Why Hiding His $133M Net Worth Actually Attracted Better Partners

We spoke to Alex in this week's episode of Moneywise. Alex is a 40-something entrepreneur who built his wealth alongside his now ex-wife, creating a successful company that's worth around $100 million today. After a two-year divorce process that required splitting both business and personal assets, Alex is navigating the dating world for the first time in nearly 20 years—but this time with a nine-figure net worth. Unlike many wealthy singles, Alex deliberately downplays his success, preferring to meet people through authentic activities like skiing, surfing, and dog parks rather than flashy displays of wealth.

Like all Moneywise episodes, Alex 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: the psychology of dating with significant wealth, how to avoid gold diggers without being paranoid, the power dynamics that money creates in relationships, and his philosophy around giving away tens of millions rather than passing it to his kids.

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. Hampton is my company. It's a community for CEOs and founders. We have over 1,000 members now and the range is everything from people running startups doing a few million in revenue to publicly traded companies doing hundreds of millions in revenue. And because I get to see all these private conversations that our members have about money, I thought "dude, this stuff is so interesting, it should be public." That's where Moneywise was born. So if you're a CEO, founder, or business owner, check this out. And if you've listened to more than one episode of this podcast, then you owe me a share. That's all I ask. Post it on your Instagram, Twitter, LinkedIn, whatever. Just share this episode with someone. New Moneywise episodes come out weekly.

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Now, below are the notes and the full transcript.

The Numbers

• Total Net Worth: ~$133 million
• Stock Holdings: ~$100 million (majority of net worth, still in original company)
• Secondary Sales: $45 million total across two sales
  • $33 million after taxes
  • One sale in 2021, one at end of last year
• Second Company: SaaS business generating ~$2 million annual revenue
• Employment: Just Alex and one partner, no employees
• Work Schedule: ~15 hours per week between both partners
• Housing: Under 1,000 sq ft, 2-bedroom house (mortgage paid off)
• Recent Investment: Full home remodel (expensive due to California location)
• Lifestyle Expenses: Very low monthly expenses after remodel completion

Building Wealth Through Partnership and Persistence

Alex's wealth story is unusual because it was built entirely through partnership with his ex-wife over nearly two decades. "Right after college, I took a solo trip on my own for about a year, traveled around a lot of places in Central and South America and then Southeast Asia for a while, and then came back, met up with her, and then the two of us took off, and we went and lived in a bunch of different countries in South America," Alex explains. During their travels, they started multiple companies that failed before finally hitting success with their third venture.

The divorce process was particularly complex because it involved splitting both personal and business assets. "It was like a very abrupt end of our both business partnership and marriage partnership, and it was not amicable and it took a while. We have two kids as well. Took roughly two years to sort of sort everything out. Figuring out how to divide up assets was was very tricky with the company involved," Alex shares. The secondary sales he took were actually part of the divorce settlement strategy, allowing him to have liquid assets while maintaining his equity stake.

His second company emerged organically from a practical need. Alex and a friend at a big tech company both needed the same tool, so they built it over a weekend. "It just started as a little side project that we used for our own companies. We had our own two companies were our first customers, and then it was a side project for six, seven years while we were working on other things and just kind of slowly grew." Now both partners work about 15 hours per week on what has become a $2 million annual revenue business.

The Anti-Flex Dating Strategy

Alex's approach to dating with wealth is remarkably understated. Unlike many newly wealthy individuals who might use their success as a conversation starter, Alex actively avoids mentioning his financial status. "Money doesn't come into it really. And the dating, like, I definitely don't advertise that I have a lot of money. I don't think that people that I mostly have gone out on, like casual dates with, would really know. I mean, I talk about how I run a small software company, so maybe there's like some implicit level of, of income, but most of the people I've dated wouldn't know what my wealth situation is."

This restraint comes from a deeper philosophy about authentic connection. "I've just always kind of have an aversion to showing off. I guess it's not in my nature. I don't know that it comes from a place of confidence necessarily, but it just never feels right to, like, brag about myself." When forced to describe his background, Alex has developed a careful narrative: he mentions growing up in rural farm country, talks about failed startups before the successful one, and quickly pivots to discussing his passions for outdoor activities.

The reveal typically happens around six months into dating, but by then it's rarely a surprise. "When you're dating for a number of months, somebody starts to get to know you and they know a little bit more and a little bit more. And so by six months of dating his person, it was pretty clear, like, oh, this guy doesn't work a lot and he takes a lot of trips. So he's clearly well off in some ways."

