A Mastermind Event Case Study about Chris Lema’s CaboPress

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This episode of LMScast with Chris Badgett of LifterLMS is a mastermind event case study about Chris Lema’s CaboPress. Thomas Levy and Ali Mathis of the LifterLMS team join Chris on this episode to discuss their experiences at CaboPress.

Thomas is the co-founder of LifterLMS and the head of development, meaning he takes care of the software behind LifterLMS and makes the magic happen. Ali is the director of projects. She handles things like the Done For You service and the LifterLMS trial.

CaboPress was in Cabo San Lucas, Mexico. The event was at a resort, and it had roughly 50 to 100 people in attendance. It was hosted by Chris Lema, who is a speaker in the WordPress community. He writes a lot about agencies, WordPress products, selling, and community building. He’s a great guy and a fantastic resource for entrepreneurs, especially in the WordPress space.

Using real-world experiences as inspiration for online products is something that has been creating successful businesses for decades. Facebook was inspired by recreating the college social experience online. The Macintosh was designed as a bicycle for the mind. The LifterLMS Social Learning add-on that was recently introduced is based on creating learning environments that mirror the way we learn best in small groups.

CaboPress was sort of a hybrid between a small conference and a mastermind. It was focused around the conversation more than a traditional conference where you sit in chairs and listen to speakers. This format creates an opportunity to meet different people and build relationships.

Attending events and building relationships within your industry creates a compound effect with the value you put out into the world. Chris, Thomas, and Ali discuss the benefits of networking and attending events like CaboPress and WordCamps. They also examine the evolution of LifterLMS and how it has shifted from a primarily service-based business to a product and service business.

Another neat aspect of CaboPress is that all of your basic needs are taken care of. All you need to do is purchase a ticket to the event and get to Cabo, and your hotel, food, and basic necessities are taken care of. This frees your mind to engage in the activities and focus on the conversation.

Thomas also shares some insights on how events like CaboPress allow you to have conversations with entrepreneurs who are at different levels with success. These conferences also have what’s known as the “context effect” which is when you are out of your normal context, and this changes your word recognition, learning abilities, and memory. Most of the CaboPress sessions take place in a pool, so you can’t bring your computer or a pen and paper. This change in scenery changes how you learn and will often improve your memory and attentiveness.

To learn more about CaboPress, check out the LifterLMS blog post on it at blog.lifterlms.com/CaboPress-Growth and make sure to head over to Chris Lema’s site ChrisLema.com.

Post comments and subscribe to our newsletter for updates, developments, and future episodes of LMScast. Thank you for joining us.

