What Happens When You Take 40 Men to Cuba?

Episode #640

What happens when you take 40 men to Cuba?

The Powerful Man had a powerful event with men in The Brotherhood in Cuba. 

Being with a like-minded group of men leads to learning and self-improvement because they can help you to unlock your potential so you can change your life.

In this episode, we’ll get into some transformational experiences with the Brotherhood in Cuba and what you can do to be with people who will push you to grow.

Hungry for more?

Head over to our BONUS page for special access to some of the deeper tactics and techniques we’ve developed at The Powerful Man. 

Also listen on:



Doug Holt  00:01

Hey guys, welcome to The Powerful Man Show where we help married businessmen save their marriages without having to talk about it, get unstuck and gain clarity in their lives. As I like to say, life is too short for average. I’m your host, Doug Holt with my co-host, Tim, The Powerful Man, Matthews. Now let’s get this started.

Guys left just different men. Different men, cups full, souls uplifted, friendships and bonds that will last a lifetime occurred. The last night some guys were up till 05:00, 06:00 in the morning, talking, laughing, playing the guitar, having a good time. These are grown men with families that have never met before, most of them having a great time. They just didn’t want it to end, and I didn’t either.

Hey, guys, welcome back to another episode of The Powerful Man Show. So glad to have you here. Tim, great to have you back. How does it feel being home?

Tim Matthews  00:56

Fantastic. I was actually getting asked that by somebody on the team today, asked me if I recovered. I feel much better now than I did this morning. I think I’m still recovering a little bit. But regardless, it feels great to be home, great to be back in the gym, back sparring, enjoying bagels, not being able to enjoy those for several months as you know why. So, it’s good.

Doug Holt  01:25

Excellent, excellent.

Tim Matthews  01:26

What about you?

Doug Holt  01:27

Yeah. So, I’m still transitioning back quite frankly. Got a little case that we talked about the subject of this is what happens when you take 40 men to Cuba. But I’m still transitioning. Coming back kids are so excited to see me, man. And last night as an example, I slept in the bed with my son. He’s going to be six next month. He wanted to — kept checking to see if I was there. And as kids do he kicks me to check or he hits me with his arm to check. So, I must have woke up, I haven’t looked at my aura ring results. So, I wear an aura ring at night. I probably woke up 20 times. So, a little tired. I’ve got a lot of mail and things like that to catch up on, stories to catch up on with my wife and friends. So, it’s always that way, though, transitioning back. But what a great trip that was. What would you rate Cuba —

So, for those who don’t know, let me describe this first. So, men that go through our program, we have a flagship program called the activation method, we have two versions. One is more personal, the other one’s based on the relationships, right, the marriage in particular. Now once men go through the activation method, some men are invited to continue on with us in an experience we call the Brotherhood. It is a one year program where guys are getting much deeper dives into areas around self, health, wealth, business, and of course, relationships.

But these guys also get two trips, two trips through the year and these are epic adventures. One of them’s the Alpha Reset, but guys continue on with us year after year. They choose to because they see the value in it. So, those guys get two epic trips. These trips are all around growth, adventure, and actually connecting with other like-minded men. These are the best men in the world, in my opinion. I am biased again, but I love these guys. I absolutely love them, Tim.

And so this time, we decided to go to Cuba. As an American, Cuba is kind of like this weird place to go to because we’re not supposed to go to Cuba, theoretically. Now we can. That’s changed over the years. So, for those freaking out thinking that we snuck into Cuba, we didn’t. We did it all legally and everything else. But we got back with what I thought was an epic, epic trip.

Now that I set the scene, Tim so guys listening to this know what the heck we’re talking about, we got 40 men, over 40 guys that took over a hotel. Guys, we literally took over a hotel. They kicked people out, we took over — Imagine having your own hotel, with all these great men, most of them meeting each other for the first time. They’ve seen each other and video, if you watch this on YouTube, very similar to this. And then you and I and Tim meeting in person, and how great it was to see these guys interact.

Tim Matthews  04:11

Incredible. I think it was a huge achievement just getting everybody there. All the messages going back and forth in the chat, various concerns, understandably. But yeah, getting these guys together, oh, man. It’s — talk about work hard, play hard. These guys work hard and play harder. They’re an amazing, amazing bunch of men and I’m always blown away with how they always get up to do the ARS, go and work out together whether it’s to a Cuban boxing gym, getting trained by a former national champion. I don’t know if he was World Champion or just the champion of Cuba. I don’t recall.

