A small podcast to help you become a better business owner

Season 1, Episode 7

Finding Mastermind Groups


Our panel discusses the value of mastermind groups, how to find one, and the black magic it takes to do it well in our experience.


Episode Summary

Our panel discusses the value of mastermind groups, how to find one, and the black magic it takes to do it well in our experience.


  • Kai Davis
  • Jeremy Green
  • Meg Cumby


Each episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they’re enjoying and recommend you check out:

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If you’re a freelancer, then you’re not just an expert in your field. You’re also a business owner, responsible for everything from bookkeeping to marketing to customer satisfaction to business development.

On the Business of Freelancing, our panel of experienced freelancers discuss the issues that they have encountered while building up their business — and give you practical, actionable advice to take your career to the next level. We also invite expert guests to provide their opinions and perspectives on how you can better succeed in your freelance career.

Episode Transcript

Kai: Welcome to the Business of Freelancing. On today’s episode we’re going to talk about Mastermind Groups. Why you want or need one. Advantages of small versus big, and how to find a Mastermind Group and the black magic it takes to do it well. On this episode, we have Jeremy Green.

Jeremy: Hey everybody.

Kai: Meg Cumby.

Meg: Hello, folks.

Kai: And I’m Kai Davis. Thinking about the very interesting times we all are in together, the phrase resilience keeps coming up for me. I know in my business journey over the last decade or so, one thing that helped me be a more resilient entrepreneur is a Mastermind Group. How about for you guys has a Mastermind Group, brought benefits for you or been a hassle? What’s your experience has been like?

Jeremy: Yeah, I’ve had great experiences with Mastermind Groups. It really helps a lot to have people that aren’t as emotionally invested in what you’re doing, that are familiar enough with what you are doing that they can give you advice and help you navigate things, especially when things get stressful and rough. Anytime that you’re feeling emotional about it, you are probably not making the best, most rational decisions that you can and it helps to have people that can sanity check you and to know you’re thinking about that the wrong way or whatever, it helps a lot.

Meg: I agree. At a minimum, it forces you get things out of your head, and explain the challenges or opportunities you’re facing. At the very minimum, people use the expression rubber duck it. Rubber duck things like explain things to an inanimate object to just get things verbally and then to be able to work your way through a problem that way.

That at a better level like beyond that it’s just good to get you like you said that outside perspective. Somebody who’s not as emotionally invested in the decision to say, well if you went through this, what’s the advantage of this option versus this option or what might be a path that you’re not seeing. Getting it that extra perspective on it from other people is huge, that you trust.

Like you said, that know you well, and it’s not just some… When you do, you are able to build those relationships over time, it helps even more. How do you guys find… I’ve heard some people say, it’s so hard to find, or how do you find this magic way of finding a Mastermind Group or find your people to partner up with and have those mutual discussions?

Kai: For me, it’s very much been a lot of it being in the right place at the right time. One of my first major Mastermind Groups where I actually met Jeremy was a Nick D’s email list. He sent out an email, “I need to start a Mastermind Group anybody interested?” A handful of us said, “Yes.”

We came together, and it was an awesome, awesome experience and so valuable. Aside from being in the right place at the right time and winning the luck lottery, I found the easiest way to find a Mastermind Group is start one yourself. It doesn’t need to be a 10 person endeavor. It could be like, yo, you and a friend, once a week, once every other week, get on a call, talk through things, ask questions. Yeah, making your own luck is probably the best way to get started.

Jeremy: Yeah, for me, definitely being in the right place at the right time and getting lucky led to my best mastermind experience. Others that I’ve had originated at conferences. So, like a microcosm, a group of people that we’re all working on SAS’s. We started a little Mastermind Group that ran for a little while. I have a very similar story to just being in the right place at the right time, the Kai, like I had met Nick D the year before at Bacon Biz conf.

At the conference, I heard several people just mentioned that he writes really good emails and that, if for no other reason just to observe how he interacts with his list, it was worth subscribing and just following along. So, I thought, “What the hell I’ll subscribe and see what happens.”

Then, a week or two after the conference, he sent that email about, “Hey, I’m looking to start a Mastermind Group for people that are interested in productized consulting, if you are interested in that, or even if you don’t know what it is and want to learn more, hit reply.” Normally my instinct on that would be, “No.” But for some reason, I was like, “Maybe I’ll give it a shot.” It turned out really great.

