Dan Berger's Net Worth is $20M. His Goal? To Die With Zero.

We spoke to Dan Berger in this week's episode of Moneywise.

Dan is the founder of Social Tables, a SaaS business in the hospitality space that he sold for $100 million in 2018. As a solo founder who started with just $10,000 in savings, Dan's journey from making $25/hour to walking away with $20 million exemplifies the entrepreneurial dream.

Like all Moneywise episodes, Dan breaks down his net worth, income, portfolio, and monthly expenses and then I, your humble host, pick it all apart.

We also went deep on: his philosophy of "dying with zero," the belonging crisis he believes many entrepreneurs face, and how his early life traumas shaped his relationship with success and money.

Below you'll find my summary of the episode along with the entire transcript.

And by the way...this podcast, the concept of it came from Hampton, which is a community for founders and CEOs and people who generally have a really high net worth. I was seeing all types of private conversations about money, and I thought, this should be public. So if you want to be part of these conversations—ones that happen amongst people who run businesses that are doing tens or hundreds of millions of dollars a year in revenue, check it out. But until you join or until you get there, you have this podcast. New Moneywise episodes come out weekly.

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Now, below are the notes and the full transcript.

The Numbers

• Company: Social Tables - SaaS business in the hospitality space (cloud software for event design)
• Exit Value: $100 million (sold in 2018)
• Personal Take: $20 million net ($22 million but left $1.5 million on table by leaving early)
• Current Net Worth: Approximately $20million
  • $10 million in liquid assets (stocks, index funds)
  • $10-million in illiquid assets (angel investments, real estate)
• Major Expenses:
  • Actual spending over $1 million annually
  • $7.5 million apartment in New York City (half mortgaged, half on 1.8% loan)
  • Multiple properties in Idaho including a cabin
  • F-150 truck ($100K) and camper
  • $40,000/month household budget (discretionary)
  • $100,000/year to philanthropy
  • Fertility treatments ($350,000 for surrogate and treatments)
• Investment Breakdown:
  • 20+ direct startup investments
  • Various tech stocks (Nvidia, Palo Alto Networks, Google)
  • ETFs including QQQ
  • $80,000 in NFTs (now nearly worthless)
• Side Businesses:
  • Commercial cleaning business in Idaho ($1 million revenue, 20% margins)
  • Building a retreat center in Boise for corporate offsites

Building and Selling a Fast-Growing SaaS Company

Dan built Social Tables from just $10,000 in savings to a company that sold for $100 million in about eight years (2011-2018). As he explains, "It was a SaaS business in the hospitality space. And we basically for those familiar with AutoCAD, we were basically an AutoCAD cloud software for events, event design."

The company grew to $20 million in revenue with 6,000 customers before the acquisition. Despite being a solo founder, Dan acknowledges he had "incredible late co-founders, as I like to call them, who kind of contributed to these founding moments throughout the business."

Interestingly, Dan raised about $27 million in venture capital, with Bessemer leading the Series A round. This significant outside investment explains why he personally received $20 million from the $100 million exit.

The "Die With Zero" Philosophy in Action

Unlike many wealthy individuals who claim they want to die with zero but don't truly live that way, Dan seems genuinely committed to spending his wealth during his lifetime. "I really do believe that there's a curve. And I'm 43. Call it the next 20, 25 years where I'll be able to enjoy my money more than I will when I'm 65 or 70," he explains.

This philosophy comes from family wisdom: "My grandfather always said, you know, in Judaism you're not buried in a coffin, you're buried in a shroud. And my grandfather used to say, the shroud doesn't have pockets."

Rather than accumulating wealth for later generations, Dan believes in helping people enjoy money while he's alive: "One thing that's also important to note is that the idea that a lot of people want to leave their money for their kids, I don't think that's the best thing to do. I think it's important...about enjoying seeing them enjoy the money, helping them buy that first house, helping them get a car."

His spending reflects this philosophy - from spending $100,000 on a trip to Australia with friends to investing in experiences and properties he enjoys using. His monthly discretionary budget is $40,000, but with carrying costs on properties and other expenses, he spends over $1 million annually.

Finding Belonging: The Post-Exit Journey

Dan's most profound revelation after selling his company was discovering his "belonging crisis" - a theme that became so important he wrote a book about it. Three major early life events shaped this struggle: "I was adopted when I was two days old. My biological mom basically told me I don't belong in her room and her family. My dad abandoned us when I was two...And then, like I said, we immigrated here when I was eight and speak a word of English."

This created what Dan calls "belonging looseness" - constantly searching for where he belonged. During his entrepreneurial journey, he found belonging within his company culture but not outside of it: "I was finding belonging within my company and not finding belonging outside the company...As soon as I sold, my belonging tank emptied."

Now, Dan has developed a concept of a "belonging tank" with multiple paths to fill it: "My belonging paths are the men's group that I run here in Boise, Idaho...I run a nonprofit that focuses on Zionism and on fighting anti-Semitism...Obviously, my wife and my daughter gives me a sense of community. My hobbies like gaming And my new company, Bringing People together."

Lessons for Post-Exit Entrepreneurs

For those who have recently exited, Dan offers two primary pieces of advice:

1. Be patient with your newfound wealth: "I would not invest in alts for the first year. It's very easy to have a lot of money and be like, oh, here it is for my buddy here, my buddy there, and you just don't do the work to figure out if it makes sense for you." He suggests parking most money in safer investments while allowing a small percentage (perhaps 10%) for higher-risk opportunities.
2. Invest in yourself and your next chapter: "I think, like spending money on something that can help you open up your next chapter is really interesting too, because a lot of entrepreneurs struggle with like the next chapter." For Dan, this meant writing a book about belonging, which served both as personal exploration and as a marketing asset for his future ventures.

Dan also emphasizes the importance of recognizing your own value: "I had an executive coach who really helped me realize that I am my own best resource." This self-confidence has led him to start new businesses, including a commercial cleaning business that did $1 million in revenue last year.

Other Key Quotes

"My spending is over $1 million a year, and that's a result of early on these investments, lifestyle, buying a house for the first time, buying a cabin, buying this apartment in New York. I'm trying to sell, buying stupid things and just overindexing on a bunch of shit I don't need."

"I love having stuff because stuff allows me to enjoy my hobbies and passions and my environment with people that I love."

