E127: The Importance of Masterminds on Business and Personal Life

If you've been listening to the EcomCrew Podcast for quite some time, you'll know that I'm a big believer of masterminds. The company of people who understand your struggles as an entrepreneur and offer guidance on your growth is invaluable. In the words of Napoleon Hill:

“Deliberately seek the company of people who influence you to think and act on building the life you desire.”

I recently joined a mastermind with mid- to high-seven figure entrepreneurs and I just came back from an in-person retreat with them. I just literally landed and went right away to record this episode, because the retreat had such a profound impact on me that I had to record while everything is still fresh on my mind.

While the entire weekend had been absolutely beneficial to me and everyone who was at the retreat, let me share with you one of the most impactful activities we had. Each of us answered one of the following questions, which I think everyone needs to be asked at some point:

1. Describe your relationship with your father from his point of view.
2. What was the last conflict you had with your spouse?
3. What was the lowest point leading your company?
4. What is something you're most ashamed of about your life?
5. What is the best thing you ever did?
6. Tell about a decision that you made that you regret.
7. What is your most public failure?
8. When did you most recently feel self-doubt?
9. How do you manage your ego?
10. What are not doing, that you need to be doing, and you want to do before you die?
11. What are you doing right now that you know you absolutely must do?
12. What is one thing you want to do before you die?
13. What is the most questionable thing you've done this year?
14. Do you think that cheating is natural?
15. What are you most afraid of?
16. Tell a recent time where you lacked integrity.

As you can see from the questions, this mastermind weekend is pretty emotional for me. It's easy for me to nerd out about business, but opening up about personal things is a challenge for me. This mastermind retreat helped me get over that hump, and made me reflect on the big picture and see what actually matters to me in the long run.

Resources mentioned:

E109: My 2018 Goals

Thanks for listening to this episode. Until the next one, happy selling!

Full Audio Transcript

Mike: This is Mike, and welcome to episode number 127 of the EcomCrew Podcast. So glad to have you along with us today. Don’t forget you can go to EcomCrew.com/127 to get to the show notes for this episode. And today I'm going to be talking about the importance of Masterminds. And this is something I've talked about on the EcomCrew Podcast many times; we’ll link to a couple of those episodes in the show notes.

But the reason I want to revisit it today was for a couple of different reasons. First of all I did join a new mastermind a few months ago of mid to high seven figures sellers and one eight figure seller in the group, really hoping to raise my level by being a part of this mastermind. And the other thing is we just got back from an in-person retreat. This is something for the first time I've done in a structural with a mastermind with so many people and it was really just an unbelievable experience. And I want to talk about it while it was fresh in my mind.

I literally just landed from the trip and I came right to the office to record this so we can get it done as quickly as possible while it's fresh in my mind. So on the other side of this break; we're going to get right into it. We'll talk to you then.

So as I just kind of alluded to in the opener for this, I just landed from a trip from Mexico, and I'm pretty tired right now. I’m going to say it's been a long few days. But I really wanted to get this down while it was fresh in my mind. Again masterminds are just super important to me. I think it's important to get out of the office every now and then, talk with other people at your level, your peers, entrepreneurs that can understand the trials and tribulations of being the CEO of a company, having your livelihood at risk with all the financials and into a company, what it's like to have employees and all these different types of issues.

And what it's like to have someone sue you or someone steal your intellectual property, and understand what it's like for all these types of things that have visceral personal level. Obviously employees, we have great employees, but they're never going to feel the same way that we do when something like that type of thing happens. And so it's really important to commiserate, and talk about the stuff, and how to take care of life in your business to the next level.

And this trip for me was just mind blowing. It's the first time I've ever done anything like this at this level. And I'll talk a little bit about why as I get into it. But I'm going to probably just go through chronologically here what happened on this trip. And obviously a lot of things I have to leave out here. I'm very open and honest on the podcast. As you guys know, I talk about a lot of stuff in our lives, in our business.

But one of the crucial things for a mastermind to work well is confidence and secrecy or just keeping things to yourself. It's a confidence in not discussing what's discussed in the mastermind with a bunch other people especially on a podcast format. But I do think it's entirely appropriate to talk about who's in the mastermind. I don’t think there is anything private about that, and talk about the format that we do and just kind of the general outcomes from the trip and things that I took away because I certainly don't think there's anything wrong with me talking about what I took away.

