$100M Exit, Sex Addiction, and the Fight to Belong

29:18Somebody else is involved or something else is involved. I've never thought about that. That's a really good point. For the traditional paths, absolutely. If you're in Tiger and you get kicked out, you clearly didn't belong. You know, YPO, you clearly didn't belong. You're a country club, you clearly didn't belong. So there is this kind of idea where like there was rejection. And one of the kind of what I call belonging intelligence skills is rejection navigation. And that's navigating both things that you reject and things that reject you. So the traditional paths, absolutely, there's kind of signals that you belong.

29:52In non-traditional paths, it's a little harder, but it is a feeling, but you don't kind of get that opt-in, the kind of validation as much as you would do from traditional. because you know tommy shelby from peaky blinders can't tell you you belong but it might lead to being you know involved in the subreddit on reddit or something like that where i then kind of have the because of my connection to peaky blinders i can go ahead and be a part of a group of fans like for example i'm a huge fan of uh tony hinchcliffe the comedian and i'm like i you know chat on reddit and go to his shows and stuff so i'm part of that community um and he doesn't know me from Adam.

30:33Yeah, because I'm trying to think about your understanding of belonging comparing to, for example, contentment, right? Contentment, we can fully control because we can, through training and work, we can feel content regardless of whatever happens around us. But this is not your definition of belonging. Okay, so you're a step ahead of everybody. Belonging, authentic belonging leads to joy. And joy is different than happiness or contentment because it's a state. And happiness and contentment, maybe more happiness than contentment, but happiness can kind of come and go. But when we feel like we belong, when our belonging tank is full with the right stuff, we can experience joy.

31:22And that's the goal of belonging is to find, to be in a perpetual state of joy amazing so you are pretty much there you said your tank is full so in my scale from zero to one and i want to put you on the spot again yeah you're close to 10 yeah i'm sorry i never answer i'm like i'm like a nine yeah you're like a nine also like look i'm like i'm diagnosed bipolar so i'm on mood stabilizers i have an anxiety disorder so i'm on anxiety pills so like that probably helps me like kind of be you know happy yeah and not have like mood swings But yeah, I'm generally, I do feel like I have a very strong sense of belonging.

32:01Let's talk about your sex addiction. Do you think your sex addiction actually came from that heightened need for belonging that you also mentioned? Oh my God, you're like the best interviewer. Yes. So let me just kind of tell the audience just some background. So I'm adopted, which means I didn't have a sense of belonging from the time I was in the womb because my mom was like, you don't belong here. My dad left me when I was two. He abandoned our family. so I didn't have a nuclear family and I didn't have any siblings and my mom raised me alone. And then when I was nine, we immigrated to the US from Tel Aviv, Israel, and I obviously had to negotiate two different identities, two different cultures, and I didn't know where I belonged.

32:37I kind of was like between two places. So I always felt broken as a result of my adoption, lost as a result of, you know, neglected as a result of my dad leaving and lost because of my immigration. So I always felt broken, low self-esteem. And the way my compulsive behavior led me to initially kind of a love addiction in my 20s, where I just tried to quickly fall in love and then just leave people and move on to the next thing, kind of, you know, you know, manipulated people to women to try to, you know, fall for me. And I wasn't really manipulated. I guess it was manipulation, but it was like subconscious because like, I actually felt it.

33:25So that was in my twenties and my thirties and became a sex addiction because I think any addiction, you keep chasing a higher high. So I was in, you know, falling in love and kind of getting sex and validation from that and then moving on from that. And then, um, and then once I was, uh, I got, you know, I got married, it was a pornography addiction because I wasn't going to commit adultery. So, um, that's the progression. And it was, you know, over, over, you know, 20 years of, of addiction. Um, and yeah, it's related to my lack of belonging. Absolutely. And what, and chasing that. So, so you mentioned that your relationship with your fish satisfies your sense of belonging and that's okay uh yeah pets are definitely and sex sex addiction i assume also fed your need for belonging yeah because that's also an acceptable way to satisfy that need for you personally so let's just talk about the fish real quick since you seem to be very interested in the fish i'm very much giving you a sense of belonging because it's pets and pets strengthening your self-esteem and then uh and because when i look at my salt when i look dogs are very obviously you know, give you self-esteem, but like cats a little less.

