Masterminds: The Good, the Bad & the Ugly

Masterminds are often seen as a must-have for business owners, but should we believe the hype about what they can really do for us? In this episode and blog post, I’m doing a deep dive into the benefits of mastermind groups, along with some of the drawbacks.

As someone who’s run masterminds for over four years, and having been in my fair share of them, I have a lot of strong opinions. Personally, I’ve had a full range of experiences in masterminds, which made me want to figure out if they’re really worth the hype.

Obviously, I’m biased when it comes to the way I run masterminds as I know they work. I see firsthand the results members get in their business (and lives) through the work we do in the mastermind.

Also, I know that not all masterminds are created equal. Not every mastermind has a positive impact, in fact, I’ve heard some real horror stories.

I set out to survey people from across the Small Business Boss community to get their perspectives on the benefits of mastermind groups. I collected insights and input from 40+ people to ensure that I wasn’t bringing my own perspectives to the table.

This group included a wide range of individuals with:

• Anywhere from one to 15+ years experience as a business owner. 
• Service businesses across multiple industries, from coaching to consulting to creatives to wellness to professional services. 
• Titles including CEO, strategist, consultant and everything in between.

Based on that deep dive and their insights, here’s what I found.

Why We Join Paid Masterminds

First, I really wanted to understand why we join masterminds. Of course, I had theories on why we invest money in our businesses and in ourselves in this way, but I wanted to go deeper. 

For this deep dive, looked at paid masterminds, as many of us are part of peer-led or informal masterminds. With this research, I wanted to ensure that the data collected was speaking specifically to the experiences where they’d invested money in a mastermind.

As background, the survey respondents have been a member of anywhere from one to four paid masterminds, with the most, 45% having been in two paid masterminds. The runner-up was three paid masterminds at 32.5%.

The key benefits of mastermind groups according to those paying for them are: 

Access to a Coach or Mentor
Many times masterminds offer an affordable way for business owners to get coaching or mentoring. Also, masterminds are the only way many coaches or mentors work with people.

Accountability and Support
A major reason for joining a paid mastermind was accountability and support. Most respondents cited this as a key factor, especially those that are more than a couple years into running their business. 

Belonging and Community
Owning a business can be incredibly isolating, so masterminds offer a way to get connected, be in community and grow our networks in the process. 

Business Growth
About half of the respondents shared that they joined a mastermind to support them in growing their income.

Brand strategist Britney Gardner shared this about why she joined her first mastermind:

“I needed long-term support and a year of masterminding with like-minded businesses getting systems and processes in place for lead generation, webinars, and public speaking. It was the easiest way to spur myself on with people around me doing the same thing.”

Next up, let’s look at if these masterminds were giving people what they expected. 

Are People Getting What They Want From Masterminds?

When you’re making an investment in your business, it’s important that you understand what you expect to get out of it. As you can see from the above, this group had very clear reasons for seeking the benefits of mastermind groups.

The question then is: did these masterminds deliver?

So I asked if they were satisfied with their most recent paid mastermind experience, and the answer was definitely more negative than positive. 62.5% said they weren’t satisfied, while only 42.5% indicated they were satisfied.

For those that said they were satisfied, here were just a few answers as to why:

“The right caliber people, connection and collaboration opportunities, and amazing friendships were formed. I also got the support I desired in my business that led to an increase in revenue, clarity, and action.”

– Gemma Regaldo, Brand Photographer, Gemma Shoots People 


“The community leaders were incredibly responsive, very quick to be helpful, and the materials were all very well presented.”  

– Latasha Doyle, Copywriter, Uncanny Content


“I liked that it was an intimate group and everyone was really helpful. I loved the masterminding too, it was helpful to hear other people’s questions and feedback.”

– Dr. Michelle Mazur, CEO, Communication Rebel

For those that were unsatisfied with their paid mastermind experience, it was for a wide range fo reasons. What was shared highlighted the challenges of this type of group program from lack of leadership and expertise, to not feeling seen and heard to the mastermind not living up to its promise.

How Much Are People Investing in Masterminds?

