How Masterminding Can Dramatically Increase Your Odds of Success as an Education Entrepreneur with Ken Wallace of MastermindJam

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Learn how masterminding can dramatically increase your odds of success as an education entrepreneur with Ken Wallace of MastermindJam in this episode of the LMScast podcast hosted by Chris Badgett, founder of LifterLMS. Ken and Chris dive into the ins and outs of masterminding, and how they can benefit you and your business.

Chris credits the ability of LifterLMS to survive and thrive to participating in masterminds. On LMScast we talk a lot about the five hats course creators wear at different times during the course creation process. Participating in a mastermind can help you master those five hats in a major way.

For the unfamiliar, the five hats problem represents the five roles necessary for online course success. You need to be a teacher, an entrepreneur, a community builder, a technologist, and an expert. It is rare to find one person who can fill in all of these roles, so often people will delegate or consult with others about the aspects that do not play into their strengths.

How masterminding can dramatically increase your odds of success as an education entrepreneur with Ken Wallace of MastermindJam

Chris and Ken discuss the varying sizes of mastermind groups, and why Ken recommends a group of four to five people as the ideal. The group of four to five people is small enough that no clicks form, but large enough to prevent a mentor/mentee relationship and superiority complex to conflict with the intended purpose of the peer-to-peer group.

Another type of mastermind group is the guru-driven mastermind. These are popular upsells for online courses or memberships where you can meet with the founder or creator of a particular product.

At LifterLMS we have the Office Hours Mastermind call as a feature of the Infinity Bundle. That is a weekly call for LifterLMS power users to learn from other course creators. On the call Chris takes a list at the beginning of what people want to talk about on the call, from technical issues to strategy advice, and that determines the flow of the call.

MastermindJam allows you to join or create a mastermind group. When joining groups you can compare yourself to others in mastermind groups to see if it would be a good fit. You can apply to join groups and do a six week trial and if you find it doesn’t work out, you can always do another six week trial until you find a group you fit in well with. Be sure to head to to check out the opportunities for growth as a business owner.

At you can learn more about new developments and how you can use LifterLMS to build online courses and membership sites. If you like this episode of LMScast, you can browse more episodes here.  You can subscribe to our newsletter for updates, developments, and future episodes of LMScast. Thank you for joining us!

Episode Transcript

Chris Badgett: You’ve come to the right place, if you’re a course creator looking to build more impact, income, and freedom. LMScast is the number one podcast for course creators just like you. I’m your guide, Chris Badgett. I’m the co-founder of the most powerful tools for building, selling, and protecting engaging online courses called LifterLMS. Enjoy the show.

Hello, and welcome back to another episode of LMScast. My name is Chris Badgett, and I’m joined today by a special guest, Ken Wallace. He’s an expert in masterminding, and has a masterminding kind of software experience called MastermindJam. You can find that at Ken, welcome to the show.

Ken Wallace: Thanks for having me.

Chris Badgett: My job in this interview is to represent the course creator, and well, of which, I am one myself and also create software for course creators and course creators, people who want to build these training based membership sites and coaching programs and all these things, they suffer from a problem that I call the five hats problem, which is essentially you need five very different skill sets. In other words, you have to wear five hats or be five different people at once or build a team to address the needs of the five different hats. Those five hats are being an expert, being a teacher, being a technologist, being a community builder, and then being an entrepreneur. That’s a tall order for one person to fulfill. For me personally, I’m participating in, I’ve been to mastermind retreats and I have a couple like one more personal mastermind that I go to and then another business mastermind I go to and then a fourth just kind of mastermind event, I do with some high level players in my industry, couple times a year so I’m a big time masterminder and I’ve gotten so much value of it.

My business is still alive because of that but I wanted to ask you in light of the five hats problem, where you need to be a teacher, an entrepreneur, a community builder, a technologist. How an expert, like how can mastermind help us attack the five hats problem?

Ken Wallace: Good question. Well, I think the benefits to the mastermind for attacking that problem is you can come to the group, you come to your mastermind group with your cards open. You can trust the people there, you can be vulnerable and to really talk about the issues that you’re facing in each of those areas. I don’t think in any one meeting, in any one session, you’re going to solve everything, all the questions that you have in all of those areas, but attacking them one at a time with the other people in your group, you’re going to be held accountable and get advice that you need to grow in each of those areas.

Chris Badgett: Yeah, that’s fantastic. Yeah, it’s not like you can flip a switch and then all of a sudden you can fill in your gaps in these different areas. I think one of the things I’ve really learned from my experience masterminding, which I started doing, I don’t know, a lot of people I think maybe first year of masterminding from the book by Napoleon Hill, Think and Grow Rich, I think that’s where I first heard the concept but the benefits I get out of masterminding, definitely compound over time. There’s not like a magic event the first meeting you go to or the first connection or a new relationship, all of a sudden, everything’s different. I mean there are some big ideas that come out of masterminds that are dramatic. The biggest benefits is how that plays out over time. Let’s talk about that time factor. How often should a mastermind meet?

