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Hello and welcome to this bonus episode! I’m so excited to talk about these tales from shitty masterminds because there are a lot of them out there.

I want to bring it into the light and have a conversation around it so that you can have the information and the knowledge to keep yourself out of a shitty situation.

Maybe you ended up paying a lot of money for a mastermind and it ends up being wah, wah, wah, not what you wanted, not what you expected, and not a huge help to your business.

So, in this episode, we are going to talk about and hearing some stories about shitty mastermind experiences that people have had.

Now I need to tell you, I have conversations with people almost every single day where they tell me about a crappy mastermind experience that they have had. But, so many people don’t want to go on the record and talk about it because it’s kind of sticky and it kind of could be perceived as throwing people under the bus. I want to be clear that that is not what this episode is about. It’s about finding the right mastermind for you and looking out for other bad experiences and bad situations that people have gone through.

You’re going to hear from Rebecca Undem, Jennifer Kroiss and Nikki Erchul about their first-hand experiences. I’m also going to share with you some things that I have heard and I have learned from what other people have told me because they did not want to come on the record and talk about it.

I’m going to give you some ideas and some suggestions based on their experiences of things to look out for before you get involved in any mastermind.

“Mastermind” seems to be a trendy or sexy word right now. I see a lot of different things out there that people are calling masterminds but are not. So, first and foremost be aware of these four things that are out there masquerading as mastermind groups but really are not.

1. Group Coaching Programs
There are a lot of group coaching programs that are wonderful and awesome, but some aren’t so great. In these group coaching programs, you have one person, an expert or self-proclaimed guru, who is dispensing the advice, the suggestions, and is helping people to get unstuck.

So it’s not about the power of the group or the collective, it’s about the knowledge of that ONE person.

2. Courses with a Community
The second thing to watch out for are courses with a community that call themselves a mastermind. So it could be a course teaching whatever kind of topic, but there’s some sort of a “community,” like a Facebook group that will be called the mastermind. Basically, there’s just a whole bunch of people lumped in together, but they’re not really a mastermind group.

3. DIY Groups
The third thing to watch out for is DIY groups. You’ve probably seen these come together before. Typically some well-meaning person in a Facebook group, will say, “Hey, let’s start a mastermind!” and a bunch of other people are like “Yeah, that’s a great idea! I want to be part of this mastermind.” Those can be, in rare situations, great accountability groups, but for the most part, those are not true mastermind groups.

I see people getting into these earlier in their businesses and generally, they are a hot mess. Once in a while, there is a strike of lightning from the heavens above or there’s a unicorn situation where they work out. However, typically these fizzle and are not great resources.

4. The Rando-Crazy Stuff
Now the last category of things masquerading as mastermind groups is all sorts of crazy stuff. For example, there’s a guy out there that has a daily email that goes out to people, an automated email basically. I think that the people are supposed to reply to that and he calls that a mastermind group.

There is nothing further from a mastermind than that. It’s just a group mass email that goes out. So first and foremost, be aware that the word mastermind is overused and it’s misused. It’s often used to categorize things and aren’t even close to being a mastermind group.

What to Watch Out For

Next, I’m going to share with you some of the specifics and some of the things to really watch out for if you’re considering joining a mastermind group, there are three main things that you need to have a successful and productive mastermind group. Without these, those fake masterminds tend to go off the rails. 

1. No Curation
When there is no curation of the people in the mastermind group, that’s no good. It’s like they just are looking for warm bodies to fill a slot and to be able to pay the amount for the mastermind. There’s no curation or careful consideration of who is in the group together.

The problem with that is you can’t just put any old people in a group together and expect them to be productive. It doesn’t work like that. I mean, think about somebody you’ve worked with in the past that and you guys were like oil and water. It’s not uncommon and that it doesn’t mean that someone is a bad person, It just means you shouldn’t be in a mastermind group together.

Typically I will see mastermind groups, even good mastermind groups, looking at just a couple of factors when it comes to matching people together. They factor in things like revenue in your business, what stage you’re at in your business, industry that you’re in, and marketing approaches. Those are not comprehensive when it comes to group creation.

Those are a good start, but there’s a ton of other factors that you have to look at. They’re forgetting about things like interpersonal relationships and how people actually connect with each other. Here at Kickass, we have a matching algorithm that is very detailed, and we look at a lot of different factors from business status, to business goals, business trajectory, and to who they are as a human. There are so many factors that you have to look at to get a good group together, and if you’re just putting butts in seats, if you will, you’re not going to get the total richness of the experience.

