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Every entrepreneur reaches a breaking point—the moment when drive meets exhaustion and you realize your business can’t depend on you forever. In this episode, Michael Cole shares how he went from Navy veteran to first-time barbershop owner to financial planner for beauty professionals—and what he learned about building a business that works for you, not the other way around. Michael’s story is about leadership, structure, and freedom: creating a culture where people stay, systems that sustain, and financial strategies that secure your future. Whether you’re behind the chair or leading a team, this conversation will change the way you think about ownership, wealth, and balance. In This Episode: 0:00 - Intro 2:10 - The power of people over profit 6:00 - Lessons from opening a barbershop with zero experience 10:20 - Building culture: hire slow, fire fast 14:00 - Retention as the real measure of success 18:00 - The fear of pricing and learning confidence in value 22:30 - From operator to owner: letting go to grow 27:00 - Designing a business you can step away from 31:00 - Why every entrepreneur must plan their exit early 36:00 - Creating a strategic cash reserve for stability 40:00 - Preparing your family and business for the future 45:00 - You can look rich or be rich—but not both 48:00 - Final reflections Key Takeaways: Retention and culture are stronger than any P&L statement You can’t grow if you can’t let go Price confidently—undervaluing your work delays freedom Plan your exit the day you open your doors Build a financial strategy that protects your family and your business True wealth is freedom, not appearances About Michael Cole: Michael Cole is a Certified Financial Planner, founder of Cole Wealth Management, and owner of a Charleston-based barbershop that has operated successfully for over a decade. His work focuses on helping beauty, salon, and wellness entrepreneurs create wealth, protect their futures, and design businesses that thrive without constant oversight. Website: https://michaelcole.nm.com Instagram: / j.michaelcole Thank You to Our Sponsors Vish: https://getvish.com Phorest: https://www.phorest.com Salon Books: https://www.mysalonbooks.com Salon Cadence: https://saloncadence.com 🔔 Subscribe for More Episodes If you’re ready to build a company that gives you time, purpose, and wealth—not just work—subscribe and turn on notifications. New episodes weekly featuring real stories, practical strategies, and insights from leaders shaping the future of the beauty and wellness industry.