The Dark Side of Entrepreneurship: The Truth About Wealth, Growth & Greed

In this episode, we’re sitting inside Society Hill Hotel, reflecting on the experience of staying in the very place we run. The conversation quickly turns to the entrepreneurial curse—that constant drive for more, better, bigger. We unpack why business owners are often their own worst critics, the struggle of chasing perfection, and the fine line between focus and distraction.

From glamping franchises to fusion restaurants, we explore how staying focused (or failing to) can make or break a business. Plus, we share personal stories of past ventures, the lessons we’ve learned, and the defining metric of success that’s driving us forward now.

If you’ve ever wondered when is enough, enough?—this one’s for you.

“Nobody would trade places with Warren Buffett right now. He’d trade it all for more time.”

What You’ll Learn:

✅ Why entrepreneurs are wired to focus on flaws instead of wins 

✅ The hidden dangers of expanding too fast (or in the wrong direction) 

✅  How Away, Allbirds, and  Warby Parker struggled with focus 

✅  The truth about money and happiness—what successful people say vs. feel 

✅ Why defining your success is the hardest part

Links & Resources:

📌 Follow us on Instagram: @findingbrotherlylove 

📌 Books mentioned: Never Enough by Andrew Wilkinson & The Five Types of Wealth by Sahil Bloom