So with that said, as I mentioned in the introduction, this is a new mastermind that I joined about six months ago. It feels like now maybe it's been a month or two more or less, but somewhere around there. And it takes a lot obviously to gel with a group of people at this level. And we meet once a month for two hours a month online through a zoom meeting. It's a paid mastermind. So there's a moderator that organizes everything for us and takes care of that making sure that we're on track and everything is going smoothly within the group, which is a really nice welcome change from other masterminds that I'm in.

Some of the people in the mastermind, I've known for a while. Most of them I've just met really for the first time a few months ago when we started the mastermind. And the thing that's really good about that is these people will call me on my BS. There's other people that I've been in groups with, in masterminds and they're also friends, and it's hard for them to call me out of my BS.

A lot of times it's a situation where they look up to me in some of the masterminds, or they're just certainly not going to ever push me or challenge me in that way while this group of people certainly will have and will continue to do, which is a pretty awesome feeling. It's scary. It's something that I'm not used to. It’s taken a little while to get used to, but I can see the marked improvement in our business and in my life because of it.

So typically the way that it works with our format for the mastermind is we open it up by kind of just discussing in a couple of short sentences, maybe a minute or two just kind of what's going on in our lives, in our business, things that make us have been going well, a couple things that have been going bad, discussing our sales, our numbers for the time using like a one word how we feel right now.

The thing that kind of constantly comes up is stressed, overwhelmed. I think a lot of entrepreneurs feel this type of thing over and over. So again it's good to know that you're not the only one sometimes that might feel this way or have these problems. And then what we do is a coaching session. So there's nine members total in the group, and this rotates through. So everyone every couple months has an opportunity to get advice from the group basically, and you pick the topic that you want to help with.

And then one other person before the meeting will coach you, help you articulate your question to make sure that you are going to be able to phrase this in a way that the group can give you positive feedback, or feedback that's going to help you in a very positive way and make a big difference in your life and in your business.

And then in the actual meeting, the coach will then present the format of what we’re talking about for about a minute, then the person that needs — that's getting some help that particular month will spend a few minutes discussing the problem that they're having in their own words. And then there's a few different rounds of feedback from the masterminds.

So that's our typical format, and we've committed to having at least one in-person mastermind per year, but I think that we're going to nurture it up to two. After this trip it seemed like everyone got so much value out of this. We've become really good friends so quickly because again we all just can relate to each other so well that I think that we're going to do this again in the fall, which I think will be great and the timing is perfect. It'll be right before we go to China for the Fall Fair.

So in the in-person mastermind, first of all this was in Cancun [inaudible 00:08:12] or whatever. The scary thing was there was a travel alert that went out like the day that I landed. I don't basically go to the city during this time because there's a credible threat. No US government employees were allowed to be there. They shut down the local — it's not the embassy, but like a local field office. There was lots of police presence there. It was a little intimidating. I kind of say it’s something I would have rather not seen or had.

But it was what it was, and luckily we came back safe, and I hope certainly anyone that comes after us is going to be safe there. We don't want anything to happen to any other people as well. But happy to be back on US soil, and happy nothing happened. I went a day early along with two other people, so there was three of us that got there a day early. I decided to go early because from San Diego there's no direct flights to Cancun.

I've traveled a lot and know that there's at least a 10, 20% chance whatever it might be of delays or even a 5% chance that you end up spending a night in an airport that you weren't expecting or something because you missed a flight, and then you just miss a very important meeting like this. So I figured I’d be down there a day early, start to acclimate to the time zone, have an opportunity to talk with a couple of the other people in a smaller format for a day, and it worked out great.

It was awesome. We got there around 5:00 PM, checked in or got down to the hotel around seven because we had to get a car and get down there, checked in our hotel, went out and had an awesome dinner, some drinks, went back and talked to the wee hours of the morning up on the rooftop bar overlooking the ocean. It was pretty special. I don't know if there's really anything specific to share about that, the conversation that night. Again all this is held in confidence, but it was definitely — it was really good.

