Startup Masterminds 101

Startup Masterminds 101 A publication by

What is a Mastermind?

The “Master Mind” may be defined as: “Coordination of knowledge and effort, in a spirit of harmony, between two or more people, for the attainment of a definite purpose.”

— N AP OLEON

HIL L, THI NK A ND GROW RICH, 1937

Masterminds are small groups of people that have similar experiences, challenges, and trajectories in their businesses. Quite simply put, they are the embodiment of the phrase: Two (or three) minds are better than one.

About a decade ago, we started championing masterminds on Startups for the Rest of Us. They were popular in the Internet marketing space and we felt they would be particularly valuable to both early- and growthstage startups. Since many founders in the self-funded space run solo operations, the idea of having a squad to provide feedback — based on an understanding of our industry that few have — was too good to pass up.

Jump to a specific section WHAT ARE THE BENEFITS OF A MASTERMIND? SHOULD YOU BE IN A MASTERMIND? HOW TO RUN A MASTERMIND LOGISTICS CHOOSING A MASTERMIND FORMAT SETTING EXPECTATIONS

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What are the Benefits of a Mastermind?

There are three clear benefits of being a part of a mastermind: GROWTH

By surrounding yourself with folks that can provide you with informed advice, qualified referrals, and critical constructive feedback on your failures in a safe space — you are just setting yourself up with both the resources and guidance you need to focus on growing your business.

ACCOUNTABILITY

As so many solo-founders know, keeping yourself accountable with no outside forces can be really challenging. We’ll talk about some of the formats of masterminds a little later — but during most mastermind meetings, there is a point in time where each member is in the hot seat, discussing past goals and their progress, setting new goals and tracking them, and reporting back to your mastermind with updates along the way. By asking your mastermind to help you be accountable to your business, you’re also committing to holding them accountable.

MENTAL

Humans are generally social beings. Napoleon Hill mentions that the convergence of two individual minds creates a third, invisible force that combines the strength of both of its components. When you share your vulnerabilities and your joy with other people, you magnify your own experience and make it the experience of those around you. The power that comes from those shared experiences can be just as compelling and empowering as your individual success.

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Should You Be in a Mastermind? ‣

Are you sales plateauing and you can’t seem to break through?

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Do you struggle with hiring and outsourcing responsibilities?

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Do you find yourself adding tasks to your to-do list faster than you complete them?

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Do you ever find yourself feeling isolated working on your startup?

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Does critical feedback from your customers sting like a personal attack?

If you answered yes to any of these questions, you would benefit from joining a mastermind.

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How to Run a Mastermind HOW MANY PEOPLE SHOULD YOU HAVE IN YOUR MASTERMIND?

There are many opinions on this — some organizations will consider their entire c-suite members of their “Senior Leadership” mastermind.

Some communities will establish masterminds of 10-20 people, but in those cases the focus is less on the individual and more focused on lifting all boats.

Here at MicroConf — we recommend groups of three or four. This allows you to hear a few different perspectives, but is still familiar enough that you can maintain a sense of focus on one another. If a mastermind has 5 or more people, members may find they are not getting enough individual attention.

HOW OFTEN SHOULD YOU MEET?

This is something that you and your fellow mastermind members should decide. Successful masterminds have run on weekly, bi-weekly, and monthly schedules. It really depends on the mastermind you join, what each of your members can achieve between each session. We find that meeting once every other week helps keep you connecting on a more frequent basis and allows you to set micro-goals that can be achieved in that two week span.

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Logistics Masterminds take work. It is not just a conversation between friends — each meeting of your mastermind should be treated with the same level of professionalism as any of your sales calls or demos. Here are a few things to consider when setting the logistics of your mastermind: SCHEDULING

Your masterminds will do you no favors if the members are not regularly meeting. When you commit to joining a mastermind, you are being trusted by your fellow members to be an active participant. On the onset, figure out a) when you are going to meet, and b) how often you’re going to meet. Try to find a time slot that can be reserved as a recurring meeting for your mastermind so that you’re not trying to schedule each meeting on the fly. And show up — the success of everyone in your mastermind hinges on each of the members.

TECHNOLOGY

Make sure that your tech stack works for everyone. Tools like Zoom, Slack, Facebook Groups, Skype, and other conferencing tools work great.

TRACKING YOUR PROGRESS

The things that you achieve in your mastermind can and should be tracked the same way that most project plans are. Use a tracking tool — whether it be a Google Sheet or Trello or whatever you’re most comfortable with. Take notes, record your conversations (so long as everyone is on board), update one another each meeting on the goals you have set in past sessions. Your ultimate goal is to build and grow your business — don’t be afraid to quantify the outcomes that you hope to get from your mastermind.

