The Fellowship Formula: Why Every Founder Needs a Mastermind
Why every founder should be in a mastermind, what you can expect from talking regularly with other founders, and how you can make your mastermind one of the best business assets you’ll ever have.
by Alex McQuade, Program Director of the TinySeed EMEA Program
Have you ever thought to yourself– “Running a business is lonely :(“ or “I wish I had someone who understood what I’m going through, my Mom just doesn’t get it!”.
We’ve all been there. Running a business can be isolating, and even if you have a co-founder, it often feels like you don’t have anyone to talk to who has context on the challenges and work involved in being a founder.
In addition to entrepreneurial loneliness, many founders also find themselves stuck in their own head trying to solve increasingly difficult challenges. How many times can you agonize over your broken sales process over and over without outside input to help bring in fresh ideas? If you’re like me, you can do it for an impressively long time while tricking yourself into calling it work.
Even the best founders benefit from a breath of fresh air and new pairs of eyes on their challenges.
“But Alex, I don’t have anyone like that in my life!” I can hear you say.
Well, dear reader, that’s why you need a mastermind. ✨
In this post, I’m going to make the case for:
➡️ Why every founder should be in a mastermind
➡️ What you can expect from talking regularly with other founders
➡️ And how you can make your mastermind one of the best business assets you’ll ever have.
Masterminds: The secret sauce of TinySeed
Hanging out with a few of our amazing TinySeed founders
Hi, I’m Alex. I’m the Program Director for the EMEA-focused arm of the TinySeed accelerator.
Every 6 months, our team welcomes a new batch of ambitious early-stage startups for a year-long program of mentorship, community, events, and… you guessed it, masterminds.
At the end of each batch, we receive overwhelming feedback from the founders about how impactful their masterminds were. “I didn’t even consider the masterminds when I applied for TinySeed, but they ended up being one of the most valuable parts” and “my mastermind group is crucial for solving challenges faster and better.” for instance.
Masterminds repeatedly prove themselves to be a foundational asset for TinySeed founders. Aside from the subjective feedback we get in our surveys, we can also see this through the fact that the majority of TinySeed masterminds continue to meet after the accelerator year is over.
So at this point you might be thinking, “Ok, but how will a mastermind actually help me?”
Let me use the power of analogies to lay out the benefits for you.
Lord of the Startups: Why you need a fellowship
So imagine you’re Frodo in Lord of the Rings. And you’ve just been tasked with the nearly impossible burden of carrying a very powerful ring to the top of a volcano while lots of things try to get in your way and destroy you.
Did Frodo carry the burden of the ring alone? No! He had a fellowship of other creatures with diverse backgrounds and skills to help him along the way.
By now, you’ve hopefully figured out that in this analogy you are Frodo, the fellowship is your potential mastermind, and the ring is your business. (Just please don’t throw it into a volcano.)
For the majority of people, leading a business is a big burden. You have to carry the weight of an organization on your back, knowing that the decisions you make and the effort you put in will largely determine its fate. That’s heavy!
But just like Frodo, you don’t have to (and probably shouldn’t) carry this weight alone. It’s possible to find your own Fellowship to share the journey with, hold you accountable, and share their skills with you to help get you further.
It’s time for a workout: How masterminds turn you into a lean, mean, entrepreneurial machine
Joining a mastermind is kind of like joining a CrossFit gym.
CrossFit!? That cult fitness trend from the 2010’s?
It’s still popular!
Yes, exactly. Hear me out.
You may have never done CrossFit, but chances are you know someone who does or have read a snarky article arguing whether it’s a fad or not. That’s all beside the point, which is that a lot of the main benefits that people get out of CrossFit impressively match masterminds. Let’s go over them and learn how you can get your business in shape!
1) Accountability
A large reason CrossFit is so effective is because there’s accountability built into it. You’re surrounded by other people trying to improve themselves and urging you to keep pushing forward. Even beyond individual workouts, CrossFit has long term accountability built into it. CrossFiters become friends with their fellow attendees over time, and with that comes a pressure to make sure you keep coming and putting in the work.
In your mastermind group, your fellow founders will focus on both your short and long term accountability. In TinySeed, mastermind groups share what they’ve accomplished since the last call, what they’ll be working on next, and their main challenge at the moment. This structure allows for the group to hold each other accountable between calls, and also to observe each other's progress on long-term goals over time.
