Michael O’Shaughnessy on Growing a Landscaping Business

About this episode

Michael O’Shaughnessy discusses the growth of his landscaping business and the challenges of entrepreneurship.

In this episode of the Kanawha Valley Hustlers podcast, I talk with Michael O’Shaughnessy and talk about how his business grows from a small lawn care crew into a company that handles landscaping, hardscaping, patios, retaining walls, drainage, and more. What I like most is how honest he is about the business side of it. He admits that even after years in, there is still more to learn, and he talks about the trap a lot of owners fall into by trying to do everything themselves. He makes the point that growth really starts when you bring in people who know things you do not and learn to trust them. We also get into the real challenges he deals with now, especially staffing and the seasonal nature of the work. On top of that, he shares a few lessons from the field, like how simple marketing tools such as door hangers can work, and how a bad truck purchase can turn into a headache fast. His mindset is clear: keep growing, stay hungry, and keep moving forward.

People in this episode

Host: Joe Justice

Guest: Michael O’Shaughnessy

Topics covered

• landscaping
• business growth
• entrepreneurship
• staffing challenges
• marketing strategies

Keywords

• landscaping
• business growth
• staffing
• marketing
• entrepreneurship

More episodes of Kanawha Valley Hustlers

• Saving What Matters with Jesse A. Lewis · June 11, 2026 · 8 min
• Building Better Real Estate Systems with Shelby Pritt · June 9, 2026
• Mykah Ballard on Building a Message That Reaches the Right People · June 4, 2026
• Early to Bed, Early to Rise, Work Like Hell and Advertise · June 2, 2026
• Peyton Ballard and the Power of Saying No · May 28, 2026
• Bryson Cutler on Manufacturing, Marketing, and Handmade Glass · May 26, 2026