34:34But, um, you know, I look at my saltwater tank, I'm like, Oh my God, I created a world, you know, all these fish are hanging out and like, I, it's kind of, it's kind of like a God complex and, you know, I can control these like 230 gallons of saltwater. And yeah, I feel like, you know, I created something and it gives me self-esteem. So it's a little far fetched, but that's how I view it. Um, as it relates to, um, any kind of addiction, frankly, I don't think it gives you, it gives you a fake sense of belonging. You feel loved, but then you lose it just as fast. So I think that any addiction needs to be addressed.

35:05And I would, excuse me, I would argue most people have some sort of compulsion that is uncontrollable and should be addressed, you know, work, eating, you know, drugs and alcohol, medication, you know, even like people are addicted to these days, they're addicted to like, you know, like the gym, like, you know, nonstop, like bulking. And it's just like, there's so much addiction around and it really needs to be addressed. So where do you draw the line between healthy feeling of that tank for belonging and unhealthy ways like addiction? I think everybody knows intuitively, you know? Okay. I think for me, I didn't know intuitively because I didn't, I mean, if you ask my friends, like I destroyed friendships because I constantly put my addiction ahead and I prioritized it out of many other things like building relationships creating intimacy with with people I dated creating intimacy with my male friends so you know I think so I knew that I had this problem people would have said Don's got a problem but I don't think that um I think everybody intuitively knows I mean anything in without moderation is, you know, dangerous.

36:22What pushed you to address your sex addiction? I went, um, to a program called, uh, PCS, which is called, which is like basically inpatient therapy for like, it's 60, over 60 hours of therapy in six days. And, um, I, uh, yeah, I like opened up to one of the therapists. There was the first time I was able to open up to a therapist, um, and kind of realized it's what I have. Um, and then I just checked out a meeting, you know, if anybody's interested, uh, uh, you know, you can go to any, there's so many different meetings, but, um, um, I went to an SAA meeting, sex, sex addicts anonymous and, um, and, um, realized that I was a sex addict.

37:06So then I had a conversation with my wife, like a disclosure and then started working the steps. So it happened quite recently. It happened after your exit. Yeah. When you actually had the time, when you had the time and space. It's my nine month chip for survival. A nine month chip. Okay. Yeah. All right. Yeah. Because I wonder if, if the fact that you have more freedom now helped you address that sex addiction. Well, sure. But I think it also would have been dangerous, right? Like if I'm, I mean, for a while I didn't help. it fueled my freedom my freedom fueled my addiction because i had all the time in the world i had money i i mean i never paid for anything but um i was able to like go on trips take my friends on trips and kind of so it made it worse at first that you had that freedom yeah and i guess probably yeah ever since i started talking about it i mean i have so many founders coming to me and saying like hey i have an addiction like can you help me a different type of addiction or sex addiction nobody talks about sex addiction nobody talks about it i know that's why i keep asking you questions i'm so fascinated that you're so honest and open about it there's no other way i mean it's serious 25 of searches in the world are pornography i mean we're in a world where men are very close to choosing pornography over you know intimacy with women or whatever do you think that do you think the root cause is a belonging crisis.

38:32Yes. I mean, the whole incelibate movement is a result of the 80-20 rule. 80 % of men do not meet anybody on dating sites. Men don't have the skill, especially post-COVID, to go approach women. They're not going out. They're trying to rely online. I mean, look at the stock market and all the dating sites. They're just tanking. And that's because people are kind of like have tinder fatigue swiping fatigue because it doesn't work for most people and then they're isolated and they resort to drugs and suicide and um and alcoholism and it's why we have more deaths of despair now than um and in any and ever before among men and men are not coming of age at the right time later as they used to as fast as they used to more people are less people are married than ever before it's a huge it's a huge problem It's a huge problem.

39:23And, uh, and, uh, and I think it's because of compulsion. Mm-hmm. Okay. So, sorry. Compulsion is created by the lack of, the lack of belonging. So people are trying to fill their tank vis-a-vis things that are kind of misconceived belonging paths, which we talked about earlier. Do you think the way our society, I mean, the Western society, the U.S. society, sees masculinity today helps or hurts the problem? No question it hurts. I mean, you know, men are, masculinity is under attack.