2) Transparency
Have you been skipping leg days? Your CrossFit mates are going to notice that when you’re having to squat low weights after showing off your overdeveloped bench press. And they’ll call you out on it!
Similarly, a good mastermind will call you out on blind spots, and areas that you need to be working on. Have you been spending too much of your time building features instead of working on your sales and marketing efforts? That’s almost as bad as skipping leg day. A good mastermind will urge you to refocus your efforts on building that business muscle.
3) Growth
You can criticize CrossFit specific workout regimes all you want, but when you manage to build a group setting that convinces people to work out on a regular basis, they’re going to grow their strength.
Likewise, a mastermind group that meets regularly and supports each other is going to see growth amongst its members. The insights, questions, accountability, and encouragement of your mastermind group will lead to you making progress. For most people, they’ll make more progress than they would have by themselves in this environment.
4) Community
Yes, crossfitters can sometimes be insufferable with their WOD summaries, group workout photos, and insistence that you come join the gang. But these are all symptoms of the fact that they’ve found a community that they’re proud of and excited by. They’re part of something bigger than themselves that makes them feel good. Excitement about communities is often hard to understand for outsiders, and hard to resist bragging about for insiders.
It can be hard to measure business ROI from “community”, but I will argue that it’ll make your entrepreneurial journey more fun. Can you build a successful business by yourself? Sure. Will you have a better time doing it with peers by your side, sharing in the ups and downs? Definitely.
At this point, you should be nearly falling off of your chair in excitement at the idea of incorporating a mastermind into your life.
Let’s wrap things up with some advice on what to do to make sure your mastermind is a success.
How to start a mastermind.
Embarking on your mastermind journey begins with one simple step: starting it.
Now I don’t want to be a cop out here, but the logistics of starting a mastermind is broad enough to be an entire article in themselves. In fact, it’s enough to be a short e-book.
Well, as luck would have it, my colleagues over at MicroConf have already written that very same e-book. And let me tell you, it’s good stuff. So instead of reinventing the wheel, I’m going to suggest that if you need a 101 course on the ins-and-outs of masterminding, you start there.
I’m going to supplement that information with my advice on running a successful mastermind in the long term. These are lessons that come from watching a large number of masterminds over years and talking with their members about what does and doesn’t work.
It’s one thing to start a mastermind, but like anything involving human relationships, masterminds take some conscious effort (and a little love) to grow over time. But just like your favorite plant/pet/child, it’s well worth it.
Embrace the vulnerability
Masterminds require a high level of vulnerability in order to be useful, so they’re not always easy. Most of us are naturally inclined to gloss over the embarrassing mistakes we’ve made and only share a curated perspective where everything is going well. This is counter-productive in a mastermind.
When it’s your turn on the hot seat, be prepared for a few things:
Share your numbers.
Resist the urge to sugar coat your challenges.
Be prepared to receive honest feedback without being defensive or dismissive.
In order to have a valuable discussion, your mastermind needs the real details on your business, warts and all. They need real numbers, real data, real vulnerabilities. Your core metrics (such as MRR, conversion rates, LTV, and churn) are all important reference points for the group to have context on where you are.
And finally, you need to be prepared to receive some tough truths. Masterminds will point out areas that you need to improve in, or give ideas that you may have not considered. Avoid the impulse to defend yourself or explain away the advice, and instead thank everyone for their opinions and give them an honest consideration.
When it’s your turn to listen to someone’s hot seat, remember that now they’re the one being vulnerable. It’s fine to joke and rib each other occasionally if that is your group's culture, but when it comes to real feedback, give it from a place of respect.
Over time as you get to know your mastermind mates more deeply, all of this will get easier.
You don’t always need answers — but you do need good questions.
New masterminds often come in with the idea that they need to be giving each other perfect answers. This is a mistake.
Sometimes people have answers, but that’s not a healthy expectation. The mastermind group is meant to work alongside you in solving your challenges. What this often looks like is exploring, brainstorming, comparing experiences, and asking good questions.
I think that last one is worth highlighting again. Sometimes asking the right question is more useful than giving an answer.