It was really good to meet one of the people that's in the Mastermind that I don't know very well. We got to spend a lot time together. And it was also cool the person I probably know the best in the mastermind was there as well which was really awesome and it was a great night. The next day everyone else arrived. We got up early in the morning and did — the hotel shuffle did some grocery shopping and stuff that prepared for everyone else to get there.

We went out to dinner and then we came back and started doing our first exercise, which is one of things I really want to talk about on this episode. It's something called the lifeline. And what you do — and the guy that presented this to us, that gave us this as an exercise, his name is Peter. He's with a company called French [ph] Sports, one of the guys in the Mastermind that I think has really become like the leader of the group, a really awesome dude.

He is also in EO which is Entrepreneurs Organization, and they do this lifeline exercise in there. And basically what it is, is the blank piece of paper, and at the bottom it's basically got like 5, 10, 15, 20, 25, 30, 35, 40, just basically five increment groups which is basically used in your life. And the idea is to plot between one and ten how you felt during that time. And you don't need to do it year by year or even month by month, but you highlight the big events in your life.

It might be when you got married or when your business was successful, or when somebody died or whatever it might be, when you got picked on in school, or I don't know whatever it might be, there could be whatever it is on the graph. And it's quite personal. It was really difficult for me to open up in this way and do this. I don't even really do that with my best friends or my wife. It's just not who I am. So it was definitely really interesting going through this exercise.

The thing that was really interesting to me after I plotted this out is it seems like I'm bipolar. I'm here there like a ten or a zero. It seems like that might be an entrepreneurial dilemma, either you're flying high with the things you're doing, or it's not working and you're not happy. And I definitely saw a theme of that as my people in our group presented. I'd say at least eight of them had similar patterns. Again, not talking about anything specific but definitely a pattern of this highs and lows thing.

For me, the highs were my last business that we did was a high. This business is a high. I feel like things are going really well right now, it's definitely a high. Lows was a bad breakup that I went through. Another low was a bad business time in my life when we had moved to Texas to partner up with someone that ended up stealing from us and really screwing us pretty badly, not only just in the money they stole, but just in a bunch of other stuff. It was a pretty dark time, definitely down there on the one or zero level.

But for the most part in my adult life, it's been above the line which is good. I try to be happy as much as I can. Other cool things that were highs were having a year off basically when we lived in the Cayman Islands and RVing for a couple of years, it was definitely awesome. Those are definitely some other cool times in my life as well. So that lifeline exercise spanned a couple of days. It takes 20 or 30 minutes per person to get through that. And it was really interesting.

Getting to learn so much about other people's lives and on a personal level, again this is obviously a way to like intensify or compress time to become close to people when you're talking about stuff like this at this level. And again a lot of common themes. I think a lot of entrepreneurs go through pretty much the same dilemmas. And it was good to know and see that. The next day we woke up and we did some activities. Unfortunately it rained on us the entire day. We really actually had pretty poor weather the entire time. But I have a saying that a rainy day at the beach is better than a sunny day at the office.

And we spent the day, we basically the entire day went to ATV riding for a couple of hours, then zip lining and went to a snow day to go swimming in a cave. I actually skipped that last activity. I was just like miserably cold and wet, and I wanted to get into some dry clothes. That was one thing I didn't elect to do, and just dried off and relaxed for a little bit while everybody else did that. We came back, did more lifeline exercise, finished that up and went to dinner.

The next day was spent full day basically from sunup to sundown and actually till four o'clock in the morning. We were joking that we were on Pacific Time the entire time we were there because the earliest we went to bed was 4:00 AM, just really good conversation over some drinks and stuff talking business and shop and personal life. So the next day we kind of went back to that same basic format. I happened to be the one, and I felt like it was a little bit unfair that I happened to be up to be coached.

And my problem again, this is my thing so I don't feel bad sharing this was just trying to do something, to talk about something more personal. In masterminds before, anything I've done like in this regard has always been based on business, things I'm doing on business, and that's very easy to talk about. It’s like, oh we're doing e-mail marketing and doing this way and sup this segment and conversion rate optimization, you should try this thing above the fold and have a contrast in the body and I could nod about that stuff forever.

