How to Build a Cash-Flowing Business That Doesn’t Rely on You with Jay Bourgana – EP 301

Interview with Jay Bourgana

How to Build a Cash-Flowing Business That Doesn’t Rely on You with Jay Bourgana

One of the great ironies of entrepreneurship is that the very business meant to create freedom often becomes the thing that takes it away. When every decision, every approval, and every problem flows through the founder, the business becomes another demanding job instead of the wealth-generating asset that creates the freedom and lifestyle it was meant to provide.​

That’s why I’m excited to welcome Jay Bourgana to the podcast. Jay is an entrepreneur, business acquisition expert, investor, and founder of Acquisition Collective. After building and exiting multiple companies, Jay has spent years helping entrepreneurs acquire, scale, and operate cash-flowing businesses while creating systems that allow owners to build real wealth without becoming trapped inside their companies.​

In our conversation, we discuss why people—not systems—are often the biggest constraint on growth, how to build businesses that create freedom rather than dependency, and why developing future leaders, investing with simplicity, and passing down core values matter far more than simply accumulating wealth.

In this episode, you’ll learn:

Why acquiring established cash-flowing businesses can dramatically accelerate financial freedom while avoiding many of the risks of starting from scratch.

How to identify when you’ve become the bottleneck in your own business and the leadership systems that create freedom without sacrificing growth.

✅ Why true legacy has less to do with transferring wealth and more to do with teaching your children resilience, responsibility, financial literacy, and purposeful living.

Featured on This Episode: Jay Bourgana

✅ What he does: Jay Bourgana is an entrepreneur, investor, mentor, and founder of Acquisition Collective, where he helps entrepreneurs acquire, scale, and optimize cash-flowing businesses. Drawing on experience in commercial banking, global manufacturing, business turnarounds, real estate, and multiple successful business exits, Jay specializes in building companies that operate without depending on the owner. Today, he also mentors founders on acquisitions, leadership, wealth creation, and intentional parenting, helping families build both financial capital and lasting generational values.

💬 Words of wisdom: “Whenever people are calling an owner for decisions, that’s a bottleneck.” – Jay Bourgana 

🔎 Where to find Jay Bourgana: Website | LinkedIn | Facebook | Instagram | YouTube

Key Takeaways with Jay Bourgana

  • Why Entrepreneurs Build Jobs For Themselves
  • The Power of Buying Cash-Flowing Businesses
  • Jay’s Journey From Banking to Business Acquisitions
  • How Founders Become the Bottleneck
  • How To Prepare Your Business for a Successful Exit
  • Finding Purpose After Selling Your Business
  • Investing After a Major Liquidity Event
  • Building a Multi-Generational Legacy
  • How to Connect with Jay Bourgana

Inspiring Quotes

  • “We rise to the level of the people around us.” – Jay Bourgana
  • “If something lived for 30 years, it’s more likely to live another 30 years.” – Jay Bourgana
  • “Technology is an accelerant, but it’s not really a reason for a business to succeed or to fail.” – Jay Bourgana
  • “Whenever people are calling an owner for decisions, that’s a bottleneck.” – Jay Bourgana 

Resources

Want My Team’s Help?

  • Tax Strategy Masterclass
     Learn the 28 most effective tax strategies the wealthy use to save thousands.
    lifestyleinvestor.com/tax

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Read the Full Transcript with Jay Bourgana

Justin Donald: What's up, Jay? Welcome to the show.

Jay Bourgana: Hey, Justin. Thank you for having me.

Justin Donald: Yeah, this is a blast. Well, you and I got a chance to hang out. We had done a Lifestyle Investor meetup in, let's see, Miami, and we went to, what is it? Mila's?

Jay Bourgana: Yeah.

Justin Donald: Which is just an incredible spot. I mean, supposed to be the top-rated restaurant out there. And we had invited some PEF Ultras to join us. And so, we got a chance to connect more, and we run in several similar circles. And it was just fun getting time, getting some good… I call it carefree timelessness, just hanging out.

Jay Bourgana: It was a great event. I appreciate you putting it together, and it was a good group of people, high quality group of people.

