No one starts a business planning to mess up. But even the smartest founders and leaders make decisions that don’t go the way they expected. The best ones take those experiences and turn them into lessons that shape how they lead, hire, and grow.
We asked business owners to share the biggest mistakes they’ve made and what they learned from them. Their stories prove that failure isn’t the end of the road. It’s part of building something that lasts.
Growth Without Structure Creates Chaos
For Blaz Korosec, the early rush to grow came with hidden costs.
“I hired for growth, but not for structure. I thought more hands would solve it, but with no defined roles, I multiplied the noise. Meetings took twice as long, communication broke down, and expectations got fuzzy. I learned I should never hire more than I can train.” –Blaz Korosec, CEO of Medical Director Co.
That experience taught him that growth only works when it’s supported by systems. Before saying yes to expansion, he now audits his bandwidth and asks whether each new hire or project will actually save time or make money.
Leading With Integrity Builds Real Trust
In the beginning, one business owner focused on closing every deal. Over time, he realized that wasn’t the right goal.
“When we first started, I thought my job was to try and make every deal work for us. I learned that our real value is in providing the best solution for the homeowner, even when that means advising them that our cash offer isn’t their best option.” –Chris Mignone, Madison County House Buyers
That mindset shift built deeper trust and stronger relationships. Being a resource first proved more valuable than any single transaction.
Holding On Too Long Hurts Everyone
For Taylor Kovar, CEO, one of the hardest lessons came from waiting too long to make a tough call.
“One of my biggest mistakes in business was keeping people on the team long after I knew it wasn’t the right fit. I cared about them and didn’t want to hurt anyone’s feelings, so I convinced myself things would get better. They didn’t.” –Taylor Kovar, 11 Financial
Taylor learned that caring about people doesn’t mean avoiding hard decisions. Letting someone go can feel painful in the moment, but it often gives both sides room to grow.
Mistakes That Make You Better
Here’s what these business owners want you to remember:
- Growth should serve your structure, not overwhelm it.
- Integrity builds a business that lasts.
- Real leadership means making tough decisions with compassion.
Mistakes are inevitable, but they’re also the moments that push you to lead smarter, build stronger, and grow in the right direction!