So part of is just like taking a chance. It felt weird at first because we all assembled in this Slack room and it was Nick who I had met once at a conference and nine or 10 other people that I had never met before in my life. Those first steps of just opening up and telling everybody about our businesses and what problems were facing, just getting over that hump felt like a big emotional risk maybe.

It worked out well but it’s definitely necessary that you have to lay it all out there and be ready for criticism and comments. Even if people don’t mean it as criticism, it can feel like criticism.

Meg: There’s so much good stuff on what you just said there. I felt like for me, it’s been putting myself out there first like in a… Both of my masterminds that I’ve been in have had roots in freelance camp, Kai’s Community for Freelancers. But just being out there and participating with people, that’s helped. So when you say, “Right place right time.” The idea of being engaged with people and meeting new people.

Both have been around to how important is it for you guys to have alignment of goals with the people that like, what helps bring a certain group of people together? How important is it for similar goals, similar types of businesses. I don’t know what you guys’ experiences are with that?

Kai: Alignment is super, supercritical in my eyes. Everybody in a Mastermind Group needs to be in the similar type of business. So if I’m running an eCommerce store, and you’re running a SAS, and somebody else’s consulting, we’re going to be on way different wavelengths already. On top of that, there needs to be similar goals.

If let’s say I’m looking to get a day job, and you’re looking to retire financially independent, again, slightly different goals, the questions, the discussions, the challenges are going to be out of sync with each other.

So, making sure you’re in a mastermind with people who have that similar type of business, you’re all consultants, you’re all SAS owners or similar goals. “Hey, let’s, reach this level as a consultant, let’s publish a book, let’s, make a quarter-million dollars as an Indie. Let’s see if I could do it.”

That helps you be on the same wavelength and just know where you’re headed. So, that resonance or that similarity is very critical.

Jeremy: Yeah, alignment of goals especially is important and alignment on type of business to a point like, you don’t want to go too similar. Like as myself being a Rails Consultant, I don’t know that a Mastermind Group with other Rails Consultants is going to do me a lot of good.

In fact, you want to avoid perceived competition with other people in the group, because that’s going to cut down on your willingness to be open and lay all your cards on the table if you feel like somebody else in the group is competing with you directly for business. Like in the Mastermind Group that Kai and I were in, we had people that were all over the map.

I’m a Rails Consultant. We had a guy that was a WordPress consultant, Kai was doing SEO, a couple of other people that were doing different types of just business process consulting. So, we were all having the same types of interactions with clients and facing some of the same questions about how do you structure engagements and how to use scope things so that it’s easy to have a one and done engagement and not find yourself roped into this never-ending whirlpool of work, those kind of things.

But we weren’t focused on, “Hey, I’ve got this tricky Rails question and I need to figure out how to solve it for my client.” That was on my side to do that part. It was about working on the business instead of working in the business, and that’s where the focus of the Mastermind Group should be.

Meg: Yeah, I have been in a Mastermind Group with a developer and I’m not a developer. It was interesting, like he says you kind of focus more on the business problems than necessarily the in and outs of the particular work you’re doing.

Kai: That’s also another lever you could pull. Even if you are in the same industry or same niche or providing similar services. If you say, “Okay, explicitly, we’re going to focus on the craft of doing business not on writing code or doing SEO, but how we become better business people.” Even if there is that strong overlap, you’re at least able to look at each other and say, “Okay, I can’t figure out how to write proposals efficiently, or I don’t feel competent enough to charge more.” You can support each other in that area.

I found similar to what Jeremy pointed out, if there is too much overlap, it could get a little weird feeling, but if there’s not any overlap, it can get a bit hard to see eye to eye so it’s case by case you figure out, “Okay, Is this good? Is this bad?” There’s definitely like a squishy middle range of we’re still figuring it out, but it feels good for now.

Meg: Mmmh.

Kai: I’m curious for you guys. What sizes of Mastermind Groups have you been in? I know for Jeremy ours peaked at around 13 members and so it was definitely on the larger side. But what other sizes have you been with?

Meg: For me, it’s been just two and three, very small. Which has been nice. It just lets the meetings be I don’t know what everybody else is, but like, an hour is a reasonable amount of time for weekly. Both times I’ve done weekly and it’s been with two to three people. That’s been nice because it feels like, there’s enough time to give everybody the space that they need and allowed to meet on a weekly or bi-weekly basis.

