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How To Run Masterminds That Actually Bring Business Benefits

What’s one of the most effective ways to stay on target for your goals and learn from like-minded people?

Mastermind groups.

But wait… what the heck is a mastermind group? A mastermind is a group of people who have similar interests and aspirations. Napoleon Hill from Think and Grow Rich describes it as ‘the coordination of knowledge and effort of two or more people, who work toward a definite purpose, in the spirit of harmony.’

Having been part of a few masterminds in the last couple of years, I can tell you that they’re incredibly powerful and will bring you business AND personal benefits.

Let’s talk about what some of these benefits are:

  • Camaraderie – you’ll naturally start to develop friendships with the people that you meet with on a regular basis.

  • Accountability – your group will hold you accountable to the goals that you’re trying to achieve. After all, you’re all motivated individuals who would love nothing more than to see your friends hit their dreams.

  • Different perspectives – everyone in your group has had different life experiences, which means they have a different world view. Listening to varying perspectives can open up your mind to new things that you would’ve never thought about on your own. For example, in one of my groups, I learned about factoring invoices from an individual with a strong financial background.

  • Access – everyone in your group has access to resources and relationships that can benefit one another. People like to do business with people that they like and if they’re in the same group as you, they’ll be happy to open the door for you more often than not.

In this post, we’ll talk about how to get started with an EFFECTIVE mastermind group.

1. The Different Types of Mastermind Groups

First, there are a few different types of mastermind groups and they each have their own advantages and disadvantages:

Established Organizations

Organizations such as Entrepreneur’s Organization (EO), Young President’s Organization (YPO), World President’s Organization (WPO), and Vistage are all popular entrepreneurial groups that have been around for awhile. To qualify for these groups, your business needs to meet each one’s criteria. For example, EO requires businesses to do above $1.5M in annual revenues (or manage a certain amount of assets or have a certain amount of funding if you’re a startup).

Having been a part of Entrepreneur’s Organization for the last few years, I can tell you that the experience has been valuable because of the history of the organization. That history lends itself to well-structured processes and templates, incredible events, a network of over 10,000 entrepreneurs world-wide, and additional benefits.

The biggest benefit is having access to a group of people that you call your ‘forum’. This is essentially your mastermind. A forum can cap out at 11 people but includes individuals from different businesses and doesn’t allow for competitors. If you need more members for your forum, EO will send more people your way to interview them.

I’m a big proponent of structure because without it, most mastermind groups can fall apart. If you happen to meet the qualifications for these groups, I strongly recommend taking a look.

What I love about established organizations:

  • In-person meetups

  • Set criteria to join

  • Not just business topics; personal topics are brought up frequently

  • Price barrier weeds out tirekickers

  • Everything spoken in the forum is confidential so you can speak freely

  • Diverse people with different business backgrounds

What I don’t like about established organizations:

  • Lack of new blood coming into these groups; average age is 42

  • Diverse businesses in forums means that you won’t be able to get laser-focused advice tailored to your specific industry

Hear about new events, press opportunities, business opportunities and more from a talented group with over 1,200 members. Here’s what the YEC membership criteria looks like:

  • Be 40 or younger

  • Be the founder, co-founder, owner or co-owner of his or her business

  • Generate at least $1 million in annual revenue, or…

  • Have at least $1 million in financing, or…

  • Have successfully sold a business for at least $2 million in the last 3 years

  • Have a business with headquarters or an office located in North America

Here are a few of my favorite Facebook groups:

  • Cult of Copy – Where copywriters hang out to talk about writing copy that sells.

  • Digital Agency Owner Insiders – Where agency owners talk about the trials and tribulations of running an agency.

  • Internet Marketing Superfriends – Where you’ll hear about the latest ramblings in digital marketing. Especially helpful because it’s such a fast-paced industry that changes frequently.

  • Podcaster’s Paradise – John Lee Dumas’ Facebook group of podcast owners.

As you can see from the above, my favorite groups are tailored to what I’m interested in (digital marketing). Although your taste will vary, just keep one thing in mind: if you aren’t getting value from one group, leave it as soon as you can. It’s VERY easy to get bogged down by the minutiae of noisy groups.

