Lessons learned from 6 different mastermind groups

Multiplier Magazine
8 min readAug 17, 2017


This was originally posted at Entrepreneurs in Motion.

For anyone who doesn’t know what a mastermind is — it’s a small group of people (usually 3–6 people) who meet and talk with some frequency in order to to help each other improve and achieve goals.

When I originally heard about the whole concept of masterminds, I thought they were for weak people who needed hand-holding or excessive encouragement to take even tiny steps — but boy, was I wrong. Good masterminds are about smart, driven people helping each other be the best they can be.

Over the course of my business so far, I’ve been involved in 6 different mastermind groups — not all at the same time, obviously. Some of them have been long-term, others have been for limited periods, like a 3-month “sprint.” I’m not going to talk about each one individually; instead I’m going to pull out some of the best practices from my experience.

My first mastermind was one I formed myself. I was about a year into my business, and I was doing a lot of research and reading on other websites. In the process (interacting in Twitter and blog comments) I came across three guys who were all interested in building lifestyle businesses, and we were all in the pretty early stages — so I emailed everyone and proposed a mastermind. They were all down for it, so we started meeting up on Skype since we were in four different countries at the time.


Sometimes people seem to be sort of waiting until they “come across” a community, but if you want to be in one, why not just make it happen? Reach out individually to a few other people who you think would be interested, and get the ball rolling.

I can’t say enough how much that group meant to me. We Skyped weekly for nearly two years, and it was a phenomenally productive time of exchanging ideas, critiquing each others’ stuff, setting and accomplishing goals, debating the finer points of business strategy, and just generally supporting and helping each other as we all worked hard and tried to figure things out.

In addition to our calls, we actually e-mailed each other a LOT in between. I just did a search in my Gmail and there are well over 700 e-mail threads between me and these guys. We’d use the phone calls to take deep dives into each of our businesses, and we’d use e-mail for the little questions that would come up in between… although sometimes our e-mail threads got deep, too; we discussed everything from disillusionment to romantic relationships to long-term dreams. There were some really amazing discussions.


I highly recommend, in mastermind groups, having BOTH a regular call AND one “informal” communication channel. That could be e-mail, or it could be something like a closed private Facebook group or a slack channel — whatever works best for everyone.

Whenever I’ve been involved in a group that has both a call and a less formal channel, I’ve felt like we interact way more. We connect more; we get far more knowledgeable about each others’ businesses and lives, and can give better input as a result.

So whatever happened to that first group? Well, eventually travel plans and time zones made it harder to schedule calls, and we sort of naturally stopped meeting regularly. But we’re in touch and still e-mail each other for advice and updates. I consider these guys friends, I respect them, I’m rooting for them to succeed, and I’m really thankful for all their support.


Even though masterminds, as I’ve said, are NOT for weaklings, you can really get an emotional boost from them.

Some of that is in the form of support when you’re down, because let’s face it, even successful entrepreneurs will have dark days, sometimes dark weeks/months. There are times when you lose a ton of money. There are times when you have to lay people off. There are times when you can’t seem to get motivated to work. There are times when you’re working your hardest, but it’s not making a difference.

Having people to lean on during these times is key. Especially because some of the challenges that entrepreneurs face are things that non-entrepreneurs can’t relate to. So your mastermind group can really help keep you going when you’re struggling. I can’t tell you how many times I’ve shared my frustrations or failures with my mastermind group and they’ve given me real, solid encouragement.

The flip side is that good mastermind discussions can generate an amazing positive energy. When brilliant suggestions are flowing, and you come off the call having gained clarity or having some promising new things to try — it feels awesome. It’s a boost, it can get you fired up for your day or for your week.


I’ve also been in an industry-specific mastermind. Basically, I was invited to participate in a mastermind with other online English teachers. At first I was a little worried about competition, but then I realized that we all took such different approaches that there really wasn’t direct competition — and plus, the English-learning market is huge; it’s big enough for all of us.

I understand that this won’t be the case for every business — in some areas, it would probably be uncomfortable or unwise to mastermind with direct competitors. But try having a theme to your mastermind.

