If you’d like a copy of the documents I use to run my mastermind, you can download them by entering your email below

An online mastermind group is a small number of trusted advisers who meet regularly with the goal of improving each other’s lives or careers. The collective brainpower of the group—otherwise known as a “mastermind”—is turned towards a single problem. A mastermind group can solve problems and take advantage of opportunities in a way that an individual person can’t.

They are based on the simple premise that a whole can be greater than the sum of its parts. John Lennon plus Paul McCartney is not additive, it’s exponential.

They have been around in various forms, under various names, for hundreds of years.

In 17th- and 18th-century France, intellectuals and leaders of public life gathered to debate the issues of the day in Salons.

Ben Franklin called his meetings Juntos, which had roughly the same purpose: “to debate questions of morals, politics, and natural philosophy, and to exchange knowledge of business affairs.”

You can imagine that anyone who attended Franklin’s Junto had a distinct advantage over those who didn’t. They knew the other power brokers and had the most up-to-date information in the colonies.

Masterminds have existed across industries and across time, sometimes formalized and sometimes not. At critical times in the early 20th century, titans of industry would come together and make decisions that had far-reaching implications for the country.

During the 1907 Panic, Pierpont Morgan of the Morgan banking dynasty (now JP Morgan and Morgan Stanley), and a small group of bank presidents singlehandedly stopped the collapse of a nation’s economy. On the morning of Thursday, October 24th, the president of the New York Stock Exchange informed Morgan that he feared an imminent collapse. Morgan demanded he keep the Exchange open and called a meeting of bank presidents for 2pm that afternoon. By 2:16 p.m., they had a solution.¹

The “Secrets” Behind Mastermind groups

Accountability

If I’m trying to get myself to do something I don’t want to do, I imagine there is a scale, and I ask, “What can I put on the other side of this scale that is even more undesirable?” Basically, I ask myself “How I can make it harder to not do this thing I’m avoiding?”

Imagine if every time you ate cookies and ice cream, a picture of you eating it got sent to everyone you knew. The embarrassment side of the scale is much heavier than the ALL-YOUR-CAKE-ARE-BELONG-TO-ME side.

Failures that are attributed to a lack of knowledge often stem from a lack of accountability. Organizations continue to launch health awareness campaigns as if the problem is simply that people don’t know that kale is healthier than cake.

I find that I often know what needs to get done, but don’t do it. Getting healthy, growing a business or advancing in your field probably isn’t that hard, logistically speaking — it’s hard emotionally and psychologically.

Having a mastermind makes The Work — the most difficult, challenging, highest leverage work — easier, by making the alternative even worse.

Given the choice between making the sales call, publishing the article, or showing up and telling a group of people I respect that I didn’t do what I said I was going to do, it’s easier to make the sales call or publish the article.

Discover Easy Wins In Your Business

The mastermind sees opportunities you won’t see in your own life.

There’s a common phenomenon in private markets that a business will have a big growth spurt right after it’s acquired. Almost always, there are obvious, low-hanging fruit opportunities that the owner didn’t implement because they were blind to them.

Online mastermind groups that run consistently for years provide you with a group of people that have a rare combination of attributes: a deep understanding of your business, and no emotional attachment to it. To get that combination anywhere else usually means giving up equity.

With the mastermind’s help, you’re able to see the obvious improvements that a potential buyer might see in your business.

Make Better Decisions

The biggest leaps in the arts, sciences and business are made by spending more time on clarifying problems, not finding solutions.

People who focus on clarifying the problem instead of figuring out the answer end up more successful in their careers.

In 1970, psychologist Mihaly Csikszentmihalyi went back and talked to a group of artists he had previously studied when they were in art school to see how they were faring in the real world. There was a huge gulf: about half of them had left the art world entirely, and the other half were succeeding at a high level as professional artists. What was the biggest difference between the two groups?

The second group was composed of problem finders, people who actively sought out weaknesses and problems in themselves and their work.²

Being part of an online mastermind group forces you to clarify your business problems enough to explain them to someone else on a regular basis.

Problems are best solved not by immediately seeking a solution, but by clearly defining the problem first.

When asked what he would do if given an hour to save the world, Einstein replied: “I would spend 55 minutes defining the problem and then five minutes solving it.”