What I like about online groups:

  • Can access from anywhere at anytime

  • Easy to ask one-off questions

  • Can find groups that are very laser-focused

What I dislike about online groups:

  • Free groups sometimes means a lot of unhelpful noise

  • Non-committal attitude that stems from the casual nature of the group (but that comes with the territory of having big groups)

  • Takes a while to find the groups most suitable for you

Slack Groups

Chat apps such as Slack are growing rapidly and that trend isn’t likely to go away anytime soon. It’s a simple communication tool where individuals can join chatrooms for their workplace or even join groups for subjects that they’re interested in.

Slack Chats are a great way to discover and join private Slack groups. Then there’s Slack List, which is a handpicked selection of the top Slack groups.

In case you’re wondering, it’s free to sign up for Slack (although there are pay-to-join groups too).

What I like about Slack groups:

  • Can access from anywhere at anytime

  • Easy to ask one-off questions

  • Can find groups that are very-laser focused

What I dislike about Slack groups:

  • Chats scroll by really quickly and it’s unlikely that you’ll read the history

  • Free groups sometimes means a lot of unhelpful noise

  • Non-committal attitude that stems from the casual nature of the group (but that comes with the territory of having big groups)

Self-organized Mastermind Groups

For me, I found that EO was like my own personal board of directors which was great for pushing my overall life forward but not so great for diving deep into a subject that I know well: growing businesses online. So I set out to create a mastermind group of like-minded individuals who had a solid understanding of digital marketing.

Here’s what I learned about setting a criteria for my own mastermind group (I’d recommend setting criteria for ANY type of mastermind group):

  • The people need to be of the same skill level – If there are 5 A-players in the group and 1 C-player, the C-player will be singled out almost instantly and it’ll build resentment. It’s on you to set the right criteria so that you don’t make the mistake of bringing the wrong person into the group.

  • Everyone’s business needs to be at around the same level – If you have some people who run businesses that do >$10m vs. someone who works for a public company vs. someone who is a contractor, you’re going to have some level of disconnect in the group. Ideally, your group is made up of individuals who have experienced similar struggles and are on a similar trajectory as you.

  • It’s tougher to get people to commit because there’s no price barrier to join – Unlike EO where I’m forking over at least $6k+ a year, there’s less of a commitment for these groups because it’s something I put together myself. A possible solution to this in the future is to get people to pay a set amount to be a part of the group.

  • It’s important to take meeting notes – I was the scribe of the group and dropped everything into Trello after each meeting. It’s helpful to look back on how things have progressed from the previous meetings.

  • The accountability commitments are the biggest benefit – The one differentiator in this group was the accountability commitments that we ended up setting at the end of each month. Each individual would note one specific and measurable goal wanted to accomplish by next meeting AND the consequence if they failed to meet that goal. This was incredibly refreshing and almost everyone hit their goals each month. There was only one scenario where someone paid out $1,000 to the group for missing their commitment (ouch!). Here’s an example:

    • Accountability goal: I’d like to launch 1 e-book with over 200 pages by our next meeting.

    • Consequence: If I miss, I’ll pay each group member $250.

What I like about self-organized mastermind groups:

  • Can be free or paid

  • Handpick your own people

  • Set your own rules

What I dislike about self-organized mastermind groups:

  • A more relaxed environment means it’s easier for people to flake

  • Tough to find new members (versus EO/YPO feeding members into your forum if you run low)

Bonus: Group Dinners

Think about it for a second: who wouldn’t want to be able to engage with others who are doing interesting work in the same space AND get a free dinner?

Here are some things to note if you want to host your own dinner:

  • Try to stagger the seating with people who don’t know each other – Let new relationships blossom!

  • Cap the table to 7-8 people to keep it intimate – Our group was a little too big with about 12 people. With 7-8 people, everyone gets a greater chance to engage with each other.

  • Take some time to get everyone to introduce themselves – Start with yourself first to give everyone a structure to follow. Here’s an example:

    • Who you are

    • What you do

    • What your biggest struggle is

  • Make sure you emphasize when the dinner is ending (but people are free to stay longer and hang out) – Everyone has different obligations. Telling people when they are free to leave gives them a sense of relief because they won’t feel like they’re offending anyone.

