How To Fill, Sell, Operate And Retain A Successful Mastermind Group

Oli Billson

Hi I’m Oli 👋 I run several paid Mastermind Communities that make around $800k /month collectively.

In this post I’m sharing with you how to fill, sell, operate and retain your very own successful Mastermind Group.

I’ll be covering:

  • How to fill a Mastermind Community

  • Captaining your group and managing Mastermind Operations

  • Protecting your recurring revenue with a Retention Playbook

To illustrate I’ll be spotlighting one of my Communities called NextLevel Scale™.

Quick background about my Mastermind and Me…

I started my current Mastermind NextLevel Scale™ about 5 years ago back in 2018.

Primarily to help other info Business Owners who are scaling to 7 and and 8 figures with their own Masterminds, Group Coaching Programs, Memberships and Online Courses.

The investment has risen each year, but currently stands at $48k for 12-months Membership.

Right now we have 50 active members which contributes to around $2.4 million in annual recurring revenue.

My role is to lead and facilitate the group with a Team that comprises of one full time Coach and a part time assistant.

But I didn’t start here.

My journey goes back over the past 20 years from being in the info business.

Since then I’ve ran virtually every kind of 'expert model' you can imagine:

Full Format Franchising, Online Memberships, Area Exclusive Licensing, Online Courses + Digital Products, In-person training centre, Group Coaching Programs, a National Association, Home study courses, Marketing Agency, Publishing Partners, Live Events, Equity based Consulting, Retreats, Private Consulting, Certification programs, Printed Monthly Newsletter Subscriptions…

…and obviously Masterminds Groups.

The high ticket Mastermind Community model is hard to beat.

It’s almost like “alchemy“, and the timing to grow your own Community like mine is especially fortuitous right now.

My goal here is to summarize the lessons I've learned, share what has worked, and what to avoid.

Fair warning: this post will likely be long, so be sure to bookmark it now in your browser to refer back to later.

Let’s dive in…


The first thing you should look at is the type of member you actually want.

To understand this, you should consider why people seek advice, guidance, coaching, and mentorship in the first place.

It usually boils down to some of these reasons:

  • Uncertainty

  • Confidence

  • Wanting a sounding board

  • Obtaining specific detailed instructions or access to information

  • Transfer of specialist skills

  • Encouragement

  • Validation

  • Laziness

  • Overwhelm

  • Accountability

The attributes we look for in potential NextLevel Scale™ Members are:

  • They consider themselves a Student

  • Have ambition

  • High emotional state

  • They are an optimist

  • The have the ability to buy / invest and make associated investments congruent to what we teach / or are required to get the results

  • They are a ‘Resource investigator’, meaning they ‘believe there’s a better, faster, shorter way’ of getting to where they want to be — from Me and others in the group

  • They are decisive and responsive

…and most importantly, they are coachable

Now that you know the motivational levers of what people want, and also what You are specifically looking for in a Member, you can begin to weave in some benefits to begin attracting people.

I’d recommend using these universal benefits that relate to joining any type of Mastermind Community:

  • An antidote to entrepreneurial loneliness

  • Access to the highest level information not found elsewhere

  • Power of combined experience from everyone else in the group

  • Speed of combined experimentation from others in the group

  • Practical sharing of resources, rolodex, connections, JV’s and other potential Partners

  • Intimate access and proximity to You not available elsewhere including external experts

  • Elevated status associated from telling others they are part of something

  • Bundled programs, services, perks and discounts

  • Unique or appealing experiences

  • Community — Community is virtually bulletproof from economic downturns and is someone's single biggest asset in any market adjustment.

To bring all this together, you’ll want to create an Offer Sheet for your Mastermind.

You can use these questions to help you map things out:

  • What is it?

  • Who is it for?

  • What problems does this solve / Why does it exist?

  • How does it work / Where does it happen

  • Who are you and why should I trust you? (Credibility)

  • What is this going to do for me? (Benefits)

  • How is it different? (Differentiation)

  • What results can I count on? (Results / Proof / testimonials)

  • When can I expect results? (Timeline)

  • How many people can join?

  • Investment (annual fee + payment options)

Here’s 5 proven offers we use to bring in new Mastermind Members:


Many Mastermind Groups are filled by ascension.