40:05Men, look, men are always going to be men, okay? Yeah. Like, you can't force men to not be men. Sure, you can stop assault, DV, abuse. You need to stop that. Of course you need to stricter rules, um, education, whatever, but you can't stop the men, you know, biological nature to like want women and chase women. Um, um, so yes, I mean, there's a war on masculinity, uh, you know, men, uh, feel, um, left behind, not heard. and as a result feel attacked. And it's why people like Andrew Tate, who's a fucking asshole, and Donald Trump, who's literally a serial abuser, the backlash is very real. You know, I'm a mother of three boys, as you know.

41:03And my older one is 18 now, so he's an adult. And I have to say that my boys have taught me to really appreciate how important, but also how beautiful masculinity really is. I'm so grateful to them because I've seen how three men developed over time and I understood them in ways I never understood before. And I have to say, largely thanks to my husband, but also maybe thanks to my own realization and learning from my boys, at some point we consciously made the decision that we're going to really support our boys being boys. And if the society attacks them, we'll do anything and everything to help them feel proud of being men and understanding what masculinity actually is.

41:52And I have to say it worked. And I love seeing how now they channel this beautiful masculine energy into entrepreneurship and relationships and all the things they're doing. And they also feel now the difference between them and many other boys around them who were not raised that way, which for me makes it even more important for the society to open their eyes and see that we're really failing our boys in a way that will be very dangerous for the society at large. and actually really horrible for women because women don't want weak men. We want men that have self-esteem, that are proud of being men, who are not sexually addicted because they feel uncomfortable or even incompetent in dealing with the opposite sex because the society puts so much pressure on men to not be themselves.

42:52You're absolutely right. And I have several things. Thank you for sharing that. So a couple of reading suggestions for the audience. Richard Reeves of Boys and Men is a great book, not just about the masculinity problem, but how to solve it. David Data's The Way of the Superior Man is about men being men. Brilliant, brilliant book. So, you know, there's also No More Mr. Nice Guy, which is a little more underground, but that's a good one too. The show Adolescence on Netflix really talks about this and the incel movement and how women bullying men for incelibacy is really creating a problem. Let me be very clear.

43:39Masculinity is vulnerability. Masculinity is intimacy. It's about, masculinity is really about giving um in literally and physically and figuratively and um and there is a reason why nature created us the way it did um but it is about a balance and the masculine energy works really well feminine energy but we both need both sexes need both in order to be highly functioning adults yeah no no absolutely but most men will have masculine energy as their dominant energy and it cannot be suppressed because that's one of the reasons we have loneliness epidemic and you know the belonging crisis that you are so generously trying to to solve and I love it that you're talking about it so openly and and writing the book and thank you well I think the super important.

44:41Well, thank you. I think the key is for, um, the way to solve the belonging crisis is for each person to take it upon themselves, to solve it for themselves. It's bottom up. It's not top down. Um, it's not like a presidential address, you know, that's going to change. It's not like a UN resolution. It's a grassroots movement from each individual to find their sense of belonging and do the work. Can we now switch to a completely different topic? Sure. Which is very pragmatic and financial. Most of my guests on this show admit that after an exit, they went down financially before going up, if they went up.

45:31Not everyone did. How about you? I feel better about myself. How about you? It happened to me too, by the way. I'm definitely one of those. So honestly, I fucking swear. I don't remember how much money I made when I sold. I swear. Okay, I never had that one on this show. That being said, I am worth roughly, depending on the stupid policy, I am worth roughly like 19, 20 million. And that's roughly where I was. I was like more 20 where I think, I don't even remember, but I'm in Tiger. So you have to be 20. So I was like, I've been like 20, let's just call it 20, you know, depending on the value of like assets and stuff.

46:19And roughly, let's just say I sold and I was that, I think it was a little less, but let's just say I was sold. So it is true. I mean, the idea that in seven, well, eight years, because six years, because I had a million and a half in deferred income. So, um, and I had another million and a half that I left on the table, but let's just call it, you know, so I million. So from, from 19, where I got my last million and a half for the last six years, I've essentially maintained my network. And that's because of several things, but most importantly, well, because of stupidity, um, I put money towards stupid investments, uh, like friends and family just trying to show off, whatever.

