Your relationship with money: A lesson from selling my first MSP

When I was deciding if I should sell my first MSP, I was completely focused on the numbers. Every conversation was about multiples, EBITDA and maximizing the purchase price. So, when I spoke to one of my mentors about the decision, I expected more of the same financial analysis.

Not the advice I expected

Instead, he gave me some advice that I didn’t understand at the time. He said, “Gary, whether you get ten percent more or less from the sale of the business was not the most important thing.” I remember thinking he was crazy…wasn’t that exactly what mattered most?

Then he told me that when that wire transfer hit and I received the proceeds from the sale, my relationship with money would change—and that would be the most valuable result of the sale. I had never heard anyone use that term: “relationship with money.” It sounded like something you’d hear in therapy, not in a business discussion.

In the decade since, his advice turned out to be true, and it made me spend more time trying to understand not just the math, but also the emotional aspects of money. The sale did change everything—not just my bank account, but how I thought about risk, security, and what money really meant to me. This journey led me to read some books and speak to a lot of people on this topic from all walks of life, from successful entrepreneurs to financial advisors to people who grew up with very different economic realities than mine.

Where money beliefs come from

Through all these conversations, the biggest takeaway is that people have deeply held beliefs about money based on where they grew up, what they’ve experienced, and even the time they grew up in terms of what economic cycle they’ve lived through. These beliefs run deeper than we realize and often contradict what makes logical sense. Someone who lived through the Great Depression will view money completely differently from someone who grew up during the dot-com boom.

What I’ve learned is that we all think we make decisions rationally, but we don’t, especially around money. I’ve worked on educating myself on money and investing, reading everything from academic papers to behavioral economics books. I’ve made mostly good decisions, but I can point to a few situations where I made emotional decisions when the math said to take another route. Fear made me too conservative in some investments, while overconfidence led me to take unnecessary risks in others.

It’s not just about the spreadsheets

Here’s my point: We all have a relationship with money that can sometimes keep us from making the best decisions. It’s not just about having more information or better spreadsheets, but about understanding the psychological and emotional factors that drive our choices.

We need to build self-awareness about our own money beliefs, get advice from the right people who can see past our blind spots, and find the balance between math and emotions. Just like I learned when selling my MSP, the numbers matter, but they’re not the only thing that matters.

Related: The emotional side of selling: How to make sure you’re ready to step away