Avoiding Gold Diggers Without Becoming Paranoid

The fear of being used for money is real but manageable, according to Alex. He's had one clear experience with someone who seemed more interested in his lifestyle than in him personally. "There was one person I dated who I think had grown up pretty wealthy and then had like some big saga where her, her dad, when he died, was living in another country. She was supposed to be one of the beneficiaries and receive a lot of money, but didn't. So she like went from like this world with a lot of wealth to then having to like make her own way."

The red flags were subtle but consistent. "All of her suggestions for like, where to stay, what to do" involved significant expense, and crucially, "she never offered to pay." Alex learned that the offer to contribute financially matters more than the actual contribution. "The offer is important. Absolutely. Yeah."

Rather than becoming paranoid, Alex focuses on lifestyle alignment. "My hope is that I'll meet somebody who is into the same lifestyle that I'm into, which is to do a lot of traveling, but not to be spending a lot of money on it. I'm happy driving up and down the coast, camping in a van for weeks on end." His current partner exemplifies this approach: "One of the things I really liked about her is that even when she, like, knew I had money and then, like, eventually knew how much money I had, like, she just never seemed impressed by it at all or, like, didn't care about it at all."

Meeting People in the Real World

Alex has deliberately chosen to meet potential partners through shared activities rather than dating apps. "A self-imposed rule, is I want to be asking people out in person. So I've gone on a few hinge dates, but really just a few." His success stories all involve organic meetings: "The first person I met on the chairlift, the second time we were on the chairlift that morning together, I was like, oh, hey, like, you want to keep skiing today? And then that just turned into dinner and then dating for a few months. The second person I dated for a few months, I met surfing... The last person I did too, who I'm dating right now, I met at a dog park near my house."

This approach serves multiple purposes beyond just meeting people naturally. It allows Alex to connect with people who share his outdoor lifestyle preferences, and it means the initial attraction is based on personality and shared interests rather than any perception of wealth or status.

Long-term Relationship Considerations

For serious relationships, Alex recognizes that financial alignment becomes crucial, particularly around his plans for wealth distribution. "I think once you start thinking about how to like, manage money and what you're going to do with it, I think a big thing that I'm going to need to figure out over the next few decades is how to give away a lot of money. I don't want it going to my kids or very little of it."

This creates a unique vetting challenge. "I do think in a long term relationship, if I'm trying to figure out how to give away tens of millions of dollars, somebody who could be a partner in that is important to me." Rather than direct questioning, Alex looks for people who "exhibit those characteristics already in their life and doesn't mean is actively engaged in philanthropy, but is like knowledgeable about challenges in the world and some aspect, whether that's poverty or climate or whatever, and is thinking about it and actively trying to come up with ways to to participate and either give time or resources to something that they care about."

Managing Power Imbalances

The wealth gap in relationships creates inevitable power dynamics, but Alex has strategies for minimizing their impact. "There will always probably be that imbalance, right? I think the ways it would show up the worst is if there's like a real mismatch in how you want to live your lifestyle. If I was wanting to spend a lot of money and bringing this person along and they were attracted to that lifestyle, there'd just be this imbalance where I'm paying for everything."

His solution is lifestyle moderation. "I'm trying to live a pretty low profile life. I'm still living in this small house. Instead of buying a new big house, I just remodeled it." By keeping his lifestyle relatively modest, the financial impact of treating partners remains manageable, and it attracts people who are genuinely compatible with his values rather than his bank account.

Other Key Quotes

"I think the thing I would, I would tell myself, would maybe just to be to like give myself some confidence then, which is that like, you're going to meet women, it's going to happen. Be patient. Do it in the real world."

"Pretty much is the rule. That's been the case. I like to just pay for things like, I have a lot of friends who I hang out with who aren't making nearly as much money as me, and if we're hanging out, I'm like, really happy to get the check."

"Not dishonest, but like, selective in what I say."

"There is always in early dates that urge to like flex a little bit. And so I'm like, try to be very thoughtful about that. Make sure that I'm not like, I'm like, oh yeah, like I sold a company like I never, I never say that."

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Full Transcript

[00:00:06] Alex: This feels like good for you. You've clearly done well. And just like, not impressed or like, seemingly unimpressed by it.