Transcript

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(Transcribed by TurboScribe.ai. Go Unlimited to remove this message.) So we're sitting in Society Hill Hotel. We are. You had to spend the night here last night, right? I did, I slept right downstairs and it is a interesting experience to stay in the hotel that you run because I gotta say it's exciting but it's also a little bit annoying because it's easy to like pick out every single detail like the sounds, the bed, you know, the way the shower, the water pressure is. I mean, I have to say overall, I was pretty happy but there's definitely some areas that we can make better. I feel like that's always the case when you experience your own product or service. It's hard to enjoy it. Like you intend your customers to enjoy it because you get so caught up in what's wrong with it. That's at least how I always feel. Yeah, for sure. And we were just eating last night with a restaurateur and like the restaurant was great. I was like super excited but he's there taking pictures of almost every dish. Every dish, he's taking a picture so that he can, you know, have a critique for it and be able to get feedback on. And, you know, I definitely think that you gotta experience your own product but it's definitely not like, I'd say always a joy because even though maybe most people come into a hotel like this and be over overwhelmingly like positive about it, I think we're overwhelmingly negative about our own things whether or not it's a hotel or a piece of art that you do or really anything that you create. It's like, it's that leaning towards negativity about our own work. Or just, yeah, I feel like that's the critical eye of an entrepreneur that is never satisfied and probably should not be ever satisfied because nothing is ever perfect. No, it's not. And I think back to sort of like the striving for perfection is what an entrepreneur is always trying to do. And I think the areas that I personally have felt where I lose my eye on that ball is when I try to do so many things and I lose focus because even like this restaurateur last night, you know, he's a restaurateur, he does restaurants. And so he's like so fixated on that plating, on the food and everything like that. He's striving for perfection. This is a hotel that we're focused on. We're striving for perfection here, but I think sometimes it's easy for us to get distracted. Be tempted. Be super tempted. I mean, like we've talked on this podcast about wanting to open up another hotel. You know, I think maybe here today, we're gonna talk a little bit about like why that decision might've been a little bit flawed and how we're not gonna open another hotel right now. Because there's so many things here at Society Hill Hotel that needs to be addressed and needs to be improved on before we can actually do that. Testament to my experience last night. I just feel like we're there, we're almost there, but we're not there yet. Yeah.♪♪ I feel like there's stages of perfection that like you can kind of check off because it's never gonna be perfect, perfect. But getting it to a standard is what I think you have to strive for. And that standard here, both in how it looks and feels and how it is through the guest's eyes, but then even the standard from a business perspective, I think is really important. Understanding like, okay, what are the top line and bottom line standards that we're setting for this business or the goals that we have? And that's, I think it's the combination of those things, both the experience for the customer, but then also the business standards that determine whether or not a project or a business is meeting that level of satisfaction, where I feel like we weren't comfortable with the level that we're at here to say, it's time to jump to another project that we needed to stay focused on this property first to get us to that standard. Totally, yeah. And before we go on, I'm gonna go turn off a bathroom fan because otherwise it's gonna drive me crazy. Luckily no one's used that bathroom today, so. Yes, exactly. It's not on for any specific reason. It's not on for any, maybe you might've used it, but you know. We did a Mexican last night. Yeah, we did. Well, it was actually Mexican-Chinese. Fusion, it was awesome. Mexican-Fusion-Chinese. I never would've thought that that went together. I thought the concept was really cool. It's fascinating. It's like from Baja, California when all the Chinese that built the railroads in America got like kicked out of the country and went down to Baja. He said 70% of the population in this area was Chinese and they set up their- To America initially. Yep, and then got basically kicked out and ended up in Northern Mexico right outside of California and set up a Chinatown down there. And the dishes were so interesting because it was things that, I don't feel like go together, but worked really well. Like the chips and salsa that you would typically get at a Mexican restaurant instead were like- Wonton chips. Wonton chips. And there was three different dips or salsas with them, but one of them was like duck sauce that you would get at a American-Chinese restaurant. That was exactly it. Wonton chips and duck sauce, that's actually not like a Chinese thing. That's like not a real Chinese food. That's an American-Chinese food. So it's like American-Chinese-Mexican fusion. It's not even like Chinese and Mexican, it's American-Chinese-Mexican fusion, which is really interesting. So, I mean, it's got focus. It does, yeah. It's got a perspective, it's got focus. If it had a hamburger on the menu, it wouldn't work. It would lose that focus. And I think that's honestly, that's been my biggest weakness in entrepreneurship over the years has been lack of focus. I