Leo & Randy On Trial & Error (Season 2020, Episode 9)

In this episode of the What Anyone Can Do podcast, host Leo Bottari and co‑host Randy Cantrell explore how purpose‑driven peer mastermind groups—particularly the WIN Mastermind led by Alexander Keenan—create psychological safety that enables rapid trial‑and‑error learning. They use the classic Marshmallow Challenge as a metaphor to illustrate how children’s willingness to experiment without hierarchy outperforms adult teams that over‑plan. The conversation delves into the mechanics of the virtual Circles platform, the structure of a WIN Mastermind session (quick introductions, a 10‑minute “spotlight” pitch, and focused asks), and the value of sharing experiences rather than prescribing advice. Both hosts reflect on personal traits (introversion, troubleshooting background) and how fear often blocks people from joining such groups. They also announce Leo’s upcoming book, credit collaborators Jeffrey Hayslett and Thomas Anglero, and share upcoming speaking engagements. The overarching message is a call to action: do the things anyone can do—experiment, fail, iterate, and lean on peer support.
Chapters
Welcome to the What Anyone Can Do podcast with Leo Battari and me, Randy Cantrell. This show picks up where our previous show, You're the Peer, left off, highlighting the simple truth that who you surround yourself with matters, and that if we enlist the support of others, give back to those who give to us, and pay it forward for the next generation, we can do anything. Author and keynote speaker Leo Battari and I talk with a diverse group of thought leaders who will share stories and insights that will help you succeed in business and in life.
How?
By doing the things anyone can do, but most of us never will.
Season 2020, What Anyone Can Do, the podcast representing Seton Hall. Star of the show, Leo Bottari. The website is leobottari.com. L-E-O-B-O-T-T-A-R-Y. My name is Randy Cantrell, coming to you from Dallas-Fort Worth, Texas. It's getting a little warmer here. It's not sunny, so— well, you're— I don't— it doesn't look all that sunny there today.
It isn't sunny, but it's nice out, you know. So I thought, let's just sit outside here a little bit and change the scenery a little bit. Yeah, Seton Hall, of course I'm an alum, so that's why I have the Seton Hall hat today. We lost to Villanova the other night, missed a 3-pointer right at the end that would have won the ball game. But, you know, we got a Big East tournament coming up and we got the, you know, the NCAA. So that'll be— I'd rather hit that shot, you know, later on. And of course I do go back and forth between Seton Hall, who I was an alum and I taught there for 7 years, but now I teach for Rutgers. So I do have to go back and forth with the Rutgers gear every once in a while as well. You know, love both places for their own reasons. But, yeah, it was kind of a tough call the other night. They were behind most of the game, though. And they totally came back in a way that, you know, it's kind of just watching great teams kind of figure it out. And they're never out of it. And they're always just digging and always in it for each other and doing what they need to do. You know, we thought today not to, you know, talk basketball so much, but last time, or it was either whether it was last show or one very recently where we talked about psychological safety and teams. And I thought it may be interesting to kind of extend that conversation a little bit around what that can afford us to do. And one of the things that, um, you know, I've actually kind of marveled at recently is what Alexander Keenan has been able to do with the WIN Mastermind group. He basically just decided he wanted to get in this. He wanted to set up virtual mastermind groups for purpose-driven entrepreneurs who could learn from one another, help one another, connect with each other across different countries. In Europe, he's gotten certainly some folks in the US, me included, you know, involved in it. It gives me an opportunity to participate in a peer group, which obviously I desperately want to do, but I cannot really be a reliable participant in like a Vistage group or an EO group or something like that because of my travel and things. But to be able to get online, you know, and be able to participate in a virtual session that I think is very efficiently facilitated, you know, has been great. But what's been interesting to watch with Alexandra and what I love It's a little bit— it reminds me of that typical— not typical, but that quote that's associated with between baby boomers and millennials. You know, like we were taught kind of good things come to those who wait, and millennials are good things come to those who act. And I think watching what Alexander has done with this company has been, I think, very much about that. He's acted, and just like You know, you and I, before we got started, we talked about the marshmallow challenge, which has been around for a while. And just to recap what that is, it's basically when you take teams of 4, let's say, and you give them 20, you know, sticks of, you know, uncooked spaghetti, if you will. I think it's like string tape, and they get a marshmallow. And the idea is who gets to— who which