Here are a couple examples:

Broad-industry theme: you could mastermind with other ecommerce store owners, who all sell different products. Or other SaaS founders, even though your software is totally different. Or other consultants, when you each consult on different areas. Or you could stay in one industry (like the education industry) but one person sells software, one person sells courses, one person has a brick-and-mortar school, etc.

I’ve found that having everyone aligned in some way when it comes to the industry or business model allows you to get even more specific advice, because the members have deep knowledge of, or experience in, that industry or business model.

Specific goal theme: for example, you have totally different types of businesses, but you all want to improve your e-mail marketing. Or rework your SOPs. Or optimize your team. Or create a new product in 90 days. Masterminds that are based on specific goals, are often good for time-limited periods instead of indefinitely.

Even if you don’t have a particular theme, you want to make sure the members are roughly in sync when it comes to phase of business and approach to business. If you’re in a stage where you’re pushing forward really hard, it might be hard to relate to other members focused on putting the brakes on their businesses or maintaining it at the current level.

It’s also not great for people who are just beginning a new side project to be in masterminds with really advanced folks who are at 7 figures with a bunch of employees. The experience gap ends up being too large. Not to say that you can’t get anything out of it, but it’s not ideal.

With this English-teachers mastermind, we were all in the same industry and we were in similar phases of business — we had products for sale, and we were looking to improve conversions, create some new products, and grow our teams and businesses. In addition to the calls, we had a private Facebook group for those informal conversations — that Facebook group’s still going today, and I love being able to get input from my peers.

The other thing I appreciated about the English-teacher mastermind group was how organized it was.


Our calls started on time and they finished on time, and there was sort of a mastermind “leader” who always set up the meeting time, sent out the link, and actively kept the discussion on track.

I’ve been on other masterminds where nobody takes the lead, and it ends up being disorganized. Something like scheduling the meeting takes tons of e-mail back and forth, or we’re never sure whether we’re meeting on Skype or Google Hangouts or something else. I was in one mastermind that dissolved after a single meeting because nobody really stepped up to make the second call happen.

The other benefit of having a leader is this: if you don’t have someone gently keeping the discussion on topic, it can easily devolve into chit-chat. Don’t get me wrong, I absolutely love casual chit-chat — but it’s usually best to do it after the official call. Basically say, “we’ll have a focused mastermind for an hour, and if anyone wants to keep hanging out and talking about other topics after that, it’s cool.”


I’ve been in a couple in-person masterminds as well — just a one-time session at a conference, where 7–8 people sit around a table and take turns in the “hot seat.” Each person gets about 2 minutes to quickly present their business and its challenges, and then everyone else bombards the person with questions and advice for the next 20 minutes.

This is a very intense experience, but it’s definitely worth doing. You have half a dozen smart people all focusing their brightest thinking on helping solve your problems. When you’re doing it in person, there’s even more focus because nobody is distracted by other stuff on their computer or things happening in their environment. And it’s amazing when everyone brings their best to the table.

So invest your best — think deeply about your fellow mastermind members’ problems, give them your sharpest ideas, and care about their businesses. Really imagine it was your business — your baby, right? — what would you do in that situation? Share it with the person.

When you give your best energy, you can make a real impact in someone else’s life — it’s exciting! During mastermind sessions, I can sometimes get as excited for other people’s businesses as I am for my own. Plus, the more you give, the more likely that the other members will invest that same brainpower in your issues when it’s your turn on the hotseat.

When it is your turn, then bring your best listening abilities. One of the biggest wastes of time in a mastermind is when the person on the hot seat gets defensive or tries to argue with or dismiss other people’s feedback. It kills the whole dynamic and it makes the other members not want to give you suggestions. So if you’re the one being analyzed, just shut up and take notes. Write everything down and analyze it later, even the suggestions that seem to come out of left field.

Obviously I’ve got a lot to say about masterminds, but it’s time to wrap up so let me review the main takeaways:

  • If you want to be in a mastermind, start one.
  • Have both a regular call and an “informal” communication channel.
  • Don’t underestimate the emotional energy a mastermind can provide.
  • Try having a mastermind theme.
  • Be organized and have clear leadership.
  • Invest your best.

Have you had experience with mastermind groups? Leave a comment and share your thoughts!



Multiplier Magazine

Host of Entrepreneurs in Motion, the podcast for location-independent entrepreneurs who are action-takers, not excuse makers.