Jay Bourgana on Pursuing Ambition Without Losing Connection at Home

0:00 Jay: A lot of people just don't talk to their spouses. They don't tell them everything. You know? So of course they're not gonna tell anything to their kids, and of course the spouse resent them and the kid resent them. And, and then they build this big business, and they're successful, and it's like, "Why are my kids not talking to me?" Michael: Welcome to Gap to Gig, the show for dads navigating the in-between season when work, identity, and priorities start asking different questions. Here we talk about what that season looks like and how to move through it with intention. I'm your host, Michael Jacobs, and today I'm talking with Jay Bourgana, an entrepreneur, investor, father, and founder of Acquisition Collective and Raising Lions. Over the past twenty-five years, Jay's built, operated, and acquired businesses across manufacturing, real estate, and home services.

0:44 He's completed more than twenty acquisitions and has helped scale the real estate services platform to about three hundred and fifty million dollars in revenue before exiting. But after years of building companies, leading teams, and navigating the pressure that comes with growth, Jay's focus has expanded beyond what it takes to build a successful business. He's also asking what it takes to build a meaningful life without sacrificing the people you're building it for. Today, Jay helps entrepreneurs learn how to buy and operate real businesses while he and his wife homeschool their two children and think intentionally about work, education, freedom, and raising kids with the agency to lead their own lives. Jay, welcome to Gap to Gig. I'm so glad you're here. Jay: Thank you for having me. Michael: My pleasure. So you know what it takes to build valuable companies, right? But much of your work today seems rooted in the realization that building a successful business and building a meaningful life aren't necessarily the same thing.

1:30 So I want to start there with that distinction, you know, when that became clear for you. Today, you seem more focused on the bigger question, how do you build a meaningful life without sacrificing the people you're building it for? When did that question become personal for you? Jay: Yeah, it was very interesting because it, it became acute for me post-acquisition. I had built this large business and exited and I was kind of liv-, living this semi-retired life. And I was having these as like a purpose crisis, if you will. And, you know, what do I do? What am I doing with my life? And what is my purpose? And I didn't feel fulfilled in, you know, especially doing nothing.

2:13 So it kind of really made me question, you know, myself because I was, you know, I was in Hawaii. I was enjoying, you know, the, the, the Hawaii life, drinking mai tais on the beach, but I wasn't fulfilled. Michael: Sure. Jay: I wasn't happy. And at the same time, I was enjoying myself with my kids, and I didn't wanna, you know, go back and build something just for the sake of building something to be busy. So I had this two-year period where to go dive deep in, you know, in this question and, and to understand what drives me, to understand what, what's purpose for me, and so forth. Michael: It's really interesting 'cause, you know, usually when I talk to people that have, you know, hit that peak, hit that, that goal that they had for themselves, whether they started their own business and sold it, or they reached the pinnacle of their career in terms of, like, where they are in the business, maybe they've taken over a business or they've taken over a department or whatever it may be, it's, we get that question of, well, what's next, right?

3:20 You're always chasing, right? It feels like you're always trying to get to that next level. Then once you hit that level, it's harder to figure out kind of like, what is that, that next thing? When you look back at those years of building up that business, what do you think you were chasing then, and how did that kind of and how did you, like, define success as you were building up, Jay: Yeah that's a great question. Michael: your business? Jay: Because that's Tony Robbins has this framework around drivers. So he talks about having four personality drivers and two spiritual ones. And all of us, when we first start, our first driver is certainty. You know, it's this drive to provide for ourselves and, you know, to e-, you know, food and shelter, the lower, the, the lower of the pyramid of needs, if you will.

4:07 You know, and then and then as you provide for that, then the next level is significance. You know, some of us have this chip on our shoulder. Our dad told us that we probably are not gonna be successful, or we, we, they, they didn't give us attention or whatever, and we wanna prove them that we're worthy of their attention. Or some of us didn't get love from our mothers and, you know, we're trying to be successful so we can get love from others. So you have this, you know, significance drive, or you have this love and connection drive. And then there's some, a group of people that are a little bit on the crazier side, where they just need variety. They need, always need something new. They're never satisfied with the same. So those four drivers can get you to go from not doing to doing, not achieving to achieving.

4:54 So essentially, that's like the first rocket that gets you out of the if you will, the financial gravity. And, and it can get you there. But the problem is that once you become, you know, semi-comfortable, fi-, financially free or so forth, those drivers lose their power, lose their, their fuel, and then you find yourself, you know, floating with no, n-, nothing to drive. There's no engine that will drive you. And so that's where, know, I think that's where you, you, you go back and rethink your, your, you know, your mode of thinking, your thinking of your motivation, your, your drive. And so the other two drivers, and which I discovered when I was, you know, when I dove back in, I went back and I looked at my life as an entrepreneur, my life as a, as a business owner, and I, you know, looked at all the things that I miss and all the things that I didn't miss.

5:49 So I didn't miss the stress, I didn't miss the problems, I didn't miss the issues. I didn't miss the, the, the burden of responsibility for payroll and, you know, and all that. And, but I do miss, and I did miss being in the arena and learning because when you're running something, when you're in the, in the arena, you're constantly absorbing data, pivoting, changing, adapting. You're, you're, you're trying to understand the landscape. You're trying to understand what's going on around you and what other people are doing so you can evolve and grow. So I miss that. And then the other part that I miss w-, is the, the transformation that I was having on people, you know, on my employees, on my clients, on my suppliers, on all, on my ecosystem. You know, the, the, the impact that I was having. And Tony Robbins calls those two drivers growth and contribution.