But talking about personal problems or struggles is not something that is in my DNA. It's not something I've done a lot of in my life. And it was super interesting to do that. And basically the thing I was talking about was that I'm 40, I'm looking back at a body of work over a long period of time. I’ve come to realize I'm pretty definitively like how obsessive I get with things. And this was the thing that I chose to talk about.

There's been several times I've been obsessive about my business. There's been other times I've been obsessed about playing tennis or scuba diving or when I went to Alaska and was hiking there, obsessive about that. And it's typically one thing that I get obsessive about, and the balance gets completely screwed in every other aspect of my life. I look at the last few years, and while we've done amazing with our business, the quality of life if I look at just I've gained some weight, and I’m not in as good shape, and things that are important to me have been sacrificed.

I'm sure my wife feels the same way or feels like maybe I haven't paid enough attention to her even though she's in the business every day which is another challenge because we're just always around. You take it for granted that she's always there, verses in a typical normal healthy lifestyle, you have eight hours or ten hours a day away from your spouse. When you come home, it's almost like when your dog reaches they're happy to see you, but if you're around all day they're not that excited, and you just take it for granted that they're there all the time. So this is definitely a challenge.

This is the stuff that we talked about. And the one thing that really resonated, that someone I mentioned in there was during just the recent time when I went and did this Alaska trip, I was able to train and be focused and obsessed with that and also work at the same time. Over the last few years I feel like that was probably the highest point of my life in the last few years doing this business where I was able to do both.

So we really strategized about how to have a better balance and do both. That's really probably the biggest key there. I had some really interesting suggestions. They’re kind of personal, so I don't really want to talk about them too much on the podcast, but definitely going to be working really hard over the next few months on trying to balance that a little bit better. I get immense enjoyment out of my business, but again I get obsessive like I'm obsessive about our stats and our goals and they're very public.

Everyone knows that we published our 2018 goals. We'll put that in the show notes. They're pretty lofty goals, and it's just full of trying to hit these numbers and constantly looking at that day in and day out and it requires a lot of time, a lot of mental capacity. And I think that technology has exacerbated this, having an iPhone in your pocket or always on the table lighting up all the time, making sounds, buzzing you with an Apple watch whatever it might be, constantly having that sensory, it's hard to get away from.

I was talking about basically how the first thing I do when I wake up in the morning is touch that phone, and the last thing before I go to bed is to touch that phone. It's definitely not healthy. So I’m definitely looking at ways to fix that in that balance. So that's probably about as much as I want to get into that. I will talk about this more in future episodes. But again, a little bit personal, so I want to kind of keep some of this as close to the vest until some of it has come to fruition and I kind of work through it. And also just to make sure that there aren't any issues sharing some of the stuff.

The other thing that was really interesting, so the other thing that I guess just real quick that happened was there was another person that presented. I definitely can't talk about any of that. It was definitely really interesting conversation though. It was something that I could relate to and hopefully was able to help a significant amount, because it was something that we're going through at this exact moment. And it's cool being able to again talk to other people at this level, and be able to help and also get help. So it was definitely pretty darn cool.

So the next thing that I want to talk about real quick that was really interesting was the last I would say half a day to a day of this, because we finished up our standard meeting format and then it was like, okay, we went out to dinner. And Peter just being the way that he is and from EO had a lot of other experience to lean on other things that they've gone in his EO group. And so what he did was he started throwing up these questions.

And the crux of the idea is to write these questions out on index cards, shuffle them, and pass them out. We did it a little bit differently because we didn't have that available right at that moment. But I'm going to read you all the questions that he kind of posted here. Again not going to talk about any of the answers or any of the things, but you can probably understand why by the end of this. It was a pretty emotional recharged room and really interesting.

So let me just kind of go through these, there's a lot of them. And the reason I want to go through these, these are things you probably should be thinking about yourself, things that you might want to ask other people or have other people ask of you. If you're in a mastermind, play this game. It's a good opportunity to learn more about the people in your mastermind, to also talk about things that aren't business. Again I think that entrepreneurs end up being too off the deep end with business. That was definitely a constant theme through this trip.

