516 | The Secret Vacation That’s Transforming Entrepreneur Families

In this powerful episode, Driven To Win founders Chaz Wolfe and Jake Isaacs open up about the deeper purpose behind their work... helping entrepreneurs win not just in business, but at home.

They unpack the story behind the Family Mastermind Vacation, the one-of-a-kind experience where entrepreneurial families combine growth, rest, and legacy-building. From the first cruise to Bermuda to now serving hundreds of families across the country, Chaz and Jake share the behind-the-scenes vision, the challenges of integrating business and family life, and the lessons learned along the way.

If you’ve ever felt the tension between scaling your company and being present with your spouse and kids, this conversation will re-ignite your purpose and show you what’s possible when ambition and intentionality align.

💡 Learn more about the Family Mastermind Vacation — where entrepreneurial families grow closer, dream bigger, and build legacies together.
👉 gatheringthekings.com/familymastermind

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Connect with Chaz Wolfe (Host): 

Website: http://www.gatheringthekings.com

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LinkedIn: https://www.linkedin.com/in/chaz-wolfe-86767054/

YouTube: https://www.youtube.com/@gatheringthekings

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Welcome to “Driven To Win Podcast”, the hub for elite entrepreneurs tackling the isolation that business owners experience at the top. Hosts Chaz Wolfe and Jake Isaacs tackle emotional intelligence, resilience, and self-mastery through interviews with top industry leaders that prove it's possible to be the ultimate version of yourself and reach success with authenticity. 

Vacation With Entrepreneurial Families
Entrepreneur families grow closer, dream bigger, & build legacy together. Join our Family Vacation.

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Transcript

Speaker 1  00:00

Hey, brother, I appreciate you sitting down and chatting with me. Here I is, here you is. Hey, man, you know, one of the things that makes gathering the Kings extremely unique inside of the marketplace is our desire to want business owners to not only win in business, but also in their families. Yeah. Why is that important to you as a mission statement?

Speaker 2  00:23

Well, I think that if you consider success, like, what is success, if you consider the definition, it would not be limited to just, you know, financial gain or power or leadership, the things that come from maybe a business succeeding, it includes, you know, impact and legacy and love. You know, not to be like super cheesy, really, but your ability to to serve others, obviously, even through a business like you get to do that to your you know, your team members and your clients, but, but I don't think there's any greater calling to serve and to love other than your spouse and your kids. Kids lead to your grandkids. Your grandkids lead to your great grandkids. And I think there's just a lot of opportunity there to fulfill who we are meant to be as an individual, as a patriarch, as a matriarch, you know, as someone who wants to change the culture of their family, someone who wants to, you know, impact the world, impact even just their own family. It's it's a it's a big part of how we think.

Speaker 1  01:25

Why do you believe that this idea of success in business and success and family simultaneously is so counter cultural?

Speaker 2  01:34

Because I believe that most people look at it as a choice. I can either have one or the other, because they believe they have to go all in. They've got to be obsessed. They have to be focused. And I think those things are true in my own experience, I spent basically a decade building multiple businesses, becoming very successful financially in my 20s, but it was at the detriment of my marriage and my kids, and I wasn't like a terrible dad, and we weren't on the brink of divorce, per se, but my wife felt like a single mom. You know, she took family photos without me. What? Like? That's wild when you really think about that and sure on the other side of it, the story was, while I was doing it for them, I was doing it for my wife, I was doing it for my kids. It wasn't like I was just running around endlessly wanting money and fame and cars and power and women. I was over here building but unto quote, unquote, my wife and to my kids and to my family, my legacy, my story has never changed in my mind, but my the output of my intentionality had to change otherwise, the story was about to be adjusted. You know, the story wasn't going to be a successful marriage and a successful, you know, family, because where that eventually ends is, you know, a spouse that isn't seen isn't feeling connected to raising kids on their own. It's kids that don't only have one parent, you know, the other parent is maybe buying everything, but, but they're never around. They're never, never there. And so I think most entrepreneurs see it as one or the other. And I got to, kind of like, make my choice, and I come over here and I'm at least going to pick a good life for my for my kids and for my wife or my my husband, depending upon who's in the business. But it's like, no, no, that's not how it has to be at all. In fact, the only thing that matters, really, is that intentional obsession go all in focusedness that we talked about, that just has to be applied to both areas. And we have just, you know, Julie and I have just figured out some very intentional ways to be able to be obsessed about our marriage, to be obsessed with our kids, with our family, with our legacy and our business and our health and our faith and all the other things too, right? Because it doesn't have to just stop there. But I think this family business component is is something that a lot of entrepreneurs that are family oriented down to earth, they're growth minded. They want to figure this out, but when they look at their scenario, they're like, Ah, I feel like I'm messing it up. I feel like I'm messing them up. I feel like I'm not giving my spouse what they need, or or I don't know, I don't know what to do, right? Because if I, if I, if I step off the gas over here, then these things fall apart. And so it's a two fold answer. In my opinion, we build the business in a specific way that allows for it to grow and make more money, but with less input, so that we can be intentional with our time and with our effort in our family.