[00:00:13] Sam Parr: Dating is already this weird and vulnerable thing. We're getting to know people sharing details from our lives. Small things like the types of books and movies we like, to the big things like our family, our traumas, and of course, our finances. For us, that part can feel like you're holding on to a bombshell, and it's not really that big of a deal if it doesn't change who you are. But money is weird, and it makes people feel weird. So there are a couple of anxieties that come with sharing how wealthy you are. Like, if people are going to take advantage of you, or if the power imbalance will make things feel awkward. And then there's the anxiety that you're going to come off kind of douchey or braggy because of the way that you address it.

[00:00:49] Alex: There is always in the early dates that urge to like, flex a little bit.

[00:00:53] Sam Parr: And that, my friends, is what we're going to talk about on today's episode of Moneywise.

[00:01:04] Sam Parr: I'm Sam Parr, and this is Moneywise. Look, you can scroll through Instagram for just 30s. You're gonna see a ton of junk out there to teach you how to become rich, but not a lot that teaches you how to handle life after you've already made some money. I'm co-founder of a company called Hampton. You can check it out. Join Hampton. It's a community of CEOs and business owners. Our members range from startups with just ten employees to publicly traded companies with hundreds of millions in revenue. And so because of that, I'm able to see all these awesome private conversations about money. And I think a lot of them should be done in public. Hence this podcast. With moneywise, we provide advice by speaking to real people who have made a lot of money, and they are radically transparent about all their numbers, meaning their monthly expenses, their portfolio, and also, more importantly, all the personal issues and problems that come with being successful and how they're trying to solve them. And of course, if you're a CEO of a startup, check it out, join Hamptons.com. You'll be put into a group of eight people who have similar sized businesses as you do, and then you're also gonna have access to thousands of other members and hundreds of in-person events. Oh, and by the way, if you listen to more than one episode of this podcast of money wise, you are in debt to me. You owe me one, and all I ask to pay that debt is just a share. I work really hard on this podcast, and if you could share it on your Twitter, on your Instagram, on your LinkedIn, it would mean the world to me. So just go ahead and share it and I appreciate you. Now let's get to the episode. So today's guest is my friend Alex, and he's worth around $133 million. Details in a minute. What's interesting is the majority of that wealth came from a company he founded with his now ex-wife.

[00:02:37] Alex: Right after college, I took a solo trip on my own for about a year, traveled around a lot of places in Central and South America and then Southeast Asia for a while, and then came back, met up with her, and then the two of us took off, and we went and lived in a bunch of different countries in South America. And during that time we started our first company that failed and then started our second company that failed. And then kind of at the tail end of all that travel, we ended up getting married, moving back to Springfield.

[00:03:06] Alex: And then our first son was born about a year later. During that time, we started our next company and that one was successful.

[00:03:18] Sam Parr: Part of the reason I wanted to start this podcast is because people are often lost when they go through that weird period of building something and suddenly being worth a crazy amount of money. Your lifestyle changes, your relationships change, your anxieties change. And for the most part, you're going through this all alone because only a few people out there actually get lucky enough to create this type of wealth. But Alex is different. He went through all that with his life partner until things changed.

[00:03:44] Alex: It was like a very abrupt end of our both business partnership and marriage partnership, and it was not amicable and it took a while. We have two kids as well. Took roughly two years to sort of sort everything out. Figuring out how to divide up assets was was very tricky with the company involved and figuring out what each person's roles and responsibilities were going to be. Yeah, it was tough. Now it's very amicable. We lived close to each other and say we had like a great friendship. It feels good.

[00:04:13] Sam Parr: And that means Alex is back on the dating scene and this time everything's different. But adjusting to his new single life hasn't been all that bad.

[00:04:23] Alex: I met my ex-wife when I was in my senior year of college, so my dinghy experienced before that. I was just a kid. I didn't know anything about myself, really. It's really fun to date as an adult when you know yourself and know what you like and don't like, and you can just like really quickly, like make decisions about that.

[00:04:41] Sam Parr: We're going to talk about his dating life and what he's learned. But first, let's get a better sense of his new lifestyle, starting with the details of his $133 million net worth.