think it even goes back to United by Blue. There's strengths and weaknesses when it comes to lack of focus. I feel like sometimes people get so narrow-minded on things and they say that they're not willing to try new things because they have this super, super strong head focus. And then there's entrepreneurs that do something that seemingly seems not focused, but then it works really well because it's so novel and unique. And the combination of say, even combining American-Chinese and Mexican would actually maybe arguably seem like a lack of focus because you're not Chinese, you're not Mexican, you're not American. But it creates a new category. And we tried to do that with United by Blue and we did it successfully for the most part when we took lifestyle and outdoors and sort of this love of nature and combined it into a new brand. And that wasn't the lack of focus. I think that was like the category-defining opportunity, but then it was not doubling down on what was working in that category and trying to reinvent things that probably we didn't need to get into. Like we were killing it with graphic t-shirts. It's not to say that if we had continued to just do graphic t-shirts, we probably would have, it probably wouldn't have worked because the competition was coming and things like that. But I think we just, we got into too many things. I mean, how many products did we have? How many SKUs did we, individual SKUs? Hundreds, hundreds. I mean, honestly, like every given season, there was probably three, 400 SKUs that were like individual items, not, you know, that's sizes and colors, but like it just sunk us by the weight of the amount. And it's not to say that a retail store, like a department store or a bigger brand doesn't have more, but at our size, at like a 10, $20 million company, we were probably doing 80% of our sales in 20% of the SKUs. I mean, everybody knows that. It's actually interesting too, because when you think about that and you would, if you would talk to somebody who knew United by Blue and you ask them, what is United by Blue? What's it known for? I think you would uncover that lack of focus, but that initial focus that we have, because most people, if you ask them what United by Blue was, it was a clothing brand that removed a pound of trash from the oceans for every product that they sold. And that was the core of the brand and the core of the focus. We didn't waiver from that focus for 12 years, for the entirety of our time running United by Blue. And even since then, since it's been acquired, they've continued with that mission and that focus, but that was the defining kind of descriptor of the brand and the focus where we lost focus was on the product mix perspective, because people didn't say, oh yeah, United by Blue, that bag brand, that bison brand, whatever. We had so many different products that we added to the mix that we didn't have a product focus. Whereas, I mean, and some of these brands are to have been total bust. And that's a whole nother story from a direct consumer's perspective. But like when you say Warby Parker, you know, you think glasses. You don't think, and they do, they have some cool mission and, you know, a donation model and all this stuff, but you think of glasses and, you know, you say Tom's shoes. You think of their, like their classic Tom's shoe, or you say- They also, but they did the same thing. They got to a point where they're like, we got to expand. Are they a coffee brand? Well, they tried coffee, you know, and that failed. They tried, what else did they try? They tried other stuff too. And like, and there's plenty of way, not a way, the shoe company, Allbirds. Allbirds, yeah. Allbirds shoe company, but then they launched clothing and, you know, they've obviously failed since then in many ways. So like, there is so many examples of companies that they start super focused and they explode in popularity. And then they do try to do more. We had that in a micro scale. Whereas Away, actually, you mentioned Away, but that's a good example. Like when you say Away, you know, luggage. That's, I don't know, maybe they do more now, but I still think of Away as just suitcases. And I think they are for the most part still. Like, I think staying focused, it's like, but it's funny in entrepreneurship and being an entrepreneur, it's like, you're never content at, it's never enough to do something and then like feel like there's other opportunities that are worth chasing. I think that's the real paradox of entrepreneurship is you can be so successful with something. Like I look at even like the Rex Hotel, that was a life-changing sort of like opportunity for us where it makes us, that profitability of that one property is probably giving us, you know, putting us in the top earners of the country, right? Like maybe not 1%, but like in the top few percent of income for our family. But it feels like a side note in a way. It's like a stepping stone of entrepreneurship for me. And now it's blossomed into like wanting to do like a massive hundred million dollar franchise opportunity, which is what I'm working on now. So it's like, when is it enough? And I think actually in regards to that, I'm reading a really interesting book that you would find interesting too. It's actually called Never Enough. It's by Andrew Wilkinson who started MetaLab and then he started Tiny, which is a holding company for different- Yeah, I know Tiny, yeah. Yeah, Tiny. So, and they bought like Dribble and then the book is really interesting. I'm almost done with it, but it's basically about his journey from making a hundred thousand dollars and feeling like he was making more than his dad ever made and then going into being basically a billionaire and how that journey, it never felt like