  • Limit alcoholic drinks to single glasses/cups – People are free to order whatever they want, but throwing bottles into the mix is usually not a good recipe for an ‘easygoing’ night.

  • You’re paying for the bill – You organized the entire meeting so it makes sense for you to fork over the dough for the bill. The price you’re paying pales in comparison to the relationships you’re developing with the ENTIRE group.

  • The fortune is in the follow up – It’s easy for people to just go their own separate ways after a nice dinner, but that’d be a big lost opportunity. Make it your job to connect everyone via an e-mail thread afterwards so everyone has each others’ contact information.

2. Examples of Rules to Follow

Each mastermind group is different and has its own set of rules. I’m going to be specifically talking about rules for in-person meetings because forums and chat groups are typically more laid back. Here are a few guidelines to steal:

  • All technology is off for the duration of the meeting – Unless you’re the scribe, keep the technology off because it can become distracting. Just think of all the times that you’ve had a 1-on-1 meal with somebody and they take out their phone mid-conversation. It’s annoying! Mandate a rule that all technology is OFF so everyone can be fully present.

  • Full Confidentiality – In our EO forum group, everything that we talk about stays within the group. You’re not even allowed to tell your spouse about what’s going on because deeply personal issues are discussed.

  • Penalties for being late – Everyone is taking time out of their busy lives for this meeting and shouldn’t have to wait for one person. Here’s a template:

    • 1st offense – pay for everyone’s drinks

    • 2nd offense – goes to a vote

    • 3rd offense – you’re out of the group

  • Strict attendance policy – Everyone should commit to a strict attendance policy or else the group can fall apart easily. My personal mastermind fell apart because I was too lax with the rules. On the other side of the coin, my EO forum has been together for 3 years. Rules make a difference. Here’s a template:

    • 1st offense – nothing; everyone is allowed one miss per 12 months

    • 2nd offense – goes to a vote

    • 3rd offense – you’re out of the group

  • Annual or bi-annual planning – As the group gains experience, it’s important to bring up important topics that are bugging the group. For example, someone might not be getting along with another person or some people might not be getting value out of the group. These issues should all be aired out so the group can figure out appropriate next steps. Doing this will only make the group stronger but letting issues linger will cause the group the disintegrate.

  • Change it up by bringing in outside coaches – Spice up your meetings by bringing in outside coaches or mentors from time to time. For example, our EO group brought in a forum coach to teach us how to optimize our group and correct things that we’ve been doing incorrectly for years. I was initially skeptical but it turned out to be very enlightening.

  • Be proactive about fixing inefficiencies – It’s easy to sit back and let the group ‘go with the flow,’ but if you want to get the most out of it, be proactive about fixing things that you find ‘wrong’. For example, we use technology to support communication and file storage. More on that later.

  • Do stuff outside of the group – In-person meetings don’t have to be tied down to conference rooms. Doing fun stuff with a group of like-minded individuals is a great way to blow off steam and strengthen relationships with everyone. For one of our EO forum meetings, we decided last minute to fly up to Napa Valley. Be spontaneous!

This schedule is based on a 1-hour mastermind that can be done in-person or on the phone. Let’s go over each activity:

  • Roll call – Roll call is for the scribe to take notes on who is actually in attendance and who isn’t. This also serves as a good time to remind people about the rules of each meeting (confidentiality reminder, technology off, etc.)

  • Ice-breaker – Use one word to describe how you’re feeling at the moment. For example, if everything is going crazy in your world, you might used the word ‘overwhelmed’. As you go around the room listening to everyone’s ice-breaker, you’ll get a sense of where everyone is at.

  • Status updates – Each individual gets a set timeframe to go over the significant things they’ve accomplished, an update on their accountability tasks, updates on key metrics, etc. The time per update can be adjusted based on the size of the group. Although it says 3 minutes here, it can go up to 6-7 minutes.

    • Note: it’s strongly recommended to have a timekeeper because some people tend to talk more than others.