Justin Donald: Yeah. I mean, one of the things that we talk a lot about, I was sharing this, I was talking with someone before, but there’s a lot of masterminds out there. And the common thread that I have noticed is most of these people kind of live on what the mastermind makes, and so they'll take whoever will pay whatever the fee is. But I had this other idea. We've got passive income, so I didn't start Lifestyle Investor because I needed to make money. So, then I was like, "Well, why don't we just, like, up the bar and just only bring in people that we think are a heck yeah and really fit the bill, and we can be super picky?"

And that has really played well because, any time someone new shows up to an event as a guest or someone shows up as a brand-new member, they're always like, "Wow, every single person I could spend more time with." And it's like, yeah, that makes a lot of sense because when the threshold is high, when the standard is really high, it's amazing who you attract and then who you retain through that process.

Jay Bourgana: Yeah, 100%. I think there's definitely, it makes complete sense when you think about it. We rise to the level of the people around us. So, when you elevate the quality of the people in the room, your level, you have to rise to that level. And that's what matters really. And that creates that as you do that, it changes your life, improves your life, it creates this value, and it creates retention into the group as well. So, yeah, makes a lot of sense.

Justin Donald: Well, I love that you were able to join us and meet some of our people. And it was really a pleasure being on your show just a moment ago. So, I'm so excited. Like, we're kind of going back to back here, and I'm just so excited to get into questions I have for you because you're a wealth of knowledge on the business front, but also on the parenting front. So, I want to touch on both sides of things. But I do want to kind of talk about how you got to where you are. You've had some exits, and you've been very successful in your endeavors. And you really believe in something that I believe in, which is the beauty of cash-flowing businesses, and really, like, not even chasing exits.

Like, get a good business that's healthy, that cash flows well, and it's amazing what can happen. And so, I kind of want to start there on your thoughts around this. Because when you acquire an established business with predictable cash flow, with financial freedom, with more lifestyle flexibility, you can keep doing it longer and longer. So, why do you believe so many entrepreneurs end up building jobs for themselves instead of true assets?

Jay Bourgana: It's a very good question. I think a lot of it is just fear, and a lot of it is avoidance of pain. I think training, coaching, and retaining people is not easy, and it's a skill that you have to develop as an entrepreneur. Getting rejected by somebody who you trained for five years, and you poured into, and then that person leaves because there are better things, better pastures, it kind of breaks your heart. And a lot of entrepreneurs don't like that feeling, so they try to avoid it. And I think the entrepreneurs who are the most successful are the ones that make peace with that, and they just pour into people. They're 100-zero type person. They put 100%, they expect nothing, and they just keep developing.

They fall in love with the concept of talent acquisition and retention and development. And it's rare. It's rare to find someone who's technical, good at what they do, but also has this component of people.

Justin Donald: So, what makes acquiring a cash-flowing business such a powerful accelerator for someone who's seeking more freedom in their life and more optionality in their life?

Jay Bourgana: Well, there's nothing like a cash machine. You know? They're not that many of them out there in nature. They don't exist naturally. It's very hard to build. It takes years. We talked about how many years and how many mistakes you have to make and how much sacrifice you have to make to get to a level where it scales enough where the business has the right team and the right mix and the right management to go on its own, and then eventually kind of keep growing. So, if you're acquiring a business that's already gone through that sequence of the growth phase, the stabilization phase, the profitability phase, you're essentially shortcutting the process.

And because they don't exist, because there are not that many of them, they tend to, you know, if something lived for 30 years, it's more likely to live another 30 years. So, if something's been around for only one year, there's less likelihood of that happening. Yeah, so I think having, to me, I think of it, I heard one time that a date farmer, when they plant an orchard, the person who plants the orchard never sees the fruit. It takes about 40 years for a date orchard to mature and start giving out fruit every year. So, the person who plants it never gets to see it. And that stays in a family for generations. You don't sell something like that. And so, to me, if you can shortcut the process and buy an existing orchard, that's the way to go because it's so much hard to build, to plant and grow and maintain.

