Why Only 33% of Family Businesses Survive: The Succession Conversation with Bobby Mascia
10 Feb 2026 · 41 min
In this episode of the Wealthy Entrepreneur Podcast, host Bob Gauvreau interviews Bobby Mascia, a former franchise operator turned wealth‑planning advisor and author of Unchained. Mascia opens by describing how a failed succession plan in his family’s Dunkin’/Baskin‑Robbins franchise sparked his desire to build a business that could run without his daily involvement. He recounts growing the family franchise from 20 to 40 locations, stepping away to launch Green Ridge Wealth Planning (a fee‑only fiduciary), and later returning to restructure the family business under a new family‑office entity, Masha Capital Group. The conversation dives into the concrete systems that enabled Mascia’s businesses to become “owner‑independent”: hiring the right people for the right seats, using the Entrepreneurial Operating System (EOS), the Culture Index assessment, and other tools such as DISC and the “big ticket” post‑it exercise. He explains why only 33 % of second‑generation and 13 % of third‑generation family firms survive, and offers practical advice for owners to make their companies “exit‑ready” before an arbitrary clock ticks, especially as the 2030 wave of baby‑boomer exits and AI disruption looms. Tax efficiency, reinvestment, and the importance of aligning personal and business goals are discussed. Mascia also shares the emotional journey of writing Unchained, the book’s positioning as a memoir‑business guide, and his broader “big hairy audacious goal” to help 1,000 owners become exit‑ready by 2036. The episode ends with actionable take‑aways for entrepreneurs, family‑business heirs, and advisors.
Chapters
The first thing is that I was a product of a failed succession plan. I always knew it was going to be dad's business was part of the reason why I wanted to get in was why I never wanted to get into the family business was to carve my own path. Get in your business to a point where if you are exit ready at any moment, it's really your best growth strategy. So how do you get there sooner than later? You're not going to learn if you're always winning. If you're always winning, you're never really going to hit the pinnacle of your success.
Foreign welcome to the Wealthy Entrepreneur Podcast. My name is Bob Govreau, I am your host. It is great to have you with us today where we're going to talk about all things entrepreneurship. I just want to remind you that this is the place where we dissect the elements that contribute to entrepreneurial success from mindset and leadership to profits and revenue. Now we've got an excellent guest who's going to be joining us today. Someone who has lots of experience in family business. We're going to hear about his story, his family story and has also ventured out of family business, started his own and then brought the two back together. In today's episode we are going to talk with Bobby Mashia. Bobby, or Robert is an entrepreneur who blends Wall street level financial expert expertise and the real world intensity of franchise leadership. Bobby and his Family own an 18stor Duncan franchise portfolio and has founded a wealth planning firm bringing a unique vantage point of how business owners can build companies that run without running them. In this episode we will explore his entrepreneurial entrepreneurial journey, how he created a self managed business structure and his deeply informed perspective of the do's and don'ts for family business dynamics. Bobby is also an author of the book called Unchained. We're going to chat a little bit about that and how we can get our hands on that. But without any further ado, excited to bring in Bobby Masha to the podcast. All right everybody, I'm really excited to bring Bobby Masha into the show today. My friend. How are you doing?
I'm doing well. I turned 47 tomorrow so the it's kind of messing with my mind a little bit. But other than that I think you know A.J. nothing but a number I think is what Ms. Jackson seems to.
Well, happy, happy early birthday. That's exciting. 47 is just a number. You know, I feel like I'm committed. I don't know about you. I'm committed to this reverse aging sort of plan where I continue to try and get in better shape of my life every year and it's going okay.
Yeah, amen to that. I start to look at it as we spend so many years in school and you get out, I was 21 when I got out. And you start a new life of now your adult life. And then when you get married and you have kids, you start your new life as your now parent life. So I rather look at it in phases and stages than the entirety because then you start to think about, all right, I'm well beyond my mid life, depending where I start my life. So if I start my parental life at 16 years ago, I got some pretty good time. Not quite midlife.
You got time. You know what, it's funny because my son's 18 right now. He's pretty competitive, he's a pretty good athlete. So he keeps me young because I'm committed to not letting him outlift me at the gym, you know, and it's hard because he, he recovers so much faster than I do. But that's okay.