Naturally, everyone I’m sure reading this loves the idea of acquiring Mastermind Members at virtually no cost of acquisition, because you’ve already ‘bought the customer’ in the first place.

The reality is, this really depends on so many different dynamics, but it may surprise you that a $6k front end Coaching Program only has about 10% ascension rate to a $30k + Mastermind.

So if you currently have a $6k program right now, I’d strongly recommend focusing on this till you reach around 150-300 clients before making a higher level Mastermind offer.

I could write a whole post about front end offers, but that’s for another day. What I will say is the best front end offers that work in unison with Masterminds have a pathway.

They should solve one specific problem then it should create another problem, and that second problem is something your Mastermind solves.

It’s very deliberately crafted this way. Done right you’ll have a self perpetuating flywheel that feed itself, done wrong the economics simply won’t back out.

Again, I don’t want to go too deep here, but I do want to touch on how you actually ascend people quickly. Your first port of call is Internal lead generation from your existing list / audience or following.

This is best place to start find new prospects for your Mastermind. There’s a bunch of ways we can ‘invite’ people to join.

Here’s an example of one:

  1. DIRECT – “COLD”:

Masterminds can obviously be sold with no ascension involved at all.

When you by-pass the ascension ladder, you have to be prepared for a significant-sized cost per sale, but you also have to be very careful of attrition.

It’s easy to get carried away adding people the group that don’t meet your entry criteria. This leads to churn and often creates a revolving door of clients coming and going.

Obviously, this is completely opposed to the traditions of a True Mastermind, so you need to be super careful.

That’s because a Mastermind is only as a strong as the weakest link.

To give you some idea, our CPA for a Mastermind client from cold ranges from $3k-6k.

When I say cold, I don’t just mean paid ads.

That’s just one cold channel. In some niches the best ‘quality of members’ — that will pay, stay and refer are often acquired via Direct Mail. Yep — that’s still a thing.

Here’s an example of our Printed Monthly Newsletter we use to do internal lead generation from:


The power of this is in its psychology.

First, few people apply for things they don’t intend to do or buy if accepted. Second, time invested equals commitment.

That’s why your Mastermind Application should actually slow the sales process down.

Adding friction will certainly reduce applications, but usually reveals a higher caliber prospect.

The application itself should highlight and reinforce the individual’s problems, frustrations, inadequacies and business deficiencies, so that their sense of need to be in the program heightens as they complete the application. You have to be clever, not clumsy about this.

If you team this up with doing Group Sales Calls (not one-2-one’s) it’s a powerful and highly potent combination. The framing is much more about an interview rather than a strategy session.

For clarity, when I say application, this could be free or paid.

However, this is not your typical VSL → Application → Scheduler.

Often they can’t book a call right away. The application gets reviewed and then we move forwards to a call if they qualify.

During the Application Call / Interview itself we strongly recommend using an Enrolment Presentation Deck via Zoom.

Here’s an example of a Sales Deck:


I actually used a Live event to sell my very first few Members into NextLevel Scale™ in 2018.

We had 20 apply and I took 15 at the time, it was a great success and something I teach people how to execute.

Live events allow you to showcase other successful Members, and if you do it right you can create a success panel of Members which basically does the selling at the event for you. It also supercharges the emotional atmosphere to hear their stories.

Still today we run a live event called NextLevelBusinessLIVE!

It’s a small 2-day workshop with around 30-50 people.

At the event we invite attendees to apply to join NextLevel Scale™ and it still works amazingly well.

These live events can be teamed up to maximize your time when running an in-person Mastermind.

For example in March this year I was running NextLevel Scale™ in Miami, I then went immediately after to do a NextLevelBusiness LIVE event in Tampa.

We closed $240k in revenue which worked out to $11k per head.

Total cost to fill and run the event was around $18k.

Here’s an example of an event Sales Page:


This is technically borrowed from the Franchise industry but translates perfectly for selling high ticket Masterminds.

It can also be used as a great front end offer to your Mastermind.

Typically people pay a refundable deposit to come for the day, there is full disclosure about the opportunity, meaning they know they are coming to make a decision about joining your program.

Here’s an example of an invitation to a Mastermind Discovery Day:


This offer is often used with great success in specific niches where there is some kind of physical operation that you are showing off.

