Interview

Mike Calhoun has spent twenty-eight years in sales and the last ten building Board of Advisors, a peer group for operators that began with quarterly meetings in Tampa and now holds quarterly summits in Dallas. The company’s value proposition is unusual for its category. It does not sell content. It does not rely on speakers. It is built around one idea: the room.

At fifty, Calhoun is deliberate and difficult to impress. He speaks about his work with the clarity of someone who has moved past theory and into pattern recognition, focused less on performance and more on what actually drives results.

Q: Most people use the term “Board of Advisors” loosely. How do you define it?

A board of advisors is different from a board of directors, and most people don’t know the difference. A board of directors is accountable to the shareholders. They are the ones making sure the company is profitable and running lean. But it is hard to grow when you are not investing in yourself or the company, so you cannot always be pushing for a bigger profit every quarter. Sometimes you have to take a step back to invest.

A board of advisors is different. Think of Elon Musk who wants to go to the Mars. He rallies trusted advisors who are committed in some way, sometimes through fees, sometimes stocks, sometimes options, sometimes a hybrid. They bring their years of experience, their Rolodexes, their intellectual property. He may not call on them often, but when he needs them, they are there. A good board of advisors meets regularly so they are inching toward the larger goal. The Board of Advisors is in alignment with the founder’s vision. The board of directors is in alignment with making sure the shareholders are happy.

Q: How big does a company need to be to have a Board of Advisors?

It is not about size. If you have a great idea, you need an amazing operator first, because that is your integrator, the person who gets things done. You also need a team to keep you from getting drunk on the line of opportunity, and that is your board of advisors.

The mechanic is simple. Make a list of the top twelve people you respect enough that if they shot down a great idea of yours, you would walk away from it. They are people you trust, people who have already done something similar to what you are trying to do. Take any great idea and put it under the fire of that list.

This is not just for ventures. It is for life. Entrepreneurs have great ideas all the time that should usually be shot down if they are not making the core thing better. If you do not have a board of advisors, get one. Whether you have a business right now or not, it will be the best genesis of any new idea you ever start.

Q: Talk about your first meeting. How did Board of Advisors actually start?

I had done a lot of online business development. Three SaaS platforms, a lot of real estate. We built the first web-based, user-based version of a short-sale processing engine out of Silicon Valley. Real bang, from startup to some of the biggest players calling me up saying I was taking too much of their market share. I was working hard, but I could not see far enough out to protect myself from failure. That is why you need people around you.

When I put on the first board of advisors meeting, I picked up the phone, made a spreadsheet, called and texted. I still have that spreadsheet. I laugh at how unsophisticated it was, but it was targeted at the right conversation. They were the people I was actually scared to let down.

I tried to call it a mastermind at first. These were big operators, and they had no idea what a mastermind was. So I changed the pitch. I told them I was having a meeting on the beach with the people I had been taking care of for twelve years and that I wanted them to come meet some of them. That was much easier than selling something I was not even sure of myself.

One of the guys who came had six thousand dealerships on his platform. He told me he was normally the biggest guy in the room, and at this meeting he was sitting taking notes, trying to figure out what he could learn from the others. That was when I realized the magic. Get the right people in the room. That is it.

“You need a team to keep you from getting drunk on the line of opportunity. That is your board of advisors.”

Q: You do not host speakers. Why?

We have never had a speaker. Every member joins as an advisor to the board. When someone qualifies, we make it official. I interview them and we take a complete inventory of what they bring to the table: their intellectual property, their years of experience, their Rolodex. Going through that interview, the person starts to realize how valuable they are. They get motivated to come to the table and contribute.

It becomes a Shark Tank kind of perspective, where they are putting something in front of the group and asking who they can help. That is what I wanted it to be. I did not want a mastermind. I wanted it to be valuable, because I did not want to be in the room myself if it was not.

Q: Why five days, quarterly?

Five days gives us about ninety percent attendance, because someone can usually make the front of the week or the back of the week. If I did three days, they would miss it for a competing obligation. If I did seven, attrition kicks in. If I put it in the middle, they can only make one day. Five days lets them come for two and a half on either end and still log meaningful time.

If they come every quarter, they stay. If they miss one, now they are on a six-month gap and they have lost momentum. It is like going back to the gym. You love it once you are sore, but the hard part is getting back there. Their head is full of excuses. They are too busy. But I am the one who gives them their time back.

“I did not want a mastermind. I wanted it to be valuable.”

Q: What is the trade-off you have had to make as the company has grown?

I am the guy who needed all the help. I did not come from an advantaged point. So my instinct is always to look for the guy I used to be and help him.

What I have learned is that the more an operator has to work with, the more we can expand. When they have teams, resources, funds, intellectual property, the speed at which we can get things done is wild. Versus jacking around with someone in the corner trying to convince them of what is possible. You have to know what to do with your time. It is a wild dynamic, because we also do not want to exclude anyone. But your dollar replenishes. Your time does not.

Q: What advice do you give the early-stage entrepreneur right now?

Number one, you have to be using AI. Get familiar with one as your daily companion. Whether it is Grok or Claude or whatever else.

As an entrepreneur, the entire process is convincing people of your idea and getting them to execute on it. The problem is never that the idea is unclear in your head. The problem is getting it played out by the team. With AI as a companion, you have a constant. You can challenge it, have it challenge you. It accelerates how quickly you can crystallize what is possible before you put a dollar behind it. Then you can vibe code something, run market research, and identify the strategic joint venture partner whose audience would fit your product. You can move at the speed of light putting a business case together. You do not have to waste time or money.

The other thing I would say is about content. Right now, everyone is looking at a video and asking, is that AI or is that real? In a year, ninety percent of social media will be AI. The reason live content will win is that it is the only way left to be real on social media. You will have your variants, your robots, your agents. But the real you, in a live format, is what people will pay attention to. The platforms know it, and they will reward it. Get good at going live, or get good at putting your ideas through the fire of AI. Better, do both.