team can build the tallest structure in like whatever time you give them, like 18 minutes or 20 minutes or whatever you give them. And, um, so they'll go build the structure. The only rule is basically you have to have the marshmallow on top. So when they have tested over years now, groups of CEOs, business school students, uh, kindergartners, right? So as you might imagine, you know, you think about this, Who is the group that on average builds the tallest structure? And it's the kindergartners. And it's hilarious to see why that is. And of course, especially in business school students, I think are among the worst. This is a pretty funny part because they're all about, you know, you've got, let's call it 18 minutes. And so, you know, so everyone's, everyone's got their calculator out, everyone's got, you know, on their computer and they're trying to devise this plan for what the structure is going to look like, and then they build it only to put the marshmallow on top, the thing collapses, and now all of a sudden they got like 2 minutes to recover and figure out how they're going to build something else. And of course time runs out and it's pretty much all over. And for those who end up building something, I think on average it's about half the height of what the kindergartener is able to build. CEOs do a little better. The only group that beats the kindergartners, thank God, is architects and engineers. I'm just grateful for that, that for people who are actually in the biz, they know a little something about structure and how to create something that can stand on its own. But the reason the kids do so well is, first of all, no one's concerned. They don't get into a big fight about hierarchy and who's in charge and all this other kind of stuff. They don't feel like they're going to devise a strategic plan, you know, for the spaghetti and the marshmallow. They just start doing stuff. And as they're putting it together, it falls. They put it together, it falls. They put it together and like, okay, we built the structure that high. How do we add to it? How do we change it? Or how do we do something so that as the clock winds down, they know they've got a structure that works. They put the marshmallow on it. They're good. And there we go. It's kind of fascinating when you think about the reason why that doesn't happen in most companies, or why it doesn't happen, you know, among groups of adults. And it's because there isn't any real psychological safety there. You know, there isn't any feeling that I can just suggest something, or I can make a mistake, you know, without making a mistake. We got to come up with the plan that everyone agrees on and everything. They're not worried about consensus building and all that other nonsense. They're just doing it. And the reason I raised that particular thing, excuse me, point, is that I think when you look at Alexander and what he's done with Win Mastermind Group, he's just doing it. He's just figuring it out as it goes. Something works, it works, they go with it. Something doesn't work, they change it. And they're constantly working on that and refining and adding people and getting input from people who are real users as opposed to sitting around you know, in a committee of people, if you will, who convinced themselves about all the viability of what they do and why and the language and the narrative around it and the strategy and everything. When, you know, Alexander really just did it, just did it, you know, and there's something to be said for that. And it's pretty cool to watch.
Oh, I'm envious. I mean, I'm super envious. You and I were talking before we hit record. You know, I began my career pretty much as a troubleshooter. I was kind of a fixer. And when you start out with that role early, and I was naturally probably wired for it, I don't know that the guy that gave me the opportunity knew that, but turns out I was. Turns out it was a really natural skill set, you know, to fix problems and move on and iterate and innovate. You know, it was something existing. But I learned really early, man, from 0 to 60, I'm horrible. I'm absolutely horrible. You know, I'm not a sprinter at all. From 60 up, and I'm dynamite, you know, I'm great.
But I think the problem—
thinking about—
yeah, go ahead.
Well, I was thinking about this. I was thinking about the psychological safety of it. And I think that plays into it even at an individual level in that, you know, of caring too much how you look or how you you appear. You know, a guy like Alexander, I mean, he didn't care.
I'm sure there's something going on in his head, but he's fearless, no doubt about it.
Yeah, I mean, he's just— if it doesn't work, it doesn't work, you know, right? Where I know that I don't have that. I don't have that. I'm working toward it, but I don't have that. And so for me, kind of leveraging the power of other people And this whole we concept and the cycle, I mean, there, there's big safety in that and being around people like that so that you can see it is safe. You know, it's, it's, it's kind of like dad going into the water before the kid does. Right. You know, it's like, okay, I see that, that, that could be safe. I mean, even for a guy like me at this age, that's a pretty powerful thing.