Doug Holt  04:55

I think he was. Yeah, he was a champion of Cuba in 84. And again, to set the scene, guys, when these men come to this, and I’ll get back to you, Tim, but the listeners don’t know what you’re talking about. So, what we do is we set the itinerary. We just got back from Iceland in October, so this time, it’s Cuba. We’re going to Canada next. And so for this, I know Canada is a big country. We’re going to Banff region next.

So, when we got there, these guys had an option. We divided half the group. So, in the morning, and it’s optional, half the guys go to a legit Cuban boxing gym. I’m talking straight out of the movies legit with a Cuban national champion. And I think he had placed in the Olympics, I’m not sure, or some kind of record board. But this guy was amazing. Didn’t speak a lick of English. We had translators there and all that fun stuff. And so he had half the guys in there in the boxing gym. And the other half of the guys went to a Cuban gym, like right, so this is an independent business in Cuba that hosts workouts like CrossFit style workouts and other things. And we can talk about what that was like as well. But continue on with your story, Tim.

Tim Matthews  06:07

Yeah. These guys, it just blows my mind, right. They arrive they’re obviously very excited to see one another. Man, I’m just thinking about the jokesters in the group and the pranks to play on each other and the banter they have and it’s fantastic. It reminds me of sports teams, the way that they’re for one another. Anyway, the fact that they get up and do the ARS together, they go to the boxing gym or the workout and then the way they show up to do the work, because obviously, they’re there for four days. So, they arrive usually, let’s say Thursday at 05:00 PM. Friday will be day one, Saturday day two Sunday day three, checkout Monday, right. So, there’s three full days, three and a half days, if you will.

But it’s over those day one, day two, day three, where we have a section where we take them through something transformational and the theme of Cuba was release the bricks. And it was led — day one led by Arthur, day two led by myself, day three led by you. And to see the way that these guys leaned in and did the work. All of these guys have been through an Alpha Reset. So, 40 or so of them, all of them have been through an Alpha Reset, and it’s kind of like Fight Club, we don’t talk about what happens there. But equally those guys because of our [inaudible 00:07:22] it’s kind of like a secret language, right?

And to see, to even consider the depths that they went to in Alpha Reset to really get to the root of what has create a lot of the issues and the pain in their lives and release that, then see how they were able to bounce off that as a platform, if you will, into Cuba, and continue to dive deep and peel back the layers just like an onion; it’s fantastic to see how they show up, lean in, they step to the line, they do the work, they get the result.

And then on the evening, they are out — well, afternoon, evening, if you will, balancing that with mafia tours and bike tours and all sorts of other fun stuff; going and visiting Ernest Hemingway’s house and all sorts of amazing things with different dinners. And it’s just incredible to see the way that these guys get to balance out work hard play harder, in my opinion. And it was a great moment, for me just being there with all those men. And considering the conversation that we had three or four years ago, Doug about, hey, let’s — maybe longer, four or five years ago.

We didn’t have this then. We didn’t have a Brotherhood of men who were like-minded businessmen who were leaders but they didn’t come from a place of ego. They don’t come from a place of pride or competition or any of those things. Instead, they come from their heart. And what I mean by that is they’re the WOLF, right. They’ve shifted from the head which is more the DEER and the fear and the path of force and the agones and so on, into being in the body and in the heart where there’s strength and courage and the WOLF, Wise, Open, Loving and Fierce and to have to be there with those guys doing epic — having epic adventures, epic adventures. So much so I’d never even considered going to Cuba. And I left there thinking how have I never considered going to Cuba?

I didn’t realize the amount of things that we did were a bucket list thing for me. I never knew it because I never would have experienced any of them. And that’s what it’s all about, these adventures with the Brotherhood doing epic adventures with epic people in epic places, creating memories that will last a lifetime. We had so many men whose wives or even girlfriends were so excited about them coming away to the trip because you always return home full, energized just with an amazing presence. Guys who prior to Cuba hadn’t had sex for four years since Cuba. I think he’s had — one guy’s messaged me saying he’s had sex 11 times in five days, I think, or seven days.

Doug Holt  10:18

Yeah, I know who you’re talking about.