  • Challenges/Wins (Option 1) Although this is listed as an option, you can add both ‘Option 1’ and ‘Option 2’ as part of your mastermind. Each member gets a set timeframe to cover their biggest challenge at the moment and their most significant win. This is a nice extension of the ice-breaker because it dives deeper into the sentiment of each individual. If Bob has a challenge and you know the perfect individual to help him out, you’ll make a mental note of that. On the other side, Bob might’ve just discovered a game-changing marketing tactic that will provide immense value to the group. Although it says 3 minutes here, it can go up to 6-7 minutes.

    • Note: it’s strongly recommended to have a timekeeper because some people tend to talk more than others.

  • Mastermind (Option 2) – One individual presents a big challenge that they’re facing and presents for 5 minutes (can be longer). For example, Bill could be facing inventory issues for his e-commerce site and talks about how he might go under if things don’t shape up in the next 2 months. After Bill presents, the entire group will go around the table asking clarifying questions and then each individual will have a chance to provide feedback or speak from experience. In EO, most forums operate on the gestalt protocol, which means that everyone shares from experience and does not provide direct advice. I’ve found gestalt to be liberating at times when I’m just listening for key elements from each person’s story so I can devise my own action plan. Sometimes, it’s better to craft your own idea versus copying someone’s template from their own situation because every single situation is different and has its own variables.

  • Accountability Commitments – Each individual shares one specific task that they want the group to hold them accountable to. Ideally, the goal is a SMART goal so there can be no question about whether they finished their task or not. After each goal is set, a consequence needs to be put in place if the goal is missed. For example, Bill’s accountability commitment will be to launch a new course with 15 videos next month and if he misses he’ll owe each group member $250.

    • Note: almost nobody misses these because it sends a message to the group that, well… you aren’t that committed.

  • Housekeeping – This is the time to plan for the next meeting: scheduling, discussion items, next presenter, retreat, etc. The scribe will then close out the meeting notes and the meeting will be adjourned. This is also a great time to talk about any potentially lingering issues in the group and what should be fixed.

Bonus: Go Hang Out!

After a long meeting, it’s good to decompress with the group. It’s not all business 100% of the time; you’re hanging out with real people. I find talking to my forum mates and learning more about their lives is an incredibly rewarding experience because everyone is so different (the type of business they’re in, the stage of life that they’re at in, etc.).

Setting up a dinner after the meeting has always been effective. What better way to cool down than to break bread and have a few drinks with guys that you open up your heart to? Don’t miss out on this opportunity.

4. Tools To Use

If used efficiently, tools make masterminding A LOT easier. Here are a few from my toolbox in the last few years:

  • Box/Dropbox – Having a central storage folder that everyone can access has made our life WAY easier. Whenever we need to access update sheets or presentation sheets, we just pull them from here. Each forum member has their own folder and stores their updates in there. It’s very interesting to pull up your past updates just to see how much you’ve progressed in the last few months/years. You can also use Google Drive for this.

  • Slack – Slack is the fastest growing B2B SaaS business…ever. But all you really need to know is that it’s a fantastic chat application. It’s a great way to keep the forum updated on new happenings outside of meetings. Big life updates such as a new baby, closing a big deal, traveling to a nice vacation spot, etc. are great and keep the group connected. I previously felt like we were missing something because we only met once a month. Slack fills that void. Alternatives: HipChat/WhatsApp/WeChat

  • Trello – For my Internet marketing mastermind group, we used Trello to store all our meeting notes and our accountability commitments. You can also use a tool like Zapier to hook in Trello with Box/Dropbox so the cards will automatically populate as notes.

  • Facebook groups – Facebook groups are like an online forum where you can post threaded discussions that are easy to scroll through. Chat apps like Slack are more ‘in the moment’ and you won’t usually find people scrolling through the feed to find old news. Facebook groups serve as a nice complement to any type of chat app you’re using.


“You are the average of the five people you spend the most time with.” – Jim Rohn

Hanging out with like-minded individuals is one of the most effective ways to grow both professionally and on a personal level. The different perspectives and ideas you get just from participating in masterminds is unlike any other. If you’re going to do something great, find a group of people and go do it together. You might just find some lifelong friends and opportunities you would’ve never dreamed of!

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