For example, you have a Lawyer with a thriving practice.

He has a specific Marketing System teaching other lawyers as part of his Mastermind.

He then uses the ‘Fly on the Wall’ day to invite other lawyers to get a sneak behind the scenes on how the day-to-day works, then they are invited to join the Mastermind.


Inside NextLevel Scale™ we provide 3 x 3 Day in-person Member only Mastermind Events each quarter.

However, each year during December we also add a 2 day Bonus Event to the calendar.

It’s the only Mastermind event where we can sell Guests into the event.

Then if they like the experience they can join for the following year.

Typically we charge $3,997 for a ticket which is then credited against their annual Mastermind payment if they join.

I like doing these Bonus Events in December as it coinsides when people are doing strategic planning and goal setting for the following year.

The Mastermind then becomes the obvious support mechanism to help achieve their goals.


This is an easy way of building up great relationship equity up with other peoples communities and clients.

Find adjacent and congruent paid communities that you would be a compliment to (not a conflict of interests with).

Then provide great content that helps people, make friends, and share the next logical next step towards working with you.

The reason this works so well is because of the endorsement from the people they already pay, invest with and trust.

You can then become the Authority, Expert and Celebrity in their eyes which deepens the relationship quickly.

I’ve had a some great clients that have joined NextLevel Scale™ from being a contributor to the people’s communities.

Here’s a few ways you can suggest contributions:

  • Guest Webinars

  • Guest Podcasts

  • Guest Speaker

  • Guest Writer

  • Sponsor

A good example of this would be GKIC and Dan Kennedy.

I was a contributor for the No B.S Newsletter for nearly 2 years. Each month their Members got a value packed article from me in their mailbox.

I also spoke on stage at their flagship events, created the updated A-Z Info Marketing Blueprint Product, and did many guest appearances on Member Webinars.

Another would be Digital Marketer. For 4 years I spoke on stage at Traffic and Conversion, never selling anything — just providing really good stuff others were charging for.

I also ran specific workshops, did podcasts and wrote for their blog. If you do this strategically I’d create a Dream 100 of Paid Communities you can add value to and begin your outreach.


The best way is to add a link on the side of your Skool group like we have here:

We use this page: to help members sign up to the referral program and to see their potential referral gifts.

After signing up they can receive instructions of how best to refer us. Each time a members refers someone to the Mastermind they get rewarded with a Gift bundle that we’ve carefully curated.

Our members can afford any of these items, but the fact they are curated together is something they love.

So as they refer more members within a 12 month period they move up to more expensive bundles.

The referral process happens organically, but it’s important to have a ‘system’ in place to promote the process.

The question is always, how do you know when to ask for a referral? Well, the best time is when you see a Member experiencing success inside your Community you should reach out via Skool and DM them.

But we’ve also found over the years NPS scoring is a robust and simple way to not only get feedback, but also referrals.

If you are unfamiliar with NPS scoring it’s a simple question you can ask your community to gauge their overall happiness.

We run this on autopilot every 90 days via our CRM, but you could also use a tool to manage this for you.

When notified that we have a "Promoter," those members are automatically followed up with to see if they know anyone who would be a great referral.

I pulled a quick Lead Source Report on how many people over the past year that have joined NextLevel Scale™ that came from referral, check it out:


My NextLevel Scale™ Mastermind Community is structured in the following way.

Our members get…

  • Daily Community Access

  • Course Vault in the Classroom

  • Past Mastermind recordings in the Classroom

  • 2 x Weekly Coaching Calls on the Calendar

  • 4 x In-Person Mastermind Events

  • Member concierge via Skools DMs

It’s a hybrid evergreen model where Members can join at any time during the year. Meaning, there’s no big intake at the beginning of each year.

Here’s how the structure breaks down:


The community get’s access to me and my team inside Skool.

They ask questions and we provide answers + other members get to collaborate and solve each other’s problems.

My favorite way to provide feedback is with detailed answers using a Loom Video.

Additionally, we offer Concierge Support via Direct Message in Skool. This is with my assistant for anything private or sensitive that Members want to request.


Each Week I run 2 Live Coaching Calls.

These are recorded and added to Skool.

Also a back catalogue of recordings from 2018 have also be migrated to Skool.

This provides excellent meta data through the transcriptions for people to self serve.


