In this episode , we sit down with Harry Olson of Hugo Tree, a second-generation tree service company based in Minnesota, he talk about the real journey of building a sustainable tree business. What started in the late ’90s during the Dutch Elm Disease crisis grew out of necessity, grit, and a willingness to take on the jobs no one else wanted. For years, the company stayed intentionally small, focused on hazardous removals and word-of-mouth work—until a new generation stepped in and began reshaping what the business could become.

We dive into what changed when ownership transitioned, including the move from paper-based systems to digital operations, the importance of branding crews and equipment, and why marketing only works when your operations can actually back it up. This conversation goes beyond ads and websites and gets into the unglamorous but critical side of growth—quality control, equipment investment, hiring experienced people, and protecting your reputation in the community.

If you’re a tree service owner navigating growth, dealing with long backlogs, or trying to balance marketing with operations, this episode offers honest insights from the field. No shortcuts, no hype—just real lessons from a company that learned how to modernize without losing the values that built it in the first place.

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From Hazardous Jobs to Full-Service Growth: Harry Olson of Hugo Tree