Justin Donald: Yeah, totally. And Warren Buffett says it best, like, buy great businesses at a good price, right? And instead of trying to reinvent the wheel or get into something that you have no idea what you're doing and starting from scratch, as opposed to, like, you may not know what you're doing, but it's actually working. There are systems in place. So, let's talk about you and your story. Like, how did you get to the level you're at? I know you've had some business exits. I know you've been in at least a couple of different businesses. Maybe it's more than that. So, I'd love to hear some of your journey, your path, how you got to where you are today, and how each of us can hang out in a post-exit founder group with, I'm always sensitive on what we share openly, but one of the higher-tiered groups in the ultra-category.

Jay Bourgana: Yeah. So, I essentially came to it the long route. I wasn't lucky to be around people that understood entrepreneurship or understood money. So, I grew up as a young person seeking that information and trying to figure it out from first principle. And the first question that I asked myself when I was a teenager is, "Where is money? Money's in the bank. Let me go work for a bank to learn how to make money." And so, I went and worked for a bank, and I observed the people who had money and the people who didn't have money. And I noticed that entrepreneurs and business owners had a different lifestyle than people like high-earning executives or employees did. So, I said, "Okay, I need to learn entrepreneur."

But in my banking experience, I got to see P&Ls. I got to see how businesses are run. I got to finance acquisition. I had to help people with their liquidity needs and so forth. But I knew that I'm not going to build a bank. That wasn't something I'm going to do. So, I needed to go somewhere else to learn how to operate something different. So, I went in manufacturing, and I learned operation from the ground up, supply chain management, and my clients were the Walmarts and the Targets. So, I learned the hard way where if you make a mistake, they charge you back with like hundreds of thousands of dollars. So, I learned a lot of like how to operate at a high level, how to execute at a high level, with high standards.

And then I got the opportunity to go to China for a project, and I ended up staying there for about five years, ran a large operation that shipped about $1 billion worth of products to the US, to all the different retailers. And I got to manage in a different culture, in a different environment, and I noticed that pretty much we're all the same. All people run the same way, and you can lead teams the same way in the US than you do in any other country. And that gave me a lot of confidence in my executive managerial competence. And so, post-2008, I came back. Everything after 2008 became a turnaround target. Everything was a mess. People were looking for efficiencies, for ways to kind of like how do we work in a new environment?

So, I spent about five years doing turnarounds, manufacturing, distributions, all kinds of companies. And I saw essentially the same patterns over and over. This lack of culture, this lack of having the right team, the right people, the processes. I would say 80% of the challenges in any business are people-oriented, and probably 20% between systems, hardly ever has any technology. Technology is an accelerant, but it's not really a reason for a business to succeed or to fail. So, after 10 years living in hotels, I wanted to come back and have a place to live, and I was looking for a place to live. And a friend of mine who's a CFO told me, "Hey, I was looking to rent a place on the beach,” and a friend told me, "Hey, you should buy instead of rent because we just printed a lot of money in 2008 to 2013, and there's going to be a lot of inflation in assets." And it put the real estate bug in my head.

So, I went and bought real estate, but also started a real estate company, and then started scaling. I came at the time when the Zillows and the Realtor.com and the Redfins were just starting. And they didn't have any use for their leads, and we end up taking those leads and converting them into money. It was early days, and eventually I saw that the cost of acquisition was going up, so I started doing acquisitions to increase the amount of LTV out of the clients. And so, we started that acquisition engine. I looked at acquisition from my banking days as a financing acquisition. I looked at them in my consulting days in turnarounds as well as integration, and now we're dealing with the sellers, and we're going through that dynamic of, like, the psychology of the seller.

And in the process of buying companies, we had competitors, and one of the competitors saw us and saw who are these guys, and they essentially made us an offer to acquire us. They bought 70%. We kept 30. We kept doing acquisitions with them within their platform. And then when COVID happened, they stopped. And so, that's when I sold the rest of my shares and essentially retired in Hawaii for a while until I found that I needed more purpose, and I had my post-exit blues. And then I decided to come back and come back to the acquisition role and do some roll-ups and so forth. So, that's kind of like how I end up in this acquisition space.