"I did kind of come to the realization that with my new venture, my wife should get something. And I just did a stock grant for her with that business as well."

"I think men are in a crisis. I think a lot of the men that are struggling don't talk about it."

"I constantly searched for [belonging]. I am an anxious blogger. I have a high need to belong, but an insecure attachment style. And because of that, I'm seeking, seeking validation."

"I kept the nut, the principal. So it's $20 [million]...Do you fear running out? Who doesn't? Yeah of course."

"Fuck yeah dude. I mean, I had an executive coach who really helped me realize that I am my own best resource."

Links You Might Like

• The Quest - Dan's book about belonging
• Social Tables - The company Dan founded and sold
• Die With Zero - Book by Bill Perkins that Dan mentioned

Full Transcript

[00:00:00] Dan Berger: Sold it for 100. 100 million. My spending is over $1 million a year. I didn't know where I belonged. I constantly searched for it.

[00:00:09] Sam Parr: It's like a traumatic first ten years of life. It seems like you believe that you are not a one hit wonder and that you can make it again.

[00:00:17] Dan Berger: Fuck yeah, dude.

[00:00:21] Sam Parr: I'm Sam Parr, and this is, money wise, the only show on the internet where we get high net worth people to break down their monthly income, their expenses, their asset allocation, and everything about their personal finances. I had the idea for this show because I run this thing called Hampton. It's a community for founders and CEOs and people who generally have a really high net worth. And I was seeing all types of private conversations about money, and I thought, this should be public. This should be a show. This should be money wise. And so if you want to be part of these conversations, conversations that happen amongst people who run businesses that are doing tens or hundreds of millions of dollars a year in revenue, check out Hampton, join Hampton Hamptons.com. But until you join or until you get there, you have this podcast. You have Moneywise and today's episode is with Don burger. Don started and then sold his company for over $100 million. Now on this podcast, we have a ton of people who say that they want to die with zero, meaning they want to spend or donate all their money before they die. I hear it a lot, but Don is the guy who I actually believe. I actually believe he's going to die with zero. And in this podcast, we're going to dive deep and we're going to figure out why. Also, if you're someone who has started and sold the company, and you're one of those people who struggles with what to do after they've sold and you're looking for the answer of what to do next, I think Don might have a secret that's going to change your life. So let's hear what it is. It's time now for part one of the story. You heard it in the intro, but Don had a company that he sold for over $100 million. Here's all the details about how much money he made.

[00:01:59] Dan Berger: It was called social tables. It was a SaaS business in the hospitality space. And we basically for those familiar with AutoCAD, we were basically an AutoCAD cloud software for events, event design.

[00:02:11] Sam Parr: And how big did it get.

[00:02:12] Dan Berger: So 20 million or 6000 customers and sold it for 100 100 million.

[00:02:18] Sam Parr: How old was the business?

[00:02:21] Dan Berger: Started in 2011 and sold it in 2018.

[00:02:23] Sam Parr: Wow, that's super fast. Was it bootstrapped?

[00:02:26] Dan Berger: No. Raised a little under. Well, about 27. Not including venture debt with Bessemer leading the A.

[00:02:33] Sam Parr: And you sold for $100 million. How much did you say you walked away with? 20.

[00:02:37] Dan Berger: I walked away with 20. Net like that was the final number. I should have had a little more, but I left about a million and a half on the table because I left a year early. So I really walked away with 22 and ended up with 20.

[00:02:48] Sam Parr: Were you an entrepreneur before that?

[00:02:50] Dan Berger: I mean, I don't consider anyone an entrepreneur until they exit, so the answer is no.

[00:02:55] Sam Parr: But you were a founder of a small business that was.

[00:02:59] Dan Berger: Almost like, you know, I was building websites. You know, I think what makes the story slightly more unique is that it was a solo founder. But that being said, I had an incredible late co-founders, as I like to call them, who kind of contributed to these founding moments throughout the business. But yeah, I was a solo founder, you know, web design agency where I, a bunch of my friends from IRC and like Instant Messenger were helping me code.

[00:03:19] Sam Parr: How much money were you making?

[00:03:20] Dan Berger: $25 an hour.

[00:03:21] Sam Parr: Okay, so you were just getting by? Kind of.

[00:03:23] Dan Berger: I started social tables with a $10,000 I had saved.

[00:03:26] Sam Parr: Wow. All right. And in eight years. Or was that eight years, or was that six years?

[00:03:31] Dan Berger: Yeah. It's like Q1 2011 to like Q4 2018. So I call it I call it eight.

[00:03:36] Sam Parr: You sold for over $100 million.

[00:03:38] Dan Berger: That's 100 million on the nose. Yeah.

[00:03:40] Sam Parr: Did it make you happier to have that money after making 100 grand? Even 30 grand a year? Not too long ago.

[00:03:48] Dan Berger: Yeah. I mean, I think my first. My deal, my deal toy was, was a car. I never owned a car, so I bought a car. What'd you get? It was like a guess.

[00:03:58] Sam Parr: Probably a Lamborghini or a Ferrari.

[00:04:00] Dan Berger: No, no, I'm not that much of a douchebag. I got a Tesla.

[00:04:03] Sam Parr: Oh, come on, that's even lamer. In a weird way. That's like the, uh.

[00:04:06] Dan Berger: I got the model X, though.

[00:04:07] Sam Parr: Oh, it's the same. It's. I'm trying not to. That's the. I'm trying not to. Flex. Flex.

[00:04:12] Dan Berger: Yeah, yeah, yeah.

[00:04:13] Dan Berger: I think one of my exes, like, saw me driving down like DC, like blasting house music, like a total tool. And she was like, wow, that guy is, like, completely lost it.

[00:04:21] Dan Berger: But you're your door.

[00:04:23] Sam Parr: Is still.

[00:04:24] Dan Berger: Like this Falcon wing.

[00:04:26] Dan Berger: I crashed it with under ten miles in it.

[00:04:28] Sam Parr: Great. That sounds great. As planned.

[00:04:32] Dan Berger: As planned for somebody who got their driver's license at 35. Yeah.

[00:04:34] Sam Parr: Were you single?

[00:04:35] Dan Berger: I was.

[00:04:36] Sam Parr: That's pretty.

[00:04:37] Dan Berger: Wild.

