Starting and Running an Impactful Mastermind Group

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If you’ve ever considered joining or starting a Mastermind group, you know that they’re often rife with problems. From choosing a schedule that works for everyone to staying on top of your take-aways and tasks, these groups vary in success for individuals. But if run correctly, a mastermind can be one of the best things that has ever happened to your business.

Taylor Pearson joins me today to explain why the mastermind  experiences  vary extensively for so many entrepreneurs. Taylor shares his expertise and talks about why so many masterminds fail the entrepreneurs within the group. From the structure to member selection, we dive into how to start a mastermind group that will revolutionize your business.

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The Full Conversation

(With your hosts Andrew Youderian of and Taylor Pearson of

Andrew: Thank you so much for being with me today on the show. And today we’re going to be talking about masterminds. Masterminds, I’m sure many of you know about them. Kind of brain trusts groups of people you meet with regularly to keep you accountable to make sure you’re getting things done in your business, to gain insights from other perspectives, to help you improve your business more or less.

And on the chat with me is Mr. Taylor Pearson. Taylor’s done a lot of stuff but right now is writing a fantastic blog over at, working on a book, and has a lot of experience in this field with masterminds. And so we talk about why they’re important, how to best structure them, some of the problems that arise, how to get the most out of them, and make them actually work for you and work to make it so your business is going to see the results from those. So without further ado let’s go ahead and dive right in into today’s discussion on masterminds. So Taylor, for folks who might not know, I think most people do but for those that don’t can you give a quick summary of what’s a mastermind and why do them? Why are they important?

The History of Masterminds

Taylor: So masterminds are old school. The first place I ever heard of it was Napoleon Hill’s Think and Grow Rich. And he uses this example of Henry Ford is in a courtroom and he’s getting grilled by a lawyer who’s asking him all these detailed questions about exactly how the business works, how the industry works. And he says, “Why would I remember all the stuff when I have a team around me who can remember all this stuff.” And this is kind of like the genesis of the mastermind. That, “Why would you keep your head full of all these details when you can instead surround yourself with people that are more talented at specific elements of those.” And then it kind of evolved under Jay Abraham, who did a lot of stuff with masterminds and bringing people from different industries together. And if you look at one industry over time, it kind of evolves together. Like every tech startup has the same landing page. By bringing people across different industries, you tend to see big wins in the way people can cross-pollinate in these small mastermind groups.

Andrew: It’s a total rabbit trail here, but that book, I know you’re a huge reader, Think and Grow Rich. I remember reading it. It was a long time ago. I read half of it and got into it. And this is the book where he’s like, “You wake up every morning, you chant to yourself, I will become wealthy or have this much money.” Am I remembering that right?

Taylor: Yeah, it’s a bit woo woo, would be a nice way to say it.

Andrew: I read half way through it and I’m like, “You know, this is a little too much.” To be fair, I didn’t read all the way through it. Does it get better? Is it a better book or am I just too sensitive?

Taylor: I read it five years ago. I have not gone back and read it since. He is right. It’s one of those things where part of it’s good. Part of it’s bad. And filtering through what is what is tricky. That’s not the book I would start with in retrospect.

Taylor’s Experience with Masterminds

Andrew: Yeah, interesting. Huge fans of that book are probably going to just roast us in the comments here, but that’s all right. So, okay, masterminds. It’s a chance to become a brain trust more or less, especially with people with different skills. What’s been your experience with them? How long have you been doing them? How many have you been involved with?

Taylor: So I’ve been doing them for the last three to four years. I’ve been in four long-term, anywhere from six months to the longest one is one I’m still in now that’s just over two years. And my general kind of premise experience with masterminds is basically that Jay Abraham is right in that big wins come from this cross-pollination and that it’s really easy when you’re looking at a problem you get fixated on this one point of attack, this one way of coming at the problem. And being able to bring that problem to a group of people you trust, that share your values, can show you a new route into that problem that might be ten times easier, ten times more efficient than the path you were on.