47:00I over-indexed on philanthropy a little too quickly. I went on a shopping spree of dumb shit. I bought a boat for$160 ,000 that I had 11 hours on that I just sold for$95 ,000. I bought a replica of the spaceship Apollo for$160 ,000 that has been sitting in storage for five years. So, but by the way, I only put 50 % down on that, but I need to pay it once it arrives. So I went on a shopping spree. I bought multiple properties. I bought a property in New York that I couldn't support. You know, I could, but it was just like eating away 22 grand a month. So stupid investments, deal toys, um, and a lifestyle that I don't shy.

47:56I I don't even fly first class. But a lifestyle that doesn't shy away from, you know, nothing crazy. I mean, I'm wearing a freaking T-shirt, like nothing crazy. But look, my wife and I did 11 IVF cycles. We used a surrogate. That right there is half a million dollars. Oh, wow. You know, we're going to do another surrogate, a couple more IVFs. That's going to be like$700 ,000. Yeah, but that one is worth it. Of course. I mean, yeah, that, that should be like my net return from like a normal portfolio, liquid portfolio of like 10 million. That should be like my annual return, you know? So like, yeah, I mean, so the bottom line is I'm worth roughly the same, but I've also adopted a die with zero mentality and I don't mean it like everybody else.

48:45I fucking need it. Okay. My grandfather used to say, you know, in Judaism, we, we don't have a coffin. We are wrapped in a shroud. The body's wrapped in a shroud. when we're dead and my grandfather used to say there are no pockets in the shroud and he was like he was he was like a male like nurse and like came to israel with like pennies in his pockets so and his wife my grandmother was like a painter so yeah he just made you know people heard that like let make the last check bounce you know i i want to truly die with zero or maybe die with like a million. That's kind of like zero for me. But I mean, and ideally I preserve my nut.

49:29I'll always have 20. But yes, to answer your question, stupidity led to keeping the, stupidity and risk led me to keeping my nut. I also had a lot of luck. I invested in NASDAQ like three years ago and it's gone up like 300%. So I've also had a lot of luck. I bought some great land that I was able to sell. I bought a piece of property for 350. I sold it for 750. you know so there's been upside and i've had some good good decisions exactly maybe it's not just luck you made good decisions and you made bad decisions and you're basically you're breaking even yep that's right okay cool interesting can we talk about die with zero because i find that people misunderstand that book in two different ways one way is that it actually does not talk about not leaving anything for the kids right because actually the author specifically talks about how kids can be taken care of so can we talk about this i know your daughter is only five months and maybe you haven't had a chance to develop you no no i mean lots of it but i'm curious where you are at the moment yeah so i think about it like you know a trust fund for you know, some like for some for for each kid, a small one, a college fund for them to be able to go to college and then purchases for them throughout their life in key moments that I can see them enjoy.

51:00Perhaps a down payment on a house, perhaps a small investment in a business, perhaps a car, perhaps obviously their wedding. So, you know, family, huge family trips, you know, with friends and family. So there are things you, it's all about, you know, that was your result. It's not just about like a negative, like a negative slope of spending or, you know, or like of net worth. It's about a bit of a negative, like a downward, a downward slope, like opposite of a hockey stick, because you want to spend more money when you're able bodied. Yeah. So you can enjoy your money and not like, what do you mean, 90 spending money like, I don't know, on applesauce?

51:48I think this book is fantastic to break that post-exit momentum that many of us have, like chasing more money, getting richer. Also, we often start panicking after an exit because we suddenly realized that we had this company that grew so fast. And now, you know, we have to manage our investments and it feels like hard work. We feel incompetent. so I like that book as something that breaks the momentum after an exit and I always recommend people to read it but yeah the second way I mentioned that I think many people misunderstand it and to me it's very important is that later on sometimes years after an exit some people who follow that book religiously but misunderstanding it I think end up in a place where their life is very empty.

52:44Because if you just focus on what next experience can I get from the world, it's actually a very selfish approach. It's like, what else can I get? What else can I accumulate? Maybe not money this time, but experiences. What else can I take from the world? And then there is no sense of contribution. There is no sense of purpose later on. And I've seen actually lots of exited founders going through this. they look at this book as a Bible and then you talk to them two years later and they're like, oh, I'm so empty. I'm so bored. There's just that, that much you can enjoy, um, all these travels and experiences.