Well, you know, so one thing that really struck me about what you talked about with regard to the problem problem-solver pieces. I remember reading something, I think it was in Peter Senge's The Fifth Discipline book a while back, where we talked about my being part of that learning team, you know, at Seton Hall. And they basically said when you have to create something, you literally have nothing and have to turn it into something. When you're a problem solver, you have something and you're trying to make it go away, right? So it's almost, you know, the argument was that it's a bit of a different mindset than bit of different skill set even to think about, you know, what that looks like. But, you know, it was great to have you participate the other day in a WIN Mastermind group just to kind of check it out and see what the format looked like. And, you know, for our listeners who are familiar with circles, which we've had a podcast on circles, and we fun to do one of those sometime again where we just literally have a whole group where we do, you know, a meeting, you know, do a little panel discussion sometime with it. But using the Circles platform, you know, versus what we're using here with Zoom with just the two of us, when you get 7 or 8 people on that and it's well facilitated and you've got the right agenda and everything, I don't know, what was your— I don't know, so I guess first of all, what was your expectation going into the session in terms of what it was going to look like and how it was going to run or what value we're going to get from it? And then what was the reality of it?
Well, because we've got such familiarity, you know, with, with Dan and Circles, and it's, uh, it's Circles with the dot between the ES. It's an ES domain. We'll put links in the show notes.
So I know you know the platform. I meant the whole Win Mastermind Experience part of it. Yeah.
You know, and the platform played a role in the facilitation because the way Circles works on the right-hand side, you've got the agenda and, you know, Alex is starting this clock, you know, and he's— so it was a really tight hour. You know, I was, I went in wondering, okay, an hour is going to go by in a hurry. And it did. I was skeptical as to what could be done probably in an hour, to be candid. I think you were too the first go-round because you and I remember us talking offline about it. But once I saw it, yeah, I got it.
It's efficient. It's a different value proposition than, you know, it's not a Vistage group meeting, it's not a, you know, EO, it's not a YPO forum. It's very different in that regard. However, The value of it is not small, and the value of it can— in many respects, it can be a gateway for people that want to also protect. You know, these things don't have to be this or that. This can be this and that. And so I think once you get introduced to the idea of these groups and how they work, and you can do it in a way that's efficient, you know, as I mentioned for me, you know, I'm just grateful that I've got this for right now when my travel schedule doesn't allow for you know, the other. But that's been our— someday I hope we do them both, you know.
Yeah, but that's been our intrigue. Our intrigue has been what is this going to look like, not only now but in the future? I mean, everything around us is changing, you know.
We—
I remember people thinking autonomous cars, wait a minute, you know. Well, now I don't know very many people that are cynical or skeptical about autonomous cars anymore, or electric for that matter. And a decade ago, everybody was skeptical about it. 5 years ago, a lot of people were skeptical about it. And the same kind of innovation I think is happening in this space, especially, you know, the peer advisory space, these groups. What is that going to look like? I think he's proving How, you know, however it looked in the past is not necessarily how it's, it's going to look. And the great thing for you and I as kind of evangelists for the power of people surrounding themselves with other people that can help them is I think there's going to end up being something for, for anybody and everybody. I realize, okay, Vistage isn't for everybody. YPO is not for every EO is not for everybody. It's for a lot of people, but yeah, it's a, it's a tight hour. It's a lot, a lot accomplished in that hour leveraging. And I knew this from you. I knew leveraging the networking part of it. Um, but not overly so. Not, I mean, it's not, it's not a, I'll rub your back, you rub mine kind of a thing, but it still is kind of a little bit of an emphasis that felt good to me personally of, do you have a resource? Do you know a re— do you, do you know somebody that can help do that? And that's a real-world practical benefit, you know, that I saw. And I realized not everybody's doing that. Uh, but I thought that was, he clearly is doing that. It, It works. It clearly works.