Speaker 1  04:31

Yeah, man, I think it's really beautiful, and I wish that people who don't know you like I know you could see your calendar and how you back up what you're saying today with like, actual time blocking and activities that you prioritize on your calendar. So I just think what you're saying is really, really beautiful. Thanks. So I want to take you back a little bit. We're going to go walk kind of down memory. Lane, you and I are on the phone. We're planning one of our earlier peer mastermind group events. I'm laying out some activities that we're going to do in Georgia, and I'm all excited about trying to, like, plan a day of service. And we're like, man, wouldn't it also be cool if we could, like, build this thing where families could take vacations together, right? And the thing that I love about you is that seed of a thought to implementation is a lot shorter than it is for me. And so this is, like, February, and we're having this conversation, and you're like, that sounds like a good idea. Let's do that. And I was like, Okay, well, like when, like, what year? And you're like, No, like, this year right, right now we're gonna do it now, like, we're gonna do it this summer, and it's like, February, and I'm freaking out because, you know, we're doing all these other things, and we plan a family vacation, and that first year, we took a cruise to Bermuda, and it was incredible. And we didn't know what we didn't know. But I think the the overwhelming thought walking off of that boat at the end of the week was, holy cow, there actually is something pretty special here. And fast forward, we've done it now for three summers. We just got back from our third trip. What are you proudest of as we continue to stack this family mastermind concept on top of each other, I'd say

Speaker 2  06:25

I'm probably most proud of the room or the table being curated with such incredible families. That sounds maybe like, well, of course, right, but I'm the one that's personally talked to every family, interviewed every family who wants to come with us. And it's funny, because you always get the ones that are like, you know, just send me the details and I'll decide if I want to come I don't need to meet I'm like, well, actually, my wife and kids are going to be there. And so no, I'm not sure I want you to be there yet. So you can spend 30 minutes on Zoom and get to know me, and I can get to know you first. Know you first. And if that's not your style, then that's completely fine, but, but you're definitely not coming on this family mastermind. So I think that the the curated quality of the room, and that has been backed up by every single person who has come, and we get the same kind of response at our other events, too, but the family is just so unique because, you know, like, as an entrepreneur, you're like, Is my spouse gonna fit in? Is my spouse gonna like it? Like, are we they don't really do the business thing, or maybe they are fully in the business, like, but, but what are the other spouses? What are my kids gonna think? Like, they're just gonna want to go to the pool, but like, are they going to want to grow and learn? They're gonna think it's school? Like, ah, you know, there's so many dynamics that go into like, all these people you know these you know, four or five, six people of your family coming on this trip, and so for multiple families to come together, to experience each other, you know, for the kids and for the adults to have a general same response of like, holy cow. I don't know where you found this family or that family, or this family, but like every single conversation I've had, these are just really high quality people and and now I have relationships with people from all across the country, of people who are doing life like us. It's probably the number one thing that I hear from from entrepreneur families is, you know, yeah, maybe we've got a few business owner friends, but they don't have kids like us. Or we have friends in our family, or we have family, or we have friends at church, or, you know, whatever, but they don't own a business. And there's just like, this major gap of, there's nobody in my life really doing life like me, business kids trying to integrate, you know, the family. I really want to take care of my spouse, but I'm building a business at the same time, and, you know, all the things that go along with that. And if you can get into a room, sit at a table with other entrepreneurs that haven't necessarily figured it out, but are in the process of figuring those things out, and then, of course, we bring you know, tactics and sessions and speakers and experts to the table to help you know the room figured out. But it's the quality of those, those people, that make for the quality of the environment, which just makes room for transformation.