[00:04:38] Dan Berger: If I may share, when I broke up with my long term girlfriend. Kind of mid-journey. Well, you know, this podcast I love about everybody opens up. So I gifted her stock as a gift for just her just helping out so much. While I was single, I felt a great deal of indebtedness.

[00:04:55] Sam Parr: To like a long term partner.

[00:04:57] Dan Berger: Exactly.

[00:04:57] Sam Parr: Which I don't like. Using the word partner is too progressive for me. But when I think of my now wife, when she was my girlfriend, when I was running my business, there's a lot of men, you know, most of the people in our world are men, and they say stuff like, why should she get half of it? And I won't debate what percentage a spouse or partner deserves, but they definitely deserve. There's been so many times when I was like, I'm done with this. I'm quitting laying on the floor of my kitchen and my wife being like, sometimes aggressively like, you know, you're being weak, stop being weak or coddling me when I needed to be coddled. And so they definitely deserve something. So I think that's pretty cool that you gave her stuff, right?

[00:05:35] Dan Berger: Yeah.

[00:05:35] Dan Berger: I mean, that wasn't kind of my attitude walking into my current marriage where I we have a prenup. But I did kind of come to the realization that with my new venture, my wife should get something. And I just did a stock grant for her with that business as well.

[00:05:48] Sam Parr: That's fascinating. I think that's a great way to handle things, because they're totally more than just along with the ride. But like, it's hard to do stuff, and it's a lot easier when you have someone at night, like whispering in your ear like, you got this.

[00:06:01] Dan Berger: Yeah, or saying you're not spending enough time with me. Which also is kind of like back in my addiction, if you will, both to work and to all the other addictions I had, which we can touch on if you'd like. But, uh, I was not willing to hear other perspectives.

[00:06:14] Sam Parr: Yeah. And I think it's good to have like a big thing that you talk about is like belonging. But it's nice having the accountability of someone who knows every detail about you and can encourage you, who can tell you what you're doing is foolish, who can just kind of keep it real. I think that that type of like voice is very, very helpful.

[00:06:32] Dan Berger: Yeah.

[00:06:32] Dan Berger: The when I was researching my book, I learned of a new term called communal relationships. And your primary relationship is a communal relationship, which means that it's not quid pro quo, it's not transactional. And that's what is beautiful about partners or spouses, whereby a healthy, secure relationship is not transactional. And you can give and not not expect to receive at that specific moment.

[00:07:00] Sam Parr: The point right there is exactly why relationships in your personal life are vastly different than the business ones. This feels obvious to say, but blurring those lines, the personal and business lines and Don's opinion is a huge reason why many entrepreneurs struggle personally and sometimes can create toxic work environments. We're going to talk about that shortly.

[00:07:21] Dan Berger: I would like waterboarded.

[00:07:22] Dan Berger: And the people in the Kool-Aid.

[00:07:24] Sam Parr: Now, we might be able to admit that that type of behavior, while honestly it could contribute to a lot of financial success, maybe is not great. And when we do talk about that behavior in a few minutes, I promise you it's not going to be like, oh, you know, bad behavior equals bad. Don thinks he's discovered where that behavior comes from and how to get rid of those tendencies altogether. But first, some more fun stuff. The math, the numbers, the financial transparency. That's why people love money wise. Don sold his business in 2018, which today is around seven years ago, he walked away with around $20 million, and yet his net worth has not grown at all. Here's why. Hypothetically, if you made $20 million in 2018 and you had invested all of it into the S&P 500, I'm just ballparking. But in the realm of doubling your nut is where you would have been assuming you spend $0, which is not practical. Your net worth purposely has not gone up, which means your spending has gone up. You went from living $100,000 a year lifestyle to potentially $100,000 a month lifestyle. Just guessing.

[00:08:38] Dan Berger: So yes, you're right, I probably I think S&P has gone up like 40% over the past five years or something like that. And so you're, you know, you hit the nail on the head first and foremost. I made a bunch of stupid mistakes, like putting a ton of money into alts. Like being like, oh yeah, let me throw 25 here, 50 here. And now, just sitting on a bunch of illiquid assets. I also made the mistake.

[00:08:59] Sam Parr: Being startups or being crypto startups.

[00:09:04] Dan Berger: Startups.

[00:09:05] Sam Parr: Yeah. Okay. So potentially not gone to zero, but just you can't access it now and there's a chance that you'll have some moonshots. Is that how the portfolio is looking?

[00:09:14] Dan Berger: Yeah. I mean I think I have like 20 or so direct deals and one silly fund that I put in a quarter million dollars into. That's gone completely dark, but it's through AngelList. So I think they're still kind of hope because you can follow the money. But yes, there is hope. But half my portfolio is liquid and half my portfolio is not liquid. The other mistake I made is I bought a trophy apartment in New York City for $7 million. I think it was seven and a half. Yeah, 7.565.

[00:09:44] Sam Parr: Did you pay cash?

[00:09:45] Dan Berger: I half of it was funded with a mortgage, and the other half was funded with a fixed 1.8% loan, which was incredible during Covid because just to highlight a point, I sold in 18. I stayed for a year until Q4 19, and then Covid hit Q1 20. And then I was in negotiation to buy meetup.com and that deal fell through. So I was kind of stuck during Covid with nothing to do. But basically, yes, my my spending is over $1 million a year, and that's a result of early on these investments, lifestyle, buying a house for the first time, buying a cabin, buying this apartment in New York. I'm trying to sell, buying stupid things and just overindexing on a bunch of shit I don't need.

[00:10:27] Sam Parr: So you had 20 now you still have 20. That's in, like, liquid stuff, and then another 20 that's in private stuff. Is that right? Bingo. And the illiquid stuff includes a $7.5 million apartment.

[00:10:40] Dan Berger: Yeah, but it's some loan. So it's a liability. Yeah. But yes, it's collateralized. There's a mortgage on a 30 year mortgage and then that's like 4 million. And the rest was a collateralized portfolio that I just paid off in like three and a half.

[00:10:54] Sam Parr: And then you have a bunch of angel investments and anything else. That's crazy.

[00:11:00] Dan Berger: Let me think. If anybody wants to buy my NFT collection of Picasso punks that I spent $80,000 on and went to about a dollar, I will gift it. And like, so that's a stupid investment I did invest in. Remember when people were trying to buy the Constitution?