I solve half the problems which I think I have while I’m clarifying them in preparation for masterminds. Once the problem is clearly defined, the solution is often obvious. Having a regular mastermind forces you to regularly get clear and define the problems in your business and career.

“A rising tide lifts all boats”

Jim Rohn’s famous quote that “You’re the average of the five people you spend most of your time with” echoes JFK’s line that “a rising tide lifts all boats.”

Athletes “play up” to stronger competition and “play down” to weaker competition. We conform to the company we keep and an online mastermind group lets you create that company deliberately.

At one point last year, I had a mastermind call where someone on the call talked about how he had heard a competitor went out of business and had immediately gotten on a plane, to go see their biggest accounts in person and try to win their business.

When you talk to someone over and over and realize that they’re just a human like you, and they’re doing really impressive things, you realize you can do it too.

I had been sitting in my apartment thinking about how to grow my business, and after talking to him I remembered there was an event the next weekend where I could meet a ton of potential clients.

I hadn’t even considered going until talking with him. Afterwards I realized that getting on a plane is often a great way to grow a business.

I was on a plane three days later.

Advising Is a Great Way to Learn

“[I]t is much easier to identify a minefield when you observe others wandering into it than when you are about to do so. Observers are less cognitively busy and more open to information than actors.”³

Dan Ariely, Author of Predictably Irrational, has found the same thing in his research: you’re more likely to make good decisions if you take the outside perspective.

Asking yourself, “What advice would I give to someone else in this situation?” is often the best way to figure out what to do.

“When we’re recommending something to another person, we don’t think about our current state, and we don’t think about our current emotions. We actually think a bit more distantly from the decision and often make the better decision because of that.” ⁴

More than a few times, I’ve given someone else a piece of advice only to realize that the exact same piece of advice applied to me, but I was blind to it. I learn as much or more when someone else is the focus of the mastermind than when I am.

How To Start (or Find) Online Mastermind Groups

1. Pick a theme

Every successful mastermind I’ve been in has had a clearly defined theme that describes a pain point everyone is trying to solve.

It can be industry related: e-commerce, publishing, speaking.
It can be stage-of-life related: starting a business, changing careers, selling a business.
It can be skillset related: sales, marketing, operations, personal productivity.

Make sure you pick one that you are excited enough about to commit to long-term (3-5 years).

Most online mastermind groups take three to six months to hit their stride where everyone understands everyone else’s situation and personality. If the mastermind is good, it will last for a few years, so don’t start one around a passing fancy.

2. Make a list of people that would be a good fit

The most important criteria for member are shared values and trajectory. You want people whose answer to the question “where do you see yourself in three to five years?” is similar to your own.

I’m agnostic on how much industry matters. I’ve done them based on industry before, and it’s good because often someone has had the exact same problem and can solve it for you very quickly, but it can also lead to groupthink: the tendency of everyone to conform.

Conversely, having a multi-industry group means that there won’t be as many quick wins, but you’ll get more diverse perspectives, which may be more valuable over the long run.

If you have no idea where to start finding people, here are some ideas:

1. In person – this is (by far) the best option. Having an in person connection at a conference or meet up and making sure everyone gels leads to much better online masterminds in my experience. You can lay the groundwork in person, then keep it going online. Is there anyone you’ve met in person in the last year you’d like to have a regular call with?
2. Free Online Communities – This could be a facebook group or other forum where people that relate to your theme hang out.
3. Paid Online Communities – By-application communities like the Dynamite Circle (Travel-minded Entrepreneurs) and eCommerceFuel (eCommerce Entrepreneurs) will frequently facilitate mastermind groups based on members’ businesses.

I generally start my online mastermind groups very small — just two or three people including myself that I know are perfect fits, and then only add to the group when someone is a really terrific match.

If you have one person that you’re not sure about and add them, the change in dynamic can ruin the whole group. I usually invite potential members on for two calls in order to see how they fit and afterwards require a unanimous vote from the group to make them a permanent member.

I’ve found four to five to be the ideal group size. If you’re at a dinner table, four or five is generally the biggest you can get without splitting into two conversations. The same seems to be true of masterminds if you don’t want them to splinter.⁵

3. Set a schedule (weekly, bimonthly, or monthly)

It’s important to have a dedicated meeting time. If you have to reschedule it every week to meet everyone’s agenda, it will fall apart. Having a set schedule also helps to send a message that this is something to either take seriously or not at all.⁶

If someone isn’t excited enough to commit to the schedule, they probably aren’t a good fit anyway.