Tim Matthews  10:20

I’m like, wow. And it’s the same with many other guys. Because it’s those little conversations that you’re able to have when you’re on the coach driving to one of the adventures, right? Just be able to sit next to some of the guys and just strike up conversation and be there with them. And in 20 minutes, you can share insights. Be it us, sharing insights with them, or the men sharing insights with each other, whoever it may be. You’re just immersed in the conversation for three or four days, it’s impossible not to walk away a different person with different insights. And actually some guys that are there, they’ll speak to another guy who’s been sending his wife, or got his wife some flowers delivered, or due to be delivered the following day, right?

So, what does that guy do? Immediately goes online, orders the flowers, gets the flowers delivered while he’s away. Just little things like that. But it just creates the environment that he walks back into. It builds the desire and the anticipation from his wife who is at home waiting for him to return. So, it’s a dream come true. It’s amazing to spend time with those men. Iceland was fantastic, Costa Rica, Marrakech in Morocco, all of them. I could go on and on and on. It’s incredible what we get to do, and I’m very grateful for the men that choose to be a part of it with us.

Doug Holt  11:45

Yeah, so to set the scene — I agree with you, 100%, man. You and I and Arthur got there a few days earlier. We did a few tours. I did some around the island. I thought I saw all that Havana had to offer before the guys got there. Frankly I was kind of like, okay, we have a full itinerary. And when I mean full guys listening to this, from 07:00 AM to about midnight, we have things to do every day. Right? And I’m thinking oh, I’ve already seen all of Havana, right? Okay, great. You get up at 07:00 AM, and you go to a gym. My group divided up, and went to the gym on the first day. And it was just awesome. You were working out and you were training one of the guys in the inner circle. I was working out with — and Arthur and I were doing double-unders.

But like some of the equipment was so rustic that they made do with what they had. And you felt like you were doing almost like a prison yard workout. You transition that from all the guys since we took over this whole hotel, having breakfast together. Right? Laughing and joking and — But guys also having serious subjects about their kids. One guy’s kid was self-hurting themselves. And a couple other guys said, hey, look, I’ve had that problem. Here’s how I overcame it, and helped my kid. And other guys were having problems with business. Hey, here’s how I’ve overcome that problem, or whatever else it was. Now, the theme was release the breaks, so we would jump right into a session. The first day you and Arthur just crushed it. And then we go out and we do a tour. And then after that, we do an epic dinner. And when I say epic dinner, we’re talking amazing, amazing dinners with amazing conversations.

Now we have guys from all over the world, different races, different religions. We also have guys that are there, as you said, that are playing hard. When we say playing hard, they’re having some drinks, right? That’s there — They’re not doing anything crazy other than that. We also have guys that don’t drink at all, right, guys that drink in moderation, some guys that may wish they drank a little less than they did at times. But there’s no judgment. There’s no judgment between the men. We’re all laughing, having a good time and taking care of one another. It’s truly like having a fraternity of brothers that’s there, hence the name, the Brotherhood.

And as these guys get to know each other better, one of the parts of it is there’s no judgment. Everybody knows why they’re there. These are all guys that came together to better themselves for themselves, for their families, for the businesses and for their communities. And now you’ve got 40 of these world leaders together in Cuba in Havana, having a great time. And we do the same thing on day two, we just switch. So, I went to the boxing gym and oh my God, Tim, that was so much fun. You know, you guys were on the pads with this guy.

I had another local guy pull me aside and I was doing bag work and he’s like, “Okay, try this.” And it was like broken English and he and I were trying to communicate and he was helping me with my form. And I boxed before so it was just super cool. It felt like you were in one of these old Rocky movies, right? You know, you’re hitting this old bag that’s duct taped and weathered, you know, but so many champions have come out of this gym. And that’s how they trained. And then you go into these sessions again and you’re learning, the growing, the guys are pushing the envelope so they can release the brakes.

One of the things we told the guys is you’re going to come here with one distinct thing, one thing that’s holding you back, and we’re going to release the brakes, release that so you can move forward and the guys did. And the tours were amazing from — I mean, imagine having a Cuban cigar — a Sommelier, if you will, to be on a rooftop of one of the most famous hotels in the world. This is actually where the mob met, Meyer Lansky and everything else or it used to be the Vegas. You’re actually having a cigar tasting. Now, whether you smoke cigars or not, there are guys that were there that just chose not to partake in the cigar smoking, but one of the experience. We’re on the rooftop, we have the whole thing to ourselves.

