Masterminds: Gasoline on the Entrepreneurial Fire

Entrepreneurs have really weird lives. We have big visions of empires and legacy, and are willing to hustle like no one else to get there.

The problem is, no one else is like us. We end up lonely and often lost, because there’s no roadmap for what we’re doing.

Our friends and family don’t really ‘get it’, and so even though the vision sustains us, it comes at a cost.

Even when you’re diligent about learning how to run a business, problems (and opportunities) crop up that you just have no experience dealing with.

That’s where masterminds come in.

Now, I’m not saying that masterminds are the answer to every entrepreneurial problem… but a good mastermind can come pretty damn close.

Why Masterminds are Like Gasoline for Entrepreneurial Fire

The best masterminds are a gathering of people of similar trajectories that help each other build their businesses. They can happen online or offline, but they’ll achieve a few things:

  • They’ll keep you focused and accountable
  • They’ll fend off entrepreneurial loneliness
  • They’ll give you perspective and fresh ideas for your business
  • They’ll help you identify the strengths, weaknesses, threats & opportunities in your business and industry
  • They’ll help you get out of your own way

Most importantly, they set a fire beneath you… and then throw on the gas. There’s no motivation like the expectations of your peers.

How do I know this?

Well, in the last few years, I’ve run multiple masterminds. Not only have I made a great income from this, the members of the groups have gone on to build game-changing businesses.

They’ve 10x-ed their revenue, disrupted stagnant industries, hired superstars and changed their lives.

I believe that a good mastermind is like a secret weapon, and you can use it to build your empire.

Instead of relying only on your own knowledge and ability, it gives you access to a powerful pool of expertise. It gives you perspectives you would never consider as a lone operator.

As an entrepreneur, you can use masterminds two ways:

  1. To build significant authority and revenue for your personal brand by running high-level, paid masterminds
  2. To access a powerful brain trust by participating in someone else’s mastermind. This allows you to grow your business far beyond what you could have come up on your own.

In this case study, we’re going to explore what makes a great mastermind (and a bad one), how to run one, how to make it extremely valuable for your members, and what to focus on in each call.

By the end, you’ll have a clear roadmap for establishing and running your own successful mastermind, or what to look for when joining one.

What Makes A Mastermind Successful?

Most masterminds fail within the first few months. The person who set it up gets sick of ‘herding cats’ and trying to keep everyone organized. The members get sick of turning up and often feel like they’re not getting the value they signed up for.

Masterminds that don’t have a leader fall apart quickly: members stop showing up, people don’t prepare for the calls, and everyone feels like they are just wasting their time.

If there are too many members, the calls are too long, or they happen too often, people will drop out quickly. Each member needs to participate fully, engaging with everyone else’s problems and coming with clear intentions. There’s only one way to do this…

Someone has to take the lead and be responsible for the behaviour of the group. They have to direct the conversation, be willing to call people out, and make the hard calls if someone is not participating.

There are two other key factors in creating a successful mastermind: a clear focus for the group, and a dynamic structure. We’ll get into these shortly, but first, let’s dig into how you can create a successful, long-lasting mastermind.

The Most Successful Masterminds are Pay-to-Play.

This is one of the most important things to factor in when you’re starting a mastermind. Paying for something increases its perceived value, and so your members are more likely to take the group seriously when they have to put money down for it.

There are two ways you can go about charging, and it really depends on your intention for the mastermind.

Charging for profit:

As I mentioned before, running masterminds can be an excellent income stream. If you charge $500 to $1000 per member per month, you will create a solid revenue stream from a few hours of work each week.

However: you must provide exceptional value in every call, and focus exclusively on your members’ businesses – not on improving your own.

Do not charge for profit if you are looking to extract value for yourself. That is not how it works. Only charge for profit if you are confident that you can create an exceptionally valuable environment for the members and that they will get more than their money’s worth.

We’ll cover the logistics of running a group shortly, including…

  • How many members you should have in each mastermind
  • How to vet potential members
  • How to structure the calls
  • How to ensure you’re consistently providing excellent value.

Not-for-profit fees:

Even if you’re not looking to profit from your mastermind, charging for it will still improve the commitment of the group.

Charge a monthly or quarterly membership fee, and donate it all to a charity of the group’s choosing. If people don’t pay the fee, they don’t get to participate – just like any other business model. Just because it is going to charity doesn’t make it negotiable.

The Facilitator Is The Determining Factor of Success.

Humans do not do well without clear leadership.

This is particularly obvious in business settings – without a vision and clear guidelines, things get messy very quickly, and masterminds are no exception.

No mastermind will work without a designated facilitator. If you’re the one who put the whole thing together, then this is your responsibility, and you must take it seriously.

