Didn't Want to Sell. Then Life Changed.

The Turn: Blue Collar to Billions · May 12, 2026 · 21m

Jay Maier started a tree service company in Rochester, Minnesota at 29. No business background. Parents were educators. He paid himself $36,000 a year on $180,000 in revenue and reinvested everything else into equipment and people. He scraped, clawed, and grew—slowly and conservatively.

The real shift came around 2005 when Jay stopped doing the work and started developing the people who did it. He realized his best value wasn't trimming trees—it was making sure everybody knew exactly what to do. That mindset change took him from a self-employed tradesman to a business owner. By 2013, he was…