Justin Donald: And I love hearing this because the more that you share on this subject, like, the more people are going to recognize that you're an industry expert, right? And so, like, as you're buying businesses, like, you're talking about buying cash-flowing businesses because you're buying cash-flowing businesses, right? So, I think that's really important. And so, I do want to talk a little bit about, like, designing ownership for freedom and not burnout. Most people that get overworked or become a slave of the business that they own, burnout creeps in. Maybe they call it something else. Maybe it's a loss of the love of the game. But ultimately, it's that. You're working more than what you want, or what you envisioned business ownership like is different than what it's actually like.

And so, I want to talk about how we structure and operate a business so it generates cash flow, without requiring constant owner involvement. That's the one thing I've loved is, like, building these businesses that didn't require me. So, what do you think are the biggest warning signs that a business owner has unintentionally become the bottleneck of their company?

Jay Bourgana: Yeah. And I mean, any time decisions are... There are a lot of decisions that are waiting for the owner to be made for things to move forward. That means the owner is a bottleneck. And so, any time the owner's phone is ringing, and his inbox is full from his people, especially the inbound stuff, within the business, that's a problem. So, in an ideal world, your people should not need to call you, should not need to email you, should not need to wait for you on decisions. They should know what to do and how to do it. So, you should be calling them to just check in, but they shouldn't be calling you for decisions. And I think whenever people are calling an owner for decisions, that's a bottleneck.

Justin Donald: No, that's good. What are some of the first changes that you make upon acquiring a company to, like, increase cash flow or reduce the owner's day-to-day involvement?

Jay Bourgana: Yeah. So, just trying to understand the team, understand the owner's involvement first, and understand what they do, and then understand the team and see what capabilities the team has and what's missing. Sometimes there are hidden capabilities. Sometimes there's a lot of talent within the team that has not been given the opportunity to lead and to manage, and they just need the opportunity turned on to activate. And so, to me, I'm like, I just map out what the role of the owner is, and I try to give some of those decisions, reallocate the decision-making, reallocate the roles. And then I'm always in the search for a bench. So, any time I'm interviewing or hiring, and I also train people who interview and hire to look for that managerial, that middle management, and higher management bench.

And so, I remember, like, many times where I interview people and I tell them, like, "Listen, in a year, you're going to replace me, you're going to be in this seat, and you're going to be doing this role." And nothing excites me more than that, to give that possibility to somebody and then see that growth in them. So, I think, like, one of the things that we don't do very well in that we used to do back in the day, like old GM, old Ford, or like old European companies, they used to have these academies within the company where they're developing people. They had their own like GE or Mercedes. They had their own management program that will take raw talent and turn it into a GE-caliber executive or a Ford-caliber executive.

And I always felt like every business should have that, should have that development program, understand what is their ideal talent profile look like. From an ICP, what does the ideal talent profile look like? And then what is the path that we need to give this person or that talent to rise to what we want it to be? So, for me, there's a really great book by Daniel Pink called Drive, and he talks about the three things that are needed to motivate people, and none of them have to do with money. There's mastery, which I call growth, and giving the people the opportunity to learn and grow. There's autonomy, giving people the freedom and the responsibility to call their shots and make decisions and learn. And then purpose, and that's one thing that a lot of companies don't do is articulate what is the reason to exist for a business.

Any business that's out there in the world has a reason to exist. There's some good in the world that it does, but we need to articulate that. What is that value for that business to exist, and how does the impact that we make on our clients, on our community, on the people around us? Now, the owner, the CEO, the founder has to articulate that to the people and continuously repeat that message so people understand that when they wake up in the morning, we are making the world a better place. We're changing. We're having an impact. There's someone out there that need me to get up and work hard and do this. And I think a lot of companies don't do that, and then so they're missing that juice that activate people just a tiny little bit more, that extra 5%, 10% that gets people juiced up to come to work.