Jeremy: Yeah, I’ve been in a couple of smaller ones that were four and five people. Neither of those worked out nearly as well as the one that Kai and I were involved in. I don’t know if that’s related to size or not, but I suspect that there is an element of size being there. My theory is that when we had 12 or 13 people in the group, that that meant on any given day that at least two or three people, were going to be somewhat active in Slack and be around to engage in conversations and answer questions and let somebody bounce ideas off of them.

Then on days where several people were having a slow day, it wasn’t uncommon that we’d have eight or nine or 10 people actively engaged. Those were very productive days just for idea generation. For me, part of what’s valuable about Mastermind Groups is getting to be a fly on the wall in somebody else’s business and see them approach and deal with problems that I haven’t dealt with yet. Because then I’ve got a better mental model for, “Okay, I understand I’m going to handle this situation or avoid this situation if I can because that looks like it’s not fun.”

So that helps a lot. You have to find some way to sustain some minimum level of activity and engagement, or it’s really easy for it to just Peter out and go to nothing. That’s what I saw happen a lot with these four and five-person masterminds is that the Slack room would be busy the first couple of days, and then after that, it just didn’t seem like there was any momentum there to keep things going.

On the other side of that one of the challenges that we had in that group was with 10 people joining a call. It’s hard to even give everybody five minutes to talk about their business. Calls were a challenge, but the Slack portion was really good.

One of the ways that we addressed the call issue is we started doing what we called the hot seat where one or two people, it would be their turn for that call to talk about what’s going on, ask questions that everybody else could help get into. Then everybody else would just do a two or three minutes, “Hey, here’s what’s up.” General status update. Then I’m going to take the rest of my questions or whatever to Slack until it’s my turn on the hot seat.

That worked pretty well. But it definitely feels different than if you’ve just got three or four people and every week, you’re getting a little bit of magnifier time.

Meg: I hadn’t thought about because I haven’t done it with a lot of async communication. I hadn’t thought about that as a way to have a larger Mastermind Group is by obviously having some Slack or some other async communication with each other.

Kai: It’s nice just a rabbit holing on the tools for a minute. I’ve always loved having an active Slack for a mastermind, just exactly as Jeremy put it, it’s nice to be a fly on the wall. Just see, okay, what conversations are happening? What’s the pulse of these other members in their businesses and pull information out? Or just remember the continuity? Oh, three months ago, you were worried about X happening? This looks the same? Let me raise a question or say, “Hey, this is similar to that. Do you want to dodge it?”

So it’s good to have conversations like that, it’s good just to have space where there’s explicit permission to ask questions, answer questions, or even ask like nosy questions. “Hey, sorry, you’re selling the service offering? What are the margins look like on that? I got no clue.” Not a standard or appropriate question, but in the context of a Mastermind Group where that permission is given, it’s a lot easier to both ask and share when other people ask with you.

Meg: Hmm. I don’t know what about that just sparked off this thought of because it goes back on to why is it valuable to have the accountability and to move things forward in your business that are the important things, but not necessarily the urgent things, like those things that will actually start to move you closer to where your goals are, as opposed to just getting sucked into client work all week. That has been probably the biggest benefit for a Mastermind Group for me.

Kai: Yeah, it’s a strong external motivator to head in a specific direction not even the right direction in your business knowing that there are other folks asking how’s it going? Or you can just say, “Oh, I don’t want to move towards doing something like this in the next month.” You’ve got some nice voices nudging you forward there.

Meg:  Just saying like, “I intend to do this.” It’s so much easier to not break the promise to yourself when you’ve made it in front of other people. Not that anybody’s there to… Everybody understands that things happen, life happens. Though priorities shift, but it does avoid just the not doing it because you’ve just haven’t gotten around to it.

Jeremy: Yeah. It’s invaluable to have somebody there to say, “Why haven’t you done the thing?”


Meg: Or some version of that? [laughs] Some less [inaudible].

Kai:  Okay, I thought that as the ringtone for the week.


Meg:  Why haven’t you done the thing? I love it.

Kai: Another strong benefit I’d call out of masterminds is really continuity. Even if nothing major has happened, you’re just like, Oh, I’m moving forward to have other people who could say, “Okay, I know where you were a year ago. I know the general area you’re headed towards and I know what that intermediary path has been for the last 6-12 months, whatever.”