[00:04:51] Alex: So I still do own quite a bit of stock, and that's probably the majority of my net worth is still in that stock. That's probably about 100 million or so is 100 million at the last funding round. And then I did take some secondary as well. And that was like a big part of like the divorce settlement. I was figuring out how much secondary to take. So I took about 45 million in secondary. So after tax it was about 33 million. That secondary sale, it was actually two different sales, 1 in 2021 and then one at the end of last year. Those two sales and then the stock is still the majority of my my net worth. I own another company as well. That's quite small. It's a SaaS company. It does a couple million a year in revenue. It builds to 2 million or a little under 2 million this year. And that mostly just cash flows. So I have a partner on that. We both take like pretty reasonable salaries from that. It has about eight. Just two of you agents. Just the two of us. Yeah.

[00:05:42] Sam Parr: Or and no employees.

[00:05:43] Alex: No employees. Yeah.

[00:05:45] Sam Parr: Damn, man, you're a hit maker.

[00:05:47] Alex: Well, it's funny, because both of these are companies that are ten years or older, but I haven't been a hitmaker for a long time.

[00:05:54] Sam Parr: The cash flowing one is ten years old.

[00:05:55] Alex: Yeah, it was a side project. It was a tool that I originally needed from my previous company, was like looking for options for it. Reached out to a friend and I was like, hey, I need this tool. And he was like, oh, that's funny, and I need this tool. At my company. He worked at a big tech company. So if we were just talking about this, we need a tool like this as well. And I was like, oh, here's what I've been thinking about how it should work. What do you think? And he was like, yeah, let's build it. River concept this weekend. And so it just started as a little side project that we used for our own companies. We had our own two companies were our first customers, and then it was a side project for six, seven years while we were working on other things and just kind of slowly grew. And then after leaving my last company, we both started working on it and we say full time, but we both probably worked like 15 hours a week on it.

[00:06:41] Sam Parr: Alex's life is incredibly simple now, and up front it wouldn't be super obvious that he has the type of wealth that he does. His house in particular is very modest.

[00:06:50] Alex: It's a little under 1000ft², two bedroom house. It's pretty tiny. And so I have like a a proper backyard.

[00:06:57] Sam Parr: And so I imagine if that's where you live, your living expenses are quite low.

[00:07:00] Alex: Yeah. I paid the mortgage off a few years ago on a I'm just completing my doing here a little bit of sound outside. I'm completing a full one year remodel. Like gutted the entire place. Redid the outdoor space that was obviously fairly expensive. It's California, it's an expensive place to build. But now that that's done, yeah, my my monthly expenses should be quite low after this.

[00:07:26] Sam Parr: Now Alex is not a show off type of guy. And maybe that comes with the age a little bit. He's been married and divorced. He has some kids and basically he's not a 25 year old who just made $100 million, which means he's a bit ahead of the game even though he's new onto the dating scene. I remember being young and goofy, and if I had a lot of money when I was young and single. I absolutely would have used that as a flex in order to meet people, which of course, I definitely would have came off a little bit douchey and attracted the wrong type of woman. And if the anxiety is that people are going to want to use you for money, being flashy with it is just going to make that come true, I think. But even though he's not being braggy about his bank account, it doesn't mean that he isn't using his wealth to give him at least a little bit of an advantage.

[00:08:10] Alex: I think not by like talking about like specific financial status or success. I think like the flex is like talking about how I only work a few hours a week, take a lot of trips, like, are you talking about things that I've done recently?

[00:08:25] Sam Parr: That's pretty obvious advice. If you don't want to come off as a rich douchebag, don't be one. And as a result, you'll attract better people. However, your wealth isn't something you can downplay forever, so you will have to have a discussion at some point rather than keeping it a secret. The question is when. Here's how Alex typically goes about it.

[00:08:44] Alex: Money doesn't come into it really. And the dating, like, I definitely don't advertise that I have a lot of money. I don't think that people that I mostly have gone out on, like casual dates with, would really know. I mean, I talk about how I run a small software company, so maybe there's like some implicit level of, of income, but most of the people I've dated wouldn't know what my wealth situation is.

[00:09:06] Sam Parr: Dude, I'm shocked that you don't. This is just clearly the difference in your confidence and my confidence of not wanting to, like, brag about it.

[00:09:14] Alex: I don't know if it's confidence. I wouldn't necessarily describe it as that, but yeah, I've never been able to. In fact, we were talking about our mutual friends at the start of this. I was at dinner with them. Um, it was at a Hampton dinner, and everybody was going around and saying what they did, and I talked about myself, but I omitted my my big company and didn't say anything about it. And our friend was like, wait a minute, are you going to talk about the company? He started it. I was like, oh yeah, and I did that too. I don't know, I've just always kind of have an aversion to showing off. I guess it's not in my nature. I don't know that it comes from a place of confidence necessarily, but it just never feels right to, like, brag about myself.