It’s not a secret that I believe the current culture of high-priced masterminds in the online business industry is some serious bullshit.

But, as a good researcher does, I wanted to understand what kind of money was being spent on masterminds, especially when so many people were indicating they weren’t getting what they wanted out of it.

Here’s a breakdown of the monthly cost for masterminds from participants in the survey:

To help put that pricing in perspective, I also asked two key questions about what was included as part of the mastermind.

First, I asked if any 1:1 calls were included. I was pleasantly surprised by this answer with 62.5% of people saying they were, and 37.5% saying they weren’t. 

As someone who immensely values that 1:1 connection and support, this was refreshing to see included in many masterminds.

Next up, I asked about in-person events. Many higher-end masterminds do a hard sell on the live event component, so I wanted to understand if this was the norm. Truth is, I also had an ulterior motive with this question, as retreats are typically part of the masterminds I run. Here in the age of COVID, in-person retreats are no longer possible, so I wanted to figure out if in-person events were the norm.

40% of respondents shared that in-person events were part of their mastermind, while 60% said they were not included.

Because I’m nerdy, I took the time to compile the data to see if there was a connection between being in a high-ticket mastermind, and having an in-person event. As suspected, the people who indicated there was an in-person event typically paid at the higher-end of the pricing range.

Would You Join a Mastermind in the Future?

Based on the mastermind experiences that many of these individuals have had, I was genuinely interested in knowing if they were open to joining a paid mastermind in the future and whether they thought the benefits of mastermind groups were worth the price of admission.

Despite so many people having negative experiences, the answer was still an overwhelming yes.

75% of people said they’d join a mastermind in the future, which shows that these groups can work, but they’re not without their problems. 

The maybes, which were 15%, indicated that some specific parameters that would need to be met in order for them to join a mastermind in the future. As for the 10% that were a hard pass on future masterminds, they were pretty much O-V-E-R this type of support.

What Can We Learn From This About Paid Masterminds?

Whenever I get curious and get outside perspectives from others in the industry, I’m always surprised by what I learn.

I’m incredibly grateful to the 40 people who provided input for this post and episode. (You know who you are!)

What I learned from the participants in this survey was no exception. It really highlighted some key issues with how masterminds are run in the online business industry, and how there’s a need for discernment when deciding to join any mastermind.

When you look at the challenges and problems highlighted by those unsatisfied with their masterminds experiences, there are some common threads that stand out.

Poor Program Design
Many times the design and container for paid masterminds is haphazard. It’s simply a bunch of things that are thrown together by someone who wants to run this type of program.

Participants shared three shortcomings with program design: recycled or generic content, an overwhelming schedule, and thoughtless programming.

As someone who runs masterminds, I can tell you that I spend an extreme amount of thought and care into designing how I run each cohort.

For the Agency Mastermind which runs the full year, I started planning for 2021 in late Q1 of this year. I carefully assess what’s working, what needs to be changed, what we need to add and so on.

I’m always gathering feedback to ensure that everything we do is both impactful and intentional. A critical component of my planning for each cohort is ensuring that the content is timely and unique to the mastermind.

Inadequate Leadership
I’m going to use the term leadership here for lack of a better word for the people offering paid masterminds. Much of the feedback related to negative mastermind experiences came down to poor leadership.

In some cases the leader was out of their depth and didn’t have mastery of the subject matter, or they were simply recycling information from other programs.

In the words of Leadership Development Coach and Consultant Bekka Prideaux about her experience:
“There was no real masterminding. A Facebook Group, mediocre livestreams, with a bundle of B-School regurgitation isn’t a mastermind.”

Then, there were the people who were faced with the fact that the mastermind was all sizzle in the sales process, but once they were on the inside, it felt short. In multiple cases, this lack of substance was accompanied by a mastermind leader who was absent and took weeks to respond.

As Bekka also shared:
“The founder of the mastermind positioned it as the best way to work with her, but they only showed up when she was launching her next course or higher paid mastermind.”