Most mastermind groups that are out there are not doing careful curation putting a lot of consideration into the chemistry of the group. Yes, you can get some benefit out of an okay group, but just think how much better it would be if you could really go deep with people about what wasn’t working in your business and where you are struggling. That is where the juicy goodness comes in. So most groups out there aren’t carefully doing curation. They’re not carefully considering the group and that is something to absolutely watch out for.

2. All Input from One Place
The second thing that I see a lot and I hear a lot of stories about is that all the input is coming from the coach, guru, or expert. It’s set up in a way that that person is almost elevated above everybody else in the group and they’re the go-to person. They’re the one who’s always answering the questions, getting people unstuck, providing the feedback, the input, and the education.

Those kinds of situations are great if you want to model your business exactly after that person’s business, that might be a good fit for you. If you’re the kind of person that likes the richness of variety and diversity and wants a lot of different input, a lot of different feedback, a lot of different viewpoints, that’s not going to be the right fit for you.

3. Structure
There has to be somebody whose job it is to make the machine run, making sure everybody is getting what they need. Typically, it’s a hot mess if one of the participants in the mastermind is also trying to play the role as facilitator. I’ve seen it many, many times over. It just does not work. You need to have a separate, dedicated facilitator and that person needs to handle all the details, the flow of the meetings, the notes and resources.

This is not just getting together all willy nilly and talking about things. You are not in a mastermind group to rant or bitch about personal stuff that doesn’t matter. Having a structure and facilitator actually be responsible for the flow and success of the group is so incredibly important. Without that, it can completely go off the rails.

I’ve heard so many stories about people who’ve had bad mastermind experiences because they were lacking these kinds of things. I want you to be aware of that so you can go in anytime you’re considering joining a mastermind group and asking questions about structure and facilitators.









Today I’m going to share with you a little bit about my experience participating in both a Kickass Mastermind and a mastermind that was not facilitated by Kickass Masterminds.

It was about two years ago that I first got involved with the first mastermind group. We were formed as an added benefit to a membership program that I was enrolled in. That is the first major difference between what I’m experiencing now being part of Kickass Masterminds and the other mastermind group.

My first mastermind group had very little thoughtful curation that went into why we were brought together. We were essentially put together because of the time that we enrolled in the program as well as the stage of our business that we were in. That leaves a lot of room for disaster just in terms of dynamic. Our group was small, there was only four of us, myself included. We got along just fine, but the stage of a business, business maturity, and also just revenue goals, was just not enough.

It isn’t just about where you’re at in business, it’s not just about where you’re at revenue-wise. It is about your personality. It is about how you’ll show up for each other. It’s about your individual skills and how they might complement or augment the skills and talents of the other people in the group.

With Kickass, there is just a lot more thought that went into the people that I’m investing a lot of time with every single month. They feel, not just like business besties, which we often say, they are like home to me. These women are everything to me, personally and professionally. After having spent almost a year with them, the experience is completely different. Just from the dynamic of the group alone.

Secondly, the biggest change for me is the structure and the facilitation that Sara and the Kickass Team have in place for us in our mastermind now. Previously, there was nobody playing that role. There was nobody in that role to facilitate and just make sure that everybody was on track. Sara does a fantastic job of holding us accountable to what we say we’re going to do. The structure that’s in place to help us be successful is completely different than what I experienced the first time around.

Those are the two big things, but lastly, the guest experts that get brought into our mastermind are amazing. First of all, they’re driven by us. We tell Sara what it is that we’re interested in. She’s only bringing in experts based on what we really need to hear. Whereas a mastermind that is an add-on to some other person’s program doesn’t have this dedicated focus is going to feel completely different. You’re going to feel less supported, less structured, and you’re going to feel more like it’s a place to rant instead of a place to be strategic. It’s more reactive instead of strategic.

If you feel like you’ve been in a mastermind before and you have kind of a bad taste in your mouth after your first experience, it’s only because you haven’t experienced a true mastermind. That’s what you’ll get with Kickass.

You can find Rebecca at rebeccasundem.com


Sara: Tell me about a mastermind experience that you had that wasn’t so hot.

