You can't save your way to your dream life anymore. The truth is, you’re gonna need to learn to make more money. The Travis Makes Money Podcast is not your typical personal finance show. Rather than shaming you for buying a Starbucks coffee or pressuring you to become a billionaire, we focus on empowering you to make more money so you can enjoy life today while preparing for your future. You don’t have to cut back so much that you miss out on the present, and you don’t need to become the next Jeff Bezos either. Hosted by veteran podcaster Travis Chappell, each daily episode features interviews with regular people just like you – yes, you – who have learned how to make more money in unique and unconventional ways. From turning side hustles into an extra six figures to building massive business empires, these conversations dive into the mindset shifts, hard-earned lessons, and simple strategies that helped these individuals succeed. With over 1,000 podcast episodes under his belt, Travis has developed a unique ability to pull out inspiring stories and practical advice you can apply to your own financial journey that you just won’t hear anywhere else. Whether you’re looking for strategies on side hustles, skill building, investing, building generational wealth, or just motivation to take your next steps, this podcast is your resource. Tune in daily for insights, actionable tips, and inspiration from some of the most successful and interesting money-makers on the planet.
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You can't save your way to your dream life anymore. The truth is, you’re gonna need to learn to make more money. The Travis Makes Money Podcast is not your typical personal finance show. Rather than shaming you for buying a Starbucks coffee or pressuring you to become a billionaire, we focus on empowering you to make more money so you can enjoy life today while preparing for your future. You don’t have to cut back so much that you miss out on the present, and you don’t need to become the next Jeff Bezos either. Hosted by veteran podcaster Travis Chappell, each daily episode features interviews with regular people just like you – yes, you – who have learned how to make more money in unique and unconventional ways. From turning side hustles into an extra six figures to building massive business empires, these conversations dive into the mindset shifts, hard-earned lessons, and simple strategies that helped these individuals succeed. With over 1,000 podcast episodes under his belt, Travis has developed a unique ability to pull out inspiring stories and practical advice you can apply to your own financial journey that you just won’t hear anywhere else. Whether you’re looking for strategies on side hustles, skill building, investing, building generational wealth, or just motivation to take your next steps, this podcast is your resource. Tune in daily for insights, actionable tips, and inspiration from some of the most successful and interesting money-makers on the planet.
This episode features host Travis Chappell and producer Eric having a rapid-fire, hilarious, and surprisingly deep “Would You Rather” session built entirely around money, investing, and lifestyle tradeoffs. Using a list of AI-generated prompts, they unpack how real people should think about risk, retirement, lifestyle creep, and building wealth with their actual constraints in mind.
On this episode we talk about:
Whether to take $10 million today or $1 million a year for life
Swinging for a 10x moonshot vs. locking in an 8% return forever
Being “early to the next Apple” versus compounding slower, safer returns
Choosing between keeping your investments or keeping your business
Building one $100M company that burns you out vs. multiple smaller businesses you love
Working 80-hour weeks for a few years to make work optional vs. coasting forever
Unlimited VC money with no control vs. slow, bootstrapped freedom
Fame with no privacy vs. quiet wealth no one sees
Driving a paid-off Toyota with rentals vs. renting a house with a Lambo
Taking a $250K job you hate vs. $75K doing work you love
Top 3 Takeaways
Safe, consistent returns beat reckless moonshots—especially early on. Travis leans toward guaranteed growth and stacking cash first, then taking bigger swings once a solid base is built.
Your best wealth-building lever at first is income, not investments. Until your portfolio can support you, your business and skills are the engine that funds long-term wealth.
Money decisions are really lifestyle decisions. Tradeoffs like privacy vs. fame, burnout vs. freedom, and hating a high-paying job vs. loving a lower-paying one matter more than raw dollar amounts.
Notable Quotes
“Get to a hundred grand, then put as much money as you can into the safe thing before you go start playing around.”
“The goal isn’t retirement; the goal is to make work optional.”
“There’s a massive difference between having to work to eat and choosing to work because you love what you do.”
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Travis Makes Money
You can't save your way to your dream life anymore. The truth is, you’re gonna need to learn to make more money. The Travis Makes Money Podcast is not your typical personal finance show. Rather than shaming you for buying a Starbucks coffee or pressuring you to become a billionaire, we focus on empowering you to make more money so you can enjoy life today while preparing for your future. You don’t have to cut back so much that you miss out on the present, and you don’t need to become the next Jeff Bezos either. Hosted by veteran podcaster Travis Chappell, each daily episode features interviews with regular people just like you – yes, you – who have learned how to make more money in unique and unconventional ways. From turning side hustles into an extra six figures to building massive business empires, these conversations dive into the mindset shifts, hard-earned lessons, and simple strategies that helped these individuals succeed. With over 1,000 podcast episodes under his belt, Travis has developed a unique ability to pull out inspiring stories and practical advice you can apply to your own financial journey that you just won’t hear anywhere else. Whether you’re looking for strategies on side hustles, skill building, investing, building generational wealth, or just motivation to take your next steps, this podcast is your resource. Tune in daily for insights, actionable tips, and inspiration from some of the most successful and interesting money-makers on the planet.