6:42 So there's, there's, you know, there's growth driver that, you know, you can grow and there's no, there's no mountaintop. You can constantly be learning, growing, developing as a person. And then there's the contribution, a driver which has no mountaintop either. You know, when you, when you are driven by certainty or significance, there's always that top. You know, there's a certain amount of money where more money doesn't add any value to you. There's a certain amount of fame where more fame doesn't add any value to you. There's more, there's a level of variety that no, v-, more variety add value to you. But in terms of growth and contribution, those are, you know, I call them like clean fuels as opposed to the dirty fuel of, you know, significance, uncertainty, and so forth.

7:25 Michael: It's interesting to me, like you clearly, you l-, you enjoy the mental stimulation, the, the challenge, figuring out, you know, solutions to the problems. You know, you mentioned like that you didn't necessarily miss the responsibility of taking care of payroll, right? I mean, I don't think anybody re-, would really miss that, that responsibility, but being in the arena, I think were the words that you used, of like getting in there and like doing something, right? And seeing the impact that you make. I'm curious, like during that time when you're building up this business, right, you are focused on solving those challenges that are in front of you, right?

8:08 Growing this thing to what you want it to be, what you hope it can be. But there are, at that same time, you also, you're surrounded by people, right? Whether it's at work, at home, or, you know, outside the house, whatever you, you may be involved with or who you're, you're friends with, but like, what were the people closest to you experiencing while you were going through building this business? Jay: Yeah, and I mean, you know, I started building my business around the same time when I started family. You know, I had a baby when I first started my first year. So there's definitely, a lot of… it was very interesting. So it's, it's combined.

8:48 You know, like anybody else who had a newborn, they, they all kind of feel that when you hold your baby, when the doctor gives you your baby the first time, you see that switch. And there's a switch that turns on in your brain where it's no longer about you. It's about, you know, keep, keeping this thing alive and keeping it you know, it's all about them. It's all about, you know, th-, this life that you brought to, you know, on Earth. So, so it's on the one side stressful, and on the other side it's fulfilling because it's no longer about you. There's no ego. There's no, you're not self centered. You're not thinking about yourself. You're just thinking about your family. So on the one side is s-, is this huge responsibility.

9:31 On the other side, it's freeing, and you know why you're doing it. So, so in the beginning it was, you know, obviously, you know, you're working hard. You're trying to figure out how to balance things with your, with my wife and how to be present as much as I can while I'm building. And you, you know, and my goal was always to, I knew that I didn't have a lot of time to do everything that I wanted to do, but I want, I knew that I wanted to put as much as much connection and as much depth of present within the times that I, the time that I had available. So, so it became more on the quality versus quantity, most, more about achieving that high level of connection to, you know, to, to my child as well as to my, to my wife as opposed to, you know, just being present all the time and just being present at all.

10:31 Just being, you know, attentive, just being there. Michael: Absolutely. Did you carve out specific times to be there for your family and be there at work? Jay: What I figured out there I wanted to give my family and my… the best of me. And I know myself as a, a morning person, and so my mornings are my, my best. You know, my peak attention, my, my best mood, my high energy. So I dedicated my mornings. So I woke up early. I spent time with the baby. I gave a plenty of time to my wife to get her day started slowly on her own pace. Did everything that I could do, you know, to help and support.

11:12 And then on the weekends, I would, you know, I would try to take, you know, Isabelle when she was little with me to, to work and, you know, hang out with me, give her color. And as she grew, give her things to do and so forth. And, and we've developed this ritual of like our coffee dates on Saturday. You know, it was me and Isabelle, and then, you know, my wife will have a date night in, in the evening. And so I have this kinda like kinda Sunday I don't do anything. So mornings dedicated to family. At night I'll be like the, you know, you know, wrestling, put her to sleep, you know taking stuff, taking care of as much as I can around the house. But that, that Saturday ritual stayed.

11:54 And then it stayed every, every Saturday we'll go coffee, and I'll tell Isabelle, even when she was a nine-month-old, I'll tell her about my work and about my industry and about what I do and so forth, even though she didn't understand anything. But over time, our conversations evolved. And then when Jack was born, he came with us. And then when I sold my company, that m, that Saturday ritual became a daily ritual. So we started doing it every morning. We would have these 7:00 to 8:00, and it became 7:00 to 9:00 every morning to have conversation with me until today. So right now they're 11 and 13, and we're still having these daily conversations every morning. And those are essentially our like very valuable time that we have together, that we connect and, you know, we, we cover so much ground in those two hours.

12:42 Michael: That's amazing. I, I love everything about that. I love the idea that you created a ritual, right? 'Cause, like, it is so easy, you know, particularly in this day and age, to get so wrapped up in the every day, right? Of like, okay, I've got all these things I need to do for work. I've got all these things I need to do to take care around the house, or I need to get my kids to their activities. I need to get these things. Sometimes we need to find a way to slow down and make time to be with the people that matter to us because at the end of the day, our jobs aren't forever, our lives aren't forever. Like, we only have, we have a limited amount of time. And yes, we still have to work, we still have to do these things, but to be able to carve out a specific ritual or something that you and the people that are closest to you, so in your case, you and your daughter, and then eventually your son, have to look forward to that's like, this is our time.