There’s so much power and just being able to have a conversation or say, “Hey, I need to talk through this thorny issue.” You don’t need to explain like, “Okay, this is what a podcast is, I have seven of them. This is why that’s important and like, catch them up on it.” Your mastermind members already know, the background details you can get right to the meat of the story.

Meg: Mmhm. Yeah, I think about that in contrast to when I’m talking with other people that probably know my business, but they don’t necessarily know the ins and outs of everything I’ve tried or what I’m working on or what my situation is, what the surrounding circumstances are. It’s nice not to have, it’s great when everybody wants to. I certainly value anybody’s input, but it’s more valuable when somebody is familiar with the situation and isn’t necessarily giving the advice a little more blindly that they can tailor it a little bit more.

Jeremy: Yeah, definitely. Because ideally the people that are in your group know about you and your goals and what you value and can help take into account more context than just, “Oh, what does that do to the bottom line?” Because there is more to life than that, and you do have to balance priorities. It really helps to have people that get that and can help you hit the target a little bit better.

One thing that it’s important that people keep in mind is that in the Mastermind Group, it’s not a mentorship, and it’s not, hey, I’ve got all these people that I can ask questions to, and somebody’s going to tell me the right answer. It’s about everybody collectively pitching in to help everybody find answers together.

One of the things that I had to get over, in the beginning, is if somebody would ask a question, my instinct would be like, “Oh, I don’t know the answer to that. I’m not going to say anything.” Really, it helps a lot if you can get over that and just be willing to spitball about things with people and say, “Well, I don’t know, but here’s how I would construct my mental model of the situation. Here’s how I would approach it. Here’s what I would hope would happen if I approached it this way.”

Just that talking through and helping people see possibilities that they might not have seen before is really helpful. You don’t have to be right. You have to be involved and engaged.

Meg: Even just asking more questions. It’s funny how many times somebody else say like, “Here, I’m thinking, should I do A or B?” Just asking, What are you hoping will be the outcome of doing A or B. Where are you trying to move towards? Are you hoping it’ll bring you more money? Are you hoping that it’ll increase your profitability get more customer? What are you actually trying to accomplish to do? Should I start a mailing list? Asking why you want to start a mailing list? That sort of thing.

Jeremy:  Sometimes it’s helpful to say, “So this may be a dumb question, but why not do C?” Sometimes the answer is, “Oh my God, I hadn’t even thought of C, that’s a great idea.” [laughs] That’s just helpful to have people around to ask questions.

Kai: So in a sense, like a successful healthy Mastermind Group, the outputs aren’t the exact answers, the outputs are conversations to help you or the group at large, have a better understanding of the situation and possibilities for what to do next.

Meg: Agreed. I’d say that’s ideal. Again like he said that combined with just having, once you do decide what path to take on something just to have that check-in with someone to see if the blockers… Yeah, it just helps you do the thing. It gives you one more reason to do the thing, and not put it off till tomorrow.

Jeremy:  So, Kai, you’d mentioned earlier about creating your own luck and starting a Mastermind Group. I know that you were involved in the administrative side of the one that we were involved in. Can you talk to us a little bit about that and how you think about molding and guiding one of these things and helping to keep conversations going and all that sort of thing?

Kai: Yeah, good question. I will have to keep myself short on this because [inaudible] in the hour of this. In terms of, kicking it off and getting started, I think it’s just something as simple as “Okay, I want to focus on this type of business. What’s like consulting, and I’m working with this type of clients, let’s say, software as a service.”

If you want to start a small Mastermind Group, figure out like, “Okay, what goal am I aiming for over the coming year, maybe it makes more money, take more vacations feel just generally better about business?” Then think of one or two, or maybe three folks that you know who may be meet all of those criteria, or some of them. They’re also doing consulting, or they’re also involved with SAS, or they have a similar goal.

Just reach out to them and say, “Hey, I’d love to start a Mastermind Group. Let’s try it as an experiment for three months if your game for it, and it would work like this. We get on a call once a week, or once a fortnight, we have a Slack channel, we can ask questions of each other in it. Really, the ultimate goal is to help support us or anybody else who joins in achieving that next level in their business.”

It definitely is a bit squishy. There aren’t absolute guidelines on what to talk about. But I found something like that works to at least get an idea started. Even just starting with one other person is great because you could get some processes down, you can just figure out what the vibe is, what the flow is.