I, I have three children. My two boys are, that are. The oldest are 16 and 14. And we were, it was, I guess like right before the summer and we're all about to go out to the pool and they both take off their shirts and there they are kind of ripped with their six pack and their, you know, their definition in their arms and. And I've got a, you know, I've got a decent body for a 46 year old, but it doesn't look like.
A 16 year old.
No. And I'm going, you know what, I am going down to low, lower my body fat. I need to be ripped. And that's been my goal ever since last summer is getting down to that, that fighting.
I love it. You know, and if our kids keep us young, that's all we can really hope for. Right. Because they do age us at the same time. But that's a different, that's maybe a conversation for a different day. It's a great pleasure to have you here with us. And I know you've had a really interesting entrepreneurial journey. I know you've got multiple stories, multiple directions, but I'd love to give you the opportunity to maybe share with us sort of how everything got started and give us your story about how you got to where you are today.
Yeah, you know, it has been an interesting journey because when leaving school, I double majored in finance and marketing and coming out of Lehigh, I think the whole training Is go to big bank, be successful, be an I banker, do your thing, be a consultant, go to one of the big five if you're in accounting and the world is your oyster. And what I found, you know, after 9, 11 happened. Both my parents went in for open heart surgery within 18 months of one another. What I found in my quest for my family always becoming, always coming first, is when I ended up back into kind of that entrepreneurial mindset, same as when I was growing up. That was really where I was meant to be. And at the time, my father was franchising Dunkin Donuts and Baskin Robbins. It was the one place that I told myself I'd never go if not for the family meeting me. And for nine years, we grew it from about 20 locations to about 40 locations. You know, something struck me. Well, a couple, couple different things struck me at the end of my, my time with the family business that really changed the course of my world. So, you know, the first thing is that I was a product of a failed succession plan. I always knew it was going to be dad's business. Who's. Part of the reason why I wanted to get in was, you know, why I never wanted to get into the family business was to carve my own path. And the other thing was toward the tail end of my time there, I started to consult other franchisees and understand a little bit about how they looked at business and personal wealth. And I realized that they just did not know how to manage and build the bridge that's in between the two. And the way that they looked at their balance sheet, I would say not in a way that kind of looks at the synchronicity of both, both worlds coming together.
If they look at the balance sheet at all. Right, they look at.
Right, exactly. I made a big decision to go back into finance. This time I was going to come in on the advisory side, cut my teeth at a couple of large institutions, didn't really like the concept of being a salesperson versus an advisor. So that's when I left and opened my own registered investment advisory firm called Green Ridge Wealth Planning. And we are fee only fiduciary. And the goal was how do we put business owners in the best position to succeed, knowing that there's like a ton of different variables in their life. And it's not just about the money that they have invested. It's not about their or just their balance sheet. It's really about starting from their business and how they view their business, what they want out of it and where we, how do we help them kind of take it from where they are now to what they envision it looking like in the future?
You know, it's funny you talked about the family business and being a failed succession plan and knowing that it was your dad's business. So funny to know now that you and I are both at a similar spot where our kids are coming into making life choices. Right. I know my son is likely going to pursue accounting and you know, I remember two different stories with this one when he was very young and this is maybe a little bit cutthroat, but that's okay. That's who we are as a family. I remember my son looked at me and, and I think he was 6 or 7, like we're talking young. And he said, dad, I think I want to be an accountant one day. And, and that's just, you know, looking up to your father and thinking, hey, I want to be like dad. And I said, oh, do you? And I said, do you want to come work with me? And he said no, I want to start my own business just like you did. And I said, well that's great, but you need to understand when you do that that you're competing with people like me and so I will take the legs out from right under you. And, and I said, and then I said to him, I was like, like, obviously I won't do that, but you have to be prepared that, you know, it's a competitive world out there. But, and that, that is what people do. They, you know, new starting up business, if it's forcing threats on existing businesses, you know, people get competitive and they will try and force you to have more struggles. And I said, obviously I wouldn't do that to you, but just be prepared for that. Now recently, you know, we've built what's a little bit bigger business. I've got 180 employees now and my son is pursuing getting his CPA designation in post secondary. And you know, the conversation sort of came up is, you know, could he come into the business? And I said he can definitely come into the business, but this is dad's the sort of. Back to your, your comment. This is my business, like happy to support you in learning and training and you can start your own. But like at this point it's too big for someone who's just coming in to be like, hey, it's a family business. It's just not a family business anymore. It's just grown that sort of style. So I can appreciate that comment a lot. And it's definitely something that we, you know, we chat about quite regularly in our household. How was it working in the family business when you did jump back in there and start growing and scaling the business? What did that look like?