[00:11:17] Sam Parr: Yeah, yeah.

[00:11:18] Dan Berger: I put money into that deal and I made I did nice.

[00:11:21] Sam Parr: So the numbers are basically 20 million I imagine in public equities, another 20 in these variety of things that who knows how they're assessed. But putting your total net worth in the 30 or 40 million range 20 liquid. Is that right.

[00:11:36] Dan Berger: Well no no ten of liquid and that's it. We could have been at 40 if I would have just done the normal thing.

[00:11:47] Sam Parr: There was something else that Don tried to buy, but as it turns out, it's not something that money can get you. And failing to achieve this with his money is what set him off on a journey to become happier and a more well-rounded person. Because at this stage, John was still struggling with addictions and a lack of self-worth. What did Don tried to buy? A sense of belonging.

[00:12:09] Dan Berger: When I moved to Idaho from the East coast, I did two things. And these are, in retrospect, maybe not the smartest things. Number one is I try to fit in more. And I started buying stuff. So I bought a camper, I bought a truck, and I was like, look at me, I'm Idaho, and I got all this stuff. And in Idaho, people like this kind of stuff. So that was number one.

[00:12:27] Sam Parr: What, like a F-250 and.

[00:12:29] Dan Berger: F-150, but with like the towing package and, you know, 100 grand and like, a nice bumper and whatever. I love that truck. It's got 40,000 miles on it. It's amazing.

[00:12:37] Sam Parr: Idaho is great for a Jewish East coaster. What, are you just walking around in? Wranglers and cowboy boots and a yarmulke.

[00:12:44] Dan Berger: Yeah. I'm like, move away, move away, you know?

[00:12:47] Sam Parr: Yeah. To be clear, it's not that he regrets buying stuff.

[00:12:52] Dan Berger: I love it. I don't mind buying stuff.

[00:12:54] Sam Parr: Oh, you like it?

[00:12:54] Dan Berger: I was up and to the right. I'm buying stuff.

[00:12:58] Sam Parr: The thing that he got wrong is trying to find a place to fit in, and a way to feel community through buying all this stuff. You can buy as many carabiners and chalk bags as you want. That doesn't mean you're going to be a rock climber. You can buy an F150 and wear cowboy boots. That doesn't make you a cowboy, but it's pretty fun owning all this stuff if as long as you remember that it's just stuff after all.

[00:13:23] Dan Berger: Context is incredibly important. I am an immigrant. I moved here when I was nine, didn't speak a word of English. I leaned into America real hard. I went to public schools, started a business super patriot over here. Not necessarily MAGA, but super patriot here. To me, the beautiful thing about America is the fact that we can own stuff. So for example, I bought land for 350 and I'm selling it, hopefully, God willing, signing today, selling it for 750. So I bought land, I bought a camper, I bought a house, I bought, I sold that and bought another house. I spent 150 grand on doing the landscaping, so I really enjoy my home. I bought a cabin in the middle of nowhere so I can just do like homesteading stuff. I love having stuff because stuff allows me to enjoy my hobbies and passions and my environment with people that I love.

[00:14:14] Sam Parr: It's the great American pastime acquiring, acquiring stuff and then acquiring more stuff to store the stuff.

[00:14:21] Dan Berger: Yes, yes.

[00:14:23] Dan Berger: And so my mom would say problems of the rich.

[00:14:25] Sam Parr: Okay. And so you like it. You're okay with this? You enjoy this. This is not a burden on you.

[00:14:29] Dan Berger: I mean, I have to manage it.

[00:14:31] Sam Parr: Do you like managing it?

[00:14:32] Dan Berger: Yes, I don't mind. I mean, it's not crazy. It's like, you know, my wife and I meet weekly and go over finances, and we have a budget that we oftentimes miss, but we have a budget and we take it seriously. I'm not like collecting weird art. Well, forget the NFT. I'm not collecting like weird art. I'm not buying rare coins. I'm buying stuff that I can use and I enjoy.

[00:14:50] Sam Parr: You don't need to justify it. You are buying weird art and weird coins for the record. Just like to put that out. There you are. I would bet money that you are doing that. Yours just lives on your computer screen instead of your your underwear drawer. And that's okay. If that's what you like to do, you should do it.

[00:15:04] Dan Berger: Well, the only coin I do have is bitcoin. That's it.

[00:15:06] Sam Parr: Yeah. So you are buying weird coins and that's cool if that's what you'd like to do. What is your budget that you try to stick to.

[00:15:12] Dan Berger: 40,000 a month.

[00:15:14] Sam Parr: Oh but you're spending probably two and a half times that a month.

[00:15:17] Dan Berger: Yeah, because I have all these carrying costs. My carrying costs for New York City is up until a month ago it was 20.

[00:15:23] Sam Parr: But it doesn't matter if it doesn't matter if their carrying costs are not like they are costs. Right? So how on earth would you create a $40,000 a month budget if you have carrying costs of 25 a month?

[00:15:33] Dan Berger: I should have been clearer. You're right. My budget, my budget for discretionary budget, for household budget is 40,000 a month.

[00:15:40] Sam Parr: Do you think that's enough? Like, do you are you happy with that amount of spending?

[00:15:44] Dan Berger: Yes. My wife and I went through a really trying time to have a kid. She went through ten fertility treatments. We had to use a surrogate. The first two transfers failed. She's about to do her 11th cycle next month. And that's an example of things I have to spend money on. You know, it's a quarter million dollars plus a surrogate 100. That's 350 to have one baby. Not to mention the travel around and stuff. So, you know, people always whenever I, whenever I talk to my finance guys, they're like oh it's one off. I'm like, yes guys. It's one off. But I got one off every fucking month.

[00:16:15] Sam Parr: And that's fine if you're happy, I guess, right.

[00:16:17] Dan Berger: Like, exactly. But a lot of people.

[00:16:20] Dan Berger: You know, give lip service or like they kind of talk. Oh yeah. Die with zero. You know, Perkins, these kind of crazy, you know, he's got a ton of money. He can say that. But I really do believe that there's a curve. And I'm 43. Call it the next 20, 25 years where I'll be able to enjoy my money more than I will when I'm 65 or 70. And sure, I'll invest in my health and all that. But at the end of the day, I want to do the good stuff over the next 20 to 25 years. And I don't need to just sit on this nut and wait for it to it to grow. Doesn't. Doesn't make sense to me.