Ken Wallace: Well, I’ll throw it back at you because it depends. The answer to a lot of these questions is, it depends if you’re, it’s a group of beginners and first of all, let me start with a definition. At MastermindJam, we focus on peer led mastermind groups of four to five people. There are a lot of conferences that say they are a mastermind event, there are people that put together Facebook groups and they’ll say this is our mastermind area. I know some founders that take a ski trip together and they call that their mastermind group so what, in the context of a mastermind group like I’m talking about, like a peer led mastermind group, that’s four to five people. It depends on the business stage you’re at and how fast your business is growing. Beginners, I always recommend that they meet weekly because your business is going to grow so radically from week to week. Your mindset will shift from week to week.

You may lose confidence in your whole business idea by Friday of the week after you’ve had a mastermind group meeting so things change so dramatically for beginners, for people that either have not yet made any dollars in their business or less than $5,000 or $10,000 in revenue. Things can move really quickly and you need maybe some weekly checkpoints to keep you focused, keep you accountable to the overarching vision, the overarching goals but once a business is “established”, say your business is grossing $2 million a year and you’ve got maybe some employees, things don’t change week to week so much, right and maybe a weekly meeting is too much, maybe it’s a biweekly meeting, maybe these are monthly sessions that are for instead of an hour a week like I might suggest for a beginner, maybe it’s three hours once a month. You kind of have to play it by ear and really be understanding and flexible with the stage that everybody’s business is in the group.

Chris Badgett: How do you qualify the best group? There’s a concept, I can’t remember which author I heard it from called plus minus equal, like you want to hang out with people that are at your level that’s an equal, whether that’s revenue or business size or whatever, but it’s also good to help some, hang out with people that are a little bit behind you and some people that are a little bit ahead of you and that creates like a really well balanced thing. I’m sure when we go to a mastermind, it’s never that everybody is at exactly the same level and you mentioned the concept of beginner versus an advanced business owner. How do we create or how do we qualify a good group? Are revenue numbers a good way to do that or like a range of this type of business or-

Ken Wallace: In a business mastermind and realize that masterminds are great for a lot of different areas of your life, right so personal development, hobbies, religion, masterminds are all great but in a business setting, we have some extra metrics and facets available to us that we can use to kind of qualify people and truly when you sign up for MastermindJam, it’s a 32 point questionnaire that you go through. Revenue is an excellent indicator. In a lot of ways, it’s a really rough way to measure but in most ways, it’s a good way to put people together into mastermind group even if your net profit isn’t much. If you’re in a business that does $10 million a year in gross sales, even if it’s an FBA business where you’re only making $100,000 on that, it’s still a good indicator of how much work that business requires, how much care and feeding it requires, how many hurdles you’ve crossed to get there, what kind of marketing budgets you’re working with, what kind of expenses you might be working with, what kind of employee issues you might be dealing with.

Revenue is a really good indicator of level like just the abstract “concept of level”, business level and to kind of the separate the beginners from the more established people. Another one is whether or not you’re full time in the business. That’s a really great indicator of where you’re at. It’s not positive or negative. It’s not a way to look down upon people that this is still a part time job or a side hustle, but it’s just the way to put people together where they can get the most advantage out of the group. We also match people based on a lot of other factors, whether or not they all have day jobs, whether or not they’re all married and have kids because people that are married and or have kids realize how that impacts the time they can put into their business, where your priorities are, whereas if you’re single living in your parents basement, you might have 12, 14 hours a day to put into just working on your site, on your dream here.

Somebody that’s married or has kids and or has kids, you might decide that I just want to work six or seven hours and then have time with my loved ones and so none of those things are right or wrong, but you want to be in a group with people with similar attention to their business and similar engagement with their business in a similar level of their business. I try to encourage people to be in a group with people that are maybe a step ahead or a step behind but in a similar journey, because going back to your five hats, you might be ahead of other people in your group in one of the hats, you might be a step behind in four of the other hats. I might be great at marketing but I’m horrible on the tech side or I’m horrible on other aspects of the business and that’s where I need help so I think it’s important to start with revenue, start with kind of lifestyle, how much time you’re putting into your business and go from there.

Chris Badgett: That’s awesome and just to drill into it even more, you mentioned the concept of a peer driven mastermind versus a guru driven mastermind, which definitely I think leads into the power dynamics within a mastermind. I’ve heard you talk about it’s better to have more than two people because that usually creates some kind of power dynamic or something, but can you speak to the peer driven, guru and then power, all that stuff?

Ken Wallace: Yeah, when we’re talking about power, we’re talking about the size of the group and it starts with the research that sociologists have done around Dunbar’s number, which discusses how many interpersonal relationships that a human, the average human can actually maintain and cultivate in their life.

Chris Badgett: It’s 150, isn’t it?

Ken Wallace: You’re right around 150, but there’s further study, in the same area of study that comes up with Dunbar’s number, they break that down into sub groups. What’s the ideal family size unit? Prehistoric humans, if they were in a tribal kind of setting, how big would that tribe usually be and why were village sizes this certain size in ancient Europe? There’s a lot of studies in group dynamics and so in a learning situation, in a small group, peer group learning situation, a group of two people is interesting because it gets really intimate really quick and it may be increasingly difficult to stay candid and open and honest with the other person. Similar to a marriage, you start to really value the feelings so you don’t want to say certain things, you do the white lies and you hold some information back to either preserve status or prevent hurt feelings on the other side.