13:34 And the other thing I love about this ritual is that it involves talking, right? It's not like we are just going to, for two hours, stare at screens while we're both in the same room or we're both gonna just watch a movie and never talk about it. Like, you are providing an opportunity for your kids to know that there's this safe space, right? Like, we can talk about things. Like, I know every day at 7:00 AM, like, 7:00 to 9:00 or whenever we have time, like, this is, like, my father is approachable, right? 'Cause it's so easy, again, to like get wrapped up in our work, right, and not be present when they're trying to tell us something, and we're thinking about work, but they want to talk about something else. Where you've crafted this ritual which allows you to get into this mindset of like, okay, you know, this is our time together.

14:17 Not my time to think about my business. This is our time to talk about whatever is interesting to, to both of us, right? Like, you might want to talk about something that happened to you at work, and they might want to talk about something that happened at school, and then you guys just end up talking about something altogether different. You just don't know, like, what comes next. But by creating this ritual, you're inviting this opportunity to occur on a regular basis or in your case, on a daily basis now, which is just incredible. 'Cause I think a lot of people, when their kids are in your kids' age range now, like 11, 13, like they're in their preteen to teen years, it gets harder and harder to have those conversations because they become more busy and more interested in things that are happening outside the house, right?

14:59 But y-, you at least have this sort of like baseline that you can keep falling back to of like this is that ritual. Like, okay, maybe you miss next Tuesday, and it's like, okay, like, 'cause, you know, they are hanging out with friends or doing whatever. Maybe they have a sleepover one weekend, so you don't have that, that, that coffee date on Saturday morning 'cause they're at a friend's house. That's okay because you know that ritual's going to occur again, right? Jay: They're gonna wake up, and the first thing they do, they make their breakfast and come sit with Dad. And, you know, they may have, it, it rarely happens. So it's like the 99% of the time we do our two hours. But if th-, if there was something, then, you know, they're gonna have breakfast, they're gonna s-, spend, you know, 30 minutes, an hour, and then they're gonna go do th-, their thing.

15:41 But that rarely happened. It just now it's, it's just part of a pillar of our, of our existence. And like you talked about, like I know a lot of parents who have problems having conversations with their preteen and teens, and it's not an issue for us just because this is what we do every day, and then it's not even, it's not even part of the convers-, it's not even something that you negotiate. Michael: You've, you've normalized conversing with your kids, right? And that's not always easy, particularly in the age range that, that your kids are at or, and as they get older. But you've made it something that's just like that's their expectation of like, "We talk to Dad every day." Like that is, that's cool, and, but it's not like, it doesn't sound like it is a dreadful thing for them, right?

16:22 They don't… It's something that's just like, "This is what we expect. This is what we want, 'cause this is what we do every day." Right? And it's not like you're forcing them to sit down and answer a series of questions. You're doing it in a way that is more ritualistic than that, more holistic for the family, right? And to create these stronger bonds for your… 'Cause I imagine as your kids grow into adulthood, right, and they go off on their own, that they're still gonna look forward to having those conversations with you because they're gonna have those memories, right, of, again, it's like I talk about this all the time of we expect, I think, as dads a lot of times like, oh, it's those big moments that are gonna be the most memorable, right? It's like when the kid wins their, their team wins a championship or something like, "Oh, I'm gonna remember that." That's not really the most… Well, I'm learning this in real time.

17:09 That is not the most memorable stuff. The most memorable stuff is like what happened during a conversation like maybe we're eating dinner together and w-, we start joking about something and we all just laugh outrageously over something somebody said or did. That's the kind of stuff that the kids remember, right? It's more mundane typically, right? And the only way to create those positive memories is to be there and, and show up and do them, and be active in the, the conversation that happens. It can't be, you know, you could sit down with your kids every day for two hours, but if your mind's not there, if you're not active in the conversation, it, there's no one's getting any value from that. Jay: Yeah, and then it's also, Michael: Right? You have to be… Jay: and it's also when, like when you have dinner, the main purpose is dinner, and the conversation is secondary, and usually by the time, you know, there's conversation around what we're eating or who's not eating what and who's like wants to eat something else, and then okay, now that we've finished eating, let's clean up.

18:04 So it kind of gets in the way of the connection. You know, when you have a, a, a, a, when you have a ritual that's completely dedicated to connection, then there's nothing that gets in the way, and then you're truly there. Like they, you know, the kids can drive the agenda of the conversation. You know, like if, you know, if they don't have anything in the agenda, then we talk about, "Hey, you know, what, what'd you dream about? What were you thinking about when you woke up? What's the first thing that came to mind when you woke up? What's the last thing that you were thinking about when you went to bed? What, what happened yesterday with your friends when you were, when you were meeting up? Tell me about…" And then you know their friends, and you know the stories, and you know, you know. And over time you, you know, you know, because you know all the other friends in the past, and then they meet some new person and it's like, "Okay, you know, from all your friends, who is this person, you know, kind of like seem like, like from the other people? Like, is this person you know, a, a Romy or, or, or Ari?"