Episode Transcript

Chris Badgett: Hello, and welcome back to another episode of LMScast. My name is Chris Badgett, and I’m joined by two very special guests from the LifterLMS team itself. We’re joined by Thomas Levy and Ali Mathis. How are you guys doing?
Ali Mathis: Great.
Thomas Levy: Very good. Very good.
Chris Badgett: Awesome.
Ali Mathis: Happy to be here again.
Chris Badgett: Excellent. Yeah. Ali is probably our most frequent guest at this point, so she’s winning there.
Ali Mathis: Competitive.
Chris Badgett: Thomas is the co-founder of LifterLMS. He’s the head of development. Ali is the director of projects, done for you, and trial, and other amazing things. But in this episode, it’s going to be a little different. We’re actually going to talk about an experience that we had as a team attending a live event. We’ve done episodes here on LMScast about the importance of virtual and live events as part of learning or as part of training programs, or as part of high-ticket programs, or course instructional design, including events. But we’re kind of flipping the script and talking about an event that we attended called CaboPress, which was in Cabo San Lucas in Mexico. It was an event put on by Chris Lema. You can find more out about Chris at ChrisLema.com. He’s a speaker in the WordPress community. He writes a lot about agencies, WordPress products, selling, community building. He’s an all-around great guy and resource for entrepreneurs out there, especially in the WordPress space.
We attended Chris’ event. This is actually Thomas and I’s third time attending, and it’s that good that we have gone back three times. Ali came down with us this year, which was excellent, but this episode is about highlighting what we got out of CaboPress, so if you as a course designer or learning experience designer are thinking about adding an event into the mix, listen to this episode as we share about our experience at CaboPress and what it was like for us, an event designed by Chris Lema.
Awesome. Just to frame in the conversation a little bit, this event was at a very nice resort. It was all-inclusive, all the food and drinks were included. All you pretty much had to do was get to Cabo on some planes. Everything else was taken care of. There were other hosts at the event who kind of led conversations, and there was ample free time for connections and relationships to form. I think there were approximately somewhere between 50 and 100 people there, so it was more of an intimate event, not one of the more giant events. Sort of a hybrid between a small conference and a mastermind.
That’s what it was, and just to kick off the conversation, we do have a blog post writeup about this, which you can find at Blog.LifterLMS.com/CaboPress-Growth. But one of the things that I really get out of CaboPress is the fact that it’s more about the conversations than a traditional or typical conference where you go and you know there’s speakers or multiple speakers, and you sit in chairs, and you get the premium content. This event was totally different. It’s about conversations around meal tables, and with experts in various fields and other people with more or less experience. I just get so much out of those conversations, which the free time also enables, that creates a lot of learning opportunities and relationships.
I’m going to turn it over to you guys. What do you guys think about that conversational format of CaboPress?
Thomas Levy: I’m extremely distracted by your giant microphone.
Ali Mathis: I am not distracted. I thought it was great. I really enjoyed the dinner conversations, and how the groups changed every night. I thought it led to a lot of opportunity to have a lot of interesting different conversations that I probably wouldn’t have had if I had just sat with you guys at dinner every night. No offense. But yeah, it was a great opportunity to meet a lot of different people, and leaders, and influencers in our field, and just chat with them about business, and just day-to-day life.
Chris Badgett: What did you think, Thomas? Any good conversations, or how did that unfold for you?
Thomas Levy: Oh, man. We’ve been a couple of years now, and I can trace back now … I actually did some writing on this the other day, but if I look back now over the past three years of our company, we’ve been transitioning from an agency, which I’m sure a lot of listeners have been kind of following our journey as a company, but transitioning from an agency to a primarily product-focused company. Some of the kind of stair steps that we’ve gone through as a company can be pinpointed, for me, to conversations and things that we’ve learned by attending this event. Hindsight is always 20-20, and you can kind of connect the dots a lot better when you’re looking back on something.
Maybe there’s some amount of confirmation bias where I’m trying to connect dots to CaboPress, but it all kind of stems around, for me, just some of these conversations, and I’ve been to a lot of conferences. I’ve been to really big conferences and really tiny conferences. I go to a lot of WordCamps, and this event for me is … It holds a very special place in my heart, because you have the opportunity here to sit at a table with some really, really smart people and very casually discuss some of your biggest problems as an entrepreneur, as a business owner, as a person in this kind of weird WordPress technology space. I think kind of the candid, the opportunity where it’s very I guess vulnerable, like a mastermind, has led for me to kind of just discover things about myself through these intimate conversations that I’m not sure I would have discovered otherwise.