Justin Donald: That's good. Well, let's fast-forward the movie a little bit. So, let's talk about the exit here. And there's pre-exit life, there's post-exit life, there's strategy for founders to maximize and optimize value. So, I want to talk about kind of navigating this pre-liquidity event, so we can get the most out of it, wring the rag dry. So, what are some of the most overlooked steps that founders can take to increase the value and attractiveness of their business before an exit? You've had several now, so I would imagine you probably did some things wrong in the beginning and did a lot more right later on.

Jay Bourgana: Yeah. Well, so my first one... This is actually a good question, a great question, actually. My first exit, I wasn't planning on exiting at all. It was a cold email. Someone cold emailed me, and I spammed the email, and then 10 minutes later, I got curious and brought it out of spam, and then says, "Okay, tell me more." And I had a conversation on the phone with someone, and then that person came the next day to my office. We spent two hours talking, and then 30 days later, I had sold to 70% of my business.

Justin Donald: Wow.

Jay Bourgana: So, it can happen real quick, and you haven't planned for it. So, obviously, you can imagine that the due diligence was painful, because we weren't ready. But we were good enough. We were exceptional enough that they really wanted us, and they didn't really care. So, I would say to be prepared, just understand, have clean books, obviously. That's something that a lot of businesses don't do, work with a really good CPA or a good financial CFO, like fractional CFO. Be prepared. Like to me, I think people have to build a business ready to sell. And from day one, you're structuring, the way you structure your financials, the way you code things, it needs to be like the best in class. So, now if I go into an industry, now I have a completely different mindset.

When I go into an industry, I always look up the public companies in that space, and I always look at their financials. I look at their P&L. I look at their balance sheet, and I copy the same structure that they have.

Justin Donald: That's good.

Jay Bourgana: Even for a small business. So, when a private equity or some group comes and looks at us, I'm like, "Oh my God. This is incredible. Why do you code this way? Why do you look at it this way?" And we explain why. And so, we wanted to emulate the best in class. So, to me, financials are important. Have a data room. Have your processes ready. Business is about client acquisition and retention, talent acquisition and retention, and capital acquisition and retention. And the financials are going to tell the story of capital efficiency. Your balance sheet's going to tell a lot about how efficient your business is.

And then you want to have systems for clean systems for how you acquire customers, understand what your CAC, understand your LTV, understand your ICP, understand how you acquire, how you retain, understand your churn, have a strategy for reducing the churn, understand what the industry standards are, and where are you, where do you play in that number. Same thing on the talent acquisition. A lot of business owners understand that client side, but they have no structure on the talent side. So, like a lot of times you talk to companies, and you say, "Okay, if I give you 1,000 customers today, I give you a choice between 1,000 customers today and 1,000 talented people for your team today, which one would you pick?" And they'll say, "Oh, I'll pick the talent because we have a shortage of X, Y, Z."

And I said, "Okay, great. Then how many salespeople do you have on this side?" "Oh, we have 10." "How many recruiters do you have on this side?" "We have none." How much money are you spending to acquire talent? So, they don't have any systems. They don't process. So, have the system, have the process, have the SOPs, have a story that you tell the marketplace why people should join you, and stay with you. And all that stuff, that packaging as a whole makes you very attractive to a strategic or a financial partner because you can clearly tell the story of why they should acquire you, why you're differentiated. The person who's coming to buy you, they're looking at 5, 10 other companies, and they can easily see how differentiated you are from everybody else.

And you can elevate your multiple. You can elevate. You can simplify the terms that you're going to get. You can enforce more. You become the platform for the whole thing, and it makes you very attractive.

Justin Donald: Yeah. I mean, that is so insightful. Thanks for walking through that. That's awesome. So, after working with founders that have experienced, like, let's just call it a liquidity event, they've had some sort of an exit, what have you learned about navigating the identity shift that these founders have, and even just, like, finding purpose again? A lot of people lose that after the exit. It's like their ego is so tied up in their business, and who they are is the business founder versus, like, who they really are as a person. So, I'd love to hear your thoughts because I know you work with a lot of people. Well, first off, you went through this yourself.

Jay Bourgana: Myself, yes.

Justin Donald: And then secondly, I know you work with a lot of people that are going through this.