Andrew: Interesting, so you’ve been part of three or four of them. Have those all been linear? Have you had multiple ones that have stacked on top of each other and if so, why? That sounds like a big commitment.

Taylor: So I’m in three, right now. And one is general business, one is specifically organized around sales and marketing, and then one is specifically organized around the future of publishing or the publishing industry. So I do tend to kind of theme them around specific topics.

Impacts on Business from a Mastermind

Andrew: And can you give me an example. What’s a tangible example of something, maybe a couple if you’ve got them, of something a mastermind or these groups have helped you accomplish recently, let’s say in the last six months or so, that you otherwise probably wouldn’t have gotten done?

Taylor: One big thing I got from a mastermind is I started consulting about a year ago and had no idea. I’d never consulted before. And basically I came to understand, was like, “Oh these guys asked me to do this thing. I think I’ll charge them this much.” And they turned me on to value-based pricing, which is an Allen Weiss concept and basically gave me the core insights into how to manage and run consulting successfully. That was something I didn’t know anything about. And more recently… Actually, the book I’m writing right now is the process of a mastermind. And the marketing is the process of the mastermind that I sat down and I wrote down this paragraph. I was like, “Well, I’ll just kind of like soft launch it to my audience. I’m going to just kind of let it dribble out.” And they were like, “No, you need to market it. You need to put some promotion behind it.” And we’ll see how that pans out but all signs seem to point that that was the correct decision. That I wouldn’t have naturally pushed myself into doing that, but having them there, they saw the opportunity and they pushed me into it.

Best Ways to Set Up a Mastermind

Andrew: So I want to transition a little bit into, okay, somebody’s convinced. They want to join a mastermind group. How do you best set this up? Because I’ve been part of groups that just have not worked. They’ve been more of a drain on my resources than a contribution. And I’m sure other people have had experiences like that too. So, we’ll dive into a bunch of them here but to lead it off. One of the things that I felt kind of really maybe counter intuitive was in your big points was your mastermind group should be uncomfortable. Okay, dive into that. Why? That seems like you’d want to have a group of trusted confidants. Why is discomfort such an important part of a really effective mastermind?

Taylor: Well let me ask you. The groups you were in that failed, they were a drain, why did you feel like they were a drain?

Andrew: They were a drain because they met too frequently. We were meeting every week. That was a problem. And I felt like I needed more time to be able to do it. They met in the morning, my most productive time. And the people in the group weren’t at the same level. Some of us, we’re just at different places. Yeah, we’re in completely different places in business. So those are the big three reasons why it didn’t work out.

Taylor: Yeah, we’re going to talk about some of those reasons later. I think the big thing I’ve seen that differentiates successful masterminds from unsuccessful masterminds. One is context, in that most of the masterminds I’m in don’t get good until I would say at least three and often six to nine months of semi-regular meetings. I’d say that’s at least monthly because you start to build a context of the other individual skill sets and also kind of the ecosystem their businesses are operating in. And you get past the obvious solutions to problems, which they’ve probably thought of.

And then, yeah, the uncomfortable point is tricky to teach people how to make other people uncomfortable. To even do it myself, I still hesitate. But when people get on the call and they’re pushing each other, and that doesn’t mean rudely. There’s obviously a kind of nuanced way to do this. But there’s that sense of social pressure and calling one another out or pointing opportunities out that people are maybe hiding from themselves. And I think a lot of times, I know this is true for me, there’s obvious opportunities and I just don’t see them. And I think this is always true at any given point. I’m sure there’s obvious opportunities in my business right now that I’m just blind to and having someone that will come in and point out and say, “Why aren’t you doing this?” Or equally, “Why are you doing this? Like, this is a waste of your time.”

Tactics for Being an Effective Mastermind Member

Andrew: For people who might not be so brash that might say, “You’re wasting a lot of your time here. These are terrible decisions.” How do you help? How do timid people get to the point where they can go over the jugular of people’s businesses? Is there any kind of tactics or hacks you have for bringing that to the mastermind given it’s so effective? Or is it just something that people kind of either do or they don’t?