To be a great facilitator, you must have some specific qualities and be prepared to do certain things that others will not:

  • You must be focused and decisive
  • You must be willing to corral the conversation and steer it back to the topic at hand when people go off on tangents
  • You must be willing to call people out when they are not following through on their commitments
  • You must be willing to kick people out if they are not participating or refuse to play by the rules
  • You must be perceptive and be able to draw the best information out of people (by asking good questions and picking up on what’s important)

As I mentioned above, you should not be looking to get value out of a mastermind that you are facilitating. If you need input on your business, join someone else’s group.

However, if you have business acumen and are good at leading people, then running your own can be very rewarding.

If you are the facilitator, you should always be looking for fresh inspiration and information to take back to your group.

Maybe you’re part of a forum or another mastermind and can pivot the information you collect there to benefit your members.

I’ve done this consistently over my years running masterminds, and leveraging external information can be very powerful.

A few more things you will need to be comfortable with as facilitator include:

  • Keeping everyone on task & on time
  • Starting and ending calls on time
  • Managing the relationships within the group
  • Paying close attention to the subtext or hidden meaning in conversations
  • Taking deep dives into a topic or problem when needed

Finally, managing the members is a critical skill.

Not everyone will be a good fit for the group: people won’t take it seriously enough to prepare for calls, will only contribute in so far as they expect to get value for themselves, or will miss calls or turn up late.

Some people will just be discordant: they’ll make things too personal, or will take things too personally. Some people will be mean in their delivery of criticism, disparaging of other members, or generally combative.

In that case, it’s up to you to remove them.

You must always put the interest of the group ahead of any individual member.

If someone is creating problems, cut them quickly. Refund their money if need be, but always, always move quickly. Nothing kills a group faster than a destructive member.

How to Choose Your Members:

The best way to avoid problem members to have a robust selection process right from the start.

To begin with, I suggest outlining a clear criteria for the kind of people you are looking for.

Build an application questionnaire based on the following information in order to find the right people for your mastermind from the outset.

Typically, masterminds are most successful when members come from a range of industries.

Otherwise, you tend to get an ‘echo chamber’ of information – everyone has read the same stuff, has similar ideas about growth and execution, and so you get very little innovation or inspiration. Cross-pollination is critical for fresh ideas.

Once you’ve selected for a range of backgrounds, you only want people who are willing to make a solid commitment to the group, and who will abide by the rules of the group….

Which means you need some rules for the group. I’d suggest building these along the following lines:

  • Must turn up to every call
  • Allowed to miss 1 call per 6 months without penalty (+ a specific penalty for missing more than this)
  • Must participate in every call to the benefit of other members, beyond talking about your own business
  • Be punctual, prepared and courteous. Don’t be cruel or combative.
  • Be honest and willing to have the hard conversations, both in regard to others and yourself
  • Give more than you expect to get
  • Stay committed. Do what you said would do, and come prepared for the next call.

Once you know that people are committed and willing to play by the rules, you need to select for trajectory or attitude. This is perhaps the least tangible part of picking your members, but it’s the most important.

Side note: It is important that your members are roughly on par with one another in terms of capability and capacity.

If you have a member that is significantly behind everyone else in the group, that person will not be able to take advantage of the group’s advice. The rest of the members will be used to having more resources at their disposal, and so their advice will be geared accordingly.

Or if one member is significantly more advanced than everyone else, the other members will either leech off them or ostracize them.

When you have people who are relatively close in capability and capacity, trajectory is more important than their current level.

For example, you might have 1 member in your group making $100,000 per year, and another making $500,000 per year. If they are both geared towards rapid growth and are constantly looking to innovate, there is a complementary trajectory and attitude there.

But if another member is making $300,000 per year and doesn’t want to grow any further, that’s a discordant attitude that will stunt the progress of the group.

Finally, select for generosity and willingness to engage.

The “giver’s gain” concept was popularized by the founder of Business Networking International. This is the idea that when you give and give and give, you will extract far more value than you would when you just take.

Without fail, the members who give more than they expect to receive in a mastermind are the ones who end up getting the most out of it.

When you are constantly looking for ways to help other people, it triggers creativity and out-of-the-box thinking.

You end up coming up with solutions for other people that you can then put to work in your own business… not to mention building incredible amounts of goodwill with the other members that you can draw on when you finally do ask for something yourself.

Select people who demonstrate a willingness to put the good of the group ahead of themselves and who can see the benefit in helping other people in order to help themselves.

How to Structure Your Mastermind:

After years of trial and error, I’ve settled on a method for running masterminds that functions smoothly and gives members maximum value.

Ideally, you’ll meet twice per month, for no more than 2 hours. People are busy, but this is a time commitment most people can handle.

If you are running an online mastermind, you can have a maximum of 8 people (plus the facilitator) per group.

5 to 6 members works better, but up to 8 is fine. More than that and the call becomes unmanageable – too many people to get through, too many people talking at once, and too great a time commitment.