Then after a couple of meetings as you have a stronger connection with that initial person, say, “Okay, who’s another person we should invite to this? Or do we want to invite another person to this and slowly grow it over time.” I found that a nice, gentle, stable way to keep it moving forward in terms of keeping it active.

For me, it’s always come down to trying to hold a space in the digital space or the physical space, and just ask reasonable questions to get to a better idea of what the other person is looking for with their next step or their current project or help them get a better idea of what they’re looking for. So that might just be being a little extra active in the Slack, making sure somebody is available or unavailable.

If somebody says, I have a question around this, even if it’s just to say I have a bunch of questions around that too. What’s top of mind there for you to almost extend permission for that other person to start sharing more details or go a little deeper? That for me has always been great in a number of Slacks or mastermind communities, just as a way to almost demonstrate to other people that it’s okay to ask questions. It’s okay if you don’t know the answer. It’s okay to just be there in the conversation.

I’ve often found by modeling that other people start imitating it or seeing there’s permission there as well. That vibe just spreads across the Mastermind Group, and as a whole people are a little more active or a little more engaged with each other. Can I explain any of that better or that tickle any spots to dive deeper?

Jeremy: No, that’s a pretty good explanation. The thing about modeling that it’s okay to ask questions and show that you don’t know the answer and provide details when and where appropriate, that definitely helps, and you need that.

Kai:  Mmmh.

Meg: I have a question about if you guys ever… I love the idea of putting a time block around to try it out and see if it works out with no hard feelings after three months or not. Somebody’s not digging it and can part? Has there ever been a situation where you get into the Mastermind Group and then maybe not everybody’s the right fit for that, has that ever happened? And if so does that person generally see that for themselves?

Kai: I’ve recognized it a few times for myself like, Oh, these folks are wonderful, this mastermind is great, but they’re all eCommerce and I’m over here in SAS land or something similar. I’ll often ask myself, okay, is there value I could provide to the other people if I have that time? Or are there questions I have around the space that or are the topic spaces mastermind is, if not, I’ll often bow out or say, “Hey, I’m super constraint on time right now, I love all of you guys, but I’m just not able to commit to this mastermind at this point in time.”

In terms of recognizing if somebody else isn’t on the same vibe. I don’t really have a lot to share there. It’s not something I’ve experienced or gone through.

Jeremy: Yeah, I’ve definitely seen people say, “Hey, I just don’t have the time to commit to this or, even hey, when we got into this, we were trying to do X and I feel like I and most of you have gotten there and I need to focus energy on other things. Love you guys, but I’m out.” That kind of thing.

Meg: Yeah, I feel like most people seem to be pretty self-aware. Like it as it is and that’s the nice thing. But by putting that time limit at the beginning, you can let people bow out without any like he said just to say like, “Hey, you know what it like?” It just doesn’t put that decision point. It gives people an articulate not that people can’t bow out earlier. But it’s nice to say this is an experiment and just see if everybody jives and if not, that’s totally fine.

I felt like I had to… The Mastermind Group that I was part of the three person, one, when we had paused for like, a couple of weeks or something like that just because of different commitments. Then I, realized, you know what this has been great this particular time, but I think our goals are starting to the verge a little bit.

So, I just felt like, yeah, that was the right time, that was the right amount of time. How long did you guys’ masterminds lasted typically? I wonder if there is at all? I don’t know if not typically for everybody, but yeah, for ranges of time.

Kai: The one Jeremy and I were in, I want to say it was four years, maybe five. A good amount of time.

Meg: Mmhm.

Kai: Another one I was in starting in 2017. We set out, I called it a charter. We sat at a charter for it to be a nine-month mastermind and then people opt-in for another year once we hit that mark, and it worked really well. Some folks just naturally, turned out or said life is busy right now, and that gave a nice opportunity to add new people into the mix. “Hey, we’re down to people who would be a good fit. Who do we know that would vibe well with us?’

Meg: I really like that.

Kai: I have seen in a couple masterminds, though similar to what Jeremy said if we hit a point where we’ve reached a goal, and there’s not a clear next step or goal to move us forward individually, or as a group, it can, Peter out. Where like, “What am I playing for? What am I aiming for? I don’t really know.” If everybody gets into that headspace, there’s just less velocity forward and it stalls.