Jay Bourgana: Yeah. So, I always remind them, there's a concept that I heard Tony Robbins talk about, which is kind of like the drivers, the personality drivers. So, there are, like, four personality drivers. There's certainty, there's variety, there's significance, and there's love and connection. So, when we don't have anything, we want certainty of shelter and food and a life for ourselves. We want to matter, significance. We want to be number one, or you want to be, like, you want to prove to your dad that you are great. And then you got love and connection, and you have variety. There are some people that are driven by variety.

Now, a lot of entrepreneurs tend to have that certainty and significance drivers, and that can push them to build big businesses and succeed in life and so forth. But then once they sell, they don't have that need for certainty anymore, and they don't have that need for significance because they've got that success and everybody knows they exited and they're successful. So, they lose the drivers. And so, a lot of times I ask them, it's like, "Okay, when you look back when you were running the business, what are the things that you really enjoyed about the business?"

And a lot of times, for me, I'll give you an example, just for me, what I enjoyed the most was I was in the game, and I was constantly learning because I'm always solving problems. When you're in business, you're constantly solving, and the environment is always changing. New competitors, new economic cycle, new trends, customers are saying different things. You constantly have to adapt and evolve and learn new things. So, I enjoyed that part where I was exposed to a lot of... I was forced to learn. And I enjoy learning anyway, but I was forced. I was in an environment to continuously learn.

And then the other part that I enjoyed was the development of people. I loved seeing the transformation in my people, seeing the transformation in my suppliers, seeing the transformation in my clients. So, I loved that transformation. So, those are essentially the two other drivers that Tony Robbins talks about that are essentially spiritual drivers, that are continuous, that never end. There's no limit to learning, and there's no limit to contribution. So, if you have to transition your life post-acquisition, then how do you design your life where you're constantly learning and adapting and evolving and picking up new capabilities, and then you're also helping others transforming, making an impact, doing something?

So, some people do it by going and acquiring a new business. Some people do it through investing. Some people do it through mentoring and being in masterminds and so forth. Some people do it through coaching and consulting. There are a lot of ways of staying in the game, learning, and constantly improving, and constantly contributing to the world.

Justin Donald: Yeah, that's awesome. And I couldn't agree with you more. And for me, it's the same thing. It's like I love to learn and grow. The more I learn, the more I want to teach. And then I just love people. I love relationships. I love helping other people level up. As I'm leveling up, I love kind of pulling people up with me. It is so fun. And then let's also talk about this, because I feel like this is maybe not spoken about a lot. You start a company, you're totally concentrated in that business, you have an exit. I talk all the time about how entrepreneurs make the worst investors. And there are learned skills, and you can learn them. I think you've done very well for yourself, even post-exit.

But what did you do from an asset allocation standpoint, or what did you invest in, once you got this big windfall of cash? At first it was 70%, then it was the additional 30%. You had previously done something before that, so you've had a number of windfalls, but now it's a different game. You're not running a company. You're managing assets. You're an asset allocator. You're an asset manager, right? So, talk us through that life.

Jay Bourgana: Yeah. And I mean, at the beginning, it was all about tax efficiency, so there's a lot of real estate, the large commercial properties, and the lower cost land areas to maximize the cost segregations and stuff. And so, anything around all the strategies around tax efficiency, I've gone through all of them, the stuff that works, the stuff that doesn't work. So, that was kind of the first phase. And then afterward, it was part stock market and then part operating businesses. I understand real estate, I understand operating businesses. I've invested in public markets. I've had some success in the public markets, so I'm not like a day trader by any means, but I allocate to things that I understand. And, yeah, I keep it simple. I mean, real estate, public, and businesses, cash-flowing businesses.

Justin Donald: And so, what did you do to create income? Because I've got to imagine, like, so any time I… And you've had more sizable exits than me. I've had several exits over the years. Nothing that is like game-changing, but all solid and all have helped me compound to the next level. I think you've had some substantial changes and substantial windfalls. And so, like, when I think about the capital I have, I don't ever want to spend it down. I want to invest it in something that kicks off some sort of a return that I live off of, right? So, if you sold your businesses prior to getting back into buying, rolling up more in your acquisition group, and actually buying cash-flowing businesses, there is this interim.