[00:16:49] Sam Parr: Can you tell me about the die with Zero stuff? So for people who don't know, die with zero is a. I say that zero is the world's greatest book title because you don't actually need to read it in order to, like, understand it. I heard the term, and then I bought the book and I was like, oh, I, I think I read the cover, I think that's adequate. And the idea being, Bill Perkins is an amazing entrepreneur, maybe a billionaire. And the idea is a lot of people wait until they're 80 to enjoy their money, or at least mentally. They think that's when they retire. They can enjoy it. His whole thinking is enjoy it now and die with zero instead of doing what a lot of people, myself included, say they want to die with X amount of money. He says that number X should be zero and you should plan accordingly. You are living that life. A lot of people say they live that life. They don't walk the walk. Can you explain to me the zero philosophy from your perspective, and how you kind of justify that on a monthly basis with your decisions.

[00:17:47] Dan Berger: Yeah, I would say that this was diver zero. Was diver zero in my head before I even read the book or had a liquidity event, because my grandfather always said, you know, in Judaism you're not buried in a coffin, you're buried in a shroud. And my grandfather used to say, the shroud doesn't have pockets. So it's kind of the same mentality.

[00:18:05] Sam Parr: And I imagine your grandfather has seen a lot of, like, traumatic events in his life, uh, and probably has a different perspective on what a meaningful life is.

[00:18:14] Dan Berger: That's right. Yeah. I mean, he came to Israel in the 30s and started working the land and, you know, working kibbutz and all that. So, yeah, certainly a different perspective. But it has been passed generationally. My mom has always told me growing up, money is just money. And at the end of the day, Sam, I do believe in my capacity and my ability, and I think that I have more in me and I can I will make more something out of nothing. As far as zero, I would say. One thing that's also important to note is that the idea that a lot of people want to leave their money for their kids, I don't think that's the best thing to do. I think it's important. And Bill talks about this in his book is about enjoying seeing them enjoy the money, helping them buy that first house, helping them get a car, helping whatever else these kind of life moments to help them enjoy and get over and not just give them a ton of money when you're dead where you can't see them, enjoy it. Finally, I think the best example of a dad with zero is would. Bill Perkins does. And it's like this party for your friends. Why not spend a quarter million dollars if you have it to bring all your friends, all your loved ones, to some place and just have a great weekend? And those are some examples of how I think Die with Zero really comes to life.

[00:19:21] Sam Parr: So my my examples might be more tame than you, but my die with zero examples. It's a I think I'm bought in to his mentality, but I'm not fully bought in. You know, it's still frightens me to die with zero. And but I like the idea of it. And so my version of this is I will take my family, you know, in-laws or parents and my family to on a first class European vacation, things like that, and just not worry and just pay for it. What's your version of that?

[00:19:48] Dan Berger: Well, the first thing I did after buying my Tesla and crashing it when I sold my company is book a trip to Australia with all my closest friends and an assistant to have two weeks in the Great Barrier Reef in Sydney.

[00:19:59] Sam Parr: How much was that?

[00:20:01] Dan Berger: Uh, like 100 grand.

[00:20:02] Sam Parr: Okay.

[00:20:03] Dan Berger: Oh, here's here's something funny. I didn't fly them first class. Wow. And I and I mean, because I'm fucking stupid. And I gave him a drink budget. That's how stupid I was back then. And then they got mad at me, like, what do you mean? I got a drink. It's so ridiculous. Like, this is the kind of shit like I should nickel and dime, you know?

[00:20:19] Sam Parr: Yeah, well, the first class thing is not nickel and diming. That could have been like an additional 100 or 200 grand in flights.

[00:20:26] Dan Berger: Totally. I still don't fly first class. I've flown first class once because I got upgraded.

[00:20:30] Sam Parr: That's insane to me. First class is my love.

[00:20:32] Dan Berger: Everybody's got their dumb. Everybody's got their dumb kind of thing. My thing is like, I'll never. But look, I think for me, I was zero. And I think your your perspective is a good one. Mine is keeping the nut.

[00:20:43] Sam Parr: Which is now the.

[00:20:44] Dan Berger: Principal. So it's well, I mean, I include my liquid in there. So it's 20.

[00:20:48] Sam Parr: Okay.

[00:20:48] Dan Berger: So I'm keeping the principal.

[00:20:50] Sam Parr: And do you fear running out?

[00:20:52] Dan Berger: Who doesn't? Yeah of course, because yeah.

[00:20:54] Sam Parr: Previously you implied that you don't fear. You said, you know, you have a mentality that I've just come around to, which is I feel as though I'm not a one hit wonder. I feel as though I can make it again. And that took me a long time to buy into. But it seems like you believe that you are not a one hit wonder and that you can make it again.

[00:21:13] Dan Berger: Fuck yeah dude. I mean, I had an executive coach who? Bill carrier, who really helped me realize that I am my own best resource. So, for example, one of the things I've done, I started a commercial cleaning business when I sold my company with a Serbian immigrant here in Idaho. We did a million last year in revenue. We got like 20% margins this year. So that's an example of something I can succeed with and I can have income from. I just started building a retreat center here in Boise, Idaho for corporate off sites, 11 rooms in downtown. I truly believe this business model will be successful and that will create income. So I'm a builder. I'm not going to stop at 43 and I will be successful because there's no other option.

[00:21:56] Sam Parr: What do you have income from right now?

[00:21:58] Dan Berger: Just like dividends and income producing investments.

[00:22:01] Sam Parr: Is that 10 million in boring public equities index funds or is it in something more exotic?

[00:22:07] Dan Berger: No. I had like 2 million in Nvidia like a lot in Palo Alto Networks, Google like a lot of tech stuff and also a lot of non tech stuff. I have like Q-q-q and other kind of de-risked asset classes.

[00:22:25] Sam Parr: Now, even though Don isn't afraid to spend his money, that doesn't mean that he's immune from regretting things that he does with it. And we're going to get to that. But it's time to get to the deep part of the conversation. This thing, it was so important and life changing for Don that like any good Post-exit founder. He felt so strongly about it that he decided to write a book about it, and that thing is belonging. Don feels that the world is in a belonging crisis. Unfortunately for him, his experience with that started very early on.