And the Sommelier and her assistants are talking about tobacco, about how cigars are rolled, what makes Cubans different, and here’s how you can taste the nuances, giving us coffee, chocolate, some Cuban rum, and tasting the differences just very subtle. As we smoke cigars and showing us how they believe cigars should be smoked, lit. It was just an amazing experience. You look around, all these guys that are sitting there together, talking, laughing, bantering, as she’s going over this and learning. And then the guys left, which was sad.

But as it happens, guys left just different men. Different men, cups full, souls uplifted, friendships and bonds that will last a lifetime occurred. The last night some guys were up till 05:00, 06:00 in the morning, talking, laughing, playing the guitar, having a good time. These are grown men with families that have never met before, most of them having a great time. They just didn’t want it to end, and I didn’t either.

Then you and I, Arthur take the guys that are from the inner circle or our one-on-one client, so these are higher level mastermind groups and they have a couple extra days with us. We continued on to the beach, the beach town. We had gotten to — we stayed at a five star resort and it was absolutely phenomenal catching lobsters in the ocean or as Arthur calls them crayfish. Catching lobsters in the ocean and having an amazing private experience on a catamaran and talking. We had dolphins swimming next to us in the boat as we were going out to this private island. And I can just go on and on how these adventures continued and the talks and the conversations got deeper and deeper as the days went on. And the guys shared more and more and opened up more and grew more.

And as you said, as these — if you can imagine guys, as you go home from a trip like this, you’re changed forever, forever. And their wives and their kids notice. They took note of the man that showed through the door. Cup filled to the brim spilling over new cultural experiences, new experiences with men, but also having conversations that matter. Guys we’re bantering about sports, right, we’re guys and they’re jabbing each other about nicknames and making fun of each other. You had guys that were very serious and guys making fart jokes. It was just, it was fun banter, laughing and poking at each other. It’s just kind of what we do. If you’ve listened to this podcast, you can tell that Tim and I joke around with each other all the time, right? It’s just — it’s a nature, it’s a brotherhood.

And these guys are doing the same, they bring that energy back home. And that’s why this guy, this amazing man who had been in a dry spell for a very, very long time, came back and his wife is sending him dirty text messages now. I don’t know if you saw that post, he shared it into the Brotherhood channel for the guys that were there. Because we knew his story, he shared his story, and he shared like, hey, this is what’s going on. Right? This is amazing. And just so proud for him and the guys that went through there. They stepped way outside of their comfort zones for the exercises in particular that you put them through, Tim. It was amazing.

Like we say it’s like Fight Club. We don’t talk about it at the privacy of the men and the sanctity of the teachings that we go through. It’s nothing that’s crazy, guys. It’s nothing that would fall out of line from any of your religious beliefs or anything like that. However, part of it is the not knowing and the trusting of going into an exercise that allows you that growth, right, it allows you that avenue to grow. And just seeing these guys go home and getting the messages and seeing the pictures was absolutely phenomenal.

Oh, and of course you guys have all seen pictures of Cuba. But if you haven’t, Google. You’ll see all the old cars from like the 50s, right. We rented 20 some, I don’t know how many cars we had, so I’m just going to call it 20. It could have been more, could have been less, but close to about 20 of the most pristine cars in Cuba, in Havana that they had. We took over the city driving around the guys honking their horns. We have pictures of these guys and they took us all to the Havana hotel, is that the name of it, where Meyer Lansky, the mob, and — [crosstalk]

Tim Matthews  19:32

Hotel Nationale de Cuba.

Doug Holt  19:33

Hotel de Nationale de Cuba, on the ocean and we were just coming in. Imagine just 20 cars honking their horns, driving around the city. The locals were taking pictures of us, the tourists were taking pictures of us, guys were just laughing and having a great time. And then we went to an exquisite, exquisite lunch right after that. It was just such a great experience.