So, did you put some money in fixed income? Were you living off of dividend-paying stocks? Like, what was the income that gave you the freedom to live? Or did you just spend from whatever the capital pile was?

Jay Bourgana: Yeah. So, I was in credit funds.

Justin Donald: Okay. We love those.

Jay Bourgana: Yeah. And I just sat there during that COVID period. And the real estate was cash-flowing. So, between those two, I was good. I was comfortable. Actually, though, it got really boring. That's kind of part of the reason why I was losing purpose, because I'm like, "I'm good. Let's not do anything." And then after, like, two years, I'm like, "No, I don't like this not doing anything." I mean, literally, I'm in one of the best places on earth in Hawaii. I'm playing tennis every day. I'm playing golf. I'm on the beach every day. I'm literally meditating in this beautiful water. It was just like Obama used to play golf in front of my house every Tuesday. There's no reason for me to not be ecstatic.

But there was a point where it was like I felt, like, empty. I was like, "Why am I not happy? Why am I not..." Like, again, I'm blessed, I'm thankful, I'm grateful. Nothing, but there was something missing. And there's that oomph, that juice for life that was missing, and that was kind of like where I felt like I needed to change. And it took me maybe a couple of years to figure that out, and then another year to decide, okay, I need to move out of Hawaii and come to the mainland again.

Justin Donald: Yeah. That's awesome that you figured that out, and you kind of wrestled with it. You gave yourself time and space to wrestle with it. And I love that you figured out, for you, it wasn't investing. Because I'm the flip-flop. It's like once I got a taste of not operating, I was like, "This is awesome. I love being a passive LP investor. I'm going to invest in a ton of stuff this way." But to a certain degree, like, I still need my people. Like, I need a network, I need a community, I need people that I'm going to learn and grow from. And hence the reason for Lifestyle Investor. It's like, hey, Ryan, who runs everything, he's awesome, Ryan Casey. But, for me, I want to be an artist inside the brand.

So, I don't need to run the day-to-day, but I want, like, influence and intention. I want to learn from people. I want to teach people the things that I learn. And so, without that, I would have way less meaning and purpose in life. There's no doubt.

Jay Bourgana: Yes.

Justin Donald: Before we wrap today, I want to talk a little bit about wealth as stewardship and building this multi-generational legacy. We talked about this a little bit on your show, and you were asking some of my thoughts on it. And I have very strong opinions on this, because I think when you hear legacy, or multi-generational legacy, it's almost always where is the money going? And I think we should be focused on that the least amount. And money corrupts if people don't know how to use it and don't see it as a tool, and consumerism takes over. And so, I really see legacy as passing down values, passing down wisdom, teaching responsibility, talking about things bigger than just yourselves.

In our case, for our family, like talking about things that are bigger than just us. So, I'd love to hear some of your thoughts about how parents can... It doesn't have to be parents, but generally it's like parents, how they're going to use their business ownership as a practical tool for teaching financial literacy and responsibility, because you do this. You do this a lot. You built this incredible group of dads that it's such a fun space to be in with all the things you're doing, all the things you're teaching. It's a powerful group. So, talk about that a little, if you wouldn't mind.

Jay Bourgana: Yeah. It's very interesting. It's very similar to the concept that I mentioned earlier with creating drive in your team, in your company. It's the same thing with kids. It has nothing to do with money. Like, I always ask the dads, "What's the goal? What are we trying to achieve here?" And a lot of times, they're not very clear on the goal and, "I just want my kids to be happy." Well, what does that even mean? Happy one time? Happy all the time? What does that even mean? So, to me, I'm like, "Okay, let's start with that. Let's start with what is my goal.” So, for me personally, my goal is to develop people that are resilient, that are responsible, that are self-sufficient, that are contributing to the world, that understand they're responsible for their own happiness.

They know how to make themselves happy, and they know where… They know that happiness is an inside game, it's not an outside game. So, they can play the inside game. They can play the outside game. So, let's start with that. So, someone who's productive, resilient, responsible, and value-adding to society. Now, none of those things have to do with money. Now, if you create a person like that and you give them a little or you give them a lot, they're going to do something with it. And they're going to be fulfilled because they understand that they're going to be driven by growth, by learning, like we talked about earlier, and by contributing.

