High School Dropout to 5-Star Tree Service Owner - Ep. 218

From dropping out of high school to running a multi-award-winning tree and winter services company — Matt Wingate, owner of Lakes Area Tree Guys LLC, joins Kaleb for a raw conversation about what it really takes to build a business from the ground up. Based in Lake Geneva, Wisconsin, Matt shares how he built a 5-star-rated company with zero advertising, a loyal crew, and a reputation that speaks for itself. The two dive into the grind of running a service-based business, handling daily chaos, managing growth, and keeping customer relationships at the center of it all. They also talk about leadership, the mindset behind staying small but mighty, and why going back to simpler values still matters in today’s world of business. Whether you’re an entrepreneur, tradesman, or just someone who respects hard work and straight talk — this one’s for you. Follow & Connect with Matt: 🔗 Socials: 📸 Instagram: @mvwingate 📘 Facebook: @thetreeguys 🎵 TikTok: @mattwingate1 🧰 We’re Proud Jobber Ambassadors! Get a free 14-day trial + 20% off your first 6 months using our link: 👉 https://go.getjobber.com/pagelservices