enough even at the stage that it's at now. It's really interesting. I'm reading a separate book right now, which I didn't tell you about, you should also read, by Sahil Bloom, it just came out, The Five Types of Wealth. Sure, yeah, I've seen that all over LinkedIn. Yeah, and I'm only a few chapters in, but he lays out the five different components of wealth and really focuses on financial wealth as being a tool to satisfy the other four layers of wealth, which are like mental, physical, family. I don't have them all off the top of my head, but those are the other pieces that he argues are more important or equally as important as financial wealth, because what he did early on in kind of the creation of the book was went out and interviewed people that had made significant exits, and the question was to all of them, how much more money would you need to feel like you'd made it and you could take your foot off the gas, essentially? And almost every single person that he talked to, it was two to three times of what their current net worth was. And it didn't matter from the founders that had exited and were worth $3 million all the way up to $50 million. They all consistently said, well, if I had about double or about three times more than what I have right now, then I would be good. But it showed him that there's an obvious disconnect with entrepreneurs when it comes to a focus on financial success that doesn't necessarily fulfill you. And he also then went and spoke to people that kind of like on a happiness index perspective were in their later years, 70s, 80s, 90s, and that were very financially successful, but asked them about what the best parts of their life were at that moment. And none of them mentioned money. They all talked about their physical health, their family, the time that they have. Time wealth, that's the other one. And I think that it's really interesting from a perspective because it, and I'm not finished the book yet, but the concept behind using, not being laser focused on financial success because financial success is not happiness. And the people that have reached a level of financial success oftentimes don't feel like it's enough. It's never enough. Like the most successful people in the world that have tens or hundreds of millions of dollars still felt like there's always a bigger boat. But you know, I know that. And I think everybody in this world could actually say that, but like, I don't know about you. I don't think so. I think a lot of people feel like they want more. I don't know. No, I'm saying like, everybody knows that, not everybody, but most people know that it's an underlying truth of life that like, you know, money doesn't make you happy. I think everybody can say that. They know that message. They've been taught that since they were young and they know when they talk to their grandparents and they talk to all the people, but it's so hard to feel that and act that, especially I think at our stage in life. And the disconnect is that this is the time where you're young, you're healthy, you have young kids that need you and stuff like that. But it's also in the prime of our careers where the financial rewards are such a tantalizing thing. And also like, for me, it's also like, because we're not salary men, like we're not chasing like a promotion and a raise, it does feel more gamified and fun in a way. Like the career for an entrepreneur does lend to be something where it becomes an obsession because you actually do enjoy it as much as you wanna make money. And I think that's my real challenge right now. And I know that when I'm 80 and I'm getting old and I'm, you know, looking at grandkids and like just wanting to have time again, I won't care at all about it, but that doesn't mean I can convince myself that I don't wanna focus on it. I'm really, it really is a struggle for me. Like I'm so fixated on, and it's not just financial. For me, it's actually, I would say, it's more of the game of building and being successful. And maybe that is a bit of a vanity thing. But then what is successful? Yeah, exactly. Like what's the definition of success? No, I'm curious. Like what, to you, like what is in your mind, what is successful? Because like, what is successful to one person? Like the Rex Hotel to a lot of people would be, like that's the top. A lifetime achievement. That would be the pinnacle. I built a boutique hotel that is beautiful in the Pocono Mountains, and people love coming here and staying here. It's big enough to be most people's retirement. And it makes great money to live a happy life. Like, so then that's not your definition of success. You've already stated that. So like what is, like in the moment right now, because I'm assuming this has changed over time. It's a moving target. Right now, what is the definition for you? Yeah, I mean, it's, you know, after going through what we went through with United by Blue and, you know, feeling like we had something that was gonna be a meaningful business with a meaningful future and a meaningful exit and going through the song and dance for that for so many, so many years. Like, I do think that what I'm building now with Ferncrest, because I didn't get into the Rex thinking that that was like a future, like that was a side project. That was really like a side note to a transition point in my career. Now, Ferncrest, I finally started to see that this is, and this is so vain, it sounds so vain, but this is like, this is the defining sort of success of my career at this moment. Like, and making it be a name brand hospitality company that's all around the United States that has the numbers that I have right now and my definition of success is 100. Having 100 Ferncrest out there in the next five years, I think I can be at 