In this episode, host Thad Miller sits down with Brent Claymon, a lifelong entrepreneur, investor, and business builder, to explore how vision, timing, and patience shape every stage of the entrepreneurial journey. From growing up in a family of founders, to selling Pac-Van in 2006, to re-entering the industry and acquiring Tyson Onsite after his non-compete expired, Brent has spent his life creating equity, surrounding himself with trusted advisors, and finding a better way to build lasting value.
Over two decades of buying, selling, coaching, and leading, he has learned that great entrepreneurship is not about chasing income. It is about thinking long term, listening more than you speak, choosing the right partners, and knowing when to move and when to wait. His 21 years of coaching high school tennis have also shaped his leadership philosophy, proving that clarity, encouragement, and strategic thinking matter just as much in the boardroom as they do on the court.
💡 In this episode:
• How growing up around entrepreneurs shaped Brent's mindset and career path
• Why the Pac-Van transaction became a defining moment in his journey
• How selling one business opened the door to acquiring another years later
• What vision, timing, and patience really look like in dealmaking
• Why his philosophy is to find a better way rather than flip for quick wins
• How coaching tennis has influenced his leadership, hiring, and decision making
• Why listening more and talking less leads to better deals and stronger teams
• What separates great entrepreneurs from good ones
• How to avoid being overwhelmed by the urgency and emotions of a transaction
• Why the first offer is often the best one and why patience builds leverage
• What sellers need to know about earn-outs, post-sale roles, and contingencies
• The biggest mistakes entrepreneurs make near the finish line and how to avoid them
If you are an entrepreneur, business owner, or leader navigating growth, acquisitions, or the next chapter of your career, this conversation will challenge you to think clearly, act intentionally, build equity, and surround yourself with people who help you see around corners.
🎧 Listen now and subscribe for more episodes of MATCHplayÂ
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