So let me read these questions real quickly here. Describe your relationship with your father from his point of view. What was the last conflict you had with your spouse? What was the lowest point leading your company? What is something you are most ashamed of about your life? What is the best thing you ever did? Tell about a decision that you made that you regret. What is your most public failure? When did you most recently feel self doubt? How do you manage your ego?

What are you not doing that you need to be doing, and you want to do before you die? What are you not doing right now that you know you absolutely must do? What is one thing you want to do before you die? What is the most questionable thing you've done this year? Do you think that cheating is natural? What are you most afraid of, and tell your recent time where you lacked integrity? And the funny thing he's closed here with is remember there are no winners, so we’re all losers.

And it kind of felt that way about the end of this. I'm not sure if it was just me feeling emotional from it, but it definitely seemed you could feel the kind of tension in the room after reading these questions. Everyone was brutally honest or at least it seemed that way. I know I was in my responses. It was hard to even verbalize it. It's like you kind of almost get choked up being honest with yourself and with everybody, because not everything is perfect in life.

And the thing that I really took away from this exercise that was really awesome to me is I realized by the end that pretty much everyone has something that they are struggling with in life, right? It's not everybody is a ten all the time. And even though I mean I'm lucky I feel fortunate that I don't suffer from depression or a lot of other types of issues and I'm usually pretty mentally stable and even keeled [ph].

But I'm definitely I'm either like I said, either a ten or a one. And I definitely go back and forth intra months sometimes. There's several times when I get frustrated and feel like I'm not doing enough job, I’m not adequate enough especially we don't hit our goal. If I got to make a decision and it was stressful which way it can go, it's interesting how things kind of seesaw back and forth. And it was neat to realize that you're not the only one going through this stuff, that everyone else has issues and stuff as well.

And it was it was definitely a really interesting way to end the trip. I felt incredibly close to this group of people by time we left, and I think the feeling was mutual among all of us. That was the end of the trip, got back on a plane, connected through Dallas, did a couple of hours of work at the airport, got on an airplane, landed here, and now we're about to spend the first part of this week a little bit of a heads up. I’m going to be recording another course. This one is going to be our Amazon course.

It seems to be highly anticipated, definitely really eager to do this. So I got the professional film crew back in town. Monday, Tuesday, Wednesday going to bang this thing out. The curriculum is all done, really excited about it. I’m going to be doing basically how to launch a product successfully in 2018 the white hat way amongst so much other things on Amazon, really looking forward to doing that

So I'm going to sign off for this episode, head home and grab some sleep. But one thing that I can say about this trip was I did not get rest. It was not a well rested lay by the beach and sleeping kind of trip. We were up early every day, went to bed really late. In fact I went to bed at 4:00 AM last night, and the alarm went off at seven, and that was just kind of brutal. So until the next episode everybody, happy selling, and we'll talk to you then. I hope you guys enjoyed this. We’ll be back with another episode on Thursday. Thanks guys.

Michael Jackness

Michael started his first business when he was 18 and is a serial entrepreneur. He got his start in the online world way back in 2004 as an affiliate marketer. From there he grew as an SEO expert and has transitioned into ecommerce, running several sites that bring in a total of 7-figures of revenue each year.


  1. Like all the podcasts, I enjoyed this one. I would have like to hear how to find a good mastermind (other than through google). Or, if you find one, how to tell if it will have value. What are some items to look for when you find a mastermind group. I appreciate the excellent podcast.

    1. I think the big key is to become part of a community first. There’s no shortage of ecommerce communities both stand alone (ecommerce fuel is our favorite), on Facebook, and locally. And after try and form one/join one that has people with similar businesses. If everyone is sourcing from China and you’re drop shipping sometimes it can make it difficult to share strategies and tactics. I know you’re probably looking for something more concrete for how to find a mastermind but the best ones seem to happen fairly organically

    1. I don’t know a list but definitely checkout ecommercefuel.com and try to become a member there. There’s a lot of masterminds organized there.

  2. Raw. Great episode. What we all want to talk about—but don’t. This is a great read for anyone going down this path: Deep Work | Kal Newport.

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