“Alone we can do so little; together we can do so much.”

–Helen Keller

3 Steps to Start a Business Mastermind Group – Stephanie Pellett CreativeThere are a few decisions I’ve made in my business life that have made an outsized impact on my growth as an entrepreneur. I did a brand photoshoot, which allowed me to see myself differently. I started to prioritize DIY business retreats, which have given me space to think & plan. And I created a business mastermind group, which has by turns reassured me, cheered me on, and helped me figure things out.

All of these decisions have involved being seen by thoughtful human beings that I trust. That’s not a coincidence! The more I do this work, the more I believe in the power of community for empowering us to be our best selves. No person is an island. Even if we’re “solopreneurs”, we need others in order to make our business the best it can be. We need to support and be supported, to witness and be witnessed. We need the wisdom of others, and the chance to provide our own.

Starting a business mastermind group is one of the best things any entrepreneur can do for their business growth. And it’s free! But before we get into the tips, let’s start here:

What is a Business Mastermind Group?

Definition of a Business Mastermind Group – Stephanie Pellett CreativeA mastermind group is a peer-to-peer mentoring group. It’s designed to help each member solve problems or brainstorm ideas with the help of the other members. The idea is that if you’re feeling stuck or scared or confused, you bring it to the mastermind!

It is my most ardent belief that there is so much knowledge and wisdom in every single person. Even if you feel blocked in your own business, you still have so much to offer, since we can almost always see things more clearly in others than we can in ourselves. Every mastermind group I’ve been a part of has been chock-full of ideas and solutions. Take it from me: when smart, driven people come together with the intention of helping each other grow, it’s magic.

Even better? Mastermind groups can be completely and totally FREE! That’s right: transformational change and paradigm shifts, for the low, low price of…a cup of coffee? A daypass to a coworking space? The rent you already pay on your apartment for the use of your living room once per month? It’s amazing how much change can come from such little financial investment. Sure, you’re investing emotionally, but the financial costs are more than reasonable.

So if you want to accelerate your progress and break through your blocks, here are three easy steps for starting a mastermind group of your own.

1. Find your people

3 Steps to Start a Business Mastermind Group – Stephanie Pellett Creative

The most important part of starting a mastermind is finding the right people to take part. You want to be working with people whose opinions you trust, with similar values to your own. You don’t need to have the same or even similar business models, but you do want to have similar business philosophies. It’s important that you feel comfortable being honest and vulnerable with your fellow masterminders, and that you feel you can be honest with them, too!

Mastermind groups are built on trust, which will build over time. It’s okay to start on more of the “shallow” side and progressively go deeper as you get to know one another. But the important thing is that you never, ever feel judged or shamed by your fellow members. Mutual respect and admiration is a cornerstone of why the mastermind method works.

And last but not least, it’s important that all members be equally committed. You can collectively design your group with whatever kind of time and energy commitment you like, but just make sure that all your members are on the same page. You want to be able to rely on the other members of your group to show up for you.

If all of that seems like a tall order, here are some additional tips:

  • Start small: Napoleon Hill, the originator of the mastermind idea, classified a mastermind as “two or more people coming together in harmony to solve problems.” Two or more! Meaning that two is enough. If you only know one other person who fits the bill, start there. When it’s the right person, you’ll be amazed by how much progress you can make.
  • Find like-minded community: If you don’t know many people who also run a business, see if you can meet them! I met many of my business besties at Tuesdays Together, a global meetup with local chapters. Or you could try a coworking space that hosts events in your city, like Make Lemonade here in Toronto!
  • Go online: If you’re not meeting cool business owners where you live, don’t be afraid to take it virtual. Many successful masterminds are run over the internet. Reach out to those online business friends you’re inspired by, get a Zoom account, and have at it! All the same rules apply.
  • Keep it focused: Although you can have masterminds of all kinds (personal, relationship, parenting, etc.), make sure you’re clear on the purpose of the mastermind you’re starting. If it’s a business mastermind, it’s okay to require that all the members be focused on their businesses! Having that clarity means your sessions will be more powerful and helpful for everyone.