19:02 It is, so it's, you have this common, you know, language with them. Michael: Yep. Jay: You know, and you're, you're embedded inside, you're aligned with their life. And, and there's, and then you can sense resistance over time. Like we were talking about teens and pre-teens. Teens, you know, get to the stage where they want more freedom. And I can, I can, I've prepped for this, you know, five years ago, where we started talking about how to earn freedom. You know, how to build, you know, res-, capability, how to build responsibility, how to have good judgment, how to be reliable. You know, if, you know, what would it take, you know, what would it take for you to have… W-, what is freedom?

19:44 How do we define it? What is… How do you make, you know, how do you define freedom? And then how do we, what would it take for Dad and Mom to give you 100% freedom the way you define it? And then let's you and I work together, let's all of us work together to build the capabilities for you to be able to, because nothing will make us happier. We align ourselves with their goals so there's no conflict. We're not, we're going toward the s-, we're pushing toward the same goal. I want you to be free. I want you to have, you know, e-, external connections and relationships and so forth. So, so, it's a lot of fun. Michael: Yeah, absolutely. I, I appreciate that, to me, it sounds like you are, because of the way you involve your kids, you are using their language to communicate with them, right?

20:31 Because you're asking them questions and you're saying, "Okay, how do you define freedom?" Right? "Let's get you… How do we get you from A to, to Z?" Right? And so it's just like in business when you are marketing to customers, the most effective marketing speaks the customer's language, not what you as the marketer thinks is the correct language, what the customer understands, right? You're speaking their particular language. And you're doing the same thing with your kids by asking them the questions of like, "How does that make you feel? What does that do for you? What would you like to see? What are your goals? What are your dreams?" You know, "What are the things that are holding you back?" And I think also because you're normalizing this conversation, you're also creating opportunity for them for when times aren't going well, they know where to go, right?

21:19 And they aren't going to make rash decisions or decisions that, you know, may be a little bit riskier 'cause they know that they can come back to you, because you have these conversations, even if it's not during that ritualistic two-hour period every day, if they need something, they know where to go. They know they can come back to dad and be like, "Hey, you know, I'm dealing with something. Can you help me figure this out?" Right? They are going to be much more comfortable to do that because you've normalized conversation on a regular basis, right? And yes, I understand it's a luxury to be able to carve out two hours a day with your kids, and sometimes it's not feasible. But like you said, it didn't start with a daily two-hour thing.

21:59 It started with Jay: Once a week. Michael: one Saturday, right, Jay: Yes Michael: as a coffee date, and then you kind of gr-, let it grow from there naturally. Sometimes it'll be into a daily thing, sometimes it won't. And it might be daily now, and then when the kids are in high school and there are all these different activities, maybe it doesn't become daily. Maybe it's a little less frequent, but it's gonna be just as impactful and just as important. Jay: And since, since Michael: It… Jay: you brought the business part, I just wanna like so that I don't forget. You know, it's, it's very ma-, it matches also the same principles of leadership and management. You know, so what you're, you know, when you have a team, you know, not all y-, all your team members are driven by the same things. They don't, they're not motivated by the same things.

22:41 And but in general as a, as a, and there's a, there's a great book by Daniel Pink, it's called Drive, and it s-, did, and it was based on a study that was done worldwide about what motivates people. And they found that three things motiv-, motivate people, and none of them are money. So one is mastery, which is what we talked about earlier, growth. They wanna see that they're growing, learning, developing, moving up. The second one is autonomy, feeling, you know, having autonomy, freedom over what they do. And the third one is purpose, and in feeling that what I do matters and has, has purpose. Now, if you have, if you have mastery, if you have opportunity for mastery or you're actually growing, and you have autonomy and you have purpose, more likely than not, you're gonna make more money.

23:28 You know what I mean? Michael: Yeah. Jay: So money comes as a result of those things which kinda, kinda creates this virtuous circle for motivation. So the same applies with kids. You know, kids wanna learn and grow. Kids wanna have freedom and autonomy. And then kids wanna have a sense of purpose. What am I here on Earth to do? What is… How can I create value? How do I drive? How do I, how do I matter in the world? So, so I think when you, you can, you can, you can use the same tool, toolkit in parenting as well as you use it anywhere else. Michael: Yep, absolutely. There's a lot of crossover there, which leads me to the next question of, I'm really curious, you know, you've said that the, the same habits that create strong companies can either strengthen or kind of crowd out your, your family life.

24:17 Which habits do you think transfer well from business into fatherhood, and which ones become more dangerous when you, when you bring them home? Jay: Yeah, I honestly, you know, good, good business practices are, you know, are the same as good family practices, and there are no, honestly, there are no, unless you bring bad practices, then it's bad everywhere. So an organ-, a family is an org-, is an organization. The same apply in a nonprofit, and apply in a sport team, and applies in business, and applies in the family. So the main one is who we are, what are our values? You know what I mean? So what is our mission statement? What is, what are our values? What do we stand for as a family?