Yeah, he's— he's— I've already had some introductions made and some things where we've been helping one another do some things that I think has been really beneficial so far. I mean, just after a couple of meetings, and, um, you know, I even had, as you know, uh, yesterday, it usually what happens in the way they run the meetings basically is, um, you know, you may or may not have the exact same people in every single group, right? Particularly at this stage of the game. But you get people who've been vetted, they've been onboarded, they, you know, participate, you know, in the— they know what it means to participate in the process and how to go about doing it and have shared values around it. But so everyone does a quick 1-minute introduction and then they have what he refers to as kind of the spotlight. And you get 10 minutes to frame, okay, here's what I'm doing, here's what I'm working on, and here's my ask of the group. And that ask could be anything. You know, and I know my ask was talking about, hey, I've got, you know, chapters I'm writing right now, and I would love to get, you know, input from, you know, people who, right, I mean, they're in different industries, they're different ages, they're, I mean, they're different countries. I mean, you know, and just to get a feel for some of these concepts and making sure that they are explained and illustrated in a way that resonates. You know, with people. I mean, it's easy to be in your own head with this kind of stuff and you get it all down and I can look at it and fall in love with it, but it doesn't matter if when people look at it they go, yeah, I don't get how you got from here to here, like you need to fill that in or you need to do— and that is hugely helpful. So, you know, again, whenever we can get that kind of, you know, input and then, you know, I mean, really everyone in the group, you know, said, yeah, I'll take a chapter and read it. I'll do something. And when you have, and when you come prepared with a specific ask, and I think that's really key. You don't show up to a meeting like that and get into the spotlight without being pretty prepared with, here's what I want to say, here's my ask, here are the questions that I'm likely to get that I want to be prepared to answer, to get clarification on maybe what some of the needs I have are. But I think when you do that, people can, first of all, their willingness, you know, I mean, they're on that call because they want to gain something for themselves, but they really want to serve others. They really want to be helpful. And it's a, you know, it's a great thing. And I say that, of course, of all, you know, obviously I go to a ton of Vistage group meetings and Tech Canada meetings, you know, mostly. But you go into every one of those sessions and everyone is so unbelievably generous with one another. And when you think about all the nonsense going around in the world today, in our politics and everything else, it's kind of nice when you can actually walk into a room or be in a virtual meeting and actually see people really being incredibly decent to one another. It's nice.
Yeah, there is that. Well, and the other thing that struck me was not just in the meeting, but after the fact stuff. And I think people that haven't experienced any of these kinds of— I don't care who, I don't care who's doing or who's facilitating it. I mean, whether it's virtuous-cynthia-cynthia or any of the others or WIN Mastermind, I don't think by and large the general public really understands the power even after the meeting, that the power is not only in the meeting and your time together, but that psychological safety, to kind of come back full circle to our point, transcends just your time together, whether that's virtual or just in a face-to-face room. Yeah.
And I think getting back to where we, you know, we started with this conversation too, I think what these groups do is give you the courage to act and try things and and go through that iterative process in a way where you might be otherwise hesitant. You know, and I think it's a good reminder for us that it's not about figuring out and getting it perfect and getting the right answer. It's about really trial and error. I mean, it just really is, you know. And, you know, when you think about, you know, the old line, you know, no plan survives contact with the enemy. And they refer to that in terms of whether it's— I don't care if it's a business plan or a student plan or whatever it is. Once you put it in front of folks, in all likelihood, you're going to have to make adjustments and changes. You just don't want to be in a situation where, like in the marshmallow challenge, you've got 1 minute left and you put the marshmallow on top, the thing crashes, and you've got no chance of being able to put it back together. And whether that's time, money, whatever that may happen to be, that is that limiting factor for you, you find that if we can just get started and keep trying things and doing little things over time. And I think these group experiences remind us that, first of all, how important it is and how much more likely it is to work. And what we can learn from it if we're willing to be vulnerable and just wrong and just make a whole ton of mistakes before you know, we get it right, you know.
Well, when we've got, you know, when we've got some people that were originally from Spain, from India, you're in Southern California, I'm here in Dallas-Fort Worth, Alexander of course is in Amsterdam. And so you've got these cultures other than you. I'd never met any of these people, they'd never met me.
Um, I'd met like half of them, I think.