I don’t know, man. For me, it’s really, really enjoyable. I haven’t really figured out … We’re a couple weeks out from now our third CaboPress, and I haven’t really figured out exactly what happened there. It’s one of the reasons I think we wanted to sit down and talk about this. But if I look back on some of the previous years, there are some really, really big things that we were there, and we’re like, “Okay, now that we’re out through this and out of this, here’s what we’re going to do over the next six months or a year.” I think we’ve been able to realize a lot of those things. I’m really excited for this next kind of six or eight months as we kind of get to implement the things that we’ve discovered and learned and thought about at CaboPress this year.
Yeah. I don’t know. It’s just a great event. I’m really, really glad to have participated in as many years as we have.
Chris Badgett: Another point to those many years and tracing decisions back, I’ve realized that based on some of the conversations there, things learned, things that we brainstormed and came up with while decompressing, there’s this thing called the law of compounding, where the longer we survive as a business, and grow, and evolve, just the very act of survival and staying with it, staying in the game, continuously innovating, challenging assumptions, that momentum starts to compound on itself, and things that helped us get a little step forward now are turning into much bigger results projected many years out, or relationships, the people we met that now we’ve seen in multiple places, developed friendships with, business relationships with. Those things start compounding on each other. It’s not necessarily just slow and steady linear growth. Some things grow exponentially out of CaboPress. That’s just one thing I’ve noticed.
Thomas Levy: Yeah. I agree. I think there’s a leveling up of sorts. I think that’s probably with anything, but we can kind of look at the compounding effects of CaboPress. In retrospect, where I am kind of personally, where we are as a business and a company, is a very different place this year than it was two or three years ago. That’s kind of interesting about CaboPress too, is there’s an intermingling of product-oriented and service-oriented companies, and I look, when we first went, we were primarily service-based and just doing custom websites and large custom projects and things like that. I think one of the things was, over the years, we’ve always kind of wanted to move towards focusing on LifterLMS full-time, but we met a lot of people that were either in transition or already through that transition, and then over the years kind of level up and build on what we’ve learned in the transition, and now being through the transition, get to kind of share, or mostly through the transition, kind of share our experiences and things like that, but yeah. Tangentially related to what you just said, I think.
Ali Mathis: I think it was after you guys came back from CaboPress last year really that we really started making the big shift towards becoming a product-based company.
Thomas Levy: Yeah. Yeah.
Ali Mathis: You guys came back with a lot of really strong ideas and plans for that, I remember.
Chris Badgett: Yeah. Those strong ideas and plans, I’m going to go to one of my other points, which is … Well, I call it the “new context effect.” It’s like, “Okay, we’re going to just totally pull out of our ordinary life, our ordinary locations, our ordinary surroundings, family, relationships, whatever. We’re going to go to this thing for five days. We’re going to get on a plane. We’re going to go to another country. We’re going to hang out with people.” It’s like a completely new context, which is almost like giving yourself permission to have the space.
When I think about CaboPress, I think about it’s really important to get the most out of the event, to make the space, to make sure the business is stable, things that need to be handled while it’s happening are going to get handled, and I can really be present, but also just take advantage of that new context. Like you said, from your perspective, Ali, when we came back, it was like, “All right. That was then. This is now. Some decisive changes have been made.” That new context, or just break from the day-to-day, is often more helpful for innovation.
Thomas Levy: On that point, I’ve been to so many conferences where I just pop my laptop open and continue in the day-to-day while somebody’s up on stage, delivering really, really valuable information, but I’m not gathering any of that, or processing any of that, because I’m reading emails and things like that. I think one of the things that’s really special about Cabo is that for anyone who doesn’t know, most of the actual content, the sessions, take place in pools, and you can’t really bring a laptop into a pool. I have actually heard some criticism about that, where people are like, “Oh, well how am I supposed to take notes if it’s in a pool?” And things like that. Of course, some people bring their phones into the water and stuff like that with their little waterproof cases, but for me, an individual who is very, very prone to distraction, that’s one of the really, really special things about it, is that I actually need to go out of my way to distract myself at CaboPress, and maybe coupled with some laziness, it’s like, “Oh, it will just be easier just to sit in the pool without a phone than to worry about destroying my phone the whole time.” Although they do have waterproof phones and stuff like that and whatnot.