Jeremy: Kai, have you ever had to deal with conflict resolution or hard feelings in a Mastermind Group and try to negotiate the peace and get everybody back to play nicely with each other?

Kai: A couple times. It’s a challenge, especially, I shouldn’t say it’s a challenge. It can be hard but I don’t think it’s impossible. It requires a willingness as a moderator or admin in the Mastermind Group to be present with the other folks understand, like, okay, you’re veering this way, and you’re veering that way because of some belief you have. It’s not that you’re wrong here. It’s just the expression of it that might be coming out a little incorrectly or a little harsh.

I’ve often found success in not even coaching, just being present and encouraging the other person to see that their idea is valid, but the way they’re expressing it might not be and encourage folks to step away from the computer, take a little bit of time, go on a walk, just to give themselves a more mental space.

So challenges and conflicts do come up in any group of humans. That’s just human nature. Being okay with it, being a little prepared with it, and being willing to roll off the punches does work well. In some charters, I’ve even said things like, “Hey, the oops out rule is fine.” Sometimes I’m going to unintentionally say something wrong or piss you off, please say like, “Hey, oops, that hurt me or ouch that hurt my feelings.” I’ll say, “Oops, oh, sorry about that. I will do better moving forward.” But it’s impossible to expect there to never be conflict. But is it entirely possible to expect that most conflicts can be resolved with the communication?

Meg: That’s the biggest thing. Nothing good can come from not communicating well. Like setting expectations, setting boundaries, telling people, “None of us are perfect and we’re all human beings.” Just big news there. Sorry to break it to everybody.

[laughs] Sometimes you can get caught up and just not see people interpret words differently.Yeah, everybody’s got different personalities and what might seem like you’re trying to just give something helpful. It may have come across in a more… May not come across the right way.

Just checking in and just saying like, I don’t know what the mechanisms are for that. But it’s always helpful to say would this be helpful? What kind of feedback are you looking for here? That can help avoid some of that like let’s say giving advice that’s not necessarily being sought for. There’s lots of different ways you can take that.

Jeremy: Yeah. That’s tricky because one of the things you want out of a Mastermind Group is to occasionally get some unsolicited advice.


Jeremy: Dude, you are totally screwing that up or whatever it is. Yeah, it is important that you just want everybody to have an openness to new ideas and the idea that, okay, just because I’ve been doing it this way, doesn’t mean I always have to do it this way. That sort of thing.

Meg: We’ve brought up a couple of times just being open to constructive criticisms, like, I don’t know if that’s really the right, or like, maybe you’re… I’d encourage you to push yourself in this area or something like that. We all need a little pressure, or sometimes just some. I think too when you get eyes on, let’s say, your website or something like that, just being open to that feedback that might be like… Maybe that’s more of this word of criticism might come in, at least in my experience is saying, well, this doesn’t really speak to, you need to improve this and this.

Speaking to someone who’s edited a lot of things and used to be an editor like, your boards can be very precious to you when you’ve written them and worked so hard on it and it can be really hard to hear somebody say tear it down a little bit, kindly. It’s hard to say like, “Oh, this doesn’t really work and you need to change this, and you just spent six hours on it.

[laugh] But you need to be open to that. Because like if your friends in your Mastermind Group are thinking that, what the heck are your customers thinking?

Kai: Yeah, true. While it might be harsh to hear, like, the sales page is ugly. It’s better to hear it from a friend or a colleague in a Mastermind Group than six months from now and a customer’s like, yo, your sales page sucks, or to have it be sucky and never hear it from anybody. It’s better to get it from a friend better to get that nudge.

Meg: Yeah. To be open to that uncomfortableness. It’s like, “Okay, let’s put it out there and get the feedback and it’s okay.”  When I go with the editor’s brain to it’s so much easier to point out what for people evaluating copy friction, it’s so much easier to point out what needs to be fixed versus what’s working fantastic [laughs]. So just to be mindful when you do that.

Kai: You can think in a big picture on like what a mastermind contributes to the value of a mastermind. I’m realizing this conversation helped nudge me in a different direction. I used to think of masterminds more as a real resource sharing collective or coming together sharing resources. But more and more, I’m starting to see masterminds as a way to get exposed to new information.