Taylor: I think, to some extent, it is something you just learn over time. It’s something I’m definitely still getting better at and not particularly good at. One tactic that I found was effective and I’ve only done this once. I did it about six months at a mastermind I was just revisiting. It was, we went through and we answered the Dan Sullivan question for each other. And so the Dan Sullivan question is: If we were having this conversation and you can use different time periods but 12-weeks, a year, where would you have to be for you to be satisfied with your progress? What opportunities do you need to cease? What dangers do you have to overcome? And what strengths do you have to maximize? And going through and answering for the other people on the call – at this point we know each other fairly well, we’ve been doing the mastermind call for a year – was amazingly valuable because you were able to see other people’s trajectories and other people’s opportunities in their business that they were blind to. Like, “If I were CEO of this business, what would I do?” So, I think, having it written down, we answered these independently and then we sent them to one another and talked about them on the call. It’s a little bit easier to write critically than it is to say it out loud in person. So I think writing it down first does tend to make it easier.

Best Sizes and Formats

Andrew: That’s a great tip. What about size and format, and leader, and meeting regularity? In terms of those kind of mechanics, what have you seen work really well and not so well?

Taylor: So I like weekly and bi-monthly, so weekly or every two weeks. I know some people like the quarterly format so that might be something to play around with. I know you said you thought weekly was too frequently. I definitely always do it in the afternoons. I don’t know of anybody that has super productive afternoons.

Andrew: Yeah.

Taylor: And so that seems to be generally a good time. In terms of size, smaller is better. For me, four to five has generally been optimal. Two to three is good. Six is good. And then, once you get over six it feels like there is just too many people. Certainly, for like a weekly, like a 60, or a 90, or a 120-minute call. If you wanted to do like a quarterly thing or as like a all day, Saturday. Every person goes for an hour. You can maybe get up to eight people. But four to five tends to be where I fall.

Andrew: Yeah, when we did the masterminds for the private forum, as we continue to do them, we max them out at five. Just because… Yeah, that’s what I found too. I’m part of one right now that’s five people and it’s worked out. Worked out great. Enough people to get various perspectives but not so many that people can’t chime in or can’t help when needed, which has worked out well. Same thing with experience level. Kind of matching people with the same level we found has worked out well. So people are in the same stages of their business.

Mastermind Duration

Andrew: What about duration for you? One thing with anything in business is few things last forever. Maybe a mastermind that works for a couple of years, maybe people diverge, maybe your needs change. For the private forum one’s we set it up where there’s at least a test period where, for the first couple weeks, you see if it’s a good fit. And then, maybe you reevaluate after that. Have you set up with any of your, seen it work, where you build in ripcords? So you say, “Hey we’re going to do this. We’re all going to commit to do this for three months, for six months, for a year. And then we’re going to reevaluate and only come back together if it makes sense for everyone there,” so that there’s not this expectation that it has to go forever if it’s not a good fit?

Taylor: I have. The most recent one I started we did that. We just started with a three-month time period because it is very. . . the idea of a lifetime commitment is a little daunting

Andrew: Yeah.

Taylor: So I do like giving those ripcords. I guess the caveat I give is my experience has been, repeatedly, that there does seem to be something at least three months in, and often more like six to nine, where you really get that deep level of context and that seems to be an inflection point. But at the same point, I think there’s been a couple masterminds where I’ve been on for a couple months and it became very clear it just wasn’t a good fit. Like people that wanted to be very social and they wanted to video chat and talk about social hour. If I’m going to be social I tend to prefer to do it in person and not over video chat. When I get on a mastermind, it’s very much like, “Hi, hello. Nice to see you.” And you see two to three minutes of warming up and then we’re into the call and it’s all business.