20 to 30 in the next 12 months. And then, you know, having it be worth a hundred plus million dollars enterprise value. And when I say that, it's like, well, what does that even mean? Does that give me time? Does that give me like family? Does that give me happiness? I don't know, but like, that's where it's like, as an entrepreneur, it is that never enough mentality because I guarantee you when I get to 100 and I have that, it doesn't mean that I'm done and it doesn't mean that I'm satisfied. And as much as I psychologically know deep down inside that those lessons of, you know, happiness, family, time is what everybody in their later stages of life want and they could care less about the money, guaranteed like we talked about maybe a few weeks ago, you know, nobody would trade places with Warren Buffett right now, nobody. Like nobody our age, even if they were dirt poor would say, I wanna be Warren Buffett, I would trade places with him. He's 95 or something like that because there's expiration dates on everything. So, and he would trade places with anybody our age for zero. He'd lose his entire wealth. I'm assuming he would do that. And so, yeah, I mean, like it's not about the money, but then it is. And like, as much as we know, just like any addiction or anything like that in life, you know what's wrong for, I don't wanna say it's wrong because it's not necessarily unhealthy. You're right. But it's not necessarily what we're gonna care about in 50 years. But then, so, but what you just described to me as success was purely tied to money. It's tied to money, but it's tied to success metrics that the success will result in money. Right, like- No, but you said a finite, you said $100 million. I said $100 million, yeah. And that does feel like the threshold. Like I wanna build $100 million company as well. Exactly. You know, like that's because we have built companies that have done a million dollars. We've built companies that have done $10 million and $20 million. Right. We haven't built a $100 million company yet. So it feels like that's the next huge success threshold from a business entrepreneurship perspective. It does feel like it. And it's like, you know, to say like, oh, I wanna make it a billion dollar company seems like maybe skipping a step. But man, I don't know. I do have this like burning desire and I don't know where it comes from. And I think a lot of entrepreneurs just have it. And it's, I don't wanna say it's greed because it's truly not, like I'm not, I'm very not materialistic. Like I think you know that like from the cars that I drive to like, you know, yes, I like nice things occasionally, but like, I'd rather spend my money on experiences. Like I'd rather be in a position to always fly like first class if I wanted to, you know, basically buy, I already buy whatever I want without thinking about it. And so I like don't have any needs, but it's more of the definition of success and the by-product of that being financial. But really at the end of the day, maybe it is a little bit of a vanity thing where it's like, I just wanna have that check mark that it's like, okay, you built it, you did it. It was successful. And I think there is a chip on my shoulder from United by Blue that's driving part of that. But I'm not saying that if United by Blue did exit for 50 million or some bigger number that I still wouldn't be doing what I'm doing. I just think it would be a different form, like a different mentality around it, which is right now it's very motivated by like, I didn't get that success yet that I thought I was gonna have. And I think now it's time that this next one has to be. Like, I actually feel like failing with this would be, is totally unacceptable. Because like, you can fail once and failure is celebrated in entrepreneurship. But I feel like unless you actually follow that up with a success, Tiger Woods will bogey a hole. He'll follow it up with a birdie in his heyday. Same thing goes for a team, right? Like if you, okay, Eagles lost a game, then they won the Super Bowl, right? They lost one of their last games in the season and then they won out. They lost, I mean, like that's imprinted on me. I think that Jalen Hurts is a really unique leader. And, you know, sometimes a little bit too cliche with his soundbites, but his whole thing has been keep the main thing, the main thing. And that's just a definition of focus. And he was laser focused. I mean, I don't know if you saw the pictures or video from him in a team meeting last year after the Super Bowl loss two years ago. And somebody snapped a picture of the lock screen on his phone. And the lock screen of his phone was him walking off the field with the Chiefs confetti raining down on him after losing the Super Bowl. Like that's- I kept that on his phone the whole season. I think he- Still to this day. Oh, really? And like, that's an insane level of focus. Like the only thing that mattered to him, the main thing was the main thing. And the main thing was winning a Super Bowl. That's what mattered. Right. It wasn't about the money. He signed a $255 million contract between then and this past Super Bowl. But it wasn't an MVP. It wasn't about stats. I mean, a lot of people got on him for how he plays the game and his passer rating and the amount of completions and everything. But he didn't care. He never once cared. And he doesn't care what other people say because his focus, he had a definition of success that he kept driving towards. And I think that's, I think it's an impressive way not only to lead your life, but also to act as a leader. Because I think that that level of focus from the top, you know, and you have a growing team at Ferncrest too. I think that level of focus allow, permeates through the rest of the team