Anyway, it’s kind of that forced bringing you out of the context of the day-to-day. It’s really, really helpful for me as somebody who’s kind of prone to that distraction. I really, really love that about the event, and I also think it also, since most people actually are really, really present in these small group discussions, and that actually I think makes for more value, because it’s not just one person saying, “Hey, this is what you need to do to do X, Y, and Z.” It’s a group of 15 to 20 really intelligent people having a discussion around that, and like Chris said at the beginning, somebody’s leading that discussion, or that topic, but everybody’s really participating. I find there’s just a tremendous level of engagement on all these topics, and that’s something you don’t get to experience at the average conference where it’s one guy on stage. Maybe there’s a Q&A session or something like that, or a breakout session, but this is just non-stop the whole time is like that.
Ali Mathis: Yeah. It’s not like a traditional lecture where you’re being talked at, but you’re really part of the whole experience and process, so yeah. I would never bring my phone in the water anyway, even with a waterproof case. Just throwing that out there.
Chris Badgett: Yeah. That’s too risky.
Ali Mathis: Yeah.
Chris Badgett: [crosstalk 00:13:55].
Ali Mathis: Just throwing that out there.
Chris Badgett: I think that’s an important point. It is important to … What we’ve done in the past is we’ll make sure we take some time individually or together to decompress while we’re still there, and capture some ideas and some notes, just so that … It’s important to capture that while you’re in that separation, in this different world that you can capture the insights for action later. That’s an important thing, to just kind of plan on.
Ali Mathis: Yeah. I do remember, I think it was Aaron Flynn had that little actual waterproof pad of paper that you could write on in the pool too.
Thomas Levy: Oh, I didn’t see that. That’s pretty cool.
Ali Mathis: Yeah. It was cool.
Chris Badgett: That is possible?
Ali Mathis: Yup.
Chris Badgett: Another one for me is, I call it “plus equals minus.” This is less of a “go hear some gurus talk,” and it’s more like, “Let’s have some really awesome conversations facilitated by some great leaders, but also a lot of the insight comes from each other.” I call this “plus equals minus.” Now, it depends what you’re talking about, but plus is something where you’re learning from somebody with more experience on whatever the topic is, equals is kind of somebody on the same level, minus is you might be talking to somebody who has less experience than you, but with the same two people, that might be different based on the topic, but those different levels of experience on whatever the topic is are extremely valuable no matter which level you’re at. That’s one of the things I love about CaboPress, is there is that kind of tribe of different people with different levels of experience, but all kind of caring about the same mission and trying to build businesses, and it is a business conference, and figure out how to make all this stuff work. Just those varying levels of experience is just … I get a ton of value out of that as well.
Cool. The other thing I just wanted to highlight was, there’s a great book about software design, user experience design, called Don’t Make Me Think. That’s one of the things I love about CaboPress, which is you show up, you don’t have to think about anything. In terms of basic needs, it’s all taken care of. Somebody’s going to be there at the airport to get you. The room’s there, it’s going to be clean every day. There’s food. Wonderful, amazing food. Everything’s kind of organized, so all the time that you do have is maximized. That’s really special, because if you get on a plane, you go to a normal conference, you gotta figure out your Airbnb, your hotel, “Where are we gonna eat tonight?” There’s a lot of other decisions that go into it, even if you are kind of removed. That’s one of the things that I just find so efficient and awesome about CaboPress, is it really makes the space, just in how Chris Lema has designed the event itself, that you don’t really have to think about the trivial things.
Ali Mathis: Yeah, I totally agree.
Thomas Levy: Yeah. Yeah, that’s a nice part.
Ali Mathis: Yeah.
Thomas Levy: The other part maybe tangentially related to that is that it is kind of a very closed environment, in that everything takes place in a relatively small area at a resort. You could walk to any part of that resort, although there are some hills and the stairways get a little confusing. You can very easily get lost at that resort, but I don’t think that’s Chris Lema’s fault. I think that’s just part of the experience.
For me, because I’m sometimes more of an introvert, it makes it a lot easier to participate in more of kind of the extracurricular activities that go on at conferences, whereas instead of trying to figure out, “Oh, who’s going to what bar? And where are we going to get dinner? And who are we going to eat with tonight?” You can just kind of wander through the hotel lobby and figure out what is going on, and you will be included, kind of regardless of what your attitude is, unless of course you’re like, “I’m just going to go post up in my hotel room and hide.” Which you [crosstalk 00:18:15].