24:59 You know, what do we, what's our mission? What's our, you know, what, what's our purpose on Earth? What do we d-, you know, what do, what do, what do we stand for, and what do we bring, you know, as a contribution to the world? And then, you know, so values go down, you know, to the kids. And then what are we trying to achieve? What are we working on? How do we measure it? How do we communicate with each other? How do we work with each other? What is our culture in our house? You know, so when you think of a company, you want this mission, this, this purpose. You want this goal. You want this client that you're serving, and then, y-, an ICP. What's your value proposition. What is, you know, what is the value? What is your unit economics?

25:39 And then and then you align the culture of the team. What, like, what's the ideal team member? You know, how do we connect with each other? How do we communicate with each other? How do we treat each other? And then how do we drive value back to our customer and to society as a whole? And then how do we continue developing, growing? How do we measure our progress? What are our KPIs? How do we measure our progress? How do we stop and, you know, collaborate to improve? You know, how do we continuously grow and improve, and have that continuous improvement loop in our, in our organization? Yeah, and I mean, all these principles, all the principles of a really good, healthy business apply in a family.

26:25 I, I cannot tell you one single principle that comes from a good business, like a healthy business, that doesn't apply in a, in a family. Michael: That's a fair point. I hadn't quite thought of it to the degree that you have in terms of like, you know, building this healthy culture and having a particular mission. We do that as a family, but I don't think we necessarily recognize that or, you know, may-, we might not be so explicit about it as we're trying to, as we're going about our, our day-to-day lives and, you know, our family, you know, grows and ages and, and what have you. It's really interesting to me because when, you know, I had the question because I was thinking like, you know, maybe there's more of a humanity element to raising a family than there is to building a business, but a good business is gonna have just as much humanity as raising a family, right?

27:20 If you're building that business right, you're doing it in a humane way. You're taking people into consideration, whether they're your customers, your suppliers, your employees, your coworkers, whoever it may be, right? So it's, you're right, they are both essentially organizations, maybe of different sizes, right? But the, the principles behind it typically are, should be the same. Jay: And I'll tell you what I, where I learned this. In my years of do-, doing turnaround, fixing, you know, ill, ill companies, I found that majority of the value that I generate, the majority of the improvement happens when we align the, when we articulate, why does this business exist?

28:05 Because for me, every business that exists, has customers, has a reason to exist in the world, has a job to be done in the world. So because of that, you can trace that purpose to the whole world. Literally, any business you can think of. You can think of a cleaning or a, a pi-, you know, a, like a plumbing business or an HVAC business. You can articulate how that business not only changes the im-, impacts the customer, impacts that community, impacts the world, and then you could literally give them measurements. So most CEOs and founders and, and, and, you know, and executives do not do a good job continuously articulating that purpose, that impact that that business does on the world.

28:49 And so for me, the same thing applies in the family and, and that's where it comes into that conversation around, you know, like where entrepreneurs or, for other organization, have this conflict between should I work hard and make money for my family, or should I s-, g-, work less and work for my family? That, that's, that, that's a false choice in my, in my mind because it's not articulating the why behind it. You know, so what is the goal? You know, why are we doing what we're doing? And then how do I articulate it to myself? And then how do I articulate it for my family? If my mission is pure, and my mission is clear, and I'm making an impact, and obviously I'm feeding my family as well, you know, I'm aligned with the, with the world, and then and I, and I articulate that to my, my spouse.

29:39 And I, and I, and sometimes people say, "Well, my kids are too young. They're not gonna understand." But your wife does, and your wife is talking to the kids, and she will remind them. You know what I mean? "Daddy's doing this for this, and Daddy's doing this for that." You know what I mean? She's gonna remind them what the why is, so the kids are gonna grow up not resenting you, you know, working hard, but actually appreciating the, the impact that you're making on the world. Those are same action but two different feelings. Michael: Right, but there are, I imagine, some limits to that, right, of you could make the decision to, okay, I'm gonna work hard on my business, so hard that I don't have conversations with my kids. I don't see them for weeks on end, days on end, right?

30:21 There is some, right? You have to find what works right for you, right? It-, I think what you're saying is there's an alignment, it, Jay: 100%. Michael: question you have to answer, and part of that alignment question is how you communicate that to your family and how your family communicates it back to you, right? Of like, this is, okay, you know, this is a time where I, I need to bear down, I need to spend a little bit more time with my work, and that might mean that, you know, instead of having a coffee date every day, we're gonna have it, you know, three days a week or one day a week for this temporary period of time while I focus on this, and here is why I'm doing it, right? Jay: 100% Michael: And so that there's, it, I think what, what I found over the years is that being clear and being honest with your kids, doesn't matter the age, of like, "This is something that's important. Here's why." Right?

31:12 You have to give them the why. I think it's easy for us as parents to be like, "Okay, I am not gonna be home tonight because I have a work event." Jay: "I have a meeting." Michael: Right, "I have a meeting," whatever. It's like they don't care. Jay: Meaningless. Michael: They don't care. They don't go to meetings. They, they go to school, right? You have to tell them why that's important. Like, why are you doing it, right? I'm doing this because I'm, you know, I'm building a relationship. Just like you build friendships, I'm doing this for work so that I can build something new with our business so that we can do these things, right? You have to give them the story behind it, right? Like, they understand stories. They don't understand technical calendar details. Jay: 100%. And, and, and also there are seasons in life. That's also, it's good to explain that, okay, there are some times where dad is super busy, and then because, and you can explain that.

