Finding Growth and Support in Mastermind Groups

This article was originally written for UPPERCASE magazine, where I’ve been the business columnist for many years.

Though I started my business alone, last year I found myself pouring out all my worries about an employee problem to six friends (who also run their own businesses) over drinks and French fries in Vegas. Instead of guessing at what to do, I got to hear their stories and advice, and make an informed decision. And then we all rode the monorail to see the Michael Jackson Cirque du Soleil show.

One thing I have stuck with over the last decade of growing my business is participating in peer groups to learn, share and get general support. This has been great for Aeolidia, my web design agency, and I have also made some real friendships with people I relate to.

You don’t have to be a lone wolf if you run a business. In fact, creating your own wolf pack can make everything better. Entrepreneurs, artists and makers are usually figuring out how to do everything on their own, often the hard way. There is a lot you can miss by going it alone. That is where mastermind groups come in.

Fun fact! Today I learned that the name “mastermind group” comes from a concept by self-help author Napoleon Hill, from 1925, that two or more minds coming together create a “master mind”—a third, intangible force. I’m in!

What is a mastermind group?

Unlike working with a coach or mentor, a mastermind group of peers is a reciprocal relationship and can provide more of a feeling of camaraderie. Masterminds tend to be groups of two to 10 people, so you have the ability to get to know each other well. And they tend to meet on a regular schedule, perhaps one to four times a month. Masterminds can meet in person or on video calls.

In a group like this, you can share your experiences and get new ideas for what you are working on. You can ask questions, learn from others’ mistakes and keep each other accountable. You may be able to skip time-consuming research or avoid costly mistakes when others in the group share their own experiences.

It can be interesting to get an outside perspective on your own business, since you can be too close to see it clearly. It is helpful to get a sanity check: am I doing things wrong, or is this just how the industry is for everyone right now?

I have brought problems to my groups that range from employee issues to project scheduling. I have offered my thoughts on content marketing and sticking to deadlines. I have also laughed my booty off, cried a bit and vented.

Who to include

Ideally, your group will provide you with perspective, insights that you can put into practice, lessons learned, accountability and solidarity. When looking for members, you want people who will be open, trusting and trustworthy, vulnerable, and supportive. You want good listeners who are enthusiastic about sharing resources.

Along with gathering good people, it is also helpful to think about the type of group you want and what your goals are. I have been in a variety of groups, and they all offer something unique of value. For instance, you can have a group whose members are very similar, or one whose members are quite diverse. I am currently in one of each kind of group.

One group only includes Shopify web designers and developers. We do the exact same work for the same customer base. This means that we can get extremely detailed on our calls, digging into what apps we use, and discussing changes to the Shopify Partner program. I am an open book in this group, because Aeolidia’s niche is so specific that I don’t feel competitive. It can be helpful to share a specialized problem and use your industry jargon to talk to people who have done the same exact thing as you.

On the other end of the spectrum is my Goldman Sachs 10,000 Small Businesses (10KSB) growth group. We are in totally different trades, from HVAC to transportation to the restaurant business. In the Goldman Sachs program, they told us we would be surprised by how much we could help each other, even across industries, and they were right. It turns out that business is business, and sometimes a perspective from another industry can be invaluable. While the folks in this group have no idea what apps I should use, their big-picture advice is golden and helps me see beyond my niche.

Alternatively, you may want to be in a group that is adjacent or related to what you do, but not a group of your competitors. For instance, I have been part of a group of graphic designers, which was great for networking. And I have participated in a retail group, which was eye-opening as far as seeing things from my clients’ perspective.

In any group, it is all about finding the right fit and making good use of the opportunity. Remember that giving should take priority over receiving, in relationships of any kind.

How to get started

Once you have gathered your group, you will want to sort out the logistics of how often to meet and where to meet. Monthly is usually a good start. If you want to get into a good rhythm, twice a month is often enough to stay caught up with each other without taking up too much time.

I find that until people get to know each other well, it is good to have some structure. In one of my groups, we had an accountability document to fill out before each meeting. We each got 15 minutes to share our updates and get feedback. Now we know each other well, so we can just jump on the call and dive into updates, problems and questions.

Our accountability document asked about:

• our wins since the last meetup,
• losses/lessons learned since the last meetup,
• our current pain points,
• goals that we wanted to reach by the next meetup, and
• any other notes that we had.

It can be hard to pull busy people away from their work. Knowing that you will hear people’s informed thoughts on all the above makes it easier to prioritize the meetup. Even pulling this information together on a regular basis is healthy for your business. Having some trusted people to run it by adds another layer of value.

How to evaluate

There are two groups that I have been in for more than six years each. I have also been in a handful of other groups that didn’t last more than a few months. Not every group will work out, and your time is valuable, so it helps to evaluate the mastermind group after a while.

You need to give it a chance—it takes a while to get into a rhythm and trust each other. Things should be clicking by your third or fourth meetup. When I get on the call with my agency buddies, the time flies by, and we have more things to talk about than time to talk, so that group feels healthy and useful. The people in my 10KSB group, who helped me fire an employee over drinks and fries, would rescue me from a burning building. In other groups, it can be hard to get everyone to even show up, or you may run out of things to talk about.

It helps to have a goal or purpose for the group. Is there a specific problem you are working on, or an ambitious business goal you would like support with? Maybe you are trying to build accountability into a freelance lifestyle, or just want a group of people who get it, that you can rant and rave to. Is your group meeting those needs?

Does it feel like each member is contributing equally? I have been in a group with three experienced founders, and a fourth person who was brand new. It felt like he did not have anything to share that helped us and was just taking notes on everything we had learned the long and hard way. As long as everyone can contribute helpfully, a disparity can be fine. If not, imbalances can lead to resentment, leaving some people feeling like they are giving much more than they are receiving.

Do your values match with the group’s? This is an area of misalignment that usually does not work well in a mastermind group. For me, it is important that my groups stay generally positive. It is okay to complain now and again, but I did not sign up for pessimism or bad attitudes. I have heard that you end up being the average of the five people you spend the most time with. I want to surround myself with positive, motivated people who are interested in learning and growth.

Remember, this is a two-way (or four- or six-way) street. Lead the way by giving, sharing, being open, focused and not hiding your mistakes. What can you offer, and what can you be generous with? What kinds of partnerships or collaborations might arise from your group? Like any worthwhile relationship, it takes regular and purposeful work to build trust and create a collaborative environment. It does not just magically happen because you get five people in a room together or on a Zoom call!

After giving it a solid chance, you can quit if the group does not suit your needs. If everyone else is getting something out of it, you could suggest a replacement for yourself and exit the group. If it is not working overall, you can thank everyone for giving it a chance, and call it.

A little encouragement

Following your competitors’ businesses on social media can feel disheartening. You see their highlights and successes—but everything’s different behind the curtain. Why not join them to support each other? You’ll then get insider access to all the mistakes and hard work that goes into what looks so easy on Instagram.

I really could have used a group like this earlier on in my career in business. I often feel like I am humblebragging when celebrating my success or complaining about my work with laypeople. But my founder friends just get it.

My advice to my past self (and you!) would be to not wait for these groups to come to you—take the initiative to form them, and you will likely find grateful people who are looking for this exact thing.