[00:09:53] Sam Parr: When do they find out? Typically.

[00:09:55] Alex: Yeah. Only one person has so far, and that was probably six months into dating or so. It wasn't like an abrupt conversation. It wasn't like, oh, surprise, there's this like big reveal. And when you're dating for a number of months, somebody starts to get to know you and they know a little bit more and a little bit more. And so by six months of dating his person, it was pretty clear, like, oh, this guy doesn't work a lot and he takes a lot of trips. So he's clearly well off in some ways. And then of course, my previous company, lots of other people have heard of it. And so when a company like kind of has like a public profile like that, there's like some guesses probably about your level of wealth. So I don't think it came as like a huge shock to her. And I go, so a bit surprising, but not like a big reveal.

[00:10:42] Sam Parr: Do you feel like maybe you have to be dishonest with someone early on?

[00:10:46] Alex: Not dishonest, but like, selective in what I say.

[00:10:50] Sam Parr: So let's let's say they go, uh, hey, tell me about your background. Like, what did you do? How would that story look like?

[00:10:56] Alex: One easy thing for me is, like, I grew up in rural farm country. So I can always start with that. And then, you know, I'd say I started several companies that failed, eventually started a company that was quite successful, worked on that for a number of years, was lucky to be able to step away from that and now run a small software company with another partner, where we are fortunate to not have to work full time and work fortunate to not have to have any employees. Then, then I would like refocus the conversation on my passion. So I spend a lot of time out in the mountains. I spend a lot of time surfing. I spend a lot of time with my dog.

[00:11:31] Sam Parr: So even though Alex really isn't flaunting his wealth, he's also not going to go out of his way to keep it a big secret. Yes, he's not having the official discussion until he's starting to feel like the relationship is serious. But like he said, the way he's going about dating means that the reveal isn't all that surprising. Not hiding it completely in a way is great. He's not creating a big secret out of it, and he's also not building up a bunch of pressure to the point where it becomes a huge thing when he's honest about it. And then, on the other hand, when you aren't fully hiding it, the anxiety of people using you can be more present. I've got a lot of friends who are single and wealthy, and this is a very common thing, which is do people actually like them or are they just being used? And it's a very, very, very big anxiety that a lot of these people have. We'll get Alex's personal take on that anxiety in a moment, right after a quick sponsor break.

[00:12:20] Alex: It's like why I really don't want to talk about it in early dates, you know, avoid it as much as possible, hopefully get a sense of who the person is. If they like me, I hope that it's for the right reasons and not because they see dollar signs.

[00:12:34] Sam Parr: Have you had people use you? You think?

[00:12:37] Alex: I will say there was one person I dated who I think had grown up pretty wealthy and then had like some big saga where her, her dad, when he died, was living in another country. She was supposed to be one of the beneficiaries and receive a lot of money, but didn't. So she like went from like this world with a lot of wealth to then having to like make her own way and not getting any of that. And when we broke up, I remember thinking like that was probably a great call. She would have spent all my money within a couple of years. And so that was like, I never like felt like I was used, but I felt like she was like, this is great. This lifestyle, this is what I want. We took some trips and she was like, we're flying business. We're staying in these like really, really nice hotels. And I was paying for it and I was like, yeah, this is really fun.

[00:13:21] Sam Parr: What specifically did she do that made you think you're gonna spend it all?

[00:13:25] Alex: All of her suggestions for like, where to stay, what to do.

[00:13:28] Sam Parr: With, like, the cost.

[00:13:29] Alex: A lot of money. Exactly. Yeah.

[00:13:31] Sam Parr: Did she offer to pay?

[00:13:33] Alex: No.

[00:13:35] Sam Parr: The offer is important. The offers?

[00:13:37] Alex: The offer is important. Absolutely. Yeah. For her, like knowing her, her background and like her childhood, she was really accustomed to that lifestyle. And for me, it was like brand new. I was like, whoa. Like, I never do this. Like, I've stayed at, like a fancy hotel twice before. And now, like, we're on a 14 day trip and every hotel we're staying in is like $500 or more a night. This is different for me.