31:59 You can explain how your business may be seasonal. You, or maybe there's a cycle in the economy where right now it's like your, your industry is hot. You're, you're bu-, you're building data centers right now. You know, it's, Michael: Sure. Jay: you're like, and then eventually it's gonna slow down. And, you know, Michael: Yeah Jay: we were slow, like, five years ago. Now, like, kids can understand. Michael: Yep. Jay: Just give them the benefit of, you know, information, and give them the benefit that they can understand things. And knowing that, hey, down the line, my goal, bec-, listen, if I'm doing a good job, if I'm working hard and doing a good job, eventually my goal is to that, that time, money, you know, kind of trade-off is gonna go the other way.

32:39 Right now I'm, I'm allocating more time to, so I can earn. Eventually I'm gonna willing, willing to, you know, give up a little bit of money so I can spend more time. So that money calcul-, my time calculation is also seasonal, so there's going to be a period. Give them a, a look forward that, hey, you know, like in a year or two, this is my plan, this is my goal. And then align them with you. Let them support you. Give them, you know, give them as… And same thing with your spouse. A lot of people just don't talk to their spouses. They don't tell them everything. You know, so of course they're not gonna tell anything to their kids, and of course the spouse resent them, and the kid resent them. And, and then they build this big business, and they're successful, and it's like, "Why are my kids not talking to me?"

33:19 Well, because they never, you know. They, they, you, you made it a choice, and you, you, in your mind you're doing it for them, but they're thinking you're doing it for you. So that's where, like, that why is so important, and needs to be big. You know, yes, why having for the family is great, but also bigger than that. Michael: Yeah, absolutely. And I think what's important too is you touch on this of it's not just explaining to them in the hard times when things are, when you're really busy at work, like, "Why aren't you there?" But also in the good times of like, "Hey, we're spending a lot more time together right now. We're doing all these fun things." Like it's end of summer, we're doing all these things, like, but it's not always going to be this way. There are gonna be times where I'm gonna have to put a little bit more time into work.

34:01 And it also gives them some expectation of what life could be like, right? 'Cause they are eventually gonna grow into adults and get jobs and d-, do their own thing. And they might think that, okay, well, if dad is home, you know, all the time or always doing fun stuff, like that's how life should be, and it might not be that easy, right? Or vice versa, dad's never around, right? That that's what's expected, and then their kids end up with the same experience. You know, to, to break these cycles, it is helpful to be honest with them, and it's not always easy to be honest with your kids, right? Sometimes you just want to protect them, and that's okay, but like sometimes you just need to tell them why, give them the reason.

34:41 Jay: And, and honestly, I don't think it's okay because I think so-, we're going into that other theme around, you know, protecti-, protecting versus, you know, strengthening. You know, too much protection weakened, softens, as opposed to giving resilience. But I wanna just take a step back, you know, w-, you know, yes, communicating to understand what's going on in our life, in our family life, you know, what's going on with our dad. But also, you wanna give them a higher goal because if, you know, w-, you see this a lot in the succession game. So a lot, there are a lot of people that are very successful that build these large businesses that cannot get their kids to take over or to, to participate because they resent the business because they accuse the business for taking their dad away or, or taking, you know, their time away.

35:36 So if that parent had explained much that business is gen-, how much impact that business is having on the people in that business, on the customers, on the world, how, what is the, what is the social benefit of that business on the world, the kids will feel motivated. They'll feel part of that mission. They'll feel part, like, "We did that." Like, "We also impact because this is our dad, and then our family does this, and then our family, our family doesn't just clean, you know, the pipes. Our, our family saves lives. You know, because if we have clean pipes, we, we have less diseases, we have productive population, we have all these things that happen because of our, our dad's company, and then we do this."

36:25 And so they take on the mission of the, the, the, the father as well as the owner, and they don't resent that business the way they, you know, they resent it if they don't know. Michael: Right. If there's anything I've learned over the years, it's that kids want to feel included, right? Whether it's with their friend group, but also with what their parents are doing, what their, what their parents might be building. And if their parents are running their own business or they are, you know, whatever their job might entail, you know, if they can feel included in that, and that doesn't mean you put them to work necessarily, right? You're not, if you're cleaning pipes, you, you might not be sending your kid out to go clean the pipes when he's eight years old. But you can start to teach them the impact of what your work does, like you said.

37:07 And, you know, it's… You talk about resilience and independence and giving them agency and ownership. Like, they have to feel a part of something in order to, to get those feelings. And I'm, I'm curious, like, how do you actually teach that in your, you know, ordinary day-to-day family life? 'Cause I imagine for you, I don't see you as the kind of person who's like, "Okay, we're gonna have a formal lesson today. Like, we're gonna bring out the chalkboard and, you know, I'm gonna give you a lecture for 45 minutes." Like, how do you raise your kids with ownership and resilience and independence and agency and those types of things just on a day-to-day level? Jay: Yeah, so like you said, kids wanna be included.

