Why Entrepreneurs Stay Stuck (And How to Actually Move Forward) | Christian Rawles

Christian Rawles didn’t just build a brand in the outdoor industry, he spent nearly two decades learning what it actually takes to run one, eventually buying and leading the business himself.

Christian is now an executive coach working with entrepreneurs who want to build businesses that align with their values, not just scale for the sake of growth. His work focuses on clarity, self-awareness, and helping founders close the gap between where they are and where they want to be.

Jon and Christian explore what it really looks like to build a career intentionally, and why so many entrepreneurs stay stuck even when they’re doing everything “right.”

Jon chats with Christian about:
• starting at the bottom and learning how a business actually works
• working for free or cheap to create career inflection points
• why working in the outdoor industry isn’t always what people expect
• how he transitioned from founder to executive coach
• the difference between being stuck and being unclear
• the “gap vs. gain” framework and why it changes everything
• fear of success vs. fear of failure
• defining success beyond money and metrics
• the role of presence, gratitude, and self-awareness
• why entrepreneurs need new definitions of success

Stay connected:

Christian's Website: https://www.christianrawles.com/

This episode is supported by:

⁠The Huddle⁠: If you’re at the point where going at it alone isn’t working or you’re ready to level things up in your business, go to https://findmyhuddle.com/ and fill out the application

⁠Popfly⁠: If you’re a brand trying to reach outdoor, travel, and adventure audiences, Popfly is where to do it. It connects you with the largest communities of adventure creators and handles the entire process from start to finish. To learn more:

⁠Creators click here: https://popf.ly/longrunlabscreators⁠.

⁠Brands click here: https://popf.ly/longrunlabsbrands⁠