We do Jam Sessions where guest experts come in and Mastermind with us.

A big tip here is to make sure their content is not in conflict with your philosophies.

Jam Sessions are great way to patch, update or supplement your current curriculum in the Skool Classroom. The sessions get recorded and then added afterwards.

We’ve had all kinds of guests come into NextLevel Scale™ from well know people like Jay Abraham, Rich Schefren, Mike Rhodes, Molly Pittman, but also many others who are behind the scenes, who don’t have a course, program and otherwise unreachable.

The key is to listen to your community.

Find out their current struggles, frustrations, fears and then find an expert in those specific areas you can invite in.


Every quarter there is a 3-day in-person Mastermind.

Here’s an example of our schedule for 2023:

Every quarter we do all our In-Person Event RSVP’s with Skool.

Its the most current and up to date list of Members we have.

So we create Notion doc with all the event details, here’s an example:

Then we make a post in Skool for people to RSVP, just like this:

Typically, I like to run these in-person events in different locations.

A quick run down of our past events have been in San Diego, LA, Nashville, The Bahamas, Miami, Portugal, Las Vegas, Mexico, London.

They are always at a 5 star luxury hotel, the best of the best.

This is what my Clients expect for themselves and the opulent environment is where they feel most inspired.

Usually we have 20-30 people at each Mastermind event which is a perfect number.

I like to setup the Room in a ‘U’ Shape

In terms of tools I use a TV and Whiteboard to collaborate with.

Most of the time I stay in the front of the room on a stool and then structurally there’s 3 parts to the Mastermind Agenda:

  1. Lecture by leader (or guest expert(s) and/or participant(s) with special expertise)

  2. Workshop style activities

  3. Hot Seats

Hot seats are where the magic happens.

It’s the power of Mind Merge you get from Masterminds.

Here’s how my basic format for each Members hot seat works:

— 25% Giving and sharing contacts, tools, resources, recommendations, campaigns they judge helpful to all

— 25% What’s going on with their business, including a report on items discussed at the prior Mastermind they’ve now acted on

— 25% Presenting their problem, opportunity, initiative, strategy, etc. and several related, specific questions they want to discuss to get my input and the groups input on

— 25% Masterminding on that discussion

All the action during the Mastermind Event is professionally recorded.

This includes multiple camera angles, screen sharing for the TV and good quality audio to pick up the audience questions.

This is all edited together and spliced into three parts to break up each day.

The recordings are then transcribed and added to the Skool Classroom.

After the event we also provide a Resource Doc of all the Notes from the event which is easy to navigate all the ‘nuggets’.

If someone wasn’t able to make the event they then have a catalog of everything we discussed. This sits as a link in the Skool Classroom under each video.


As I mentioned above every year we do a 2 Day Bonus Mastermind.

This is where we can invite guests that are looking to join us.

To protect the confidentiality of our members I don’t stick to the usual Mastermind agenda.


We both know the lifeblood of any business really comes down to your ability to ‘get’ and ‘keep’ Clients. I find most focus on the former, ‘getting’ - when in fact it’s the keeping that allows you to create what I call ‘Compound Continuity’.

First, a few notable mentions about retention of Members in any paid community.

  • Your Members don’t buy Features, they buy value & outcomes — these aren’t always linked to money, know what their ‘currency’ is and lean into it.

  • Members buy solutions to problems and they buy your path to achieving their goals — if you don’t have a framework and principles for success it’s hard to keep people on the straight and narrow.

  • Focus on the evolving needs of those you serve to keep members for life — you or your Community Manager has to keep their ear to the ground. What are they seeing, what are they hearing? How is the community changing?

  • Don’t try too hard to prevent departures from the group — This usually tempts pandering, letting the ‘inmates run the asylum’, constant reaction, piling on more benefits, and reducing profits. It can also make the group stale.

  • A group can benefit from some level of turnover. However, most advice on "retention" for groups comes from "experts" who have little or no actual experience in successfully operating groups. They often treat maximum retention as a holy grail, regardless of its cost in time and resources, or its impact on the group's authority. I am here to tell you that this approach is misguided.

  • Don’t be emotionally affected by ‘leavers’ — It doesn’t matter how much ‘love’ you’ve poured into them, how much money you’ve made them, how far you’ve bent over backwards for them - they will see greener pastures, or bright shiny objects and find them irresistible to refuse.