[00:23:01] Dan Berger: The reason I am where I am today is because of three things that happened to me the first time adopted. I was adopted when I was two days old. My biological mom basically told me I don't belong in her room and her family. My dad abandoned us when I was two. I don't talk to him right now. So the nuclear family, I had disappeared. And then, like I said, we immigrated here when I was eight and speak a word of English. So I had to negotiate my identities, you know, in fourth grade. Those things really gave me this kind of belonging, looseness. I didn't know where I belonged. I constantly searched for it.

[00:23:31] Sam Parr: Yeah. I mean, it's like a traumatic first ten years of life.

[00:23:34] Dan Berger: Yeah. And everybody's traumas are different, and I respect them. And everybody's traumas are, you know, their pain is at a maximum. I'm not ranking traumas here. These are mine. This is what happened to me. And I like to think about it. And this is what I write about is this kind of like belonging personas. And I am an anxious blogger. I have a high need to belong, but an insecure attachment style. And because of that, I'm seeking, seeking validation. And it's like I call them meerkats because we're like looking up. Then we're going back underground to socialize. So I have done a lot of things to try to fit in, try to belong, and a lot of where I am today is because of those things and because I took the time to figure it out.

[00:24:14] Sam Parr: And when it comes to belonging, what I didn't realize about myself was when I started a company. I don't believe in becoming friends with your employees because we're not a family. You know, we're a team, but you do for a small company, you oftentimes become friends with them and your employees sort of become it's like a general without an army. You just feel naked. You feel alone. You feel I have nothing anymore. You know I was important. Now I'm unimportant. I don't belong in the trenches with my troops anymore. Did you feel just more alone after selling?

[00:24:52] Dan Berger: I know a lot of people on the pod have talked about this, and that experience is valid, especially for me. I just take a slightly different perspective. The way I think about it is that I was finding belonging within my company and not finding belonging outside the company, and that is everything from like interpersonal relationships, my closest friends to what I kind of refer to as casual encounters, saying hi bye to acquaintances, self-esteem. Another belonging path where I was kind of seeking to be validated by the industry and by the employees. And yes, because every one of my belonging needs was being met at the company. As soon as I sold, my belonging tank emptied. And that's when I realized personal belonging has to come before professional belonging. I mean, even religious. Kind of like this religious kind of cult of a culture. I don't even talk about drinking, I was, like, waterboarded in the people in the kool aid, and I didn't realize people have belonging. I need to find belonging outside of work first before they can have belonging at work. And I flipped the script on that, and that was a big mistake I made.

[00:25:52] Sam Parr: I don't understand you made people think that they only belonged in your company, because that's how also how you felt and you thought you were doing the right thing, and that was not the right thing. Looking back on it.

[00:26:03] Dan Berger: It's exactly right. I didn't realize people have to find belonging outside of work, and when people did not do what I expected them to do, to find to like, fit in and like go to every happy hour and, like, wear our t shirts or whatever else I ostracize them.

[00:26:18] Sam Parr: And where this where a large percentage of the staff bought in?

[00:26:22] Dan Berger: I think so, yeah. I mean, we, we got a lot of culture awards. We got a lot of we had scores, a lot of friends referred friends. We had poor retention numbers. And that's partly because of my leadership style and partly because we had a young workforce that went to much better places. But yes, um, I to this day, Sam, I get texts from people thanking me. We have three marriages as a result of the company. I mean, there's a lot people are still working together, like Adobe or Pendo, and there's still that strong alumni network. So I definitely believe we were very successful in creating a culture of belonging, but it wasn't for everyone.

[00:26:57] Sam Parr: I think I'm gonna have to invent a word here, but it's called belonging lessness. And it's what Don is describing here, and it's what has caused a lot of Don's issues. It may be the cause of your issues, too, by the way, but those issues don't have to look the same. So if you're not seeing yourself in Don, that's not to say that you shouldn't think about your own sense of belonging, but Don has found a way to work on this for himself. It's what he wrote about in his book. It's called The Quest. He's going to share some of that with us, too. But first, I want to focus on how this issue has presented itself in his life. You had mentioned before that you have a God complex. What does that mean?

[00:27:37] Dan Berger: Jackie does a wonderful job preparing you for these conversations.

[00:27:41] Sam Parr: She's very good.

[00:27:42] Dan Berger: She is very good. I think the context of that and being in recovery, you kind of realize that you cannot play God. And by the way, a great path for belonging is being in recovery and in fellowship when you haven't. Let me talk an I when I had an addiction and I try to control everything around me. That's a God complex. Whether I'm addicted to work and playing God at work, or whether I am using my addiction to manipulate people, I have a God complex, and I think one of the really important things in order to be in recovery is to realize you cannot play God, and to realize that there are other forces at work that are not solely under your control.

[00:28:21] Sam Parr: What addictions are you recovering from?

[00:28:24] Dan Berger: Uh, love sex and porn?

[00:28:25] Sam Parr: Um, those sound like pretty good ones, right? Fucking rock and roll, right?

[00:28:31] Dan Berger: Yeah, yeah, that's what I thought was, uh, how men should be showing up.

[00:28:35] Sam Parr: You sure you don't want to add some cocaine and Jack Daniels to that list was there?

[00:28:39] Dan Berger: It was there. It's all I wouldn't say it was, uh, it was not addiction levels. I mean, but it was definitely par for the course with those addictions. Yeah.

[00:28:48] Sam Parr: And there has to be a clear line to you being raised like, you know, not knowing who loved you and, like, questioning, like why your parents, you were adopted and moving. I mean, I would imagine if you would look up some of your issues in the dictionary, you'd see a photo of you, like, I don't know anything about anything, but I do know that there's a very clear line of like, well, this stems from these issues, right?

[00:29:11] Dan Berger: Yeah. Hopefully it's a better somebody better looking. But yes, you're absolutely right that there is worthlessness associated with what I went through. And there is a desire to meet to solve that worthlessness through the addictions I just mentioned.

[00:29:24] Sam Parr: If you could fix any of these issues, would you?

[00:29:27] Dan Berger: I am fixing them.