Ali Mathis: I don’t know why you would do that, though. It reminded me a little bit of college freshman orientation week, where I know you guys have been there. This was your third year, but for me, I was meeting a lot of new people for the first time in a new environment, like you said, that it was a little bit of a closed-in environment. But your group of people was, you were surrounded by them, and you could talk to different people, and it was a really neat experience.
Thomas Levy: Yeah. I like the way he kind of facilitates the … He’d put you in different groups all the time, so you may have one … We had one static lunch group, and you could do whatever you want for breakfast, but for dinner every night you were broken into different groups based on different criteria that Chris I’m sure planned out in advance, but they kind of seemed arbitrary at the time, or random at the time. You were constantly being kind of like forced into situations with new people, which is part of the point of a thing like this, is, “Let’s go meet new people.” For me, that makes it a little bit easier, to get to know different people rather than just kind of cliquing up and staying with my same group all the time in my comfort zone.
Ali Mathis: Yeah. It definitely was outside of my comfort zone, but in a good way.
Thomas Levy: Yeah. Yeah.
Ali Mathis: Yeah.
Chris Badgett: I think there’s a name for that. It’s called “facilitated networking.”
Thomas Levy: Yeah. There you go.
Chris Badgett: But one of the other great benefits that I wanted to throw out there is just that it’s about making remote work. We’re a remote team at LifterLMS. Again, you’re talking to Chris, Thomas, and Ali. We don’t work in the same places. We don’t live in the same states. Thomas and I have gotten together many times over the years, but not very often. We had never actually met Ali in the face-to-face before, so what better way to do that? I just think that if you are listening to this and you work online, and you have a team that’s bigger than you or someone else in your household working together, it is important to get together in person sometimes. It’s just part of relationships, and if you can pull it off, it’s just an important thing. CaboPress is a great way for us to do that. That’s just another benefit that comes with it. When you work behind a computer remotely, getting together is just an important piece, and why not do it in style like CaboPress?
Ali Mathis: Yeah. 100%. Why not do it in Cabo?
Chris Badgett: Yeah. Yeah.
Ali Mathis: Better than doing it in Pittsburgh.
Thomas Levy: I’ll take your word for that. Yeah.
Chris Badgett: Awesome. Well, I just wanted to thank … Chris, if you’re listening to this, thank you for organizing the event. It’s always been great. It’s a highlight of the years for us, and we’ve just gotten so much out of it. We appreciate it, and also anybody else who attended CaboPress or was one of the hosts, it’s always great. I appreciate everything that you do. Some of those people have been on this podcast, which is great, and yeah. I’ve just gotten so much out of the event. If you’re watching this or listening to this and you’re thinking about going, I highly recommend it, and yeah. It’s just nothing but thumbs up, five stars coming from me.
Do you guys have any parting thoughts?
Ali Mathis: No. I agree with you 100%. I appreciate the conference and the opportunity to go to the conference, and I think it was good for our team and for our company, so absolutely second what you just said.
Thomas Levy: I would add a third. I’d also note too, though, this isn’t the only event in the WordPress space that happens every year. It’s one of the more expensive events, I would say. I don’t mean that as a bad thing, because it’s worth every penny, but if you’re out there and you’re listening to this, and you’re like, “Oh, that sounds really great but I just can’t afford that.” I would recommend looking up some WordCamps, because there’s a WordCamp, two or three every weekend, all around the country, and you can get a lot out of them. I like WordCamps. They’re great. They’re not as good as CaboPress, but they’re a great event to get to know members of the community and a lot of the people you meet at WordCamps are people you’re going to meet as hosts at events like CaboPress. Some of the same people are going to be there. Location-based, something along those lines. You might not see everybody at every WordCamp.
Anyway, WordCamps are extraordinarily cheap, so I highly recommend them, and I’d go out and check a couple of WordCamps out if you’re looking to go to an event and you can’t afford CaboPress. Or you’re not sure you want to go to an event like CaboPress, a WordCamp is a nice place to start, potentially.
Chris Badgett: Awesome. Well, Thomas and Ali, thank you for coming on LMScast. As you know, here at LifterLMS, we’re big into social learning. We talk a lot about mapping learning from the real world or offline world into the online space. As you can see from this conversation, when we go as a team and hang out with other people doing similar things, a lot of learning happens for us. It’s this kind of experience that inspires the vision of, for example, Social Learning, the LifterLMS addon.
I just want to emphasize how important learning in groups is, and what that’s all about, and again, thank you Chris for putting on CaboPress, and thank you all for listening.

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