  • Familiarity breeds contempt — avoid excess fraternization. They are not paying you to be their friend, they are paying you to be a strong leader who has authority.

So how do we stop people leaving?

The first thing is to harness a True Mastermind Community.

What I mean by that is a Community that is tightly bound together.

In my experience this is down to having the fundamentals covered.

I consider those to be ‘shared’:

  • Goals

  • Principles

  • Beliefs

  • Values

  • Outlook / Mindset

  • Identity (this is often manufactured by you)

High alignment to these commonalities create a strong immoveable, unshakeable community.

Do these things right and you’ll have a Mastermind that markets itself.

As such you’ll never have a churn issue, as the momentum from this kind of organic growth ensures you’ll always be Net positive.

So how do we stop people from leaving Oli?

I’ll break it down into two parts:

Functional pains of disconnection like:

  • Losing access to valuable resources

  • Access to past Q&As

  • Vault of Masterminds recordings

  • Resource documents

  • Course Curriculum

Emotional pains of disconnection:

  • Relationships

  • Time

  • Feeling understood

  • Freedom

  • Impact

  • Legacy

Now that’s covered… how do we track Member behaviour before cancellation?

Again I break this down into two parts:

Involuntary Churn — these are Members that end up on our Accounts Receivable list because we are not collecting payments.

Common Involuntary churn reasons are declined cards, expired cards or merchant account issues. These can be easily fixed if you use Stripe by using something like

Voluntary Churn — these are Members who are requesting to cancel or not re-enrol The key here is to identify exactly what are the contributing factors that are going into a Member ‘wanting out’ - and then fixing them.

You might have an issue with your Customer Profile.

It might be the type of Bribe, Offer or Incentive you gave when brining in people to the program.

It could be because your onboarding isn’t well structured or your content is overwhelming.

You need to identify why members are falling away. Some of the ways you can do this is setting up what I call ‘Retention Sensors’.

For this I like to use RFM.

How we use these in the context of keeping members is the following:

  • Recency — How recently did they engage with the community

  • Frequency — How often are they engage the community

  • Monetary — How much money have they spend to be part of the community

Additionally, we love using 90 day NPS scoring to have a company wide metric on the health and happiness of our community. Check out the link above for more info.

I hope you enjoyed this post about how to fill, sell, operate and retain a successful Mastermind Group.

We covered…

  • How to fill a Mastermind Community

  • Captaining your group and managing Mastermind Operations

  • Protecting your recurring revenue with a Retention Playbook

Let me know your thoughts, take aways and distinctions in the comments below.

I realize there's a good chance you've never heard of me, but it's likely that you've already ‘seen’ my work through many of my successful Clients.

A quick note about me…

  • Dad to Spencer 16, Sienna 9 and Summer 8 /months

  • Husband to Lindsey

  • For fun I like reading, family time and go-karting

  • Currently living in Portugal 🇵🇹 originally from the UK 🇬🇧

  • Founder of

  • This year marks 20 years in the info marketing business

  • I’m a zero social media guy

  • Built 5 separate 7/8-figure businesses

  • 2 business exits

  • Sold over 1,000+ franchise licences in 26 countries

  • Spent 25 Million on Facebook Ads, 10 Million on YouTube, 5 Million on other Paid Sources

Want to chat about NextLevel Scale™ and building high ticket recurring Communities?

Shoot me a message on Skool

Still not got a Skool group yet?

Use my link here and I’ll send you a special gift ($297 value):

— Oli

P.S. The biggest pay-off for me from “teaching” people how to prosper in their Communities is seeing ‘good people’ rise to prominence and influence in their industries.

So many of my Clients have gone from relative obscurity to fame and become change-agents, recognized by thousands, some tens of thousands, and been appropriately rewarded.

Seeing people turn their knowledge, personal interests, curiosities, hobbies into million dollar businesses is the most exciting feeling in the world.

YOU too can play a meaningful role in people's lives and also insure your own financial future in any economy with your own Community business.

P.P.S Using Skool you accomplish this by legitimately aiding and positively influencing thousands with your own Community. As the late Zig Ziglar said: “If you help enough people get what they want, you will get what you want.