Andrew: Yeah, I love it. I’m the same way. Really, yeah, one or the other. I don’t mix business and pleasure very well either. Okay, so those are great tips for actually setting up the format. One thing we didn’t mention, I want to make sure we hit this. What about how you structure it in terms of the actual mastermind interactions? I know some people do a hot seat where one person gives a problem and then the entire hour, or whatever the length is, is focused on that one person. Sometimes people will break it up into 20-minutes. You’re, I believe, a big fan of the hot seat format, why?

Taylor: I am a big fan of the hot seat. So the usual format I do is an updates round, or a progress round. So this is partly to build and partly to just keep that rhythm in context. Everyone will go, that’s not on the hot seat, and give three to five minutes tops of high level summary of what happened since the last meeting and then their biggest opportunity and their biggest problem. And if someone has feedback on that, like I say, “I want to get into the trolling [SP] motors niche.”

Andrew: I knew it.

Taylor: “Well, you know, I can help you with that.” So at that point, that will be something we can take off the call and it wouldn’t interrupt the hot seat. And then move into at least 45 minutes. And I find often 60 or 75 minutes for a hot seat is really good because it takes a long time I found, or at least 20 to 30 minutes, to really get into the problem. Frequently it’s this scenario of the problem isn’t the problem. The problem is something else masquerading and you need to get through the five whys of, “Why you want to do this? And, why do you want to do this?” To really get to the heart of what the problem is. And then, also, I think when you’re on a mastermind with intelligent people, like they’ve got some general idea of how to solve this problem and they’ve thought about it a decent amount and what they need is more in-depth coming from different angles. And so frequently the first 20 minutes you’ll kind of roll through all the obvious solutions and then you get everyone thinking about it. You come up with a new way to approach the problem that could be ten times more effective, ten times faster, or ten times easier.

How to Seek Out a Mastermind Group

Andrew: So finding one, getting into one… If you’re a private forum member, we’ll link up in the show notes the thread we have that talks about how you can apply for one and get matched up with some great people in the community. If you know people, maybe there’s just three or four people in your life, you know it’d be a great fit. But, Taylor, what do you do if you’re on your own? You’re working out in the sticks of Montana and you don’t know anybody. You have one buddy who barely knows about business who’s willing to listen to you. What then? What are your options?

Taylor: First of all, I have no idea why anyone would ever choose Montana. What a bizarre place to live.

Andrew: It’s because you haven’t been out here yet.

Taylor: It probably is. I think and I would say when you mentioned you had different experience levels, I think masterminds are a great opportunity to network up. And I mean that by if you’re the one that is organizing the mastermind, you’re the one taking initiative, often times you can serve as the role of the connector and just connect other people that might be farther along. It doesn’t necessarily mean to be farther along in terms of just revenue, but they could be farther along in different aspect of the business. So maybe they are better at the marketing side or they do b2b and you’re really good at b2c and finding those kinds of synergies. In terms of first steps for getting it set up, I usually start with everything, I’m sure it’s someone I know relatively well and in person. And so I usually go find somebody and go, “Oh, it’d be really valuable to talk to this person every week or every two weeks about what I’m working on and have that back and forth.” And if that’s going well then we’ll reach out and we’ll slowly add a third member. And I often times build them up maybe over the course of three months and bring people, all individually, and say, “Come check it out for six to twelve weeks, see what you think. If you like it, hang around. If not, no hard feelings.”

Taylor’s Book – The End of Jobs

Andrew: Yeah, it’s the chance to really extend the network. If you don’t know anyone, go make some friends. You’ve got to kind of build it out of your network at some level but you can kind of leverage it too to grow it. So I want to shift gears again. Awesome stuff about masterminds, Taylor, you were a huge help when we were launching up at the forums. I took a lot of this from you in terms of incorporating how we structured them. But it’s interesting to hear about your book. Completely unrelated, or at least I think it is. But you’re writing a really cool book. I love the title by the way. The End of Jobs is the title. You think about titles that. . . was that hard to come up with? It’s a great title. Did you just spend hours and hours thinking about that?