[00:13:58] Sam Parr: This was a pretty big red flag, but it's not often that simple deciphering between who wants to enjoy your money and who wants to enjoy your money with you is tough. And that's the thing. By the way, we've talked a lot about on this podcast, which is you don't make a lot of money just to sit on it. It's meant to be used to be given away, to be enjoyed. And who better to share your success than with someone you really love? Because of that, the answer to this problem isn't just going to be keep your wealth all to yourself. If you want to see how that situation works out, you should check out our recent episode with a woman named Jennifer. Being cheap out of fear brings negative energy to any situation, and that is not nice for the people around you or even yourself. It's nice to pick up the bills when you can, and Alex enjoys doing that.

[00:14:42] Alex: Pretty much is the rule. That's been the case. I like to just pay for things like, I have a lot of friends who I hang out with who aren't making nearly as much money as me, and if we're hanging out, I'm like, really happy to get the check. And I do. Not a lot. It's not specific to the dating context, but I do tend to pick up the check.

[00:14:58] Sam Parr: That means that what this really comes down to is the wisdom to understand people's intentions. We'll talk about this in a minute, but one of the ways that Alex deals with avoiding people who just want to use him for his money is trying to find people who align with him on his lifestyle. This is all really complicated, though. Be wise isn't super specific advice which makes you think about an easier alternative, which is dating people who already have wealth on their own. When I started dating my wife, she worked at Facebook. At the time, I think I was paying myself like 2 to $3000 a month, and she was making 10 or $15,000 a month. And she also came from a family of entrepreneurs, which means that she kind of saw her parents start something and kind of rise to become a very successful family. Because of that, she kind of understood the entrepreneurial journey. She understood that maybe what I'm doing is going to work out and we're going to have a lot. Maybe what I'm doing is not going to work out and we aren't going to have as much. But I think because of her background, because of the way she was raised, because she already had a little bit of money, I think it made life so much easier for us, particularly once we kind of came into making a bunch of money. It was as if she had already experienced a little bit of that lifestyle and didn't take it for granted, but also wasn't incredibly impressed by it. And I love that about her. But Alex really isn't concerned about his potential partner's wealth. He wants to meet people purely through connection, and that means ignoring apps altogether.

[00:16:27] Alex: This could change over time, but kind of a rule that I've had for myself these last few years that I've really enjoyed is a self-imposed rule, is I want to be asking people out in person. So I've gone on a few hinge dates, but really just a few. And it isn't like a very short period of time. And other than that, the people I've met like my rule is meet them in real life and ask them on the date. And so the people that I've liked dated for like a few months at a time. The first person I met on the chairlift, the second time we were on the chairlift that morning together, I was like, oh, hey, like, you want to keep skiing today? And then that just turned into dinner and then dating for a few months, and we took some trips together. The second person I dated for a few months, I met surfing, and so it was like, hey, do you want to just like, meet up and surf again? And then that kind of evolved and I was like, oh, do you want to take a surf trip with me? The last person I did too, who I'm dating right now, I met at a dog park near my house.

[00:17:21] Sam Parr: And instead of searching for people with similar wealth right now, he wants to focus on how his potential partner aligns with him when it comes to his future financial plans updated.

[00:17:29] Alex: People are kind of all over the place. I do think that it gets maybe for like a long term relationship, it could be a little bit more of a a challenge. I think once you start thinking about how to like, manage money and what you're going to do with it, I think a big thing that I'm going to need to figure out over the next few decades is how to give away a lot of money. I don't want it going to my kids or very little of it. You'll link to my kids at least. So no, I haven't had any sort of guidelines around who I want to be dating in terms of like what their background or their financial situation is. But I do think in a long term relationship, if I'm trying to figure out how to give away tens of millions of dollars, somebody who could be a partner in that is important to me. And that might dictate sort of the background that somebody has.

[00:18:16] Sam Parr: How are you going to vet a potential partner to make sure that she's on board with that?

[00:18:22] Alex: That's a good question. I mean, I think slowly, lots of conversations that are not like, hey, is this like aligning with your life philosophy? Because who knows what one conversation could lead to? But yeah, I think somebody who exhibits those characteristics already in their life and doesn't mean is actively engaged in philanthropy, but is like knowledgeable about challenges in the world and some aspect, whether that's poverty or climate or whatever, and is thinking about it and actively trying to come up with ways to to participate and either give time or resources to something that they care about.

