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This episode of Best For Business sits down with Jamie Jamitkowski, the visionary founder behind Chaotic Wrestling, for one of the most detailed and important conversations in the history of the podcast. Jamie walks through how his love for pro wrestling began, growing up as a fan, not even realizing independent wrestling existed, and the moment that sparked the idea of “we should start a wrestling company.” That idea would eventually turn into one of the most influential independent promotions in New England history.
Jamie breaks down what it was really like owning and operating a wrestling company, starting Chaotic Wrestling from the ground up, running the very first show, setting goals, and becoming more serious as the company grew. He explains his personal motto, the reasoning behind Chaotic Wrestling contracts, why the word “World” was dropped, and how bringing in outside names helped shape the promotion. We dive deep into understanding independent wrestling from a promoter’s point of view and why Jamie felt Chaotic needed to be tied to the WWF/WWE to truly grow.
The conversation covers Mike Hollow running the school, building a working relationship with WWE, and how the talent exchange actually functioned behind the scenes. Jamie explains what made the Jamie/“Adult” partnership work, finding the Polish American Veterans Club, and making difficult decisions like firing Matt Logan and RJ Deluise. From there, we get into the creation of Cold Fury, crowning the first champions, establishing the heavyweight title and other championships, and the dispute over the “Breaking Point” name with WWE.
Jamie shares incredible insight into what stood out about Kofi Kingston, how Kofi was discovered, how Antonio Thomas (Santell) got signed, and stories behind booking names like Sunny and Bret Hart. One of the most unbelievable chapters of Chaotic Wrestling history is explored in detail — Chaotic Wrestling’s homecoming featuring John Cena and Vince McMahon, including how it happened, how Vince McMahon ended up stepping into a Chaotic Wrestling event, and what that moment meant for the company.
Jamie also explains why he never stepped foot in the ring or booked himself into storylines, what his role looked like on show day, who his biggest mentors were, and what led to stepping away from pro wrestling. We talk about Chase Del Monte taking over, being inducted into the Chaotic Wrestling Hall of Fame, celebrating 25 years of Chaotic Wrestling, and what Jamie is up to now with Prop Store.
All this and more on Best For Business with Jamie Jamitkowski.
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