Taylor: I probably spent too long. I’m not sure exactly how long I spent on it. My initial strategy was I sat down with a piece of paper and made a hundred lines. I said, “I’m not getting up until I’ve written down a hundred different options.”

Andrew: And how long did that take?

Taylor: It took, I think, almost three hours. Some of them were so bad. I’ll have to go back and look at them but some of them were really atrocious. Like, it got really academic and then it just… I actually don’t think anything came out of that first one. But, yeah, back and forth and eventually that was what I ended up on. It seems to be a good lineage of the end of books.

Andrew: The end of money, the end of jobs, all this kind of stuff.

Taylor: Yeah.

Andrew: So now that we’ve teased the title, what’s the premise? What’s the book about? Is this like the last days of Steve Job’s life at Apple? Is that what we’re talking about here? What have we got?

Taylor: I’ve gotten that a lot. I know, I maybe should have been more selective with the title, but the premise of the book is basically that we’ve crossed this threshold in terms of the macroeconomic opportunity in that a lot of the conversation that goes on now in terms of entrepreneurship and starting your own business is very much a “Follow your passion,” one. It’s very emotional and it’s not as much about, “What is the real opportunity?” And, “What are the macroeconomic reasons?”

So, the rapid development of technology, globalization, all these things. People that are running their own business, especially internet businesses see, isn’t widely known that the leverage points in that sense have changed and that the people that understand those new leverage points have dramatic opportunities that they’ve never had before. And the people that don’t understand those leverage points are in more competitive, less profitable situations than they’ve ever been before. I was just looking at a report from Kleiner Perkins and I can’t remember the firm’s name. It’s from those well-known management firms saying that, basically, since 2000, the rate of jobs is like 2.4. Let me pull it up. The population has grown 2.4 times faster than jobs have since 2000. And for all of the 20th century, jobs grew 1.7 times faster than population. And that to me. . . it has some other statistics on that line, but there does seem to be this clear inflection point we’ve hit with job growth. And the growth in the economy is not coming through jobs but increasingly coming through entrepreneurship and new businesses.

Andrew: It’s really interesting and I feel like this has been a trend. Globalization and technology has been a trend over the last 20-25 years. But I feel like especially even this last year, I’ve been hearing more and more about it. Planet Money will link up to a really. . . do you listen to Planet Money at all?

Taylor: I do, periodically.

Andrew: Yeah, one of my favorite podcasts. In the last couple weeks, they’ve done a really interesting series on technology in jobs and going all the way back from the Luddites, the original haters of technology in the industrial revolution. That sort of destroying the looms when they came about because they took up jobs all the way up through today. And talking about how increasingly recovery is, especially over the last 20-25 years have been jobless recoveries because all these people lose their jobs. And then the economy continues to grow, but the jobs don’t come back because a lot of what was done is now being done by technology. And with those jobs gone because it got severe in terms of economic issues, they didn’t have to hire the people back to replace them.

And more talk about, I feel like the last quarter or so, or six months we’ve heard more about artificial intelligence. Guy’s like Elon Musk and Bill Gates and Stephen Hawking I believe, these fairly respected people saying, “Hey, artificial intelligence, even though is a far a ways off could potentially be some dangerous stuff.” So, yeah, I feel like we’re hearing a ton more about that. It just accelerated the discussions about it the last year or so. It’s crazy. How fast do you think this is going to take off? And do you think we’re going to see that the point where just really, in 10 years, the only viable way to be able to make a decent living in the Western World is to be an entrepreneur or to own your own business or to really step outside the confines of a job and take on the risk of making it yourself?

Taylor: I’m always really hesitant to make predictions because my track record is so bad. I think what is clear is that there is this transition that you were just talking about, which is from what I call complicated work to complex work. You would like this. There’s this framework called the Keneven Framework. It’s a management framework and it talks about. . . You can categorize management into simple, complicated, and complex. Simple tasks are best practices. It’s algorithmic work. It’s putting together an IKEA or Lego. Someone gives you the exact map.