53:21So tell me how you feel about it. Let me, let me comment on that. So I have three comments. First of all, as it comes to experiences, they're useless without other people. So it's less about like, you know, I don't know, like whatever, it's like a trip around the world, uh, than it is about a trip around the world with your family or with your friends. Um, and I love, uh, Bill, Bill Perkins's idea, by the way, I think he's a billionaire and he'll never die with zero, but, um, I love Bill Perkins's idea that, um, you should throw a huge party for your friends and family and like for big occasions.

53:56Cause again, it's about the memories. So that's about the experiences. Um, the other piece of it that I used, I used two and a half million dollars in my net worth to invest in my new company, you know, and I'm taking a risk. I'm building offset retreat. I'm building venues for offsites and retreats and I'm doing everything myself. So I'm not, I have no debt. I have no investors. I'm doing it all. So that's, I'm creating value with the value that I already built. And then another piece of it, and by the way, a belonging path is philanthropy. And I give more money away than, you know, than I used to.

54:32and i i mentioned i over indexed on it but still that is also a way to die with zero and you know warren buffett bill uh bill gates they're all doing it yeah they're doing it too i think i i love hearing this because i don't like when people use this book as an excuse to stop being hateful for the world and then they just turn into this parasite these parasites uh that are saying oh it's all about getting more interesting experiences in our lives and we deserve it it doesn't take us to a good place it's okay temporarily but it doesn't take us to a good place yeah i agree especially when your purpose is like fucking off and having fun that's not a purpose you know my purpose in life is to help as many people as i can find their sense of belonging um that's my purpose in life so you know sure i'm not going to get it by like traveling you know to the jungle so is this your motivation for the new business yes is there still a financial motivation in it as a secondary.

55:31Oh yeah. I mean, if it's been successful, I'll do, you know, a million bucks in income a year. Well, I mean, after partners, much less, but you get my point. Yeah. No, I understand. Okay. So, and you feel, what is really driving you? And is it, is it both the financial motivation and the, and the the sense of purpose that you get from doing that? So several things drive me. The first one is my love for the hospitality industry and my love of seeing teams come together, achieve their sense of belonging, and then achieve their goals. So that's number one. Number two, it is about more security and safety for my family.

56:12And number three, it's more about much more philanthropy. And those are the three things that motivate me. And I just love building stuff. And I love new concepts. And this is a new lodging concept. I think it's a new asset class that people don't really think about. So, yeah, I think for all those reasons, I think it's innovative and exciting. I mean, it's the first kind of like it's the first chain of retreat venues. It doesn't exist without the programming. And I can absolutely see how it would ride this wave of retreats because after COVID, people don't seem to be able to get enough of events together.

56:54That's right. If that trend stays, then you may be in a very good place with this business. Yeah, it's not just for doing ayahuasca on a weekend with strangers. It's like it is coming together to review quarterly goals, review annual goals, do those team meetings. So it's more for business-related retreats. Weekday, weekday. And then weekend is social or like forum or something like that. So how long ago did you start that? Started it about a year ago when I purchased the property. And we should be open October 1st this year, 2025. Oh, that's exciting. Well, the first one. The first one is Boise, Idaho.

57:35And then we want to do 10 more in four years. Okay. So I want to talk to you about what lessons you've learned in terms of the business. Like, what is it you are taking into a new business from your original business, from social tables, and what it is you are not taking with you to this business intentionally? So obviously, first of all, respecting everybody's sense of belonging and prioritizing whatever they want to prioritize. I think there is a paradigm shift away from, I think we're moving back towards the transactional nature of work where it's like nine to five, kick ass, and then leave and get paid.

58:16And people are not looking for as much belonging in the workplace as they used to. And that's totally fine. I support that. So I think work is becoming more transactional, which is how it used to be. As opposed to COVID where people have this great realization that they need something else in their life. So that's number one and respecting everybody's desire for belonging. The second one is obviously moving from software to hardware because I used to be a SaaS business and SaaS and now I'm in lodging. So I am taking a lot of my hospitality intuition and my hospitality contacts and my hospitality mentors and leveraging that in my new business.