So there's two versions to that. One is the initial version and one is the revive version. So the. The initial version was very difficult. It was. When I first got into the business, I was 23 or 24 years old. And my father had a mentality because, listen, he was a baby boy. It was about the grind. It was about the hours put in. It wasn't about the quality. It was about the quantity. And I did. I made my bones and did it for about nine years. But there just becomes that point where it's. It's counterproductive. You know, more time doesn't necessarily mean a better output. And I had some aunts and uncles that were a part of the business. It was a little bit tribal. It was very competitive inside, trying to, you know, gain favor. It was who was getting what. And the way that I kind of came into the family business when I did, I tried to carve a new path for what it was that we were doing. Like I said, my dad went for open heart surgery. My mother went from open heart surgery. It was one of those things where it was like, we should probably think about this a little differently. And dad was like, I can't change what we have. It's too hard. So fast forward, I leave the family business, I come back out, I open my business, which becomes a very successful business in its own right. My father says to me, hey, listen. See the house, I see the cars, I see what you're doing. How come you're not doing that for me? And I said, you mean. He goes, well, I mean, you're obviously really good at this. You helped me with my portfolio, you know, when you were working with me, why don't you come and help me out? And I said, dad, I love you. This is. You didn't. We didn't talk for a year afterward. We had the best relationship we ever had. I said, I'm not. I'm not jeopardizing that to come work for you again. And he says, no, no, I don't want you to work for me. I want you to help me with all of my stuff, like the way you help your clients. I said, that is the relationship. I'll be working for you. I said, how about this? Why don't I help you? I'll go through all the stuff, I'll ask the Questions, we can involve the professionals that you have in place. I'm not taking anything over. I'm just going to sit next to you like your Sierra, so to speak. This way I don't have to feel like our relationship has changed and you can just get free advice from your son. So we did that. And what I found was my dad surrounded himself. Kind of like what I learned and why I had gone into my own, you know, my own business. He surrounded himself with yes men. A lot of the things that he did, he unwound himself. Things that were recommended to him, he either just poo pooed or said he would do. But never. There was never any checks and balances in terms of follow through. So we started to focus on what dad had going on and how do we make sure we put some formation to it that made sense. Well, he ended up getting cancer.
Jeez.
Within a few short years, he ended up becoming terminal. That part of his life, that part of my life. We were going to sell the businesses, but because of step up in basis and other tax issues, we kind of just said, you know what, dad? We got to keep this thing going. And he says, well, who's going to run? I said, well, who do you think is going to end up having to run it? He says, but you can't. You have your own business. I said, well, I built my business to not rely on me 100%. I have the right team in place. I have the right people in place. I can come and take this over successfully. But there's one condition. And he says, what's that? I said, you got to do it my way. If anybody comes back and says Robert is doing this, you have to say he's in charge now and that's it. I'll keep you up to date. We'll have conversations. You'll never have to feel like you're in the dark, but you can't go against what it is that I'm trying to accomplish. That's the only way I can do this. And he said, you do what you have to do. And that was when I had come in and I had to put in the whole infrastructure that I was looking to put in when I was younger, which is bringing the entirety of the business together. So we're all pointing in the same direction, really treating employees like employees by putting compensation programs in place, having processes above and beyond what the franchise offered. But what it is that we did and how we handled things internally, we secondarily branded our organization as Masha Capital Group, which I Created a family office for. And you know, now our Dunkins have that logo so people know that we own the stores. And that is actually, you know, it was a lot of work. It was a lot of money and a lot of people putting a lot of faith in what it is that I was doing, which was completely different than what they were doing. And the beauty and irony of it is even spending more money and spending less time, we made more money and became more profitable and we ran with less friction than we ever have.
So let's, let's maybe dive into that a little bit because I think there's a lot of gold in there. You know, when you first, when you talked about build, building your business before having to go back into the family business and that you created it so that it would operate essentially without you by bringing the right people, putting them in the right places, in the right seats, what did that look like? Like, what would maybe be the top two or three things that you did to successfully allow your business to operate without its dependence on you?