[00:19:06] Sam Parr: Aligning with your partner about finances, and more specifically, what to do with your money is crucial, I think, to any relationship. Your lifestyle nearly completely depends on how and where you spend your money, which means finding someone with similar wants and values is a major part of any good relationship. But there is this power imbalance when one partner makes significantly more money than the other partner. And even if you have this, what's mine is yours. Team philosophy, which I think is the way to go. There's still going to be a little bit of an issue sometimes with money and that power imbalance.

[00:19:38] Alex: There will always probably be that imbalance, right? I think the ways it would show up the worst is if there's like a real mismatch in how you want to live your lifestyle. If I was wanting to spend a lot of money and bringing this person along and they were attracted to that lifestyle, there'd just be this imbalance where I'm paying for everything. It's totally dependent on what I say we do. It's a real fear I have. I think a couple of the ways that I'm personally trying to mitigate that is I'm trying to live a pretty low profile life. I'm still living in this small house. Instead of buying a new big house, I just remodeled it. My hope is that I'll meet somebody who is into the same lifestyle that I'm into, which is to do a lot of traveling, but not to be spending a lot of money on it. I'm happy driving up and down the coast, camping in a van for weeks on end. Yeah, I guess avoiding potential matches where that power imbalance would manifest more naturally.

[00:20:42] Sam Parr: It's probably always going to be there, right?

[00:20:44] Alex: Yeah.

[00:20:44] Sam Parr: It's just it's just a matter of how you adapt to it.

[00:20:47] Alex: I think you're right about that. And so thinking of the person I'm dating now, one of the things I really liked about her is that even when she, like, knew I had money and then, like, eventually knew how much money I had, like, she just never seemed impressed by it at all or, like, didn't care about it at all. Uh, when we travel, like, we've camped a ton together, that's the thing we've done more than anything else. It's never really come up in our relationship too much. Like I pay for a lot of dinners, that sort of thing. But in the way that we're living our lives, it's not constantly a thing. Saying.

[00:21:26] Sam Parr: Alex is kind of lucky. The lifestyle compared to his net worth is incredibly cheap, which means footing the bill. It's not that big of a deal for him. And so for that reason, he's not too concerned about the power imbalance overall. But what if you want to live this extravagant life? That imbalance is going to be exacerbated when you want to do something fancy, like take a trip on a private jet and you constantly end up footing the bill because you want your partner to come. And even if you're totally fine paying for things, you want to empathize with your partner, everything that you do together will ultimately be in your control. There are a lot of ways to address this, but there's one that I found incredibly interesting, and that's this woman named Anne Mahlum. She came on Moneywise a few episodes ago, and she told the story about how she sold her company, Solidcore, for a couple hundred million dollars. It's an incredible episode, maybe my favorite of all time, and you have to listen to it. However, I want to bring to you a quick little bit about this relationship stuff that didn't make the cut for that previous Episode that right after a small sponsor break.

[00:22:22] Anne Mahlum: So Brett is younger than I am. He's about six years younger than I am. So that means I've had more time to make money and my career. And it's also I've exited my company. There's not a lot of people, let alone women, sitting in my position, that have built $100 million of net worth for themselves. And so, Brett, even if he makes $500 million a year, like it's not really going to move the needle on our financial situation or what we can do. When we were going through our prenup, I was not going to feel good about if we ever get divorced, that I have to give X amount of money to this person. I no longer want to have a partnership with or and or vice versa. I think Prenups are completely stupid in that way. If I want to make Brett feel more equal in our relationship, and not that I have the power with the money. And like I get to say, because I have more of it then I need to gift Brett money in our marriage when we are starting our life together. That is his and that he can grow that money or do what he wants to do with that amount of money so that he feels empowered by that. And it's not like everything is, you know, he's got this much and I have 100 million, and I feel like a sugar mama. I didn't want that. He didn't want that. And so I have I'm gifting him money over the course of our first two years of marriage. And if we get divorced, there's no I mean, obviously, I never think we're going to get divorced, but you know what I mean? There's no payout. There's no ill feelings at the end of, like, okay, well, Ann owes Brett this amount of money because their marriage didn't work out.

[00:23:58] Sam Parr: I didn't get a prenup. And I'm not envious of you for having to have that conversation.