2. Figure out logistics

Coworking Space for Business Mastermind Session – Stephanie Pellett CreativeNow that we’ve covered the who, what and why, we need to figure out the where, when and how. A mastermind group is such a simple concept, meaning that there are nearly infinite ways to set it up! That said, in my experience there are some guidelines that can help make your meetings more successful.


The schedules of each member will naturally have an impact on what times of day you can meet, and that’s totally okay. There’s no “right time” of day to run a mastermind group, no matter what the internet may tell you. I’ve done sessions in the mornings, on the weekends, and late into the evenings, and they were all equally powerful. Once you’ve chosen a time slot that works, take some time to think through each of these factors:

  • Regularity: My mastermind group meets once per month, but others may meet every week, or every two weeks. Decide what feels manageable for everyone and book your next few dates at once.
  • Length: A good rule of thumb is to budget about an hour for every member of your group. That doesn’t mean each member will get a full hour in the “hot seat”, but it helps account for bathroom breaks, people being late, or socializing. You can always adjust if you need more or less time!
  • Energy: Mastermind meetings can really take it out of you! Make sure, whatever time of day you choose, that you’re well-rested and well-fuelled before, during and after. Take regular breaks, bring snacks, and stay hydrated.


Again, there’s no “one right place” for a successful mastermind group. How could there be, when each group will be made up of different people, each with their own personalities, styles of learning, and sensitivities? The right place for your mastermind is the place where everyone feels comfortable. Here are a few things to consider:

  • Are we okay with being out in public, or would we prefer a private space?
  • What kind of noise level are we comfortable with?
  • Is it important that we be somewhere that feels business-like, or is more casual okay?
  • Do we feel strongly about the aesthetics of the space?
  • What do we need to feel our best in a space?

3. Run your session!

Women's Coworking Mastermind Group – Stephanie Pellett Creative

Once you’ve established some of the basic guidelines for your group, the only thing left to do is actually begin. Grab your favourite notebook, a great pen, and a warm drink and settle in for the inevitable transformation that will follow.

The basic structure of a mastermind is pretty simple: meet regularly, share an issue you’re struggling with, have a discussion and receive feedback from your group, and listen and provide feedback on the issues that others are having. But within that structure, there’s room for so much flexibility. You can customize your group to you.

Here are a few tips:

  • Trial and error: The only way to improve the way your group runs is to give it time to evolve, and to be willing to iterate on your initial structure. You and your fellow masterminders are the best experts when it comes to what you need to do to make your sessions work for you. So be sensitive and check in regularly about what’s working or not working in your meetings.
  • Consider a timer: After a few months, my mastermind group came to realize that our “hot seat” time (the time that each member spent sharing about their struggles) would always expand to fit the time available. To keep us focused and on-task, we started setting a timer to map out roughly how much time we have for each person. We almost always go over by a little bit, but this practice keeps us on track.
  • Dim distractions: As with most important work, the best breakthroughs during mastermind happen when we’re all engaged with the process. For most of us, that means putting our phones away, muting notifications, and staying off the computer as much as possible. Take the work seriously and give it the attention it deserves.
  • Create a routine: Coordinating these kinds of meetings can be taxing! Instead of reinventing the wheel each time, try your best to make the sessions regular and routine, ideally at the same time and in the same place. When everyone knows the lay of the land it means that no one person is responsible for managing everyone else. It’s a team group and the coordination should also feel like teamwork.

Mastermind Magic

There is no Step 4, except to just keep showing up! Stay committed, keep reiterating the format and implementing the suggestions and you’ll experience the magical progress that mastermind groups can bring. The format seems so simple, unlikely to create massive change. But there is so much power in bringing focused attention onto the sticky areas of our lives and businesses. It’s a tiny shift that makes a huge difference.

I’d love to know: What feels most exciting about joining or creating a mastermind group? What feels like it’s still a stumbling block in the way of you starting one? Let me know in the comments below or on Instagram @stephpellett.

PS. If you’re looking for a group with even more focused support & attention, consider joining The Foundery! Not only do we have monthly mastermind meetings, we also have individual calls, office hours & resources to share. Click below to learn more about the program.

The Foundery | Stephanie Pellett Creative