You know, I think one of the things that I bought into early was the fact that, you know, most people who go into business, that being all things to all people, the control, the feeling like only I could do it the best, it's real and it really does slow down your ability to grow and to bring on the right people to have that trust structure in place so that this way those people will flourish in their own rights. And when you look at kind of, I would say most businesses, it's not, you know, especially service professional service businesses, you can unilaterally focus on one thing, right? I could have come in and said investment management is what I do, or I just do financial planning, or I just do business consulting and management, or I just do long term tax planning, or I just do retirement and strategies and tax strategies. But the reality of it is, is just focusing on one thing, especially in my world or even in your world, becomes really counterproductive to the success of the client. Because I would say the most highest dollar that I get paid and my team gets paid is to issue spot when there's going to be a problem, to then bring in the resolution to solve the problem. So when I started to look at the business, I started to say, okay, we have to be experts in all these different things and I'm not going to be the expert in every single thing. Who do I bring in so that this way the team rounds each other out and we can kind of go in as a unit to, you know, Help these business owners and their families attain the kind of success that they're looking for, even if they don't even understand what that picture looks like right now, and taking them through that process of uncovering what it is that they're hoping to get out of their business. So it was really identifying, okay, who's going to be my viable number two, and then really looking at the different seats on the bus and saying, who belongs on that seat and what type of person. Now, in the beginning, and I think this happens for a lot of people, you are constrained by the amount of money that you have to put back into your business. Your revenue is really ultimately going to dictate, or your profit is ultimately going to dictate what it is that you have to reinvest back in your business. So, you know, at first I had to bring in a partner. My partner is brilliant. And then we, you know, I said, my belief system is you find the person who is going to fit in the organization. Maybe they don't come with all of the fine skill sets that you need, but those are all trainable. You can coach those. You can't coach people on their work ethic. Being a good person, putting others in front of. In front of themselves, having that sense of camaraderie of team, being able to talk to people and not sound like they're mumbling over their own words. Find the right people, teach them the skills that they need to learn and turn them into their own ninjas. So that's how we had started the business. I just started to identify really good people and finding where on the bus can they sit? And then as we added more, there was a lot of evolution of job roles. And, you know, that to me, is what got us from just about to launch off the ground into, you know, high atmosphere, stratosphere. Yeah, that's what we're aiming.
High atmosphere, 100%. Why would we aim for anything less interesting? Right. Like, I know one of the largest risks that we see in business value or even in the ability for a business owner to sell their business, which I believe is greater than 70% of businesses never sell, which is staggering. Right. And the largest risk associated with that is dependence on the owner. And so transfer Bill. Yeah, so. So exactly what you're just talking about and explaining that you sort of introduced early in your business is the largest struggle that we see business owners facing is being able to eliminate themselves from the business. Now, recent conversation with people who, who want to work with us, you know, the sort of comments were, well, we feel like, Bob, your business is somewhat dependent on you. And I was like, well, I can understand because there's a lot of marketing material with my face on it, for sure. There's a lot of information that goes out, any of our advertisements and stuff like that. I said, but truthfully, that's just me playing that role. You know, if I were to go down tomorrow, this business operates without me, and the marketing team pivots and puts a new person in that seat immediately. Right. Like, you know, at some point before, I used to feel like, man, I, you know, I'm really important to this thing. And although I still feel like I'm important to it, it's very replaceable, you know, the skill sets and. And the role that I play. So can completely appreciate that. And structuring the business to operate without you is maybe one of the most important things that business owners can possibly do. As far as any other structure that you put into your business back then, whether it's looking at KPIs or different operating systems, was there anything specific that you introduced as part of that side of the business that helped you be successful?
