In my first two decades as a small business owner, I couldn’t imagine selling my business. And I think, like a lot of small business owners, I felt a small touch of moral superiority over business owners who did sell. In this conversation with Christine Trumbull on her valuable Mastering Your Exit Strategy podcast I had an opportunity to dig into the mind-shift and freedom that I’ve experienced in my career as I moved from a small business owner into truly viewing myself as an entrepreneur, and moreso now as a serial-entrepreneur.

“So my first company I started was my baby, it was the thing that I put all my energy into, it was built around me, I was an integral part. And then when I started hiring employees, I was looking for people who were clones of me. And I couldn’t find clones of me, I couldn’t find people who would care about the business as much as I did. And over a 20-year period, I slowly learned that good employees don’t necessarily see the world the way an owner does. And I started to see that my attachment to the business might actually be getting in my own way.

“In a lot of ways, my IT company, which was a small little thing, could grow only maybe like 1x or 2x bigger than me because I was attached to every single facet of it. It was my life.”

“…And I think that’s what started me on my path towards understanding that a business’s needs and my personal needs are not the same. The more that my Venn diagram showed me and my business overlapped, the less freedom in life I had. And the business was never really built to scale because it was always built around me.”