It’s not enough to bring people together. A mastermind requires someone to facilitate it. The leader of the group needs to set the pace for how things are done, engage individual members and be prepared for challenging situations or conflicts when they arise.

Finally, there were a few stories about the harm done by mastermind leaders that were downright disturbing.

The story LA-based interior designer Aaron Duke shared with me about his mastermind experience was chilling.

“She told me to use the law of attraction. When I was depressed and suicidal because I’d not created money, she told me to go on a vacation that I didn’t have money for. She suggested I put it on a credit card or take out a loan at the bank.”

I don’t have to tell you how very messed up this is, and more importantly how damaging it is. When we work with someone in this capacity, we’re placing our trust in them, and it’s essential that they don’t do harm to us in the process.

When we choose to engage with someone, we need to understand how that relationship will operate, including what the expectations are within the engagement, how disagreements are handled, how feedback is provided and more. We also need to know, before we buy, just how present the “leader” of the mastermind really is.

Ideally, before you enter this type of relationship with someone there should be an agreement beyond the terms and conditions on their sales page so this is outlined clearly for both parties.

The Wrong Peer Group

One thing I’ve had to learn the hard way in my business is how, for masterminds, (and pretty much anything else), specificity rules. And it’s a big reason why I created a mastermind for service business owners (first called Double It, now the BS-Free Service Business Mastermind) and then one for agency owners.

Turns out that I’m not alone in my need for specificity. One of the biggest reasons cited that a mastermind experience was both positive or negative came down to the peers within the group.

There were definitely a number of responses talking about how positive their experiences were with their peers.

“I truly value collaboration and being in community with other entrepreneurs. Masterminds really can be an inspiring and massive growth inducing environment if done right.”

– Danait Berhe, Founder + Brand Strategist, The Asmara Agency

However, there were countless responses that talked about how they couldn’t relate to their peers within the group as the cross-section of businesses was too broad.

Another issue, raised multiple times, was the fact that people within the group were at dramatically different stages of business, and that left business owners feeling frustrated.

“If I were to join any mastermind in the future, there would need to be a vetting process for the level of business. No offence to newbies, but I want to learn too, and obsessing over email providers or how to use Canva isn’t my jam at this point.”

– Lanie Lamarre, Data Driven Strategist

All of this goes to show how a mastermind with the wrong peers can lead to frustration. From my perspective, much of this comes down to the need for less catch-all masterminds, and for the creator or the mastermind to curate or screen the members of the group to ensure fit.

The fact is, if we’re going to invest in a mastermind experience, we need to ask better questions about who this is for and what stage of business they’re at. Most of all, the group should have a clear, specific container that brings together. 

Should You Join a Paid Mastermind?

As someone who’s built a business based on running masterminds, it’d be easy for me to simply say everyone should join a mastermind group. 

While I believe in the power, magic and benefits of mastermind groups, this deep dive really shows how not every group is the same. Especially in the online business world where anyone can slap together pretty much anything and call it a mastermind as a way to make money.

If you’re considering joining a paid mastermind, look past the glitzy packaging and consider the following:

Expectations
Get clear on what you want out of the experience. What type of ROI are you looking for and is this group aligned with your expectations?

Specificity
Consider if the group is specific to your needs including your stage and type of business.

Leadership
Ask questions about the leader’s level of participation. Are they present? Do they offer 1:1 support? How do they work with you between calls? 

Experience
What’s the leader’s background and experience? How are they uniquely qualified to lead this group? Does how they run their business feel aligned with how I want to do business?

Program Design
How is the program designed? What’s included and does this meet your specific needs?

By taking a harder look at any potential investment in a mastermind, you’ll be better able to improve your odds of having a positive experience. 

It’s clear from the willingness of people who’ve had negative experiences to try again that there can be immense value from this form of support and the benefits of mastermind groups can be many. Paid masterminds can offer us so much, but we need to do our homework to ensure they’re a good fit before we spend our money.

Speaking of masterminds, my newest mastermind, the BS-Free Service Business Mastermind is now open. If you’re looking for a different kind of mastermind, this may be exactly what you’re looking for.