Yeah, you know, I'm a huge believer of standing on the shoulder of giants and not reinventing the wheel. So a lot of the things that I have implemented, I kind of stole from other people. Right. I mean, that's the whole point. Rip off and duplicate, and then that's it. So, you know, early on, I would say I mostly used, you know, a fellow Canadian of yours, Dan Sullivan, or Strategic Coach. I used a lot of the mentalities that I learned over at Strategic Coach in terms of like focusing on my unique ability, the ability for me to bring my best foot forward and provide the most value and then find out what other people's unique abilities are and really build processes around them or help them to identify what the processes are going to be that are the most efficient and effective way of accomplishing the task that they're really good at. Fast forward, because, you know, we've been through, I've read it all. I've been to different, you know, symposiums and things of that nature. But, you know, you try to find things that kind of stick. And I found eos Entrepreneurial Operating System, which is an offshoot of Dan Sullivan's, which is really just putting some structure around how teams communicate. And then how do you look at your accountability chart or your organization chart? Put your North Star out there and then continue to focus the shift toward your North Star so you don't go off direction and if you do go off direction, what are the things that you need to pivot to get back into alignment with your North Star? Another thing that we have incorporated that we find that, you know, I talk a lot about the right people in the right seat. We had, you know, those big oversized tickets post its and we would go and we would, I'd take them through an exercise every year to where we'd identify kind of the things that they're doing, what they really enjoy, what they don't enjoy and want to take off their plate. Where do they see themselves being in a couple of years? And it was a lot of real. We've used Colby, we've used disc. It was, you know, trying to hone in on how do we make that person the best version of them in the workforce. And I came across the Culture Index, which is a, an interesting assessment tool. It's kind of like modus operandi. And that really helped us to look at right people, right seat, in terms of, okay, as we start to look forward and hire and we get these new applicants, the people who are applying, who should we be interviewing? And without wasting too much time, because I think we've all been on the dating scene. Whether you're dating men or you're dating women, you're a male or a woman, you get to that first date and you never truly meet the person that's across the other side. You meet the person that they want you to meet. And it happens all throughout your dating career until you move in. And then when you move in, you realize the sink is a mess. They don't put their laundry in the hamper, stack the plates in the, you know, in the sink, and by then it's, it's kind of, I wouldn't say it's too late, but it's comparison to if you would have learned some of that early on, you may have made different decisions or you may have had different conversations that could have led you to a better place. And, you know, Culture Index, I feel like, helps us to do things like that. So, yeah, I mean, you know, to your point, the person who sits at the helm, whether you're the face of the organization or not, if you're doing everything and you don't have the right processes in place, you don't have the right infrastructure in place, your business is just going to become less sellable for sure. And then it's a matter of what do you do from there. So I guide my clients to make their business saleable. And if I'm not Doing it for myself and I'm not eating my own food. It's kind of hypocritical.
Right. So listen, what does a typical day look like for you now with like, I'm assuming you're still involved in both facets of the two businesses. What does that look like today?
So I would say 80% of my time I spend in the wealth management a business. The other 20% I spend in my family office and family office. I have a couple of different businesses that we've gotten involved in and my brother in law helps to really run the Duncan side of it. And then I have brought in the COO who's a, an attorney by trade. She's helps a lot. But most recently I wrote a book.
Excellent.
And it's a lot about my, I would say it's a mix between a business book and a memoir. And it takes a lot of what I've learned, my experience, because there's no replacement for experience. And I try to bring it into relatable stories for people who are reading and they are either in the midst of growing a business, transferring a business, they're in a family business, they're thinking about growing their business to sell it. It's really meant to get them thinking a little bit differently. So that's been a lot of talking on podcasts or being interviewed in articles or you know, really doing a lot of that book promotion. Because at the end of the day, we have a goal, and it's our big hairy, audacious goal of helping a thousand business owners by 2036 to be exit ready. And for us, exit ready is not necessarily you have to sell your business or you want to sell your business, but getting your business to a point where if you are exit ready at any moment, it's really your best growth strategy. So how do you get there sooner than later? Not because some arbitrary clock is ticking, but because you want to run your business to the best of its ability. And ironically, I say not because this arbitrary clock is ticking. Really the concept came over the past couple years because we've got two tides colliding, so to speak, with 2030 around the corner. And I'm not sure if you're talking to your clients about this, but you know, 2030, every baby boomer turns 65 or older. That brings a whole new dynamic in terms of their business. Them going to market with their business, the assets that they have, the transferability of over $80 trillion, over 3 million businesses that are going to change hands, but pair that up with AI set to reach singularity, which basically means that the machines are going to be smarter than we are. By, you know, it was 2030, I think. Now it's 2028. So just the impact of that alone on business owners that are going to be looking to transfer or sell, how are they preparing themselves not only to make their business exit ready, but also for the changing environment with technology being moving as quickly as it is. So that's the, you know, that's the exit ready mindset.