[00:29:28] Sam Parr: Yeah, but like, I guess what I'm saying is I'm sort of grateful for some of my craziness. Yes. And is it Adler who says one of the reasons why, for example, someone like me, I get panic attacks on I don't like going in subways or planes. And I think it's Steven Adler would say something like, well, the reason you feel that way is because you don't want to improve. You kind of like being this way for a variety of reasons. And I think that I am crazy in a variety of ways, and I sort of like it because it's made me successful and I'm refusing to let go and change. Is that the case with you.

[00:30:06] Dan Berger: As it relates to gratitude? I have gratitude for my addiction. Absolutely, because it brought me to where I am today. It's led me to the path of recovery. It's led me to a deeper connection with my higher power. It's led me to a deepening of my relationships with people. It's led me to a community of other addicts and so on and so forth. So I'm grateful for my addiction. I'm also angry at my addiction, for taking away my self-control and wounding a lot of people along the way. And I don't think I'd be with my wife right now if she didn't have the grace to forgive me, and these allowing the space for me to show up and share these things. But without my addiction, I would not be where I am today. So I am indeed grateful for it. Like you mentioned.

[00:30:45] Sam Parr: And here's the answer that he's found to the belonging crisis.

[00:30:49] Dan Berger: So belonging tank is basically what it sounds like. It's a bunch of different fuels that go into a tank and give you a sense of belonging, any kind of delta between how much you have full and how much is empty is an opportunity to have more belonging. I won't go into the different paths just because of time, but basically there's multiple paths to belong. There are six of them. So my belonging paths are the men's group that I run here in Boise, Idaho. You know, you started Hamilton, which congratulations. What a success story for me. I run a men's group with 27 guys. We meet monthly. That's a big part of my belonging tank. I run a nonprofit for that focuses on Zionism and on fighting anti-Semitism. That gives me a sense of belonging, be part of that community. Obviously, my wife and my daughter gives me a sense of community. My hobbies like gaming And my new company, Bringing People together. It's a meetings company. It's for retreats. That gives me a sense of belonging. Those are all the things that give me a sense of belonging today. And by the way. And writing my book. Right. Writing my book is one of the ways of creating belonging for yourself is these kind of one sided relationships where you're like, you're you have belonging with your fans. I mean, you have a lot of Twitter fans, a lot of people who follow you, much like they have a connection with you, you have a connection to them, and that provides a sense of belonging in the same way that I wrote in my book, giving me a sense of belonging.

[00:32:05] Sam Parr: I would say that for me, I had 100 million people listen to my podcast last year, or 100 million views and downloads. Who knows how many people that is? That gave me close to no sense of belonging. I don't care about that number. I don't give a shit about these people necessarily. When they come up to me and they shake my hand and they say, this impacted me. I feel great about that. And I feel like, oh, I am like a servant to you. And that makes me feel good. I served you, but just seeing that number, I don't care. And I find it a little actually lonely just talking into a mic in front of a camera. So if you had to create a blueprint of belonging, part of me thinks that it has to be, or for most people has to be some type of in real life connection, not just digital. And so like if you had to make like a here's the rules or here's the, here's the attributes of what belonging feels like, likely being around someone on a regular basis physically is on that list, I would guess.

[00:33:05] Dan Berger: So just a little pushback. That's not what the research says necessarily.

[00:33:10] Sam Parr: Well, I don't know anything as well. I'll preface that.

[00:33:12] Dan Berger: So I didn't want to misrepresent. I'm not suggesting that because you have a lot of followers or downloads, you have a sense of belonging, but because you're having an impact on a large audience and people, then you get signals that it's helping. That's the sense of belonging I'm referring to that being of service is what partially is one way we get a sense of belonging. Just to be clear, there's also research that shows that while you're absolutely right, The belonging is a fundamental human need and is a social construct, which is why I reject Eckhart Tolle or Brene Brown, who says, just go get naked in the wilderness and introspect all day. That's not how you find belonging. It's only a part of it. It is a social construct, requires social connection. But people do find belonging. Sam Theroux, for example, being part of a subreddit, reading fiction and connecting with people, watching a show like Peaky Blinders and falling in love with Tommy Shelby. Those are ways of finding belonging as well, that continue to be researched because they represent these parasocial bonds with figures we don't necessarily know. So there's many ways to fill that tank. And, you know, for different people, there are different ways to do it.

[00:34:13] Sam Parr: This is an issue that Don thinks a lot of people struggle with. And in his experiences in the communities that he's part of, he's seen this hitting men particularly hard.

[00:34:22] Dan Berger: So I'm a big proponent. Well, let me just be very direct. I think men are in a crisis. I think a lot of the men that are Struggling. Don't talk about it. And I think that given what you said and what we agreed on, that there is a kind of compulsion driving a lot of entrepreneurs. That compulsion, in my view, needs to be addressed in some way. And I think that pornography, especially for men, especially in this time, given the kind of tectonic shifts that are happening in society, it's important to address some of the compulsions. Again, pornography, womanizing, or even workaholism or substance abuse. By the way.

[00:35:04] Sam Parr: I think that men are getting left behind. I think if you look at like suicide rates, if you look at education levels, you think about the fact that like, to be masculine is sort of it's not a compliment right now. I think that's not good. I also think that entrepreneurs but, you know, I hate saying founders struggle because I think everyone struggles. And I think it's bullshit to say just because of your job, you are in a different category of struggle. But I do want people to know that when they're starting a business. To me, starting a business isn't really starting a business. It's more of like a it's like an exercise of confidence of saying, you know, I have this vision for this world, and that vision could be that my artwork is going to be wonderful. It could be I'm going to write this song and I think people are going to like it. This is going to be a hit, whatever it is. And capitalism and entrepreneurship is just a really fantastically practical way to give someone the ability to put their dent in the world. And so when you're starting a business, that's what you're doing. You're going through that process.

[00:36:02] Sam Parr: And it's very normal to think, I'm not good enough. This is going to suck. This won't work, I hate this. Why am I doing this? And I try to let people know that is very, very, very normal. And at the same time, I think that I try to encourage people, particularly young men, because I can relate to that feeling of a young man is basically sometimes you just kind of kind of shut up and do it like you owe it to your family, to your coworkers, where this is just your burden, and you should have a community of people to bitch and complain about. But also you just have to suffer and you should try to find meaning and joy in that. And Tony Soprano says, whatever happened to the strong, silent type like Gary Cooper? I think that every once in a while we need to be a little bit like Gary Cooper every once in a while, and we just got to shut up and get it done, you know? Gary Cooper is a traditional masculine actor who doesn't complain. And then other times, you know, in your small circle, I think you're allowed to be weak. You know what I mean?