If you’re weekly or bimonthly, 60 minutes is a good amount of time for the call. If you’re monthly, try two hours.

4. Give it time and be willing to be honest and vulnerable

In my experience, it usually takes 3-6 months to get comfortable with each other, develop context, and allow for everyone to open up. As the moderator, the more open and vulnerable you can be the better, as everyone will follow your lead.

I typically dread my masterminds and often feel terrible right after them because the ideas I bring usually get shredded into oblivion. We often avoid this feedback because it makes us feel bad, but it’s much better than the alternative. If you have an idea or plan that is deeply flawed, would you rather a handful of people you respect and trust tell you before you start, or spend months (or years) and tons of capital to find out?

5. Start Strong

Have one person in charge and take it seriously. The difference between a good and bad mastermind is huge and it’s largely determined within the first few months.

Enforce an attendance policy – Life comes up, but if someone can’t be on 80% of calls, they probably don’t care enough.

Be constructively critical – If someone is talking about something they are working on and a doubt or thought creeps into your head, you have to say it. Imagine you were a business partner and owned half of their career/company. Would you put the business at risk because you were afraid of hurting their feelings?

Be honest – When I’m presenting a problem or opportunity to my mastermind, I try to expose all the potential flaws and insecurities I feel around it. By receiving feedback on all the weaknesses, I can either improve how I’m handling the project or stop it entirely before I waste more time and money on it.

If the first few months are conducted business-like and everyone opens up instead of deflecting, it turns into a great group. If it’s all social chitchat and no talks about the real problems keeping them up at night, it becomes mostly useless.

Running Online Mastermind Groups

If you’d like a copy of the documents I use to run my mastermind, you can download them by entering your email below

Pre-Call (Everybody)

• Before you arrive to the mastermind, prepare your progress (what you actually got done since the last call), your biggest problem and biggest opportunity.
  • Your problem and opportunity will be no longer than two sentences.
  • Each will be written down prior to the call.

Note: I really like to do my weekly review before I get on the call. When you’re preparing your problem and opportunity, you want to be able to walk people through the idea maze of your thinking otherwise you tend to get advice you’ve already thought of.

E.g., I want to increase traffic to my site because the conversions and back-end economics are already good, but I don’t have enough traffic. I have published ten articles on these topics that are SEO optimized but are not yet ranking. I’m trying to decide if I should double down on SEO or try doing more social media, specifically this facebook strategy.

• Turn off phones/remove any distractions (cell phone, email, Twitter, etc.).
• If you missed the previous call, read through the call notes from the previous week to get up to speed.
• Turn on your camera: Video is strongly preferred as it lets everyone know you are paying attention when they’re talking and also enhances the level of communication since everyone can see your body language.
• Login five minutes before: I’m currently using http://appear.in/ and Google Hangouts. I’m not crazy about either but haven’t found a better solution for video conferencing

Online Mastermind Group Structure

Use the “hotseat” format where, on a rotating basis, one person is the focus of each call and gets 60-75% of the call to focus on themselves. Forty minutes of focused attention on your problems is more than twice as good as twenty minutes. In most cases, the problem someone thinks they have is actually a symptom of a much deeper problem, which it will take a while to get down to. Uncovering and solving the deeper problem will treat many other symptoms besides the issue the person initially raised.

Part 1: Opportunities/Problems Round Table (First 25-40% of the call time)

Beginning with the person who was on the hot seat last week, everybody does a brief update. It should take around five minutes per person and no more than 40% of the total call time. You want to leave the majority of the time for the person on the hotseat to get at least 40 minutes of everyone’s focused attention.

• Progress since the last call
• What’s your biggest problem right now?
• What’s your biggest opportunity right now?

If you can help someone with something they mentioned in the time allotted, do so. If you think you can help but it will take more than one or two minutes, arrange another time to discuss after the mastermind.

The round table should end with the person on the hotseat being the only person who has not given an update.

Part 2: The Hotseat (Final 60-75% of Call time)

The person on the hotseat gives the same update on progress, problem, and opportunity.