So you're keeping yourself busy is what you're saying.
Yeah. You know, my. My kids say the same thing to me. My oldest guy, he's not. So I want to work with you, dad. Although he's not as forward about it. You know, he's like, ah, you know, I know you said you have to go, I have to go work for somebody for five years before I come and work with you. But, you know, I'm thinking, like, could be interesting. My son, my middle guy sees the lifestyle, you know, of course they. He sees, because I'm. Because like you, I'm the one who's doing the interviews, writing the book and all. He sees the glitz and the glamour, the money, the lifestyle. And he goes, I'm coming to work with you, dad. And I. Oh, yeah? What does that look like in your mind? Because I really would like to understand how you envision that happening. And he goes, well, I know, you know, I have to earn the right to be there. And I've got to work for five years before I even, you know, come over and work with you. But you tell me what I need to do and I'll do it. And I laugh and I go, danny, you don't do anything I tell you to do. So I'm not sure how much we're gonna follow through with that.
But that's good.
I love the idea.
Yeah, that's good. I like that. How did you find writing a book? Because I know for me, it was one of the most challenging things to do because it. It's sort of slowing everything else down so that you can dedicate time to putting thoughts to paper. And I hired a coach and. And everything to try and make that an easy process, but it was definitely challenging. And people I know are like, are you gonna write another one? And I said, probably, but I don't want to. How did you feel about the process?
I was in a group of people and I was telling my story, and I gave you the brief version. My normal version is usually very emotional, and it talks about the trials and tribulations that I've kind of gone through. And then when my dad passed it, you know, with the emotional toll that that took, not only on me and the family and losing my dad and his businesses and having to deal with mom and my sisters and making sure that they were all. But also with my existing business and my partner and my wife and my kids and everything. And it's probably about eight to ten minutes in totality. But at the end, a woman that I know, she said, have you started the book yet? Because you need to write a book. And I said, you know, I've been contemplating writing a book, but I don't know if I should. Then finally I said, you know what? Let me take this a little bit more seriously. So I put together an outline, and I was like, let me just think about the things that I want to talk about, because I was hot off of a lot of things. Hot off of, you know, four or five years of explosive growth in the business, my dad passing away, the changes that we made. And I lost sleep, you know, for the first year, if I told you that I didn't wake up at least three or four nights a week with a nightmare that my dad was still alive, saying, what the hell did you do to my business? I'd be lying to you. So, you know, dealing with that, and then coming off that first year and having, you know, the most profitable year we've ever had, having, you know, the employees just happier than they've ever been, coming together in teams, the committees and subcommittees that we built around certain components of that business that really reinvigorated and revitalized the energy behind it. I put together an outline. And in that outline, I said, if I'm going to write this book, it's probably going to take me forever, because I'm going to write it, and then I'm going to rewrite it, and then I'm going to rewrite it. So I'm going to get somebody in here kind of like what you said in a coach and a ghostwriter. And I went through this period of interviewing, and that was emotional. And then they would send us the copy, and I would go through and I'd make my changes. And I thought this was going to be six months. I figured, what the help of the, you know, professional team. Six months, and then I'll hire a publicist, and we'll get it out to market and we'll be rocking and rolling. That was about 14 or 15 months ago, right?
Yeah.
So it took a Lot longer. You know, not everything runs on my timeline. There were multiple professionals that we were dealing with to try to coordinate, and I found it to be a lot more work than I thought it was going to be. At the end of the day, when it was done, I felt super rewarded. Like, I felt really fulfilled that I was able to put this into, you know, written format. I started thinking about how, like, this would be great. I wish my dad would have done something like this because I could have read his perspective on things a little differently. My kids can have this. And then it went on Amazon, and people in my town and friends and people that I work with started to ask and started to order. And then I felt super exposed. And I'm like, oh, my God, what an idea. I opened myself up to the world. And this morning, before I got off the call with you, a close business relationship of ours wrote, wrote me and. And cc'd his daughter, who's a business partner. And he said, I have to tell you, I'm halfway through the book. And I'm not joking. This is the best book I've ever read.