There will often form a mentor mentee relationship and it’s tough to break out of that and it’s really difficult to let it flip flop. It rarely goes back and forth evenly and so it will just develop one person always takes the coach role and one person always takes the follower role, and that’s not the point of the mastermind group. Then once you get above five or six people, if you’re in a group of seven, eight, 10, 20 people, it starts to feel like more of a workshop and you feel less personally accountable to every other peer that’s in the group, which is fine. It’s that works for a classroom setting for example  , that works in college, that works in high schools, that networks in a lot of settings. In the old weight watcher meetings were often 50 and 100 people and that works, but you have to realize in a peer based mastermind group, what I’ve seen work best is four to five people. Odd numbers work good. Three or five, four person, I have found is kind of the ideal situation so I tell my groups to be around four to five.

The reason being is it’s too small to form like two clicks, like if you got six or more members in your group, often you’ll find the group kind of fractures into two sub groups of three each, it’s two clicks and you get like warring loyalties and just weird things start to happen if you’ve ever watched survivor or things like that. It’s just really interesting how that works so I always tell my groups to stay around four to five people and that’s to answer your question about group size and power dynamics. The other question about peer based versus guru, guru driven. A guru driven mastermind is really common because a mastermind is a really popular upsell in a lot of offerings that you see in personal development and business and entrepreneurship these days on the internet.

It feels like an easy thing to sell people but often it turns into more of a buzzword, a mastermind group as a buzzword and it’s really a workshop or just a community, which by the way, not discounting the value of those two things but let’s just be clear about what the definitions are. If you are say, a course creator, and in addition to the course, everybody who takes the course has access to your private Facebook community. Just realized that the dynamics in there may never reach an actual true mastermind so maybe let’s find a different term to use for it. In a guru driven thing, for example, Michael Hyatt has a mastermind group that he leads and Russell Brunson has an inner circle mastermind he leads for marketers and James Wedmore has one. There’s a lot of these that go around and it might be 10 entrepreneurs in a room and like a guru person, a leader person, a facilitator.

He may allow or she, he or she may allow the members of the group to go around the room and talk about their issues and help one another but the information still gets distilled through that final voice, that final filter and then relayed back as okay, this is the gospel on this one, this is the takeaway. At the end, the person that speaks last and usually wraps it up by saying, oh at the end of the day, this is what we need to learn. The person that’s in that kind of a power position, if you have that in your group, then you know you’re in a kind of a guru led mastermind. The takeaways from those are very different than you get from a peer driven mastermind. I’m not going to take the stance that one’s better or worse. I do have my opinion on that but the point being, you need to be upfront about what it is you’re looking for when you’re looking for mastermind group and make sure you get in the right one because they often don’t give you the same output.

Chris Badgett: Yeah, that’s it. This is really fascinating and it’s really relevant actually to something that happens over at LifterLMS, our software product for course builders. Our highest end bundle is called the Infinity bundle and with that, includes a access to a weekly call, which I used to call office hours and I run that every week and a lot of the power users and people who are new to this tool getting set up, they have questions, a couple things started happening. One of it was people started asking a lot of strategy questions and other just five hats questions outside of technology, which is the actual product itself. I would answer those questions and then I realized other people on the call, these are ranging from anywhere in the early days like five people, now they get up to like 30, 40 people coming in there, I realized there was a lot of wisdom in the crowd and I have no ego in terms of like I have to be the one to answer.

If this other person over here has a lot of experience with a mentor or this marketing strategy or this teaching method, it kind of organically became a mastermind and I changed the name of the product from being called office hours to office hours mastermind. I’d love your feedback on this. I want to share with you the format and then look for any tips you might have on how to improve it. First of all, I do kind of facilitate it. I come in there. I open the call and then there, what I do at the very beginning just like in person masterminds I’ve been to or we’ll take an agenda, I’ll be like what do people want to talk about and I’ll basically create the list and make sure that nobody gets left out or that we work within the time we have to get to the list. We don’t really do any like prolonged hot seats.

It’s more just like we work the list with as much time as we can within the hour and I’m more, I see myself as a facilitator even though I’m kind of the, I guess the guru, I guess it is a guru mastermind but I’m not always the one with the final answer so I think maybe it’s a little bit of a hybrid. At the end of the day, it’s become an amazing thing. People have created business partnerships inside of their people’s courses or membership site, platforms have gone from struggling to solid. People just develop relationships outside of that call and they didn’t know each other before this call. It’s evolved to a lot of different things and just as a side note, I’ve been to other like more true peer to peer masterminds and me personally, I do see how that, if I had to take a stand of which is more valuable, the peer to peer with a small group of three to five people, those are the most valuable like in terms of the results I’ve gotten from attending.

I do find that this kind of rolling admission mastermind, I have some people have come, since they joined, they just stay and they say that’s the reason they stay with everything. I didn’t know how people get out of like hospital beds to go on the car to join the call and I’m like, what’s going on here? What have I created here? I was just trying to do live technical support and it turned into a mastermind so I know I’m throwing a lot at you, but whatever that is, how do I make that even better?

