Why You Feel Trapped in a Business You Built to Be Free (+ How to Change It)

Oct 21, 2025

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Chris and I are in full-on prep mode for our Elite Entrepreneur Mastermind, and it reminded us of one truth we see every time most people start their business: they chase freedom, and end up feeling more trapped than ever. Many entrepreneurs start a business for time freedom and financial freedom, then feel like they have neither. In this episode, we talk about what we’ve learned from 15+ years of masterminds, what freedom in business actually looks like, and the two levers you can pull right now to create more freedom without blowing up your business. Get ready to rethink how you define freedom and start building your business and life on your own terms.

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HIGHLIGHTS

How 15 years of entrepreneurship shaped the way we build our masterminds.
Why time freedom is a common struggle for entrepreneurs.
Why most entrepreneurs feel trapped by their success.
The two levers that determine your freedom.
How resetting your expectations can instantly reduce pain and pressure.

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