58:57So if you had to choose between you being a natural creator, operator, or investor, talking about archetypes, which one would you be in? So there's four archetypes. I like Les McEwen's predictable success, and in it he says there are four kind of archetypes. There's operator, visionary, processor, and synergist. Synergist is all three. I think I'm I love I'm an operator I love operating I'm I think I'm a synergist even though I didn't get that on the test um I think people are just visionaries are fucking lame um like you need to you can't just be like I don't know the expectation other people should build you stuff I like to roll up my sleeves unless you're a minority you know minority stakeholder but yeah I mean so I'm an operator I love operating I nothing is beneath me I'll buy digital ads i'll edit the website you know i'll unlock a bunch of stuff for my teammates but i'm an operator so so far are you finding um doing your repeat businesses because that's not your first business after the exit easier than the first business or not it's harder because it's my own money and um yeah i i'm really scared that i'm not going to do well are you going to raise not not for the first one maybe the second one our structure is interesting because we have a management company that's above the property and each property has got its own you know llc and then the management companies it's a kind of um oversees all the properties so i can raise from different i can offer different types of financial instruments or capital instruments so yeah maybe but probably the first thing that makes sense is take out a mortgage because it isn't like residential converted into like these kind of bed and breakfast if you will with private bathrooms but yeah I'll probably raise eventually but not right now okay makes sense so you wrote a book and quite a lot of people in the post-exit community are thinking of doing that so uh for someone who is thinking of doing that would you say it was a good idea yep so you know one of the deal toys was a book um initially i'll tell you a funny story initially my book was going to be it was called founding alone it was about to about how to start your own a business without founders like i did um and then it was going to be it was called um building belonging.

1:01:36And it was about how to create belonging on teams. And then I realized that thing where I was like, I can't have belonging at work before I have it personally. So let me, my first book be finding belonging, you know, finding belonging. It's what it says here. And then I can do a building belonging. That's why I'm on bonus chapters about how to build belonging on teams. Spoiler alert. It's, it's team building events. And that's kind of like my funnel for my new business, you know? Okay. But I think a lot of people think that their stories interesting and it's not like your memoir nobody wants to read it I do have personal anecdotes that start every chapter but people don't really like and that's just to like level set and show my vulnerability and kind of relate to um to the topic so I paid like 200 like a quarter million dollars to get this book done I did a pay-to-play model with Forbes books but I I ended up writing the book myself, literally every word.

1:02:33Three ghost writers failed me. They did not capture my voice. It was very heavy research. So like that wasn't their thing. And I ended up getting several refunds for some of the experiences that I had. That being said, I have a book. I have an audio book. I have great graphics. I built the website myself. So I just rolled up my sleeves a lot and it took three years as opposed to 18 months. That being said, if anyone wants to write the book, there has to be like a shtick. There has to be something special. Is it about the industry? Is it about, you know, but nobody wants to hear another kind of founder memoir about how lost they were when they sold and like, and how their identity was gone.

1:03:12Sure. You went from a human being to, from a human doing to a human being. That's great. But I do think there has to be something special in it. And your special is those frameworks you offer. Yeah, belonging. To find belonging. I mean, it's still the same idea. Like, but to me, it's not just like, oh, you sold your money, you're a millionaire. This will save you. For me, it's like, oh, like anywhere in your life, you can pick up this book and find meaning. I think it's such a great mission you're on. Thank you. I sent you a copy. I sent you a digital copy, right? You haven't. Not yet. No, we're going to do that.

1:03:45We're going to do that. My goodness. I'm embarrassed. How about the physical one with a note? You're international. It's too expensive. It's okay. I got to save my money. okay dan this has been absolutely amazing i need to ask you i need to ask you the same question i ask everyone at the end of an interview oh it's one of those huh exactly how do you want to be remembered um

1:04:20a great husband, an inspirational dad, a hospitality innovator, someone who helped people find belonging and somebody who helped the Jewish people and the state of Israel continue to thrive. Beautiful. Dan, thank you so much. Thank you so much. This was great. You're awesome. You're awesome too. Hope to see you soon. Likewise.