Ken Wallace: I don’t know that there’s and I don’t want to get into a semantics discussion but largely it is because I don’t know that there’s a better word for what it is that you’ve created because, and being strictly, just referencing what Napoleon Hill’s definition of it was. He first started talking about masterminds in a book he wrote based on speeches he gave on the road. He’s like a touring self help guru, right and he would just give motivational, he is one of the earliest motivational speakers. He codified his slides, basically his deck into a book called Laws of Success and this was just the stuff he would speak about, obviously, they didn’t have PowerPoint or anything back then, but this is the notes that he would just always talk about. He put it into a book, a written form called the Laws of Success and in there, he was talking about mastermind groups.

Then he went further with the mastermind alliance, a mastermind group and masterminds concept in the book, Think and Grow Rich. For him, any group of people that got together would always be smarter as a whole than any one individual person and that can happen one time so if you’re like at an event and you’re all out to dinner and there’s 10 people sitting around a table, talking about whatever the issue is, business or relationships or whatever, it’s going to be amazing because just that’s the way humans are. It’s just like Lego pieces, you put together in a way and you’re like wow, we are a different thing altogether and so I don’t know that, I don’t have a problem with you calling it mastermind.

Back in the day like, I don’t know how you facilitate the discussion if and how closely you facilitate the question and answer or if it’s just kind of a free for all, but I mean we’ve seen things from like, remember the Donahue show?

Chris Badgett: [inaudible]

Ken Wallace: Where we’re just or the early days of Oprah or Sally Jessy Raphael, these talk shows would be, they’d have a topic and an expert maybe on and then the host would walk around the audience getting everybody’s ideas on that topic and handing them a microphone. The audience members would talk to each other across the room and it was like there’s a mastermind on TV going on right now. I’m always going to remember this because when I would be home like on a sick day and my mom would be watching it, right. I mean as old as humans are, these things have been happening so I don’t have a problem with you calling it a mastermind but it’s definitely a facilitated guru led event that you’re having there. I’ve seen it called like office hours is still a great name for it. I don’t know why that’s not a good name or a roundtable or a town hall. I’ve seen it called, but masterminds fine too.

I think that’s perfect. The only things that make it different from the peer led version is that in what you’re talking about, a person that comes to that event and they get business advice, they don’t necessarily know who it is that’s giving them feedback, giving them advice. They don’t know their qualifications for where they came from in that answer, you know what I mean?

Chris Badgett: Yeah.

Ken Wallace: I might be giving somebody a legal advice on how to deal with a client that won’t pay in a session like you’re describing but they don’t know if I’m an agency owner or if I just have some thoughts on it, you know what I mean? They don’t know if I’ve been there or if I’m actually a lawyer, they don’t know so.

Chris Badgett: I think that’s a real benefit of a true three to five person, the doors are locked, the relationship, there’s no new people coming and going and it’s like [inaudible].

Ken Wallace: Yeah, like the people are vetted in some way, even if it’s just a matter of over time, I’ve learned about them. The people, you know you can trust them, you know where they’re coming from, you understand where that point of view is coming from so that’s maybe an advantage of the smaller group over the bigger group, similar to a Facebook group right. You don’t know who’s reading your question, usually you don’t know, like if Pat Flynn replies me, I understand who Pat Flynn is right, but most of the time, the people that reply on just a random entrepreneur Facebook group, I don’t know them. I don’t know how much is for show and marketing speaking versus how much they’ve actually accomplished or what their business is really doing or what their expertise really is. Whereas in MastermindJam and in a peer group, you’ll find that we work really hard to vet the people and make sure you can trust that advice you’re getting.

The same thing like there’s a lot of internet forums you can go to and get advice and you’ll get tons of feedback. I mean you can go to reddit/smallbusiness or reddit entrepreneurship and you’ll get all the advice you can handle, right but there’s zero way to vet where that information came from. You don’t know at the other end of the handle that’s like, baby bear 32. You don’t know if that’s Chris [inaudible] on the other end or just some random kid in his basement. You don’t know who’s giving you this business advice. No matter how well written it is and how research that seems to be, you also don’t know if it’s like got a foundation and real experience.

Chris Badgett: I think that’s a really good point. If I ever want to get a discussion going in our Facebook group, which is not part of the product, it’s just a open Facebook group for course creators. I figured out a long time ago that if I write the first sentence as, can I get your opinion on something? Then I ask question, I’ll get a flood of, like that’s what Facebook groups are for. People ask questions, people answer, but that’s very different from a curated group that’s like, where people are like in relatively the same kind of area or whatever and that’s okay. There’s a place for that Facebook kind of just free for all.

Ken Wallace: Oh, yeah. Not to discount it. Yeah, I’m not saying don’t go to Facebook and ask questions. Don’t go to Quora and ask questions. By the way, I’ll say that Quora has a leg up because at least you see some credentials. LinkedIn has a little bit of this where you can actually click on their profile and learn more about them. It’s like who is this guy, he seems smart but can I really trust it? Facebook less so but it still has its place because let’s face, a lot of times, we’re not asking like a crucial business tactic question.

We’re not asking how should this legal letter be structure. A lot of it is just like self confidence issues like you already knew the answer. You just wanted somebody else to affirm that you’re on the right track, especially those of us who are not lucky enough to like live in the valley or be in Y-Combinator or be in some like TechStars in Boston where you have like this crucible of business knowledge all applied to you or in some kind of MBA program maybe they have this. Most of us are like far flung.