Tim Matthews  19:55

Yeah, and those cars as well, it’s like being in a time warp, right, because they’re from the 50s. And like you said earlier, they can’t get any parts or anything to fix the cars. They can’t import any car. Well, there’s a few cars that have been imported, but not many. And if you imagine these cars from the 50s, they’re kind of like the cars from Grease, the movie Grease. Just wild, bright colors, top down, it was just incredible seeing the guy’s faces lights up. And they were saying just when they thought it couldn’t get any better, that happened. It was fantastic. It was, again, that’s one of those things I never knew having done that, it’s like a bucket list thing.

But I never would have even considered it prior. And that’s what these Brotherhood trips are all about. Whether it’s racing quad bikes in the Sahara, or having the more private Moroccan cooking class where we cooked our own tagine and all that stuff. That was amazing. Or whether it was doing the boardroom event in the Blue Lagoon in Iceland in a thermal volcanic spring, talking business. I mean, this is what it’s about, the Brotherhood events, all right. Cuba, sorry, Costa Rica, all Learning to Surf together, one of the best places in the world to surf. Guys that have never surfed before are just stacking it, falling off surfboards.

Some guys are crushing it, riding the waves, but it didn’t matter. We were all just there to be with one another and just create incredible memories. Or Tulum even, right, swimming in the cenotes, the sacred waters that run underground, beneath Tulum. Been in the jungle. It’s just incredible. And that’s what the Brotherhood, a big part of what the Brotherhood is about.

Doug Holt  21:46

It really is, man. I mean, I could talk about Cuba all day. It was such a great trip, such a great group of guys. And I feel bad, we had some guys — my only regret of Cuba is not being in the military myself or associated with the military directly. We had men that had DoD contracts or men that are still associated with the military on various levels that could not make the Cuba trip due to restrictions. And I was just, yeah, I was torn to pieces that those guys couldn’t go. We didn’t know, we felt horrible about that.

And so as long as we don’t invade Canada, there shouldn’t be a problem getting those guys to go to Canada. It’s one of the reasons we picked Canada. We’re like, okay, I think this is going to be a safe place. We’re going to do epic stuff in the Banff, the area around Banff, Lake Louise and such. But this way these guys can get a chance to come through.

Tim Matthews  22:43

Yeah, I’m excited to meet those guys.

Doug Holt  22:47

They’re amazing, they’re amazing.

Tim Matthews 22:48

Really, yeah. Yeah, yeah. Animal exorcist, a few others.

Doug Holt  22:55

Yeah, my name sake Doug, I love that guy. He’s great. So, anyway, gentlemen, if you don’t have something like the Brotherhood for yourself, a group of guys who you can go out with, and not the remember when friends. Not the friends that you go play golf with and you just, you talk about old times. And that’s it, you don’t make new memories together. In fact, you probably don’t even really enjoy each other, right, going through there. Find a way to do this. It doesn’t have to be through the Brotherhood. We love this. We made this, it’s what we call our beer test. All of these guys pass the beer test.

Again, some of the guys don’t drink at all. That’s not the point of this. The point is, these are guys I would go spend time with independent or irrelevant of the events themselves. The events are amazing, because again, epic growth, epic adventures with epic men, right? That’s what the Brotherhood is really all about. Find that version for yourself. You need it. Whether you know it or not, you just need it. It is amazing to have that energy, to have that insight.

One moment literally, you could be busting someone’s balls, laughing and joking, and the next minute, you could be having a very deep conversation about something serious. Whether it be suicide, a relationship, infidelity. It could be a business acquisitions, mergers, at very high levels on all of those things. And sometimes you just want to relax and talk, right, or just hang out and have fun and enjoy yourself and not have the pressure of taking care of everybody else. And that’s what the Brotherhood events are for me, Tim, and I just absolutely love them.

Tim Matthews  24:23

Yeah, me too.

Doug Holt  24:25

Gentlemen, that’s a wrap for this episode. Thanks for letting us recap Cuba. It’s such a great thing to come down memory lane. If you want to see some pictures from Cuba, I will post them over in the Facebook group. We have a free Facebook group over at The Powerful Man, over at Facebook. Just search for The Powerful Man. It is for business owners only. You do have to apply to get in and simply we’ll just verify that your business owner. That’s it. Once you’re in, you’re in and I’ll share some pictures from that event so you guys can see it and you guys can laugh at me riding in one of these old cars. And if you want to see a picture of Tim in his pink car, that’s absolutely fantastic as well. Tim, in the moment of insight, as always, take massive action. I’ll see you next time on The Powerful Man Show.