MARK KOHLERMain Street Professionals, Main Street Professionals, Main Street Professionals, Main Street Professionals, Main Street Professionals, LLC · Owner at Main Street Professionals, LLC

I Cried When Firing My First Employee

16 Jan 2026 · 0 min

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In this personal anecdote, Mark Kohler recounts the emotional difficulty of firing his first employee while running a janitorial business he started in college. He describes his background of working as a janitor for seven years, gradually hiring and replacing staff, growing the company to about 25 active employees, and eventually selling the business before attending law school. The focal moment is the first termination—a carpet‑cleaning hire who wasn’t a good fit—where Kohler admits he cried, vividly recalling the employee’s appearance and the setting. The story underscores the human side of entrepreneurship, the challenges of leadership, and the lasting impact of early managerial decisions.

When I fired my first employee, I cried. I really did. He's like, it's okay. Yeah. Yeah. Oh, my gosh. It was when I had my janitorial business in college. I worked for seven years working as a janitor and replacing myself, hiring more janitors, and I ultimately sold the business. Before I went to law school, I had 25 active employees sold the business. But I remember the first guy I hired to help clean carpets and clean and this and that, and he was not working out. And when I had to fire him, it was the hardest thing. I still remember where I was sitting, what he looked like.