Speaker 1  09:00

Yeah. I mean, I think just being in that room and being surrounded by other people who are prioritizing the same thing that you're prioritizing, yeah, success in business, success and family, better communication with my spouse, like it's just, it's a room where the guard comes down, the armor comes off, because everyone is there for the same purpose? Yeah, I think it's really cool to see

Speaker 2  09:24

hey, kings and queens, Chas Wolf, I want to talk to you about something that's super important to me. We put a lot of time and effort, we meaning myself and my team, into this podcast, into the content that goes out every single day. And if you have been getting any sort of value or insight from this, we want it to be able to reach other business owners too. So we would love if you would like comment, share, leave a review, post, share, again, all of the things on social media, on all the different platforms, or even on the podcast mediums of apple and Spotify. We would love to be able to get our content into more hands, more. Are entrepreneurs so they can grow their business as quick as possible. Together, we are building a community of like minded entrepreneurs who are committed to growing their businesses to new heights. So let's do this. Let's help each other grow.

Speaker 1  10:11

You know, at this point, through a couple of these vacations, three of these vacations, we've served hundreds of people. Now, what are you excited about for the future of the family mastermind?

Speaker 2  10:24

When I think about families like this, you know, I don't necessarily see a conference of 1000s of families in one conference, although maybe I'm not like shutting that out, but what I am, what I do see is transformation. And in my experience, transformation is tough inside of a conference, and you maybe pick up some nuggets and you feel motivated or inspired, which I love those things. And so maybe there's a version of the family mastermind in the future that maybe is conference style. And there's 1000s of people I don't know, but I think that generally, what I'm after is the opportunity for families to get into an environment to be transformed so they can go back home and, like, keep doing the thing, you know, do the thing with their spouse. Well, do the things with their kids. Well, help their kids start or buy a business well. Or maybe the kids start, you know, working in their business well, or whatever the scenario is like, to actually do the things we talk about well in their life, and for them to now have contacts and relationships of other people doing the same thing. And so I know that, over the course of years, will will impact and help transform 1000s of families. Because the more people that I talk to, the more I recognize that this group of people is super unique. It's this down to earth, family oriented, but yet growth minded, individual. It's the person that's like, No, I'm gonna go all in Sure. Like, like, you said, we're gonna do the event. Great. Let's do it. Let's do it now. Like I want to, I want to be around winners like that, who are in their business, but who also say, at the same time of pressing every single boundary and taking all the risks I'm gonna, I'm gonna date my wife, and I'm going to, I'm gonna send her a text message every single morning, appreciating her for something specific from something from yesterday. And when my kids and when I spend time with my kids each day, I'm going to look for ways to build them, to build their character, to look for ways to bring them into how to think and how to build them as an entrepreneur, and I'm going to put them in an environment where environment like GTK, where they're teaching entrepreneurship for kids and taking care of the next generation, as we call it. So it's just like, I want to be around people like that, who that not? It's just, it's just not like a cool thing to be part of. It's like, no, no. This is the mandate. This is how we live. This is how our family is going to operate for not just our generation, but we're changing the family tree. You know, for multiple generations down, we're going to think, we're going to love, we're going to serve, we're going to do things with excellence, we're going to live the exceptional

Speaker 1  12:49

life, you know, yeah, for the person that is considering booking a call with you, what would you

Speaker 2  12:56

say? Well, I'd say, first off, don't consider for too long, because nobody likes, you know, people that sit on the fence. In fact, if you sit on the fence too long, you usually get injured. So either decide, am I focused only on my business and do I want to just make money? Do I want to just grow financially? Or do I want to do that plus get really, really intentional about my family, because it's going to be work, and I don't really want you in the environment. If you're not willing to do the work of being intentional, right, you can't, you know, be the optimized version of yourself, health wise, if you're not willing to go to the gym and eat, right? It's the same thing with your family. It's the same thing with your business. And so if you're the entrepreneur that's counting the cost of, I don't know if you know 10 or a 15, or maybe one day we'll do a $50,000 trip. Like to me, if that's all you're thinking of is, what's the dates and what's the cost, then we're just not the right people. We're not the same and that's okay. What we're looking for are families who go, You know what? I'm going to triple my business in the next 510, years, but at the same time, I'm going to make sure that my relationship with my spouse is the strongest it's ever been. I'm going to fall deeper in love with my spouse than I've ever been before. I'm going to be intentional with my children, because I want them to grow in their character and their integrity. I want to bring them into the business, or help them start their own business. I want us to take meaningful vacations together. So that's not just another trip just because we have money, but it was purposeful. We created memories that matter. It's a trip that like, moves the needle in our lives. And I want to do it with other entrepreneur families. You know, I want that. I want the family to think, well, I don't want to just go to, you know, an island by ourselves. I'd rather go to an island with other entrepreneur families like this, because they understand the impact multiple years down the road of those relationships that they'll make just in this one event, let alone, you know, joining our community and being a part of

Speaker 1  14:45

this movement. Yeah, Chaz, last question I have for you here, you have kind of a unique experience in that, on that first trip that we went on, your youngest daughter wasn't even one, right? And so we have now seen her. Grow up in this curated environment, from summer to summer and trip to trip. What excites you the most as a father, about your children being raised in this environment?