Yeah, you know, we're all brand new to each other. And yet right out of the gate, you hit the ground running. You spend this hour together and there's enough psychological safety that you all know why you're there. You know, you're all there to derive some benefit for yourself, but you're also there to provide benefit to other people. So there's the tie that binds. So the psychological safety can happen really quickly. And I'm always fascinated by how quickly We can get to a place of safety. And I, I think a lot of people really underestimate that. I think a lot of people, a lot of people, unless they see it or experience it, I don't know that they would really believe it, especially, and I'm an introvert, I'm an introvert. So I'm way more comfortable listening to somebody else's problems and asking questions and trying to understand. And if you, And you did notice, you do pay attention. And I'm not saying other people don't, but I just ask questions. I didn't offer a whole bunch. I was just trying to, I was trying to better understand. And my hope is that asking the questions helps people, but the quickness with which we can get to the psychological safety is pretty fascinating to me. And I wish more people really understood that. And then it transcends to not the advice necessarily, but whatever the person decides to do. Whatever they themselves choose to do. If I chose to throw something out there to a group like that, then I would know, okay, I got 5 people. And it's amazing to me, and I'm just speaking for myself, that in my head, those 5 people, knowing that there are 5 people who at least have my back in the sense that, okay, I can come to the next meeting, I will have colossally failed, perhaps, but it's okay. Yeah, it's far more safe for me than to think of the world out there that could be ridiculing me, making fun of me, and I could be embarrassing myself. But I know I'm not going to embarrass myself in front of these 5, or however many it is.
Well, there's a recognition too that, you know, when you try and fail, at least you're in the game. Yeah. And there's a— and people respect that, you know. And we— it's not like we all haven't made mistakes or we all haven't You know, I think the other real big factor that appeals to the psychological safety as well though is a big, you know, Alexander stressed it at the top of the meeting and throughout the meeting where when we are sharing with one another, we are sharing our experiences, we are not offering advice. Now clearly there are times where people might flat out ask, tell me what to do, and I think that's fair. You know, and if you— and people are looking for those answers from time to time. See, the sun is coming out here in California, as it should. But in other cases, it takes the pressure off the listener and the person who is, quote, you know, sharing some of their ideas, because sharing your experiences and offering advice is completely different. And just sharing, hey, here was my experience with this, and here's what I did, and here's how it came out. Is much easier to say, here's what I think you should be doing. And now all of a sudden, I feel like I own part of that. And then they try it and it's like, you know, I mean, I think when people share experiences and people take in what resonates with them and what they believe fits who they are and fits their circumstances in ways that it's going to be very difficult to really understand, you know, fully. I don't, by the way, and that's true whether it's a full-day meeting or you got an hour. But I think when people can kind of take that in, you know, do something that connects with them and they, they can own that solution so that they take that forward as opposed to a consultant or someone telling you what to do or shooting you in some way, that's helpful. And in large part, people are going to implement something more successfully if they had a hand in creating it, you know, and coming up with it and really having ownership of it. So I think that adds immensely to the psychological safety of that environment and why you can get on the phone with, if you will, the phone or on the Circles platform, I should say, with 6 to 8 people from different countries, many of whom you've never met, but you know you're all there for a given reason and that everyone shares a the common purpose, values, and behaviors, it's powerful. And it's just, it's to your point, it's like amazing how immediately comfortable you feel in that setting.
Well, and I would venture to guess that the majority of people listening to us or watching the video of this podcast have not experienced that. I mean, have not experienced that kind of, I'll be brave and bold and say, I dare say the majority of people prefer professionally, when it comes to business, when it comes to running an organization, operating, have no clue, have no clue about what that even feels like. Because if you go to your buddies, buddies are notorious for telling us what we ought to do, right? I mean, every business guy I know who's got business buddies, oh, the buddies can, man, they can solve all of our problems, you know. And happily tell us what we ought to do. But to get that kind of, I don't know, I don't know what the right word for it is. It's filtered on one hand, and then it's filtered to not should you, but it's unfiltered in the sense of it's just so readily there and available. I'm still fascinated. I was fascinated some 4 years ago or so when we first connected. And I remember asking you, one of the first things I asked you is, why is this so rare? Why do so few people in the business world take advantage of this? Now that I understand, and now that I've seen the power of it, why is this so stinking rare? And I remember asking you that question nearly every time that we talked, you know, cause I, I just, I don't know. I never could get my head wrapped around some satisfactory answer. I think now these years later, I've got some idea. And I think, I think we're, I think this is it. I mean, I think it's, it's just people fear. I think it's fear. I just think it's pure and simple fear. And I don't think people really understand the psychological safety that can happen in these kinds of, these kinds of groups.
