In this episode of The Monetize, Tim Conley sits down with Shea to dissect a hard truth: no matter how many times you pivot businesses, your problems follow you because you bring the same beliefs, emotions, and habits into every venture. They trace Shea’s journey from burned out consultant with a “Four Hour Work Week” lifestyle he hated to a creator rebuilding his life and business around genuine passion.

Tim introduces the idea of entrepreneurs as both arsonist and firefighter, setting their own businesses on fire out of boredom, then rushing in to save them. The conversation dives into the difference between delegating and abdicating, why control and ego quietly destroy freedom, and how systems, rules, and honest self awareness let you grow without burning everything down.

Together they explore practical examples from Tim’s coaching clients, failed and successful ventures, and Shea’s new multi creator travel brand to show how facing your emotional baggage, including fear of numbers and pricing, is the real leverage point. If you have ever secretly hated the business you built, this episode will feel uncomfortably close to home in the best way.