Crockett Crothers, host of The Wealthy Cowboy, joins Josh for the very first guest episode of Freedom by Design. From day-working cowboy to building one of the most recognizable brands in Western entrepreneurship, Crockett pulls back the curtain on how it actually happened — the mindset shifts, the rejection, the rewiring of his beliefs around money, and the moment the pain of staying the same became greater than the fear of the unknown. This is a grounded, no-fluff conversation about wealth, faith, family, freedom, and what it really takes to step out of your comfort zone and build a life on your own terms. Key Takeaways 1. Commit to the date, then figure it out.Crockett didn't wait for the logo, the studio, or the perfect setup. He picked a launch date, jumped off the cliff, and grew wings on the way down. Most people stay stuck because they keep climbing back down the cliff instead of jumping. 2. Information is cheap — execution and accountability are the bottleneck.You're not stuck because you don't know enough. You're stuck because no one is holding you accountable to take the next step. Coaching isn't about new information; it's about pressure, structure, and forward motion. 3. Wealth ≠ a dollar amount. It's an abundance of assets.Faith, family, freedom, time, relationships, health, and money — all of it. You don't have to sacrifice one to build the other. You can have both. 4. Your beliefs about money will either attract it or repel it.If somewhere deep down you believe money is bad or that wealthy people are bad, no amount of hustle will fix it. The paradigm has to shift before the bank account does. 5. The fastest way to make more money is to solve bigger problems for more people.Stop chasing the money. Chase the value. The money is the byproduct. 6. Rock bottom isn't required, but pain is.You won't move until the pain of staying the same is greater than the pain of the unknown. The sooner you create that pressure on yourself, the sooner you move. 7. There's almost no real risk in betting on yourself.If you try and it doesn't work, you're back where you started. If it works, it changes your life. That's not risk — that's asymmetric upside. 8. Successful people aren't that special. They just stayed hooked longer.The biggest mindset unlock from being around high performers is realizing they're regular people who didn't quit. That's it. That's the difference. 9. It sucks for everybody.There is no shortcut around the sucky period. Broke, scared, doubting, wanting to quit — that's the price of admission. Different flavor for everyone, but no one skips it. 10. Get rewarded for discomfort once, and you start chasing it.Comfort zones aren't broken — they're expanded. Each rep makes the next leap easier, until you're actively looking for the next uncomfortable thing because you know that's where the growth lives. 11. Regret lives in what you didn't do.Almost no one looks back and regrets the chances they took. They regret the conversations, investments, and leaps they avoided. Live in a way that makes for a good story. 12. Freedom is the prize.Not money. Not status. Freedom to choose your day, your people, your purpose. Build the business and the life that protects that — don't sacrifice it in the chase.