Like, really? Yeah.
And then he said to his daughter, I know you're reading this book, but I'm going to ask you a favor. When you're done with it, read it again. And then he said, get me a bunch of copies because I need to start handing this out to people. I appreciate you. And I was. And I felt like another. Another feeling of reward, of I'm helping other people view things and maybe their businesses in a way that's going to take away some of the friction that I've learned just through experience over the past couple of decades.
Absolutely. No, I love that. So you sort of highlighted a few elements in there. One you were talking about, you know, when the business, when you'd first sort of taken it over, that you had scaled it, it was moving at a really fast pace. It became extremely profitable. What are maybe your top couple of items that you would focus on when you're really, truly looking to scale a business successfully?
I would say most of the people who don't attain their goals, they don't attain it because they didn't try. I always say the one thing is regret is a bitch. Excuse my life. But, you know, regret is something that I never want to have. So when I have this inclination or this feeling that I might step out of my comfort zone to be able to accomplish what I need to do, I have to do that. I just say, hey, listen, this is some temporary pain that is going to discomfort. That's going to either A, get me to where I want to be or B, validate that there's a different way that I have to go. But I'm not going to figure that out by not doing anything. So I would say if you have an idea, if you are, you know, if you're experimental, because really being an entrepreneur is just a series of failures. And those few successes in between are what make it, are what really brings or makes it rewarding. And you're not going to learn if you're always winning. If you're always winning, you're never going to really hit your the pinnacle of your success. The more you can get comfortable with the fact that that's part of the process, I think the faster you'll go and we're comfortable.
And I would add to that too completely agree that everyone thinks bigger is better and more successful you are, the easier it becomes. I would challenge that and say that it becomes more difficult not necessarily realizing and duplicating your actions and recreating success. But, you know, the challenge is that if you're somebody who's striving for excellence at all time, it's always going to be hard to continue to keep that momentum going. And truthfully, the more cogs that are involved in the process, the more challenging it becomes to make sure that everything's moving in the right direction. But I think you referenced eos, which is really, if anyone hasn't read the book Traction, check that out too. Really great foundational sort of accountability system for a business. And I know we use, I would say, a modified version of that as well. And, you know, it's really important that, you know, as you continue to move forward and you continue to reinvest in your business, that you do stay focused on building out these systems and these accountability methods because again, you know, you have too many cogs working all at the same time. You know, they're not always going in the same direction. And I would say that that's the founder's job or the CEO's job is to try and keep everybody aligned.
You talk about reinvestment into your business, and that's sometimes it's a hard concept for people. And I think that when we look over the breadth of things that business owners are feeling and doing and executing on, you know, over their business, and just through the entirety of the financial arena, you're in the most, I would say the largest pain point. Tax.
Right?
People don't like tax. And when you think about reinvesting back into yourself via your business, you're essentially taking the profitability that you would have otherwise put in your pocket and paid to. You know, for us it's Uncle Sam. For you guys, it's the government. You know, you have a nickname for him.
Not like Uncle Sam.
No, no, not like Uncle Sam. But you end up paying taxes on versus if you reinvest back into yourself, it becomes something that starts to grow the value of that business that you're creating, which in our world is long term capital gains. When you sell some dividend recapture, but it's a lower rate than income tax. So when you start to look at like how do I reduce my income tax? The first place is how do you, where should you be reinvesting in your business that's going to pay you back in multiples? Not today, but over a period of time by putting the right foundation in place. And it doesn't have to be eos, but something is always better than nothing. And when it's nothing and you're trying to piecemeal it together, you're going to find that you're going to hit more friction. You're just not going to be as far as you hope you are. When you turn around in the next five years and you say, did I really accomplish everything that I wanted to accomplish? Did I really do everything I wanted to do?
You know what, it is quite a journey, I got to tell you. And for those of you who are part of it, we know that not everything is going to run perfectly. And we're going to all have our challenges. We're going to have our moments of cash flow. We're going to have our moments of misalignment and challenging customers and challenging employees. But it truly is an honor to be able to create something on your own and build something maybe with some really incredible people tied to something that's got a massive purpose for you and, and for others. And you know, the more that you can align all of those things together, the more successful you're going, you're going to be. And I know I wouldn't trade anything, I would train a lot of days out, but I wouldn't trade anything about this journey of building something remarkable. Right? It truly is an honor to be able to do that. Bobby, I gotta ask you, if you put yourself back to where you were starting, what would be the one piece of advice that you would give yourself back to when you started? Now, that would probably save you some heartache, but also maybe accelerate your success right out of the gates the one.