They then state what they want to dive into first: either the opportunity or problem. If there’s time, you can get to both, but it’s better to focus on one and really get to the bottom of it.

Everyone on the call asks questions to clarify exactly what the problem/opportunity is. A good rule of thumb is The Five Whys, the root cause of most problems is usually “five whys” away from the surface problem.

For example, if someone complains the car will not start:

Why? – The battery is dead (first why).
Why? – The alternator is not functioning (second why).
Why? – The alternator belt has broken (third why).
Why? – The alternator belt was well beyond its useful service life and not replaced (fourth why).
Why? – The vehicle was not maintained according to the recommended service schedule (fifth why, a root cause that once solved will prevent future problems).⁷

If the person in the hotseat doesn’t start properly maintaining the car, the surface problems will continue manifesting in other ways. The benefit of the hotseat format is that you have the time to get down to the root cause.

Other members of the call should be asking “why” and associated clarifying questions, and only once the real problem is clear should they give advice or comments.

At the end, ask if the person on the hotseat is satisfied and has a clear course on how to move forward.

If not, clarify the problem again and repeat the five whys process.

If they are, you can move on to another topic they want to talk about.

At the end of the call, confirm everyone’s attendance for the next call and update who is in the hotseat next week so they know to prepare.

Common Mistakes

Not taking it seriously – When masterminds I’ve been in haven’t worked out, or haven’t worked out to their potential, it has often been because they were not initially framed as a serious commitment, with strict attendance and tightly enforced moderation.

Adding people that aren’t a perfect fit – My best mastermind groups have always started with three or less people and took over a year to get to five people. If you know five people that are perfect off the bat, that’s great, but unusual. It’s better to start with one or two people that you really gel with and add slowly.

Not being open, honest and vulnerable – If you don’t expose your biggest fears and insecurities, they won’t go away, they’ll get worse. If you’re on the hotseat and not at least a little nervous, you’re doing it wrong.

Not being critical – In an online mastermind group setting, not pointing out other people’s hidden problems is pernicious and disrespectful. If someone is giving their time to the group, you have a responsibility to pick apart their business.

Jony Ive, the lead designer at Apple, recalled learning this lesson from Steve Jobs:

“I remember having a conversation with [Steve] and I was asking why it could have been perceived that in his critique of a piece of work he was a little harsh. We’d been working on this [project] and we’d put our heart and soul into this, and I was saying, ‘Couldn’t we … moderate the things we said?’

And he said, ‘Why?’ and I said, ‘ Because I care about the team.’ And he said this brutally, brilliantly insightful thing, which was, ’No Jony, you’re just really vain.’ He said, ‘You just want people to like you, and I’m surprised at you because I thought you really held the work up as the most important, not how you believed you were perceived by other people.’

I was terribly cross, because I knew he was right.”⁸

Not giving it time – It usually takes three to six months for a online mastermind group to mature. Everyone needs to get comfortable with everyone else and learn the ins and outs of everyone else’s personalities and businesses. Often times a mastermind will start very strong because everyone is excited, then go through a brief lull before it hits it stride.

How to Get Started

• Pick a theme
• Make a list of people that would be a good fit and invite the top two or three
• Agree on a schedule

If you’d like a copy of the documents I’ve used to start and run successful masterminds, you can download them by entering your email below. (It also includes an email template to invite people).

If you’re interested in getting paired up with other mastermind members, my friends at TMBA have launched a matchmaking service you can sign up for here.

Last Updated on January 24, 2020 by Taylor

1. Source: House Of Morgan by Ron Chernow
2. Source: To Sell Is Human: The Surprising Truth About Moving Others by Daniel H. Pink
3. Kahneman, Daniel (2011-10-25). Thinking, Fast and Slow (p. 417). Macmillan. Kindle Edition.
4. Source: Dan Ariely – Predictably Irrational
5. This depends on the format. I like to do either weekly or bi-weekly meetings for 60-90 minutes. I know a lot of people also like to do quarterly for 1-2 days. Those groups seem to work at larger size (8-30ish)
6. The exception I do make to this is for people who move to a different time zone. That should happen maybe once or twice a year though, not every week
7. Source: https://www.wikiwand.com/en/5_Whys
8. Source: Cult Of Mac