whatnot W H a t N o t in the app store, download it and you can start, start selling right away.
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And then you have the ultra wealthy who all drive like pickup trucks and SUVs or Camrys. And then you have sort of this like middle area where people just go spend all their money on cars but then end up broke later on. And then, and then you have the car collectors. It's like, then you have some wealthy people who just love cars. They're not obsessed with being perceived a certain way because they have status, because this vehicle gives them the status that they want. The, the identity and the value is, is different from the vehicle itself. They just love cars. So they go buy a bunch of cars. But my point is to say that while you are making money, you need to figure out a way to make it seem to yourself like you are broke. So it is my al. My personal philosophy also is like whenever we get our bank account up to a certain amount, that's like our emergency account, you know, anything above that, whenever that starts increasing, like once a quarter, we write a check, get rid of it, put it out in somewhere else, put it in crypto, put it into some sort of an investment like get it out of my bank account. I don't want to see it. I don't want to look at my bank account and see a bunch of money there. I want to still have this, this, this feeling of deprivation so that it keeps me motivated to go continue making money. What the research says about this the clinical term for this inversion is post traumatic growth and it's measurable. A Systematic Review of 45 Studies of Refugees and displaced people found moderate to high levels of post traumatic growth even in severely traumatized populations with showing the strongest association. A longitudinal study found that perseverance predicted post traumatic growth, which in turn improved life satisfaction. So adversity reframed as opportunity the increased overall life satisfaction. Researchers still debate, however, whether some reported growth is genuine change or a coping narrative sort of like that survivor bias and distress can coexist with growth. That it's, there's, you know, maybe some other external factors that are potentially, you know, involved in these types of reporting because it's, you know, sort of this like self reported genuine change. So some of it might be their own coping narrative to that. It's a narrative that they accept internally that, that there, there's no other way for them to cope with it other than to believe that it was something that was good that happened for their benefit. But then that belief itself sort of manifests itself in the way that they view that event, which in turn means that that's what that event means. You know, events are just things, they're things that happen. We have the determine what that event actually like means to us, if that makes sense. And then in, in history, when I think we've talked about this once before on the show, but similar to John D. Domenico Demosthenes, who is a, a Athenian orator, he was really well known for his powerful speeches in Athens, was born with speech defect. And that limitation easily could have been the thing to prevent any sort of oratorical ambition for him at the time. But he would put pebbles in his mouth to, to try to articulate words better. He did vocal training, like while he was running to increase his wind capacity and his lung capacity because obviously at that time there's no microphone. So you gotta speak and you gotta enunciate and you gotta lift your voice up so that people can hear you. And these obstacles that he had to go through because of this speech defect when he was younger ended up turning him into. All the work that he did to overcome those things became the work that he continued to do to get better and better at the craft and became, you know, one of the most famous orders of all time, especially in ancient Greece. So another example of the mess becoming the message, the struggle becoming the story. This, this continues to be echoed throughout history and not just with the people who've been on my show. So that's it for this episode. Maybe start thinking about like some of the things that you've looked at in life as obstacles. Some of the things you've looked at in your life as like, negative these things are, you know, in your mind it's like, well, this is an objectively bad event, this is a negative thing. But start asking yourself the question, how can I potentially reframe this and pull something positive from this event that happened in my life? And the more you focus on the good things, and I know it feels impossible when you're going through it. And I'm not trying to downplay any sort of bad circumstances that come about in your life, but it's the hand that you're dealt. So it happened. Now what? Now what are you going to do with it? Are you going to let it define you in a negative way, or are you going to try to look for the positive and try to let it define you more in that light? That's it for this episode of the show. Thanks so much for tuning in. We'll catch you guys on the next one. Peace.
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Hey, it's Ryan Reynolds here from Mint Mobile. Now I was looking for fun ways to tell you that Mint's offer of unlimited Premium Wireless for 15amonth is back. So I thought it would be fun if we made 15 bills, but it turns out that's very illegal. So there goes my big idea for the commercial. Give it a try@mintmobile.com switch upfront payment
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$45 for 3 months, 90 for 6 months or 180 for 12 month plan required 15 per month equivalent taxes and fees. Extra initial plan term only greater than 50 gigabytes. Me slow when network is busy. See terms.
Podcast: Travis Makes Money
Host: Travis Chappell
Episode Title: SOLO | Make Money by Turning Your Biggest Obstacles Into Your Greatest Advantage
Air Date: August 3, 2026
In this solo episode, Travis Chappell distills a recurring theme from his conversations with high-achieving guests: the most significant obstacles in people’s lives often become their greatest advantages. Drawing inspiration from stoic philosophy and Ryan Holiday’s The Obstacle Is the Way, Travis explores how reframing and leveraging adversity—rather than merely overcoming it—can lead to both personal satisfaction and financial opportunity. Through anecdotes from past guests and his own reflections, he offers actionable strategies and questions for listeners to apply on their journey toward greater wealth and fulfillment.
“For a lot of people, the obstacle becomes the way, the struggle becomes the story… It literally is the driving force behind everything that they do for the rest of their life.” (00:54)
“I would not have this career if I didn’t have this hindrance, this obstacle when I was a kid… figured out that I could do all these other voices… and then built an entire career in the comedy entertainment industry.” (08:12)
“Basketball is the furthest thing from any of us. It was just about survival at the time, just to find food for such a large family.” (08:46)
Obstacle: Persistent experience of poverty, lack of financial literacy, feeling unworthy
Transformation:
Practical Strategy:
Notable Quote:
“It wasn’t about pursuing prosperity. I was running away from poverty…The move away from pain is much more motivating than the move toward pleasure.” (11:28)
Timestamp: Garrett White’s segment at (11:28)
Insights from Grant Cardone:
Travis, on universal patterns in success:
“Several guests describe a specific inversion. The thing that caused the most early pain or limitation became, with time and intention, of course, the exact asset that made their work extraordinary.” (01:26)
On financial drive:
“In order to become wealthy, you have to live like you’re broke—even if you have money.” (15:15; reflecting Grant Cardone’s philosophy)
On redefining adversity:
“Events are just things, they’re things that happen. We have to determine what that event actually means to us.” (22:24)
With warmth, humor, and candid stories, Travis demonstrates that cultivating the ability to reframe and leverage obstacles isn’t just motivational fluff—it’s a time-tested route to financial and personal growth. Whether you’ve faced external limitations or internal doubts, the question is not “Why did this happen?” but “What will I do with it?”
“It happened. Now what? Now what are you going to do with it? Are you going to let it define you in a negative way, or are you going to try to look for the positive and try to let it define you more in that light?” — Travis Chappell (24:45)