Chris Badgett: I want to actually ask you about this topic specifically so course creators, another name for them as a group is education entrepreneur, which is a subset of a type of entrepreneur. These are people creating online courses, memberships, coaching programs, events, things like that. As the Internet has democratized publishing and how anybody can really be a course creator and try to figure out how to build types of programs, the tools are accessible. I think never before in history have entrepreneurs because of technology, because of global markets to the internet, they’ve never been so isolated say for a few areas like you described like Silicon Valley and these incubator hubs and things like that. I want to just kind of ask you in general, why do entrepreneurs get so isolated and education entrepreneurs? How can a mastermind really help get people unstuck who are feeling like, I live somewhere out in the country but I’m reading all these books and studying all these things and I’m building my side hustle business or whatever.

It’s a lonely road. It sure was for me and masterminding was huge for me, but I was just hoping you could speak more to that isolation, that entrepreneur specifically come into contact with.

Ken Wallace: Most people are raised to not be different, right. I think there’s a concept called crab barreling, crabs in a barrel, where the concept is if you’ve got a barrel of crabs and one of them starts to climb toward the rim, the other crabs will pull him back that right. Humans do this to each other, from the time you’re put together into classrooms in school, all the way through college, business, you get on a career track and I think a lot of is that just most people aren’t entrepreneurs, right?

Chris Badgett: Do you know the stats. I think I heard once, like 5% of the population and also just want to add that I didn’t realize I was an entrepreneur until I turned 30. I didn’t know what that was.

Ken Wallace: You’re right, yeah and this label you put on it right because a lot of the labels you might get from your family of this guy, he’s never happy in a job or he was always a cut up in class or he was-

Chris Badgett: He’s never satisfied.

Ken Wallace: Never satisfied. He’s always taking charge and he always wants more and you don’t put entrepreneurship label on that and by the way, there’s a lot of ways we can go with this discussion too because if a boy exhibits those traits in school, he’s labeled very differently than if young girls exhibit sees traits.

People are very cognizant of somebody stepping out. The way I was raised, very poor upbringings but everybody in my town was either a farmer or you worked at a local factory, right? The people that would label themselves as entrepreneurs were always considered to be people you couldn’t trust like, oh, he’s an entrepreneur. That means he probably sells Amway. He’s a door to door Cutco knives salesman. He’s doing anything but providing for his family, because whatever reason, he’s too good to have a job so he’s got to go and be an entrepreneur.

There was never this translation of that job that he could go and get, who’s the owner of that business? An entrepreneur. Who’s giving these jobs in the community? Entrepreneurs. Who owns that construction company? An entrepreneur. Who hires that fleet of five vans that drives around town with the Roto-Rooter and singing on the sides. Who owns that franchise?

Chris Badgett: What were they like before they had employees and success?

Ken Wallace: Yeah, yeah. People don’t make that leap in their mind so the way I was raised, entrepreneurs were not to be trusted. You didn’t use that word as a goal. Your goal was to just stay on a path, follow what everybody else was doing and hopefully you get a good job at a good factory with a good pension, or you maybe found a way that you could get hired on to one of the local farms, and if you’re super smart, and if your family’s got a lot of money, you could be a doctor, a lawyer. That’s just the way I was raised, so I go through college, I’m like I was hoping to become a music educator.

I was very deep in the education space and this was especially true there, you had to follow established teaching curriculums and you had to do everything a certain way. Get your student teaching hours in, and there was very little path to step away and to do something entrepreneurial and you were always frowned upon for that.

People who wanted to try different ways of educating kids, all these different things so, and then to realize I’m just not satisfied here at school doing what I’m doing. Oh no, by the way, I have a part time job as a web developer, maybe I should do that and then like this flood of people saying what are you doing? Even the girl I was dating at the time, she’s like if you drop the major, I think we would have to break up. That’s just ridiculous right?

Chris Badgett: Crabs climbing out a barrel.

Ken Wallace: Yeah, and then so like it just got to the point one day. I remember, I don’t know if you remember, I don’t know how old you are.

Chris Badgett: I’m 40.

Ken Wallace: Okay, so I’m 41. There used to be a site called and Excited had a job board, Excite Jobs and so I was just fed up one day and I just wanted to see if there is a job doing what I was doing with better hours in the town, the college town that I was in. It was just a part time job and I accidentally stumbled upon full time job listings for doing what I was doing for part time work just to make my rent while I was a music education major. The reason I chose music education was because at University of Illinois, it was 100% job placement rate and growing up so poor, that was amazingly important and like my high school band director, he got out of college making $25,000 a year. Me, my mom never made more than $12,000 a year and so that was just amazing, like $25,000 for one person? Yeah, it’s just like the jackpot, right? I was just, that was my path and so I was just looking for a better job so I can pay rent while I’m getting my education degree.

I go on Excite jobs and for exactly what I’m doing part time, the starting pays $40,000. It’s just like an epiphany, like this thing that I do on the side just to make rent, that I love a lot more than my actual major, I love it a lot more than teaching kids. I love it. I mean, I just love the work. You mean people are paying more for these kinds of jobs, right?

Chris Badgett: Since society started validating it.