when they know what the North Star actually is. Yeah. So I had that same thing happening within Lynton Hospitality, which is what runs Ferncrest. I was gonna buy a hotel in the Catskills and sort of loop that under, you know, the Rex and like try to grow that in conjunction with Ferncrest. And there's multiple reasons for not going forward with that. But like, I think the big thing is focus. And like, I'm hiring all these people and I'm telling them we're gonna grow the biggest glamping brand in the United States, in North America. And to have all these people joining and then have another project on the side that is not that brand, what does that say? Like, what does that do? And I think leadership focus, it is the most important. Yeah, whether or not it's, you know, all we care about is winning a Super Bowl or in our case, you know, we care about growing, like the fastest growing, you know, the name that everybody will know in glamping in a couple of years, if not sooner, is gonna be the focus. And I think it's not to say that I'm not gonna get distracted, because I know I will. And I don't think all distractions are the end of the world. Like, especially within the focus of Ferncrest, I think recently I've had some distractions that have turned into actually really meaningful things, like figuring out prefabricated bathhouses. Okay, some people would be like, why are we getting into prefabricated bathhouses? Well, you know, we've already sold now a few hundred thousand dollars of prefabricated bathhouses. And it's tied directly to- Solving the problem of opening glamp grounds faster. So yeah, so it's definitely, that, I guess, that entrepreneurial, like, curse of always trying to solve problems can be really good if it's within that realm of focus. But defining what your focus is, is probably the hardest part of that. Because it involves a lot of saying no, which I think as a entrepreneur is hard to do. It's super hard. You know, I'm experiencing that with franchisees. We have so many inquiries for franchise. So many people wanna do a franchise here or a franchise there, or they wanna start with X number of units. And like, if we just said yes to everybody, we could be at a hundred franchisees in a year. Like, honestly. But what would that create? Like, that's not gonna create a resilient, long lasting brand. It's not gonna accomplish that secondary focus, which is that financial success and like the outcome of what that success means. They have to go hand in hand. So like you, like FairX. So, you know, obviously you have a little bit of a curse. A little bit, well, I don't wanna say curse, but yeah, you are a little bit like conflicted because we're sitting in Society Hotel, it's hospitality. FairX is a different business. You have two things that are sort of butting heads in terms of focus. But if you separate that for a second, like within FairX, how are you looking at focus and how are you building that? I think one of the things that's been helpful actually to not talk about FairX specifically at this moment, but there's actually a really interesting tie between what we're doing with Society Hotel and what we're doing with FairX. And the tie is hospitality. How does hospitality relate to the healthcare industry feels it doesn't make a ton of sense. But I mean, you think about where you go, you go to a hospital and that's a derivative of hospitality. And- You playing word games with me? It could be. But ultimately what we've built and what has made FairX really unique is not the food that we're getting to people. And it's not the nutrition education that we're getting to people, but it's the way that we're delivering it. Fair enough. And how we are making people feel. And that is what hospitality truly is because it's at the end of the day, whether it's the hotel or if it's a FairX member that's getting a bag of groceries or a prepared meal or a session with a dietician, that experience and how the person feels, like back to the Maya Angelou quote of, people won't remember what you did, but they'll remember how you make them feel. And I think that's the definition of hospitality is how people feel during that experience, whether they're sleeping in this bed behind us or eating dinner at the restaurant downstairs or if they're receiving something from FairX or talking to one of our team members over the phone that's able to coach them through something. That has been the common thread. And it's honestly what the perspective I've taken into FairX and into healthcare that's felt disruptive compared to what our competitors are doing or how kind of the way that this industry has operated for a long time. Because if you think about your experiences at a doctor's appointment or trying to schedule something for one of the kids, it's been like for me personally, it's been, it can be a nightmare. Like my kids go to the same primary care practice that I went to as a kid. That's insane. Same pediatrician's office. And it's awesome. But it's also really inconvenient and it's really a pain in the ass. Like a couple weeks ago, Ella Rose got sick on a Saturday and it was a holiday weekend. So Monday, they didn't have school, but I didn't think that maybe the doctor's office wouldn't be open. And she just happened to get sick, woke up sick on a Saturday morning. So we call the pediatrician's office and ask if we can get her in. She's got a fever. It's been a few days, like she was feeling bad for a couple of days. Fever was getting high and wanted her to be seen. And they had no appointments for the rest of the day. They were closed on Sunday. They were closed on Monday because of the holiday. So you're telling me Saturday at noon that I have a sick kid that can't see her doctor until Tuesday at the earliest.