SOLO | Make Money By Failing Forward episode artwork

EPISODE · May 14, 2026 · 16 MIN

SOLO | Make Money By Failing Forward

from Travis Makes Money · host Travis Chappell

On this solo episode, Travis shares candid stories from his own entrepreneurial journey, walking through more than a dozen ventures that didn’t work out the way he hoped before his podcasting business took off. From childhood side hustles and landscaping to MLMs, door-to-door sales, and water purification, he breaks down how repeated “failures” created the skills, resilience, and opportunities that ultimately built his income today. On this episode we talk about: Why fear of failure and fear of embarrassment keep people from even taking the first swing at their goals How our social wiring, threat detection, and negativity bias make us over-index on what others might think The difference between temporary failure and the only real failure: quitting and pulling yourself out of the game Travis’s long list of experiments: landscaping, college side hustles, multiple MLMs, door-to-door solar, alarms, water machines, and more How just 3–4 of roughly 17 different ventures produced about 90% of his income over the last decade The transition from sales and MLM into podcasting, masterminds, courses, and live events Why leveraging other people’s time (hiring help) was a key early lesson in building leverage instead of just trading hours What the entrepreneurial path actually looks like emotionally: ups, downs, and the necessity of stepping back up to the plate Top 3 Takeaways The fear of other people’s reactions to your failure is often more paralyzing than the failure itself, and it’s usually based on imaginary scenarios that have never happened. Entrepreneurship is inherently experimental; most attempts won’t be home runs, but a small percentage of ventures can drive the majority of your long-term income. A failure only becomes permanent when it causes you to quit — as long as you keep getting back in the game, each “loss” becomes data, skill-building, and positioning for the next win. Notable Quotes "A failure is not a failure at all unless it causes you to quit. The only version of failure that's permanent is the one that pulls you out of the game." "You're creating a situation in your mind that has never happened and then reacting to the reactions of other people about a situation that has never happened." "Out of those 17 things, probably three or four of them are responsible for 90% of the income that I've made in the last decade." Connect with Travis: Instagram: https://instagram.com/travischappell Other: https://travischappell.com A Word from our Sponsor:Are you ready to start your own creatorjourney and make it big? Visitwww.fanvue.com today and launch yourcareer! Learn more about your ad choices. Visit megaphone.fm/adchoices

On this solo episode, Travis shares candid stories from his own entrepreneurial journey, walking through more than a dozen ventures that didn’t work out the way he hoped before his podcasting business took off. From childhood side hustles and landscaping to MLMs, door-to-door sales, and water purification, he breaks down how repeated “failures” created the skills, resilience, and opportunities that ultimately built his income today. On this episode we talk about: Why fear of failure and fear of embarrassment keep people from even taking the first swing at their goals How our social wiring, threat detection, and negativity bias make us over-index on what others might think The difference between temporary failure and the only real failure: quitting and pulling yourself out of the game Travis’s long list of experiments: landscaping, college side hustles, multiple MLMs, door-to-door solar, alarms, water machines, and more How just 3–4 of roughly 17 different ventures produced about 90% of his income over the last decade The transition from sales and MLM into podcasting, masterminds, courses, and live events Why leveraging other people’s time (hiring help) was a key early lesson in building leverage instead of just trading hours What the entrepreneurial path actually looks like emotionally: ups, downs, and the necessity of stepping back up to the plate Top 3 Takeaways The fear of other people’s reactions to your failure is often more paralyzing than the failure itself, and it’s usually based on imaginary scenarios that have never happened. Entrepreneurship is inherently experimental; most attempts won’t be home runs, but a small percentage of ventures can drive the majority of your long-term income. A failure only becomes permanent when it causes you to quit — as long as you keep getting back in the game, each “loss” becomes data, skill-building, and positioning for the next win. Notable Quotes "A failure is not a failure at all unless it causes you to quit. The only version of failure that's permanent is the one that pulls you out of the game." "You're creating a situation in your mind that has never happened and then reacting to the reactions of other people about a situation that has never happened." "Out of those 17 things, probably three or four of them are responsible for 90% of the income that I've made in the last decade." Connect with Travis: Instagram: https://instagram.com/travischappell Other: https://travischappell.com A Word from our Sponsor:Are you ready to start your own creatorjourney and make it big? Visitwww.fanvue.com today and launch yourcareer! Learn more about your ad choices. Visit megaphone.fm/adchoices

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SOLO | Make Money By Failing Forward

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This episode is 16 minutes long.

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This episode was published on May 14, 2026.

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On this solo episode, Travis shares candid stories from his own entrepreneurial journey, walking through more than a dozen ventures that didn’t work out the way he hoped before his podcasting business took off. From childhood side hustles and...

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