So, my goal is to go out, play this game in life, play this game of accumulating capabilities, accumulating skills. I always start trying to teach my kids through video games, even though my kids never play video games. But we always use the video game analogy where you're going through this game, and you're accumulating capabilities, skills. And then eventually, you're going to be able to use those tools to generate value in excess of what you need. And then that excess, what you need, you give back to society, you invest, and then the world gives you more. And so, it's a very simple game. Now, the inside game is you understand that you make you happy, you're in control of your mind.

Happiness is an inside game. You've got to be grateful. You've got to be thankful for who you are. You're good. However, wherever you are, you can make yourself happy and grateful and thankful. So, to me, the legacy piece is secondary. So, as long as I can transfer my intellectual capital, my knowledge, my values, how we do things, how do we play the game of life, and then I can transfer my relational capital. Number one, my relational skills, how to acquire high-quality relationships, and how to maintain them and retain them. And then through my network, I want them to connect with families. I want to connect with people that are high caliber to be inspired by.

And then the capital comes later. The capital is the easiest thing. To me, the capital, I want to teach them how to make capital and then how to allocate it. So, how to make money is very simple with kids. Any six-year-old can go put a table, put a lemonade stand, and start selling. And then if they do it three days in a row or two days a week for 10 months, they're going to see the trends. They're going to see what days people come and what days they don't come. They're still going to see when I get a family with a lot of kids, they spend this much, and then when I get a one-person, they spend this much. They're going to see who gives them more tip, and who doesn't give them. So, they can develop pattern recognition.

They can understand unit economics. They can understand how hard it is to make a profit. And then now every time they make the spending decision, it's from that calculation of how long it took me to make this dollar. So, if my kids are selling $200 a week of cookies on the street, and they're making, I don't know, 60% margin, let's say $120, now when they ask me to go to Disney World or they go, it's like, "Okay you want to spend $1,000 on spending a day or you want to allocate that $1,000 maybe to a vacation somewhere? Or you want to invest it in stock and compound, and whatever? What's the decision here?" Because there's always a give and take here.

So, the earlier you start this conversation, the earlier you start this teaching, the better. So, when they understand the value of the... And it's not about the money, it's about what we do with the money, but you need to understand it. You need to understand how to make it. You need to understand how to save it. You need to understand how to allocate it. And I think the earlier the better, the 10,000-hour thing.

Justin Donald: Definitely.

Jay Bourgana: Yeah. And I think once you develop a human that's capable of understanding these concepts, it doesn't matter how much money you give them or no money at all. They can figure it out

Justin Donald: That is so brilliantly said, and we agree on this on so many levels. And it's part of the reason I resonate so much with the way that you parent, and I love being in a community with you where we're intentionally parenting. And we're intentionally parenting away from entitlement. Because if we're not doing that, the default is entitlement. And so, I love that. Where can people learn more about you and all the cool things you're up to on the acquisition side, on the parenting side? Give us the goods.

Jay Bourgana: Yeah, I'm easy to find. My name is very unique, Jay Bourgana. You can find me on social media. Acquisitionscollective.biz is the community, the Acquisition Collective. You can find it also on YouTube, on Facebook, on Instagram, everywhere, on LinkedIn. So, yeah, easy to find. Ask away. Business, parenting, I'm happy to help.

Justin Donald: Love it. Well, thank you so much for your time. I love closing every episode with a question for our audience. So, if you're watching this or if you're listening, what is one step that you can take today to move towards financial freedom and really living life on your terms, a life that you desire to live? So, not a life by default like most, but a life by design. And I just challenge you to take something from Jay today, put it into practice, and move towards life on your terms. Thanks! And we'll catch you next week.

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Justin Donald is a leading financial strategist who helps you find your way through the complexities of financial planning. A pioneer in structuring deals and disciplined investment systems, he now consults and advises entrepreneurs and executives on lifestyle investing.

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