Advice that I give myself is that even though you feel like you might be not be going down the path that you believe is going to bring you the most joy and the highest reward, stay with the path. The world, God, karma, the earth, the universe, whatever, you know, whatever it is that you look at has a weird way of putting you exactly where you need to be in the time that you need to be there. As long as you're doing again, back to karma, like, what you give is what you're going to get. So, you know, as long as you're doing the right things, you'll end up exactly where you need to be. In terms of. We talked a little bit about our kids, and I think a lot of people struggle with the idea of family businesses and what it is they need to do. And the one advice I'd give, if you're, you know, if you're a family, if you're running a family business, 33% of second generations succeed, and only 13% of third generation succeed. And, you know, why do I bring this up? It comes off of you, you know, in your excitement around what you've been able to accomplish and us sharing that excitement. It starts in first generation with the excitement and the desire, and only one out of three of your children are going to have that same excitement because it's a 33% success rate. So when you start to look at your business, if you're looking at something you want to transfer and your kids are not necessarily as excited as you are, well, why not use your business for your own personal needs? Find out how to transact on it or not transact on it, and find out how to help your kids go down the path that's going to get them most excited and invigorated. Because the continuity of one business, while we know that over decades it just inherently will become more and more profitable because of time and you know, what you started with. If it's not going because there's no joy or excitement behind that engine, then that doesn't matter. So reinvest in your kids. Help them to accomplish what it is that they want to do. If it's not yours, don't force it into their hands. And the more you can plan around how you do that, the more successful you're going to become in the future. And for me, my kids, like, even if they want to take over my business, I don't necessarily know if I want them coming in. I would rather them feel an abridged version of the pain that I felt because even if they start with dad being, you know, on their side as a, you know, in their corner as a coach, they should be able to accomplish more than I did in the short. In a shorter period of time, and they'll have longer because they're going to start earlier. So reframing that idea of family business, I think, and, you know, the family goal is something that I wish more people did for their own families and the success in their own families.
I love that. Bobby, thank you so much for joining us today. Your book Unchained, maybe give us one more glimpse of it there. Where can we find your book? Is it on Amazon?
Oh, it's on Amazon. Barnes and Noble. And then we have the Pod is Unchained. And it's really about finding the failures of other business owners and understanding the trials and tribulations they went through to get to where they are. You know, the brand kind of all comes back that same theme, and that is it's not easy to be an entrepreneur, but love what you do. There's nothing better than it.
Yeah, a hundred percent. So we will put the link to your book. We'll put the link to your podcast. How else could people reach out and connect with you?
I'm on every social media. You'll find me. Bobbymassia.com b o B-B-Y m a s c I a dot com. That'll bring a link to Green Ridge. It'll bring a link to Magic Capital Group. It'll bring a link to the book, to the podcast. It's kind of like my hub, so we'll have to.
Have to have that. Yeah, the landing page. It's been an absolute pleasure. Thank you so much for sharing your story, your insights, great conversations about entrepreneurship, what it takes to be successful and to continue to scale. I know for sure there's going to be some insights and some takeaways for everyone who's been listening. So thank you so much for joining us today, so much for having me. All right, guys, this is the Wealthy Entrepreneur Podcast. I'm your host, Bob Govreau. It has been an absolute pleasure and to have Bobby on today and to talk about his journey and to share some insights about his areas of success and maybe even some of the challenges that he's had along the way. Just know that our intention here is to make sure that we're supporting and empowering entrepreneurs to have the financial confidence they need to make informed decisions, and ultimately, we can change the world together. So if there's any insights that you've had here today that you feel you could share out with anyone that you know. Grab the link, share it. We're here to empower all entrepreneurs so the more people we can support, the better. If you have a comment, want to share an insight, have any questions, make sure you drop them in the comments below. We will make sure that we address those and if any are specific to Bobby, we will get them to him as well. But for everybody who's been here with us today, thank you so much for watching. I look forward to seeing you again next week.