Ken Wallace: Well, my society didn’t. The circle I was in didn’t, and it became clear that wait a minute, my path is a little different here. There are other paths and then so I left school, I never completed that degree. I left. I went away to pursue that career. Well, in that career still, I’m being held back by these thoughts of entrepreneurs not to be trusted, but I just happened to find a job path that was better than the factory or the music teacher or the farmer, right? I still didn’t have this knowledge that you could start a business until I started talking to the CEO of that company, and I got to learn, I got to go to meetings with CEOs of Fortune 500 companies.

Chris Badgett: Was that like a mentoring relationship? What would you call that?

Ken Wallace: Not on purpose, not on purpose.

Chris Badgett: Just reaching outside, reaching out?

Ken Wallace: Yeah, me asking a lot of questions and him just having a huge ego and he just loved when people asked him questions and he felt smart. That was a jerk, right? It was like huge ego and he just loved it when people put him on on a mentor role, right? I found that he wasn’t coloring as answers. He was just eager to answer because that made him feel smart, but he was still giving me great advice on marketing and business and entrepreneurship and stuff I’d never known about.

Then so I just decided one day that wow., entrepreneurship is actually a thing that you can do and give your family a good life, not be looked down upon, feel good about yourself, feel like you’re actually helping the world.

Anyway, it’s a long way to answer your question. I think it’s just most people aren’t entrepreneurs. Most people are going to tell their kids, tell their friends to do the thing that most people are doing and that’s kind of the way humans are wired probably for a survival mechanism. Stay in the school of fish. I just think that’s the way that happens where the first time you walk into a conference, whatever the conference is, it happens to so many first time conference goers, you walk in the room and you start talking to people, maybe you go to lunch with some people and you’re like, wow, these are my people. I finally found my people. They’re all in a room together. I’m not weird. They’re all weird like that. They’re all just like me. These people are successful doing the thing I’m aspiring to do and it’s like it’s a whole paradigm shift that just changes your context and there’s just no going back after that.

Yeah, Mastermind groups are a way to take that feeling when you go to a conference for example of those are my people, like especially me living here in the Midwest surrounded by farms and factories and steel mills and whatever and to have that feeling all year long though, so I’m here in like an entrepreneurship desert working in my basement, like literally, you can see my basement and I can go and have a Mastermind group call with other entrepreneurs. It doesn’t matter that my community is not filled like Silicon Valley, I can’t just walk down the street and run into 16 other entrepreneurs. I can just get on Skype or Zoom or whatever and have a conversation with them. It’s a magical, powerful thing that’s going on right now that even 10 years ago, it was really a tough thing to get in touch with other entrepreneurs.

Chris Badgett: Yeah, it’s amazing how fast the times change and how like video, internet, VoIP technology is just ubiquitous and how small the world really is. I want to go into the social component of your  MastermindJam software and just the Mastermind in general but before I do, there was something from your story that I wanted to ask you, which was, this is not a beginner problem. This is more of an intermediate problem that entrepreneurs or specifically education entrepreneurs face where when they do start getting traction and like with you, let’s say you got that $45,000 thing or something starts working. It actually works. A lot of entrepreneurship is failure and hustling and grinding and trying to find product market fit and innovate and create value but once you do, I noticed in education, entrepreneurs are really and a lot of entrepreneurs, especially bootstrapped entrepreneurs, they don’t stop to celebrate success enough but more insidious than that, when things are working like where you are able to pay your bills, or do things that you haven’t been able to do for a long time, like eat out or eat good food, or whatever but I noticed some people will carry that stress of the hustler. They’ll just hang on to it.

It just keeps going and it’s fine. I mean, it’s kind of like a battle fatigue thing. You just kind of get in the mode and you’re just going, going, going, going but in the long term, the compounding impact of stress is not healthy for the entrepreneur. Do you have anything from your story or in all your interactions with other entrepreneurs that you can share of how to relax a bit or how to make that transition from okay, I’m validated, it’s working. How can I maintain more balance so that I’m not stressed out constantly?

Ken Wallace: I don’t have a magic answer to this, but I’ll tell you what I’ve been learning and what I’m doing. Stress is a huge, huge problem, especially when you’re isolated. Again, back to me being like in an entrepreneurial desert I feel like here, it’s very easy just to feel guilty all the time and feel stressed all the time. For me, it manifests itself as guilt a lot of times, so I will be working late. I have a day job still, and I’ll be working after the day job on my business, and then I’ll feel guilty while I’m doing it, that I should be upstairs playing with my kids, having moments with my wife. helping with dinner, and then I’ll hear the mower start up in the backyard and my wife is mowing and I was like, I’m a failure as a husband too.

I’m not even mowing the yard, the simplest things I’m not even doing because I’m in here in front of a computer. I just feel like a complete failure sometimes and it’s just all in my head and then other times, I’ll feel guilty. I’ll be playing with my kids or mowing the yard or having a date night with my wife and I’m thinking-

Chris Badgett: You’re not working on your business.

Ken Wallace: Yeah, I’m thinking man, this is time I could really use working on that new course or working on that new initiative for the business. I keep talking about how I don’t have time to get that thing done for my side business but yet here I am having Chinese food with my wife, and so you feel guilty about that and then you feel guilty about feeling guilty, right? It’s like you get in this weird spiral, and it’s like, why am I not fully present with my son here with the Legos? I shouldn’t be thinking about business so now I’m feeling guilty that I felt guilty and so for me, that’s when the people in my Mastermind groups outside of the meetings, like between the meetings, the between the meaning communication for me is just as important as the meetings for the meetings are very focused on the objective and the goal but between the meetings, it becomes a support network, and people that were in mastermind groups past, I still stay in touch with and even though we’re not mastermind group anymore, our businesses have moved at different paces, I can still check in and be like, dude I’m having a hard week, how have you been?