[00:36:54] Dan Berger: I do a couple of things come to mind when you when you said that, and I completely agree with you. It's why forums like the ones in Hampton, for example, are really important. I think that men don't have the emotional lexicon nor the emotional maintenance in order to show up vulnerably, so they need to see other men doing it first and foremost. Second of all, you know, Gary Vaynerchuk was one of my earliest advisors. I ran up to him at South by Southwest, and he agreed to be an advisor, and he made a lot of money by making that decision very early on. And I think that he was kind of like sidelined a little bit regarding like hustle porn and all that. I think that's part of being a man. It's going out there. It goes back to primordial days when we're going to find the wooly mammoth, and.

[00:37:39] Sam Parr: You got to go hunt.

[00:37:40] Dan Berger: Sometimes we got to go, got to go find it, you know? We're not coming back until we do it. And, you know, it may be a couple of downed trees and, you know, burned villages, but God damn it, we did it.

[00:37:58] Sam Parr: I'd given a teaser earlier about the things that Don would do differently if he was able to redo his exit today. Here's what he had to say.

[00:38:06] Dan Berger: Number one, I would not invest in alts for the first year. It's very easy to have a lot of money and be like, oh, here it is for my buddy here, my buddy there, and you just don't do the work to figure it out if it makes sense for you. At least that was stupid for me. That's number one.

[00:38:23] Sam Parr: Could you summarize that? I'm going to project a little bit. I want to I want to know if you agree. Do you think the He summarized that rule. You could say just basically do nothing with the money for about 6 or 12 months.

[00:38:34] Dan Berger: I mean, I think you can probably be a little more prudent about it, like maybe put it in fixed income or something like that where you can kind of you can park it.

[00:38:40] Sam Parr: I would put that in the category of nothing. I guess what I mean is like major changes in your life.

[00:38:45] Dan Berger: Yeah. I mean, I'm not sure. Like, I think you can take some and do some high risk stuff like I believe in like that. What's that app called where you, like, mimic your own purchasing.

[00:38:53] Sam Parr: What is. What are you talking about?

[00:38:54] Dan Berger: There's like this app where you mimic your own purchasing decisions and then invest in those companies.

[00:39:00] Sam Parr: That's a great idea. So instead of buying $100,000 Tesla, you invest $100,000 in Tesla.

[00:39:04] Dan Berger: Yes, exactly. Okay. That's cool. I think Tesla is not a 300, so don't do that today. But I think anybody who has a liquidity event can intuit where the world is going, especially in things that relate. For example, even during Covid, I invested in Marriott and I was in the hospitality industry. I invested in Ticketmaster. So those are examples of things that I would have done regardless, because I feel like I had some intuition. So I would say, yes, park it, do a couple alts if you want to. Like maybe like your buddy needs 25 K, great, but that's a gift. It's not an investment. And then maybe a little bit of philanthropy. I think I leaned in too hard into philanthropy. Personally. I've given I give like $100,000 a year to philanthropy, and I think I can wait a little bit until I'm older to do that. But where Israel is right now, they need it, in my view. Obviously many people would disagree, but yes, park it, do a little bit and then have some fun with it and some some risky stuff. But generally speaking, I think you're right.

[00:39:56] Sam Parr: So rule one chill on the alts.

[00:39:59] Dan Berger: Chill on the alts.

[00:40:00] Sam Parr: Mostly boring for at least one year is kind of what you've said.

[00:40:04] Dan Berger: Yes, while keeping room maybe 10% to have some fun, do some high risk stuff, buy some stuff, help a buddy you know, give the charity a little bit just to feel good.

[00:40:14] Sam Parr: Is there a second tendency or principle of what you would have done differently?

[00:40:18] Dan Berger: You know, Sam, I spent three years after the sale and kind of exploring what belonging means to me, and I fell into it. I didn't realize it's what I was missing And I think doing that and then committing to writing a book about it and spending a quarter million dollars on writing this book, and which I ended up writing myself, by the way, it was a pay to play model, although it wasn't that great. I think it's a really good way to get introspection, and I didn't want to be one of these other, like, people, like, oh yeah, I wrote a book about my success. I wanted to write a practical book. So I think, like spending money on something that can help you open up. Your next chapter is really interesting too, because a lot of entrepreneurs struggle with like the next chapter. I mean, it's a big issue, right? Like from what I understand, a lot of people come to Hampton with that issue. So let me just be very clear. The reason why I decided to write a book is not just because I want to help people find belonging, but because it is it is a key marketing asset for my next thing. And unlike most people who are like, oh, I'm a CEO of a $20 million a year company, let me go market myself. I'm first marketing myself, and then I'm going to start something else. So investing something and figuring out how are you going to show up in the next life, even if it's not totally thought out? I think is really important to give all of us some clarity and some kind of solace.

[00:41:37] Sam Parr: So just to summarize the last pieces of advice. One is the classic. Don't do anything crazy with your money right away. Even if you think some startup is going to be the next big thing, it's safer, in my opinion, to sit and be patient. You've already made millions and it's okay, in my opinion, to just sit there and relax and wait and plot. And there's going to be lots of different opportunities that are going to come across you. So it's no big deal to just not do anything for 6 or 12 months. And two is you should invest in yourself. In my opinion, you should find something that can help you find the next season in your life. Invest in your personal brand. Invest in reading. Do anything that you think will help spur some type of inspiration that could be traveling, surfing. It could be anything you want, but I think you should go and do something that gets you outside, gets you away from thinking about making more money and also not put a time limit on it. Just let it come to you naturally. It feels pretty uncomfortable to be honest. That time. It could take one month, six months, three years, who knows? But I think you should wait and slowly begin to plot. Now I'm going to end with this. You see this podcast. I've already said it before. It's inspired by Hampton, this community I have and the reason I came up with this community, Hampton, is because I started and sold the business, and after I sold my business, I was kind of lost and it felt kind of lame to talk about this stuff online, like, what do I do with my money? What do I invest in? Who do I talk to about it? How do I feel about this newfound success? And that's why I created Hampton, because I wanted a small community of people who had been there, done that, people who had similar problems as I have.