Yeah. Yeah. No, I completely agree. And you know, we were, We are putting our best face forward everywhere we go. Somebody walks up the street, how's it going? Great. You ever hear someone answer? Yeah, not so great today. And then all of a sudden, it's like, okay, right.
And if you do hear that, you don't want to be that person.
You don't want to hear it anyway. Yeah, no.
And you don't want to be that. You don't want to be that person doing that kind of complaining. So I get it. And yet in our head, we're not our highlight reel in our head. But that's what we're comparing. Everything too, because everything's on Instagram.
Everybody's awesome online. Everyone's got LinkedIn, they got this, they got that. Life couldn't be sunnier for everyone else in the whole world but us, you know. So that's right. But, um, but anyway, um, yeah, I think, um, yeah, I think our, uh, title for our show today will be On Trial and Error. I think it's kind of a good, uh, good, good theme. And, uh, I think something for us to kind of remember is if there's any message coming out of this one show today is just do stuff. Don't be afraid to try, fail, try it again. You know, do the old Thomas Edison thing, right? What, 10,000 times before we got it? You know, so hopefully we'll get it quicker than that, but you know.
Yeah, and you're, you're, and you're in really good company, you know, because all the rest of us are out here, you know, sweating the same stuff and having the same fears, but you want to learn more about Leo and the work, the work that he's doing, excuse me, peerinnovation.co will take you to the exact same website as Leo Bottari. That's leobottari.com. Working on the new book, have more to say about that in future episodes, uh, Lord willing. That comes out sometime spring, late spring, summer.
Yeah, I'd say spring, early summer. Uh, book should be completed, uh, By the end of the month, as we know, we've got Jeffrey Hayslett who's going to write the foreword. Thomas Anglero is working on— Jeffrey Hayslett, for those of you listeners who probably do know, since our podcast also runs on C-Suite, but C-Suite Network is Jeffrey Hayslett, the CEO. Could not be, I think, more generous. I think he's taken his whole career right now and just getting people to work together and connect and collaborate. In a way that I think is extremely powerful. And Thomas Anglero—
And if you want to be studying somebody that's just doing stuff, Jeffrey—
Yeah, totally.
There's a kid, buddy.
That is exactly right. Oh, he's totally— and, you know, it's awesome, right? He's just doing it. And Thomas Anglero, you know, he's basically the Director of Innovation for IBM Nordic. You know, he talks a lot more about people than he does technology, and he's a fascinating guy, and look forward to what he's going to, you know, contribute to the afterword of the book. So, you know, just, you know, really excited about those guys and their involvement. And yeah, so we'll get a lot of this stuff done. I actually am heading to Calgary into Montreal next week. I'm doing a— visiting with a couple of Tech Canada groups and delivering a workshop to them there. And then back the following week, I'm actually speaking for Rex Roundtables here at Petco Park, doing a keynote for them, and then off to Denver. So With that, um, you know, we're just, uh, it's been, been fun. It's been— I've been home for a while, which has been great because I've gotten a lot of writing done, but it'll be fun to get back out on the road too. So I'm excited about that. And, you know, good. Um, so there we go.
Do stuff. So go out and do stuff. Don't be afraid.
All right. All right, everyone, have a great week.
To learn more about our show and what we do, to submit questions to us, and to subscribe to What Anyone Can Do podcast, please visit our website, whatanyonecandodo.com. What Anyone Can Do podcast is hosted by Leo Bottari and me, Randy Cantrell. Music provided by Kevin MacLeod is Vibe Ace, licensed under Creative Commons by Attribution 3.0 license. Thanks for watching or listening. We hope you'll share the podcast.