He’s in Australia and it’s like how have you been and so we’ll just get a chance to just do just real talk and it’s like friendship and so more than a mastermind group, it’s just a great way to really build a deep level of trust and you develop that shorthand that old friends get but you develop it in kind of a short amount of time so for me, the mastermind groups have helped there too. Then you get to a certain level of stress and, and depending on what those side effects are of that stress, whether it’s affecting your health or it’s affecting your marriage or relationships, sometimes you even need to seek a professional. If it’s leading to depression, seek help. If it’s leading to problems in your marriage, get help with your marriage. It’s okay to go to couple’s counseling just to help you better talk to your spouse about what’s going on in your head because a lot of it is even though it’s just in your head, that makes it 100% real, so you need to find a way to to share with your family, your loved ones, your friends, what’s going on in your life so that your support system can really help you as best as it can.

Chris Badgett: That’s awesome. Well, thanks for masterminding with me on that one. It’s just a real issue, for everybody but especially entrepreneurs.

Ken Wallace: I still deal with it daily, especially because I work remotely so I actually have an office and a beautiful standing desk and pass to a beautiful parking garage and they have all these amenities at this office building in Chicago. I never go there. I’m always working here. I work full time at home, unless there’s a meeting at a client’s headquarters or something like that. I’m usually here working in my basement so I’ll put the kids on the bus in the morning, come down on work, get the kids off the bus in the afternoon and give them a snack, come back and work some more and I’m working into the evenings on  MastermindJam and weekends on mastermind. It’s like I look at this basement a lot and it’s really easy to just get in your head and just to start living the stress.

Entrepreneurship has been one of the greatest journeys for me but physically, it’s been a horrible journey for me. I’ve gained 100 pounds. I’m really hard on myself getting this latest platform release for MastermindJam through the software because before, it was this kind of a service so I added this whole platform component and that took almost 10 months of just like I would sleep four hours and then the rest of the day was just non stop thinking or working on MastermindJam, so even like doing my day job, my brain is working on this other thing, you know what I mean? I would get up and get the kids on the bus, immediately work on MastermindJam, go to my day job, work on MastermindJam over the lunch hour. skip dinner, you know what I mean? It’s just horrible and I’m finding I just need to force myself to have some balance, go to the gym, Ken. Go jog your ass around that block, Ken.

Things like that have to happen because the balance is just so hard to restore and so you have to heal, like I told you before we started the call, going to Cabo for us this year was amazing, just for my wife and I. It was a no brainer for us to upgrade our room and have like a slightly fancier room and an ocean view just to kind of heal our marriage a little bit because it’s been such a stressful year leading up to it and yeah, I think you just have to realize it’s an issue, identify it and then take, it’s always baby steps every day to make it better.

Chris Badgett: That’s awesome. Well, let’s talk about MastermindJam the software. Masterminding is amazing. I attribute all or just the fact that my business is still alive to masterminding. It’s the number one thing that has helped me not only survive in business but also thrive for a lot of reasons. Let’s assume you listening or watching this out there don’t have a mastermind and want to get involved. What does MastermindJam offer?

Ken Wallace: MastermindJam offers the ability to join or create a mastermind group today, this week and give you all the tools that you need to make sure that mastermind group, for the life of it, is a success that you can get the most out of it and realize that mastermind groups, as we’ve discussed, have a life span and it’s not a commitment forever, but get into a mastermind group, help you grow your business and then as you need to, find a new mastermind group that can help you move further.

Chris Badgett: That’s awesome.

Ken Wallace: Well, that’s what the platform is for. It used to be a, sorry to interrupt, it used to be a service where I would physically do the matching of entrepreneurs, and then that grew into, I created a software algorithm that people would sign up, give me an email address, I would have them go through the onboarding questionnaire, but still behind the scenes, there was this algorithm. This is like an opaque black box process. You didn’t know what was going on, but it was working on finding you an ideal match and then once it found one, it would introduce everybody and it was hands off from there. I would give people advice materials for how to hold their meetings and things like that, but it’s very much just on their own and I had no way to measure engagement. I had no way to actually help nurture the whole life of the mastermind group.

It just became obvious talking with customers that everybody was hitting the same hurdles in the same ways after they were matched, that I needed to make a software platform. I held off as long as I could, because usually the answer for a business problem is not let’s build a SaaS. Usually, the answer is a lot simpler than that so it started off with just a simple like email automation sequence and then it went into like, there was an algorithm that did the matching but there was still education involved in it and so now, it has grown into the software platform but I’m going to be injecting a lot more to it.

MastermindJam is going to be growing so much in the next weeks. We’re adding a coaching marketplace because the next question that happens when I tell people to get into a four to five person peer based mastermind group is the next question people ask is well, isn’t that like the blind leading the blind? If we’re all around the same level, what happens when we get to a point where none of us have the answer? Which is a great question.

Chris Badgett: That’s a very valid question.