And then complicated tasks are what we think of as knowledge work, broadly. Maybe someone asked you to write a marketing report and they said, “It needs to be ten-pages and you need to have five sections, and three main points in each section, and two takeaways at the bottom.” There’s a good practice for how to do that and you can look up some guidelines, but it’s not super clearly defined. And what’s happening now is it’s moving from that complicated to the complex, which is a much broader questions, an emergent practice. There is no handbook. Is it even worth writing a marketing report? Are we in the right industry for writing this marketing report? Does the tone of the marketing report… Is that going to be congruent with when they call up the sales person? Or, should we write this marketing report for an industry we’re going after or should we be using it to solidify an industry we’re already in? And these are much more difficult questions to answer and there is no best answer, right? It’s an emergent thing. I think that transitioning is definitely happening and my suspicion is it’s going to happen much faster than everyone thinks. And how fast that is, I’m not sure.

Andrew: So if people want to get their hands on this, Taylor, where is it available? Where do they go to pick it up? A cool little giveaway you’re doing to incentivize . . . completely, really, unrelated to the book but just for readers, a cool thing to think about.

Taylor: Yeah, so I’m giving away. . . I went back through a lot of books I used researching and writing the book and put together my 67 favorite books on entrepreneurship. I’m going to be giving away a copy of all of those to someone who enters the giveaway. And that’s at So if you’re interested, you can submit your email there for the giveaway. And then, anyone who enters for the giveaway will also get a free copy of the book when it’s out on Amazon. So, yeah, those are the details.

Andrew: Very cool. I was teasing you before that there’s no way you could read 67 books but, man, you devour books faster than just about anyone I know. It’s impressive. How are people going to get these books? Are they eBooks? Are you actually shipping the hardcover/paperback books? How are you doing that?

Taylor: In true fashion, I have no idea how I’m going to fulfill it. I just decided it was a good idea. And I was like, “Yeah, I’ll figure out the fulfillment later.”

Andrew: Awesome. That’s so cool. Best of luck to you, I’m excited to read it when it comes out. So again, if you’re interested in joining a mastermind and you’re not already part of the private forum, sign up. We’d love to have you. And again, we’ll link up to how to get plugged in. We actually do a matchmaking service in the forum where we look at your experience, how often you want to meet, all this kind of stuff and put you with a group of other store owners that are just like you. You can get plugged in there and we’ll link up to that. And, regardless, check out Taylor’s blog. He’s got a fantastic blog. It covers the gamut in terms of a lot of topics for entrepreneurship, reading literature, the systems. I know you’re a big system geek like I am as well, Taylor. And that’s Taylor Pearson, P-E-A-R-S-O-N dot M-E. And to win the books, again, that’s And no hyphen, right, Taylor? Just winbooks?

Taylor: Just winbooks. No hyphen.

Andrew: Great blog to read, regardless. Taylor I’m going to be wishing you the best. Looking forward to when it comes out and thanks so much for coming on.

Taylor: Thank you so much for having me. I appreciate it.

Andrew: That’s going to do it for this week. But if you’re interested in launching your own e-commerce store, download my free 55 page ebook on niche selection and getting started. And if you’re a bit more experienced, look into the eCommerceFuel private forum. It’s a vetted community for store owners with at least $4,000 in monthly sales or industry professionals with at least a year or more experience in the e-commerce space. You can learn more about both the ebook and the forum at Thanks so much for listening and I’m looking forward to seeing you again next Friday.

What Was Mentioned

Photo: Flickr/Allan Ajifo

Posted on: June 19th, 2015

Andrew is the founder of eCommerceFuel and has been building eCommerce businesses ever since gleefully leaving the corporate world in 2008.  Join him and 1,000 vetted 6 and 7-figure store owners inside the eCommerceFuel Community.

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