With 8 members, the calls can run up to 2 hours at a time. By the end of the call, people will be exhausted and the value delivery will have dropped off substantially. That’s why I recommend keeping it a bit smaller, so that you can keep the calls to about 90 minutes.

If you are running in-person masterminds, groups of up to 25 can work. You start and end the meeting together, but break up into smaller groups of 4 or 5 for the middle, with the facilitator rotating through the groups to keep everyone on task.

Many masterminds happen weekly. This often works to begin with, but over time the members find it too much. Finding the time becomes difficult, and they start wearing out.

The projects they commit to working on become more complex over time, so they also take longer to make progress. Updating every week with ‘I’m still working on the tasks from last week’ gets old fast, and people end up feeling like they’re not getting value any more. So even if you start weekly, be prepared in time to move to twice a month.

Once you’ve settled on your frequency, you need to pick a format. Again though, this should change over time. Humans are dynamic, and so your interactions with them should also be dynamic.

Run a particular structure for a few months, then change it up. That way, you keep everyone engaged and ensure that fresh ideas keep flowing.

I recommend starting with a round robin set-up. Each person gives a quick update about what they achieved since the last call, and what they plan to do before the next one. After that, anyone who has a particular problem or opportunity can put it to the group for feedback.

After 2 or 3 months of this format, move to a hot-seat format. Get quick updates from everyone as usual, but have 1 or 2 members deep dive into a part of their business that they need help with.

That member should come with a prepared list of their challenges and opportunities, and the rest of the group should come with ideas and observations from previous discussions that will help move the hot-seat member forward.

Do 1 or 2 hot-seat rotations of the whole group, then you can move onto themed sessions.

For example, you might have each member bring up their big marketing challenge on one call, then get into hiring and employee management on the next. Again, do this for a couple of months.

After that, you can go back to the round robin format, this time adding a 10-minute teaching to each meeting. Once per meeting, 1 member should teach the rest of the group something that’s working really well in their business, or share part of their expertise that the rest of the group can immediately put to use.

Always keep the format dynamic.

This keeps your members engaged and yields far more value than a static format that doesn’t change for months or years.

What to Cover in Your Mastermind:

Masterminds are not the place to cover technical or tactical implementation.

In one mastermind I ran years ago, a member had a 7-figure ecommerce store. He thought that adding particular piece of technology would allow him to grow his business substantially, and he became quite fixated on implementing it.

He would come to the calls always asking if anyone knew how to work this technology, or if they could recommend anyone who did. This became a problem, because no one else in the group was in ecommerce, and everyone else was focused on high-leverage, strategic topics.

That member ended up leaving, because he didn’t want to talk about the big-picture stuff (that would have helped him grow his business far more than this single piece of technology). Unsurprisingly, the quality of the group went way up after that.

Here are the strategic things to discuss that will give your members the most value:

  • Marketing channels
  • Sales channels & strategies
  • Business development
  • Employees (hiring them, finding the right people, managing them)
  • Building company culture
  • Finding and dealing with business partners
  • Finances
  • Resource sharing
  • Vendors (asking for service / hiring recommendations)
  • Entrepreneurial loneliness

That last one is a big one, as I mentioned right at the start. This is one of the biggest values people get out of masterminds. No one gets what we all do, so you can’t decompress with those people.

They’ll scoff at you if you’re frustrated that your business is stuck at $3 million instead of $5 million. They’ll resent you for it, too, so you need other people you can commiserate with… and who will make sure you get over it and hit the next level.

Now, occasionally there’s a place for a quick tactical conversation.

If someone is really stuck on something, the facilitator should be able to draw a solution out of the group.

For example, in one mastermind recently, a guy with a $100 million business was complaining that his staff were refusing to put up a new website to test a new marketing channel. The guy sitting next to him had scraped into the mastermind with his $1 million business, but had recently learned how to build WordPress sites quickly.

After a quick question from the facilitator, Mr $1 Million piped up to say that he could set up the site in an hour or two. Mr $100 Million sat with him at lunch, and put the website up. Mr $100 Million set up joint ventures with Mr $1 Million and both saw explosive growth as a result.

But masterminds should be largely focused on high-level, strategic conversations that free each entrepreneur from their own limitations.

Go Forth and Mastermind!

From this case study, you should have everything you need to start and run your own successful mastermind. You know how to find ideal members, how to charge them, and how to structure your meetings.

The value of a good mastermind is hard to overstate. It draws the very best out of people, both in terms of creative, growth-focused ideas, and in how they relate to other entrepreneurs.

It allows you to connect people in a powerful, profitable way. Businesses go through drastic growth, and entrepreneurs hit the velocity they’ve dreamed of.

Focus your mastermind on providing world-class value to every member.

Pursue real engagement, and protect the group relentlessly from discord and apathy. Bring fresh inspiration and deep focus to every meeting.

If you can do these things, you’ll watch your members become empowered and create unstoppable momentum in their businesses… and you’ll get to be right at the center of it all.