Speaker 2  15:12

Yeah, super good. I mean, I think I'm like a lot of entrepreneurs who like us, they're family oriented. But you know, life gets away. You know, we get busy and we have good intentions, but if we are not intentional, the intentions are just that. Just thought about it. Didn't do anything about it, but I thought about it. And so for me, having my kids in this environment isn't just Oh, like, look at the wolves. They're perfect because we're not, obviously, but having my kids in the environment, even though I might be the one teaching, or you might be the one teaching, or maybe it's not a GX t call where the kids are learning, and they're just hanging out with another family, and they're talking to other entrepreneur kids, and guess what they talk about? They're talking about what their dad talks about or what their mom talks about. And it's the same stuff, and it normalizes what I've been trying to teach them. It normalizes how we live and how intense we are, or how intentional we are, or why we don't do things. You know, you know my kids, my kids pretty much know the know the deal of why we do and what we don't do, and the kind of like the why behind it, whether that be not eating sugar or or the reason why we get up at a certain time, or the reason why we think about money the way that we do, and so I'm super excited about it, as a dad, to have my kids in this environment that I'm curating, because that's my future legacy. We're in the process right now, most likely, hopefully, in the next couple of weeks, to close a like an eight location vending machine business for for my 11 and nine year old, my six year old probably help a little bit. He's a little bit of a wild card right now. Bit of a wild card right now. A couple more years, and he'll be able to truly help. But it's like, okay, what 11 year old and what nine year old is going to learn? Inventory Management, digital tracking, money management, they're gonna have to figure out which ones need to be filled out or filled up each each week. They're gonna know what products to bring and make sure that they have them on hand. As far as the inventory as far as the inventory management, they're going to have to learn how to interact with the different locations and the people that work there when they drop them off. There's just so many things from whether we end up getting this business or something else, but it's like me curating this environment forces me to a lead, but lead them in a specific way, like I'm trying to teach all the other families to do, which ultimately just impacts multiple generations. Because, I mean, can you imagine having that type of business at 11 and nine, the things that you can learn? Can you imagine us being in an environment like that when we were 12 and 15? Right? So it's just pretty

Speaker 1  17:36

incredible, man, it's awesome. I appreciate you for doing it. Appreciate you for doing all the behind the scenes work and and, you know, the toil that comes with organizing hundreds of people to leave the country.

Speaker 2  17:48

Yeah, well, back at you, because I get to be the one that, you know, often takes the credit on the outside, but all the all the details get summed up, and all the T's get crossed, and eyes get dotted by you. So in that way, we make a great team and and the families that that come are a big part of that. You know, we're not trying to bring divas, you know, we're not trying to bring prima donnas. We're trying to bring families that they need to do any work. It's a pretty exclusive and pretty amazing trip and pretty hands off and credible vacation. But every experience is made by, in my opinion, the people. And I'm not looking to spend my personal time with any anybody who wouldn't want to be helpful in an environment

18:28

that's good. Thanks, buddy.

Speaker 2  18:32

Thank you for listening to driven to win. I hope that you were able to pull out a few nuggets to go apply into your business right away. More importantly, though, I hope that you're realizing that it takes more to be successful than just being by yourself, doing it all on your own, carrying the weight all by yourself. What I have realized, not only in my own journey from multiple businesses and multiple different industries and now interviewing over two or 300 other very successful seven, eight and nine figure business owners is that it's tough to do it alone. And so gathering the Kings exists to bring together successful entrepreneurs. In fact, we are putting together 1000 kings, specifically, who are grateful but not done. We're intentionally assembling kings who fight tooth and nail for their business, family and communities. And here's what, we believe that in the pursuit of excellence in those areas, that it ignites within us the responsibility to govern power and forge a lasting legacy. So if that relates and resonates with you, and you know that you need people around you, sharp, qualified, other very successful business owners, I want you to go to gathering the kings.com. Want you to take a look at what we're doing and see if it makes sense for you to be part of our pursuit to 1000 kings talk soon.