37:48 So responsibility is probably the first thing you can prov-, you can give them, which is just give them small tasks around the house. You know, if you're cleaning, give them a towel to clean. If they're sweeping, give them a little broom to, to br-, to, to, to do. Get them parti-, I, I remember I have pictures of my daughter, she was probably two, she could barely walk, and then she's has a little broom, and she's brooming around the house. She's cleaning, she's cutting things, she's… You know, so you give them these little jobs, and then you, you know, you try to expand the catalog of jobs that they do. So you give them like true jobs, not like playing, you know, true things. Now your job is to do this. Now your job is to organize your room. Now your job is to, you know, do the, broom this thing or, or do things around the house.

38:33 And then over time, like in our house, we don't have a cleaning person. We don't have a gardener. We don't have a, you know, any, so our kids do all that stuff. They have a schedule of chores, and they do all those things, and we don't pay for those things. They're just part of being a, a part of a member of our family. Everybody participates. There's, there's a, a schedule, and everybody knows their task and, and they take care of it, and we don't have to talk about it. And so that's responsibility for me is the first thing. The second thing is resilience. Resilience comes from essentially allowing them to fall and, and, and stand up. You know, allowing them to experience things and hurt themselves and, you know, get up and do things.

39:19 So not being there for everything. Allow them to carry things. Allow them to, allowing friction to happen and not taken away. Like one of the thing, I'll give you an example. Probably it's gonna be controversial, but, but, but if you in my mind, if you have pouches of food when kids are little, and if you have those Gerber jars in your house, and you have crackers, and you have those cheese sticks, you're losing the game. There's no reason for kids to be snacking all the time. Let them go hungry. Hunger is good for them. They can go eat from meal to meal. There's no point for kids to have, like their mom having a bag of snacks going around all the time.

40:04 I'm, you know, like I might be weird, but to me, that's a form of resilience. Like, if you're hungry, it's fine. It's okay. We're not gonna die. We're gonna get home, and we're gonna have our dinner, and we're gonna have our lunch, and we're gonna have our, you know, thing. So, so finding these opportunities and, and for friction and then not stepping in and not creating this cushy, comfortable, you know, if there's an opportunity for them to walk, let them walk. Let's not drive. If there's an opportunity for them to carry stuff, let them carry stuff. Let them carry their own bag. Don't pick up their bag. carry their own stuff. Don't do that. And, I mean, if they fall, let them get up. If they want… so, to me, those as early as you can and, and give them responsibility, resilience, those, those two are, are kinda you can do as early as possible.

40:54 Agency is a little bit later. Once you start kind of like, you know, giving them opportunities to kind of like notice things and solve problems, that's a kinda like a being aware of your world and, you know, remind them, "Hey, you could solve this. Hey, you could do this." What are the other qualities that we talked about? Michael: Well, I guess we… I mean, those are the big ones was like resiliency, agency, responsibility. I think you've, yeah, so you, you've covered those and it, it's super interesting. I'm not sure I agree with you on the hunger part. That's, no, that we're, we can, it's okay to agree to disagree, but on the responsibilities part of like carrying your own bag, of cleaning up after yourself, doing those things, creating those habits early, it's, it can be very easy to default to spoiling your kids of being like, just take care of everything for them.

41:52 But the earlier, you know, once they reach a certain age and earlier they can start to learn some of these lessons, you know, the, the easier it is for them to adapt, the more time they have to start to figure those things out, right? Like, when I coached hockey, once kids reach a certain age, I wanted them to carry their own bags, right? Carry their h-, of, of hockey equipment. And, you know, I had a season where, you know, first part of the season, the kids were definitely old enough, strong enough to be able to, to carry their bags, but they're still having their parents do it. Some of the kids were having their parents do it. And for me as a coach, you know, yeah, I'm teaching 'em to play hockey, but I'm really teaching them how to, you know, take the next steps in life, how to become more responsible, how to become good teammates, how to become good people and great sportsmen and, and what have you.

42:41 And I wanted to teach them that, you know, your parents are already doing so much for you, getting you to the practice, paying for you to play hockey, right? Cheering you on during the games. At this point in time, you're capable. You should take your own bags, right? And, you know, when I first tell them like, "Oh, you should be carrying your own bags." They're like, "Why? My, my parents will carry it for me." Right? That doesn't get anywhere. Again, it comes down to like, you need to explain why sometimes, right? Like, once you give 'em the reason why, buy-in is really quick, right? Like, everybody's carrying their own bags all of a sudden, right? Like, once I explain like, "You are old enough now. You are responsible. Like, you know, it's good for you to do some things too.

43:24 Your parents shouldn't have to do everything for you. You're ready to take that next step," right? "Believe in yourself that you can do it," right? It's like they don't actually care about carrying their bags. They, they don't even realize it's on their shoulders by the time the, you know, the next practice comes around. They just do it. It's so, you know, the, the importance of giving your kids a responsibility, right? But in a way that is not only age appropriate, but makes sense to them. Like, they have to understand the, the, the reasoning behind it. Jay: So, so, the other, the other thing that we talk about sports here, what, two things that I recommend people do as quickly as possible, which is any type of self-defense training and martial arts, whatever. I highly recommend that as soon as possible.

44:05 Three, three-year-old, four-year-old, put them in taekwondo, let them have a good time, and then switch to jujitsu or judo or kickboxing or whatever. But kids need to know how to self, to defend themselves. There's huge amount of confidence, huge, and also martial arts is, you know, by design, has this discipline has values built in, which is discipline, you know, you know, self-reliance learning skills to defend yourself. Just that's like the first concept of like, you know, self-reliance is defending yourself. You know what I mean? And don't die, you know, to be able… And then the other one is businesses. So I'm a big proponent for kids to start businesses as early as possible.