That information might be, hey, here’s a course I took and it’s great. It might be your sales pages are half baked, there are ways to make it better and they don’t suck, but you could make it a little stronger. So it is a bit squishy in terms of the absolute value of a mastermind, but more and more I’m seeing that information and feedback from other people as being the true most valuable part.

Meg: Is there anything that people can do to… We’ve talked a lot about what you can do to make things work well, but is there anything else that we haven’t talked about that can set up for success or like or?

Kai: Honestly, I’d say, be willing to roll with the punches, dear listener, if you’re starting a mastermind or joining one. The first one might not luck out, I got really lucky with my first one and it was a positive multi-year experience. But there are others that like three weeks and we’re like, “Oh, no, like, I love you. I love your business. I do not love this mastermind, let’s hit the cancel button.”

That’s okay, you’ve gotten more information, you’ve learned what could work, what didn’t work, and that’s going to help you have the next or the after that or the next after that mastermind be that much better. Be willing to see it as an experiment, be willing to, get messy, make mistakes and realize, “Hey, I know how to make the next one even better.”

Jeremy: Yeah, I was going to say the same thing about rolling with the punches and just be comfortable with the idea that what it looks like in month one is not what it was going to look like in month three, which is not what it’s going to look like in once month six and that you’re going to learn a lot as you just go through the process of trying to do a Mastermind Group.

You should plan for things to change and know that they’re going to change and realize that everybody involved is probably figuring it out as you go. It’s just because people are all unique, individual weird creatures, and you put six or eight or ten of them together and you’re going to get weird combinations that are hard to pull out of a textbook for “Okay, here’s how you should do things.”

So you got to find whatever is going to work for the group of people that are involved, and that’s probably going to be somewhat different group to group.

Meg: No, for sure. If you’re not willing to try and be okay with something not working out, it’s far less likely you’ll find that right group I would think or like. When I say right group, there’s no one right thing but find a good group that could help you move things forward. But if you don’t try and start connecting with people, like anything in life, you got to try and see what works, see what doesn’t adjust.

Without the negative feedback, you’re not going to know, negative feedback in terms of trying something and having it maybe not work. Then you’re “Okay, here’s what didn’t work for that.” What is it that Edison quote, when he’s like trying to invent the light bulb, and there was 500 things… He tried 1000 things before one worked. He’s like, after 500, his assistant said, like, “We’ve learned nothing.” He’s like, “Nope, we learned 500 things that didn’t work”.


Meg: I’m pretty sure he didn’t say nope [laughs].

Kai: Now it’s time for our picks. One thing I’d love to recommend this episode is the book Nonviolent Communication: A Language of Life by Marshall Rosenberg. I first read this book, Amazon tells me back in 2012. It has become a longtime companion of me in personal relationships, business relationships, or in a Mastermind Group.

Understanding what nonviolent communication is, helps immensely. So dear listener, a strong recommendation from Kai. If you’re a longtime listener of my podcasts, you’ve probably heard me recommend this two or three other times. That’s because it’s an awesome book. Please, go out and order it. Meg, how about you?

Meg: Yeah, Well, we’re just discussing about Mastermind Groups. In fact, one thing that’s helped me organize everything, including shared projects is Notion. Notion is like a lot of people love it. Some people aren’t into it, but I’ve so grabbed on to Notion the last six, eight months for designing both for organizing projects that I’m working on, for sharing documents of people. I love the all in oneness of it and not switching between apps.

Like I can use it for to do I can use it for a journal, I can write my… Work in it and keep track of projects where they are. That’s been a lifesaver for me for a while. So I’ve never grabbed onto a piece of software, I don’t think quite as much as I have Notion. I recommend people check it out. And Jeremy?

Jeremy: Yeah, I’m going to pick Company One by Paul Jarvis. It’s a really good book that has put into words a lot of things that I’ve thought and felt about how I wanted my business to be for a long time. I’ve never really wanted to do the whole go from consulting to growing an agency thing, but that is what is expected or at least a lot of people assume that’s where that’s going. So it’s nice to realize that other people have some of those same thoughts and ideas and it’s just really good if you’re into the, deliberately small but sustainable company idea. This is a really good book that talks about a lot of those ideas.

Meg: Nice thing.

Kai: Listener, you could find links to all of those in the show notes for this episode. Thank you so much for tuning in to this episode of the Business of Freelancing podcast. Remember friends, tune in the same bat-time same bat-channel for the next delightful episode. Until then, have a great week.