Michael O’Shaughnessy on Growing a Landscaping Business

In this episode of the Kanawha Valley Hustlers podcast, I talk with Michael O’Shaughnessy about building a landscaping business that grew from a two-person lawn care crew into a company that handles landscaping, hardscaping, patios, retaining walls, drainage, and outdoor spaces. He makes it clear that this work is about more than mowing grass. It is about solving problems, improving curb appeal, and building spaces people can use.

What stands out to me is Michael’s honesty about business ownership. Even after years in the field, he still talks about the weight of responsibility and the feeling that there is always more to learn. One lesson he learned the hard way is that you cannot wear every hat forever. He found out through experience that a business grows faster when you bring in people who know more than you do in key areas and when you trust them to carry part of the load.

We also get into the problems he faces now. Staffing stays hard, and seasonality shapes the whole business. Winter slows some parts down, even with snow removal, while the busy season brings long days and nonstop work. Still, he leans into that pace because he likes the work and the life that comes with it.

Michael also shares a few sharp lessons. Door hangers were one of the best small marketing investments he made. A used dump truck was one of the worst. He believes every entrepreneur needs hunger, self-awareness, and the ability to keep growing. The skill he is still working on is letting go of control. At the core of his outlook is a simple belief: if you can get up and keep moving, there is still a way forward.