44:50 You know, I have the, you know, the, this program that I do with the kids business school where teach kids how to start their, you know, make money, you know, you know, as early as, as, as possible. Six-year-old can go and start a lemonade stand or cupcake stand or cookie stand or whatever and, and start selling. That also gives them a sense of agency and a sense of like closing the loop in the mar-, in the real world where the market says whether your product is good or not. And that's also brings ex-, a level of, of responsibility, a level of resilience, and a level of agency, which is essentially observing and reacting to, to the world. Michael: Right, and they get some realistic experience, right?

45:33 Actually, I think to me is what I love about what you're doing with the, the Kids Business School of you, it's, you know, you could, kids can read about some of this stuff, they can hear about some of this stuff, they can see it on social media or whatever, but until they actually do it and try it themselves and, like, put in the time and the work and the effort, they can start to appreciate, like, what it takes to succeed, and maybe not everything is handed to them. Or, you know, maybe they're, they find what they're good at or what they really enjoy doing. Like, giving them that experience to find out. Like, that to me is maybe the most valuable piece of it all, right? The, everything you talked about, you know, getting some of that agency and learning responsibility and things, like, those are all super important too.

46:15 But, like, to me, getting that experience, that practical, real-world experience is just so cool. I think what you're doing is, is awesome. So I want to go from the super cool and super effective to the really weird, which is the speed round. Five quick questions for you. Nothing to do with anything, starting with what's the first kid show theme song that comes to mind? Jay: Garfield. Michael: Garfield? Oh, I love that. My favorite cartoon character of all time is Odie, Garfield's dog. He, he's the best. I don't know why. I've just always loved him. I think he's the coolest. Jay: Happy. He's a positive, positive, happy, yeah. Michael: Yes, absolutely. What was your very first job? Jay: My first job was selling, you know, cookies and, and stuff on the street, you know, but, but job, job, Michael: Oh, wow.

47:01 Jay: real job is, is, is bank, in the bank. I, I was em-, a bank emlpoyee. Michael: Oh, great. I, that was also my first job out of college was working for a bank. Would you rather spend 24 hours with a toddler-sized T-Rex or a T-Rex-sized toddler? Jay: A T-Rex toddler. Michael: Why is that? Jay: Good question. I, I can deal with toddlers. I can't deal with T-rexes. I understand toddlers. Michael: That's fair. Jay: They're predictable. Michael: That's fair. Jay: Toddlers are predictable, not T-rexes. Michael: Yes, they will tire out at some point. Jay: Yeah. Michael: What's your go-to karaoke song or the one you would sing if you had to? Jay: Losing My Religion, R.E.M.

47:41 Michael: R.E.M. Awesome. Great song. And finally, what's the weirdest thing you've ever carried around in your bag, briefcase, or pockets? Jay: Ah. What are those coins where, you know, you, you will die kind of coins? I don't know if you're familiar with the… Michael: Like a challenge coin kind of thing? Jay: No, no, just say a remember you're gonna die, you know, coin. Michael: Oh, just a reminder. Okay. Huh, interesting. Not sure I've seen that. Very interesting. Well, that was cool. I appreciate you obliging me here with th-, with that speed round. Before we wrap up, Jay, I want to give you some space to point listeners to what you're working on with Acquisition Collective, Raising Lions, Kid Business School, anything you kind of want to leave them with. Where should people go to, to learn more? Jay: Yeah, I appreciate it. So I have two worlds.

48:22 I have the business acquisition where I a, a business acquisition world where I teach people how to buy small businesses, mid-size businesses, and I do advise as well large companies to do M&A. And then I have my other world, which is the Kids Business School, where we teach kids how to start and grow businesses. You know, it's a dojo-style environment where they earn their white belt all the way to black belt through running, growing real businesses in the real world. Michael: And where can people find those? Jay: Yeah, absolutely. So acquisitioncollective.biz is the, you know, Acquisition Collective website, and then kidsbusinessschool.com, just like we say it, and that's the Kids Business School.

49:04 You can do it online or offline. Michael: Awesome. And we'll put links to both those in the show notes. Jay, I really appreciate you coming on today and talking with me and being so honest about what it takes to build ambitious things, but doing it in a way that allows you not to lose sight of the people you're building them for, right? There's always this connector between what you are trying to build and who you're building it for. And I appreciate that reminder that, like, meaningful work and still being present at home for your, your wife, for your kids, they don't have to compete. You can actually kind of bring them together. But it requires some clarity. It requires boundaries and choices that, you know, reflect, you know, what really matters most to us.

49:48 So thank you again for, for taking the time to chat with me today. I appreciate it. And finally, before you go, if you're a dad listening to this and you find yourself in between, navigating a season that feels different, head to gaptogig.com, subscribe to the Gap to Gig newsletter. Comes out every Friday, and it's a quieter space to reflect on work, life, and what really matters right now. And if this conversation resonated, consider sending it to another dad who might need to hear it. Until next time, I'm Michael Jacobs. Thanks for showing up and listening to Gap to Gig.