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Chris Cangero By Chris Cangero • June 3, 2020

An Entrepreneur’s Guide to Mastermind: Getting Started

At the start of my career, I finished school, and I asked myself, “What do I want to do”? The answer was easy: I want to be an entrepreneur; I want to figure out how to run a business. Where best to learn than from my father, an entrepreneur willing to tell me everything – the good, the bad and the ugly. 

In that sense, I’ve had coaching my entire professional career. There was a mentorship period of about eight to ten years with my father. Eventually, I made my way around the company in various roles and positions: sales, operations, service, and support. This exposure provided a well-rounded kind of experience set and deep appreciation for mentors. With that background, I came into the Mastermind program and what led to an easy transition to working with Cathy Kenton.

When you have a mentorship program, it is like anything else; it only works if both parties bring what they need to the sessions. In my experience, Cathy’s responsibility was to bring expertise, wisdom, insight, and a thoughtful breakdown of information and recommendations. My responsibility was to bring my Untitled design-8genuine interest in getting the most out of the program.

Think of it this way: every session has a cost to it, and I’m not just talking about the financial costs. There is a time cost, where the time spent must have value. When I started working with Cathy, from the very beginning, it felt natural. We were both prepared and understood what needed to be brought to the table. 

Although we have some long-winded intros, where we catch up and say hi for maybe five or ten minutes, my sessions have always been very productive and informative. Each session includes a discussion around what we are doing that week and what is happening in the industry. In the end, our conversations always return to the larger picture: where I want the company to be, what I need to do to get there, and how current events may affect that larger plan.

The way I think of entrepreneurship is like a pyramid. You have the tasks that you have to do on the bottom row, and you’re working your way up towards your end goal. First, you need to tackle the 35 things at the bottom level to bring you closer to your goal. Maybe they accomplish a subset of goals. And then you’re continually completing tasks that move your business towards that top point, the ultimate objective.

The true value of the Mastermind program is Cathy’s intuitive understanding of that ultimate goal. There is an objective down the road for where I want to be, and she knew what we had to do to get there.

For me, that end goal is a positive impact on the community that we serve. And it’s more of an achievement-oriented plan, than a financial-oriented goal. I am not looking for a coach simply focused on an exit strategy – I needed someone like Cathy that understood and aligned with that community plan. 

That’s important, from a customer, to recognize that your consultant sees your objective, acknowledges that you’re there for genuine purposes and wants to help you push that vision forward. And that alone reinforces why the Mastermind program works so well. As sincere as my intentions are, so are Cathy’s in coming to meet me halfway and help my business grow.