Ken Wallace: A valid question that happens and if you’re not a part of MastermindJam, for any mastermind group, the easiest thing you can do is go find an expert to join your meeting for like, two meetings, one meeting, say you have four people in your group. If you have an hour meeting, go to and find an expert on the issue that your mastermind is facing. If there’s four people in the group, and let’s say the person charges $400 an hour, great. Each of you pay $100, have the guy sit in your meeting, and if you’re smart, you’re going to do like two meetings, two or three meetings.

The first one is just like education, you can dive into your business with the person looking over your shoulder, he can give you individual help. It’s still cheaper than one on one coaching. It’s still more individualized attention like if you take a course or you read a blog post or you watch a three video workshop, you still have to figure out how to apply all of that knowledge to your business, whereas an expert’s going to come in and just give you the knowledge you need for your business, and by the way, since you’re in a group call, all of you are watching each other’s advice so you’re getting the benefit of well he told me to do this right now but my friend in the call who is a step ahead of me, he told him to do that so I know what I got to do next because I also absorb that knowledge too.

Then maybe have a follow up call where the expert, he or she is just available to answer questions like, hey, I did the thing you told me to, this happened. Now what do I do and it’s a perfect time to ask the expert. That’s what we’re adding to the MastermindJam services, a coaching marketplace where you can go out and bring in a coach or an expert to your mastermind group. Just a short, not forever. It’s not like a lifetime commitment to a facilitator or guru. It’s just we got this specific issue and so that’s just one of the things we’re adding.

Another thing is, I call it mastermind scripts, where it’s 135 email templates and meetings templates that help mastermind groups get through all of the other stuff like the whole life cycle about what do I say to people on the first call, how do I introduce myself?

Chris Badgett: There’s a process, so that’s awesome putting that together.

Ken Wallace: That helps apply the process to the thing, and then the third thing is, some people are reluctant to get into a group because it feels like such a big commitment. They don’t want to make a hasty decision and it’s like, well if I’m going to be in this group for like, four years, I better make sure it’s the perfect one and so they’ll dabble with three or four different groups and they won’t commit to any of them and so to kind of get people over that fear and we’re doing six week intensive mastermind sprints, where it’s just pick a topic, we’re going to form a mastermind group that just solves that one topic in six weeks or addresses that topic, gives you a quantifiable result.

The magic of it is you come away with a takeaway, almost like a challenge or workshop, but even better is you’ve done it in a group setting so you’ve grown together as a group, you’ve learned to trust one another, you have weekly check ins for six weeks and maybe at the end of it, you like that group and you just want to continue on and congratulations, you’ve got a mastermind group or you didn’t, fine, you can reach out and do another six week trial with a different group of people and so it kind of lowers that load, that cognitive load that we put on mastermind group where it kind of removes some of the awkwardness from meeting new people because it’s just six weeks. You can do anything for six weeks.

Those are the things that are coming up at MastermindJam, so on top of the software, the software allows you to interview people and say you’re in a group that you need one more member on, you can take applicants and then screen those applicants so everywhere in the system, it says apply. You don’t just go into the group room and sit down and sit at the back and watch the meeting happen. No, you’ve got apply to join the group, and they get to determine if you’re a good fit, and you yourself can determine if it’s a good fit so when you see groups that have spots available, there’s an Apply button and then right next to it as a Compare button, and so if you’ve ever purchased a tech gadget on Walmart or Target or on, like you’re picking out three different stereo system, you can kind of put them in three columns next to each other and then look at their facets and determine how they rank up against each other.

Same thing here. There’s a compare feature that allows you to put yourself in the first column and everybody else in the group and then to determine if this is going to be a good fit. Do you see that your strengths complement their weaknesses and vice verse? Do you have similar revenue numbers? Are you all in day jobs or not in day jobs? Are y’all married or not married? What’s your availability? Are you in similar time zones or is one person halfway around the world and is not available when you’re available? It allows you to make really informed decisions and really get to know the people and kind of take away some of that mystery before your first meeting.

Chris Badgett: That’s fantastic, so that’s it,

Ken Wallace: It is.

Chris Badgett: Ken, thank you so much for coming on the show. I really appreciate it and thank you for helping unpack the five hats problem. As you were talking there, I was imagining a group of five people, five course creators in the mastermind that one of them was like strong in each of those hats. If you can bring that together, I could only imagine how unstoppable that group would become as they learned from each other and what you said about the Apply buttons and everything, I think the key to mastermind’s success at least in my experience as well from this conversation is the creation of the group. Number one, the world is a big place. Number two, you’re not alone and you only need a small handful of people out of the entire world’s population that can have tremendous benefit for each other. Correct?

Ken Wallace: Yes. Thanks for having me on. This has been a great discussion.

Chris Badgett: Yeah, I appreciate it so head on over to if you’d like to join a mastermind and explore what Ken’s got going on over there. Thank you so much for coming on the show Unpacking Masterminding and also sharing your personal story. We really appreciate it.

Ken Wallace: Thanks for having me.

Chris Badgett: That’s a wrap for this episode of LMScast. I’m your guide, Chris Badgett. I hope you enjoyed the show. This show was brought to you by LifterLMS, the number one tool for creating, selling and protecting engaging online courses to help you get more revenue freedom and impact in your life. Head on over to and get the best gear for your course creator journey. Let’s build the most engaging results getting courses on the internet.

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