Jennifer: I think the easiest way for me to answer that would be when I wasn’t with people who were even somewhat in a similar space that I was from a work perspective. So, there wasn’t even a common language. You had people who were in that side-hustle phase, some people who were well-established down the road in their business, and yet you didn’t have any common denominator of either business acumen from a previous life or from the entrepreneurial life. I think that would be my number one.

Sara: That’s a big thing, it’s being in a group with people who are at a similar stage. It doesn’t mean they have to be at the exact same stage but when there’s a huge gap there, it’s almost like you’re speaking English and they’re speaking Japanese. It’s almost a totally different kind of a language.

That is a big deal and it doesn’t mean that they’re not good business people. It’s just about making sure that that fit is right.

Nicki: For me, I would agree with what Jen said, but I also want to add, that you need people who have the same amount of buy-in and are as invested in the process. I’ve been in a group before where I was super amped to be there and really excited to get the results and support the other people but it just fell super flat. They wouldn’t show up or they wouldn’t show up emotionally or energetically. It’s so hard to rally your own energy when you feel like you’re dragging other people along with you. So, it was the buy-in piece for me was also huge.

Sara: It is huge because you can’t be the only one bringing the energy. Or if people aren’t even physically showing up, that’s part of the problem.

You can feel if someone’s invested in your group and in you and how present they are. It sounds like you had an experience, Nicki, where you were showing up and present and wanting to invest but the other people there just didn’t have that same investment level, right?

Nicki: I would agree with that. I would also say, just on the flip-side, I’ve also been in mastermind groups where there were other people who took over and then didn’t allow for room for other people to speak up. So, there wasn’t that balance and that give and take. I think it can go both ways, where you can show up and there’s plenty of room, or you can show up and there’s not any room for you to be there.

Sara: That totally makes sense. In that situation, was it a peer-led or did you have a dedicated facilitator who was kind of keeping the people in line and having this kind of equity in the group?

Nicki: This was actually an online mastermind group and so it was conducted through a Facebook or seminars online. So it wasn’t a traditional, or even by definition, mastermind, but they were calling it a mastermind. It was very much like people really commandeering the Facebook group conversation. There wasn’t a lot of give and take, it was just a lot of sort of blah. Like there wasn’t a discussion happening.

Sara: Got it. And when stuff feels like it’s one-way, that doesn’t feel good either. If someone’s dominating or sucking down all the energy in the group, taking all the air out of the room, that doesn’t feel collaborative and cooperative.

Nicki: Absolutely.

Sara: I get that. Can you talk a little bit about the trust and the relationship factors that you guys have experienced in masterminds and maybe some things that didn’t work out when it came to that?

Jennifer: I think it would be that people had that different levels of commitment. Just having different levels of knowledge and experience makes it really hard, in my opinion, to put trust or vulnerability to play if you’re not feeling that coming from the other people in the room.

Nicki: Having the conversation or maybe the level set at the very beginning stating this is the purpose and this is why we’re here, these are the rules. I’ve worked in therapy a lot and anytime you’re in a group you have to have an agreement, whether it’s stated or unstated rules, that create that safety and vulnerability and trust. The second somebody violates those, it really creates the cracks in the foundation. So, I would agree that one, there has to be the kind of commonality, “Here’s why we’re all here. Here are the goals.” But then also, just the respect within the group. I haven’t had any experiences, necessarily, where there was disrespect, like blatant disrespect, but that you could sense, “I don’t want to talk about this with this person because I don’t think that: one, they’re going to understand me, or two, they’re going to care.”

Sara: Well, and that comes back to that relationship and that trust. If you’re going to really get into business stuff, which, let’s face it, a lot of it’s ugly and vulnerable, you have to have that place where you feel open and you feel like you have a confidential place where people are gonna receive you. Even if they just say like, “Oh man, that sucks. I’m sorry that’s happening.”

Nicki: Yeah. Or like, “I’ve been there. I know exactly where you’re at. I’ve gotten through it.” Or, “I understand what that chain feels like or that disappointment,” and being able to incorporate a sense of empathy into that. So, I think that that can be really valuable in groups.

Sara: I agree. I totally agree. Do you guys have any thoughts or feedback on experiences you’ve had that haven’t been so hot in terms of the structure of the mastermind? So, the facilitation or how often it meets?

Jennifer: I could go for days on this.

Sara: Tell me more.

You can find Jennifer at jenniferkroiss.com and Nicki at luxhippielife.com

Podcast audio editing and custom music by the awesome Zack David. Need custom music or podcast editing? Check him out: http://www.zackdavid.com

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