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Men of Tampa Bay 30-Day Challenge

The 30-Day Challenge is a guided experience designed to build clarity, connection, and momentum for entrepreneurs in the Tampa Bay area. Through weekly in-person gatherings, daily practices, and focused themes—Mindset, Vitality, Wealth, and Love—participants move through a steady, intentional rhythm of growth. The journey concludes with a celebratory gathering alongside friends and family, honoring both completion and what comes next.

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Wednesdays Off Podcast

This show is for entrepreneurs who want more freedom, not more grind. Each episode explores how founders and creators are breaking old patterns, reclaiming their time, and building lives that their businesses serve, not consume. Whether they’re feeling stuck, scaling fast, or already free and seeking continued alignment, Wednesdays Off is here to support them.

For founders willing to question what they’re building, and who they’re becoming in the process.

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The Rebel Experience

30-Day Challenge

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Community

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Adventures

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Our Promise

“Routine Rebel is more than just a company, it’s a personal commitment to help entrepreneurs and other freedom seekers like you live fuller, more intentional lives. The changes we facilitate aren’t just about escaping the mundane. They’re about growing as a leader, reimagining how work gets done, and designing a professional life that sets you free. This kind of growth doesn’t just transform your schedule; it transforms your presence at home, your impact at work, and your capacity to experience life with ever-increasing freedom and joy.”

-Stavros Michailidis, Founder, Routine Rebel LLC

What People Are Saying

Stavros is an amazing person and every entrepreneur can learn from him. Highly recommend. The events he puts on will help you break through your current obstacles.

Paul

Routine Rebel! Most of my personal growth has required hard work and discipline. When I heard about an excursion where participants would address a specific topic or theme for study, meaningful insights, and personal growth, but that the excursion also included adventures/activities, I assumed the two were mutually exclusive, or, if related only by design for one to offset the intensity of the other. Our theme was "address the lessons we refuse to learn" - a great topic! Kudos to Routine Rebel, a masterful demonstration! The results: It wasn't hard, it was fun. It didn't require discipline; the concept of discipline is alien in an environment of wholesome fun. And yet...the pearl of wisdom did manifest as advertised! I'll be back.

R T

I had an incredible experience with the Adventure Racing outing! The best part was it wasn’t just about racing. Routine Rebel cued up thoughtful ways to tie the experience to my business life. From structured “pre-briefs” to a post exercise deep dive, I gained a ton of insights and also learned from the others in the group. If you’re looking to advance your business mind and have a ton of fun, I highly recommend it!