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Choosing a Mastermind Format There are a ton of options to choose from when it comes to the format of your mastermind. You may want to be a bit more relaxed in your structure or, especially for early stage masterminds, having a strict agenda can be super helpful. Here are a few formats that can serve as the skeleton of your meetings: ROUNDTABLE

If you want to implement a roundtable format, you’re looking to maximize the time to focus on all members during each mastermind session. You’ll split your meeting into even segments where the member gets the floor for their block of time. ‣ Advantage: Everyone gets equal time to focus on their startup.

Encourages members to consistently attend. ‣ Disadvantage: May not be able to dig into a single individual's needs as much as you’d like.

TIMED SEGMENTS

Set up blocks of 5-10 minutes. One member takes the floor for the first block of time, allowing for a quick round of questions. Cycle through the blocks of time until you hit the end of your meeting. ‣ Advantages: Encourages more of a fluid conversation, creates a built in opportunity let the conversation evolve based on prior time block conversations. ‣ Disadvantages: You need to be pretty strict on timing to make sure everyone has equal opportunity to contribute. Time goes by very quickly.

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HOT SEATS

This is a perfect setup for masterminds who want to focus more on the individual trajectory of its members. One person is the focus of the conversation, allowing the group to dive deep into that member's needs. When you’re in the hot seat, prepare an update covering all of the details that your mastermind has agreed to focus on. After you finish your update, the group spends the duration of the conversation focusing on the how and why behind that update and helps you to advance to that next goal. ‣ Advantages: The member in the hot seat gets the undivided attention of the rest of the members — leading to much deeper conversations than you might achieve in a short amount of time.

Allows for a longer runway for each individual to meet their goals between their day on the hotseat. ‣ Disadvantages: Because only one person is the focus of each hot seat, the other members might be disincentivized to participate.

MODERATED

If your mastermind is feeling a bit stale, or you all are running into obstacles that you cannot navigate through together, it may be worth bringing in a moderator to help guide your conversations. They will establish the agenda for the mastermind session, be respected as an authority that may be able to hold members' feet to the fire more effectively than a close peer in a difficult conversation, and can help hold members accountable between meetings. Moderated masterminds are uncommon and are usually found in more advanced groups.

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MODERATED CONT.

‣ Advantages: Master at keeping your meetings organized, asks questions your other members may not be comfortable to ask. ‣ Disadvantages: It is crucial that you choose the right person for this role. They are holding the reigns of your group — you want to make sure the moderator understands who the members are, what they are trying to achieve, and can provide meaningful insights (i.e. they have a level of expertise in your industry).

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Setting Expectations We saved one of the most important elements for last here — some expectations that you should be setting. Many of those expectations have been outlined above, such as setting meeting times and dates, but there are a few other things to consider when you set the rules for your mastermind.

ESTABLISH THE GROUND RULES

Figure out the rules of engagement for your mastermind early. And set them together. Some of the rules may be dictated by the format you choose, some may be as simple as an attendance policy. Some guidelines you may consider adding to your mastermind: ‣ Set a template for your member updates, including things like Monthly Recurring Revenue, Churn, Biggest Wins, Biggest Fails, and Current Roadblocks. ‣ When you’re meeting, your masterminding. Keep the conversation focused and empower everyone to feel comfortable steering things in the right direction. ‣ Honesty and Openness are essential for a mastermind to do its job.

Make sure that your guidelines encourage a space of open communication.

CONFIDENTIALITY

This one is huge. You will never be able to be open and honest with one another without the respect and trust the conversations you have are being kept confidential. Some masterminds may find it important to sign an NDA within the group, especially if planning for an exit is a part of those conversations. The vast majority of groups operate under a

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FriendDA, or a social agreement that governs the group. Be sure to talk about what level of confidentiality you need in order to be an active member of your mastermind.

NO HARD FEELINGS

Sometimes things just don’t work out. Personalities may not be a match, people may not be able to make meetings anymore, it just may not be the right fit. Our suggestion: give it another shot. Be a bit more vulnerable. Give a little bit more. If it just doesn’t seem to be working, then your group may just need to part ways. Don’t take it personally — you can still have a meaningful relationship if the professional relationship isn’t it for you.

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We hope that this guide has given you a bit more insight into how masterminds can help your business.

If you are a Startup Founder who is interested in joining a mastermind, but aren’t sure where to start, head over to microconfmasterminds.com and you can apply to be matched with other founders like you from around the globe.