This is a useful thing to remind yourself because it takes the pressure off of everyone in the group to be a subject matter expert on every topic that will come along. You don’t need to know everything to be a valuable mastermind member. You do need to actively engage, ask good questions, think through things out loud, and share your thought process.
Stay flexible: Everything can be changed
Every mastermind group is different. Different personalities, skill sets, and goals combine into a wonderful unique soup of collaboration.
Remember that there is a lot of room to change the way a mastermind group is run, depending on what will be most useful for the group.
Earlier I referenced the MicroConf e-book as a “101 style” review of how to start a group. This material is made up of lots of useful recommendations that are useful as a starting point, but it’s just a starting point.
Over time, as your group gets in the groove of things, it’s worth having a discussion to see if there are any changes needed to make things more useful for the group. I usually recommend having the first one around the 3-6 month mark, and maybe one every six months to a year after that.
Almost everything is flexible! Structure, time per hot seat, questions, types of accountability, frequency, it’s all on the table.
Feel free to suggest changes that might help the mastermind better align with the goals or personalities of your group. These changes can be viewed as experiments, and you don’t need to feel married to them either. If an experiment isn’t going in a good direction, you can always cancel it and change things back.
Commitment, commitment… and you guessed it, commitment
The most important thing to prioritize in your mastermind is commitment.
Mastermind impersonal relationships generally develop over time and get better as the members get to know each other and their business. At the beginning, things can feel a little stiff and formal. Over time, trust builds and barriers drop. As this happens, the dynamics of the group evolve and the support you feel from your group increases. This could take as long as 6 months, so don’t feel like you’re doing anything wrong if you’re not all besties immediately.
You’re also getting to know each other’s businesses more in depth over time. How long does it usually take a new employee to learn the in’s and out’s of your company? At least a few months (if they’re a superstar), but often longer.
Although there’s already a lot of shared knowledge between group members by you all being founders, it will still take time for the other members to get a good grasp on things like your funnel, marketing, audience, sales, operations, and all the ways you run your business. The good news is that the mastermind is still valuable even before you reach this point.
If the other members are doing their job, you should be enjoying the accountability, brainstorming, and camaraderie of your mastermind relatively quickly. But like a good stew, it will just keep getting better over time.
Finally, at an individual level, commitment is necessary for you to actually see the results of a mastermind. As wonderful as a mastermind is, it’s not a magic wand. Your group is not going to change the trajectory of your business after a few calls. As time goes on, the accountability and guidance of your group will lead to tangible results. Mastermind members generally are able to navigate hurdles faster, and prioritize actions better thanks to the help of their group. Over time, this improvement in your effectiveness as a founder can have compounding results.
So what does commitment look like at a practical level?
Show up, seriously.
Make your mastermind a top business priority, not a nice to have. That means not canceling for last minute sales calls or any little obstruction that comes along (and they will come along). Unless it’s truly an emergency, your mastermind should take priority. Don’t be the person who emails the group a few hours before the call to back out because “something came up”.
Be ready to give the group your 100% attention
Get yourself into the right mindset before the call. Bring a good energy and be ready to give your group your full attention. That means not checking slack/email/whatever your distraction vice is. Everyone can tell when your attention is elsewhere and it signals to your group that these distractions are more important to you.
Bonus idea: I’ve heard about some masterminds having an accountability buy-in to make sure everyone is serious about attending. The idea makes sense. Each founder pre-commits a $500 deposit (or any amount that is financially significant to the group) that you’ll lose after X amount of calls missed.
This is an interesting way to make sure everyone has some skin in the game and isn’t going to waste the group’s time with cancellations. If anyone has done this, I’d love to hear how you set it up and the results!
Let’s wrap it up!
Over the course of this article, we’ve covered why you should consider joining a mastermind, what you can expect from your group, and how to turn your mastermind into a long term success. If you don’t already have a mastermind, my hope is that this article gives you enough of a push to go for it. If you already do have a mastermind, wonderful! I hope this article gave you some new ideas on what to expect from it and how to improve it over the long term.
Finally, feel free to share your mastermind experiences with me. Is there anything you’ve seen or done in a mastermind that made it valuable? Any unconventional formats or approaches that have worked well for your group? Let me know, I’d love to hear from you!
In the meantime, keep calm and mastermind on.