[00:24:03] Anne Mahlum: It honestly, like, was super easy. And Brett is also like, yeah, that makes more sense. Like, why wouldn't we try to find a more equilibrium in our marriage when we are happy and, you know, plan to have our whole lives together again. Who knows what the future holds? I shouldn't even say that. Like, I never think we're going to get divorced. And I know nobody ever does when they're in love and in marriage. That's why you have a prenup to plan for the whatever percent chance that that may happen. But we have things in our marriage, like when we go out to dinner, we have a shared credit card. Brett has his own money, and I have my own money. And then we have a shared sort of pot on our life together and things that we do. I don't make a big purchase, Sam, without talking to Brett, because I think I owe him that respect as my husband and vice versa. And that doesn't mean that I don't own certain property, like I own this house that I'm in on my own. Like it's only in my name. There's a condo we own together. There's different investments we may do together, but I have been in many relationships where the masculine feminine energy was off, and I didn't want to take that risk with Brett. So we knew we had to talk about money. And like I said, he'll put down the credit card when we go to dinner because it's a shared credit card that we have. And like that's part of a masculine activity for him. Like I don't really care.

[00:25:19] Sam Parr: Was dating a pain in the ass being a woman? That was just a badass.

[00:25:24] Anne Mahlum: It wasn't a pain in the ass, but there are like multiple men in my life that I have as friends who'd be like, oh, I would never be able to, like, date you. Who knows if because I'm a pain in the ass or that's actually my my money. But they talk about that of like, I would be so uncomfortable feeling like I'm not the one financially providing. And I get some of that, like, let's be real, there is biology and like feminine masculine, what that means in society telling us what that means. So I know what took like a really strong, competent man. And that's, you know, Brett is that guy. Like he's super confident in who he is and he knows his value as a human doesn't just depend on how much money he makes.

[00:26:03] Sam Parr: When it comes to power and balance in relationships. I think about this a lot because I want my wife to know that everything that I've earned is not mine, it is ours. I think there's a few ways to do this. Like, for example, occasionally a spouse will ask the money earning spouse, is it okay to buy something? And I think that the correct response is like, I don't know, you tell me it's your money. Is that what you want to spend it on? Little things like that, I think, go a long way, and it's something I do in my relationship all the time. But I'm not gonna lie, it's something I think about all the time because it's something I think about. And I want to make sure that my spouse, Sarah, that she is incredibly comfortable in the relationship with money and knows that whatever I have, it's hers, too. Now back to dating. Dating doesn't always have to be a serious thing. It can still be fun and relaxed, even if the goal is to find a long term partner. So yes, you are gonna want to plan and think of all the things we've talked about, but you could also just use your money to have fun dating in crazy, unique ways.

[00:27:01] Sam Parr: Sort of like my buddy Nick Gray. If you're not familiar, you should Google this. His name's Nick Gray, and he posted on Twitter a couple months ago asking if he could take a woman on a blind date to Tokyo for a weekend getaway. He said he'd pay for everything. They just had to show up. He wrote and posted about the entire experience from beginning to end. So when he was going to pick her up from the airport to their first time out together, he did the whole thing on Instagram. It's Nick Gray news, and it's a fun and amazing story and you guys have to check it out. Nick's very outgoing, he's very eccentric, and there aren't a lot of people who would do that. But I'm sure we've all been tempted or at least would like to live through Nick a little bit. I want to end here by saying that obviously money brings some unique anxieties into dating, but overall dating really can be just an awkward thing. Meeting people and putting yourself out there is always going to be vulnerable and full of ups and downs. Here's Alex's parting advice.

[00:27:57] Alex: I think the thing I would, I would tell myself, would maybe just to be to like give myself some confidence then, which is that like, you're going to meet women, it's going to happen. Be patient. Do it in the real world. Like that is a good way to do it. Like again. Of course, go date people in line too. But like you can absolutely meet people in the real world. It will happen. It will happen when you don't expect it to. Be patient and do the things that you love doing and it'll absolutely show up in your life. I definitely didn't believe that for a long time.

[00:28:27] Sam Parr: I don't know you well, but knowing what I know about you, I'm like, well, you're good looking. You got this cool, kind of, like, outdoorsy vibe, and you're really wealthy. Like you're gonna crush. You're gonna crush it. I'm shocked that you had a lack of confidence.

[00:28:42] Alex: I mean, you know, a divorce is like a big disruptor, right? It tears down things, and you don't know necessarily where you're at. And I hadn't thought about dating in almost 20 years. And so there was challenging.

[00:28:55] Sam Parr: Anything that you wish you knew then about, like when to reveal or talk about money or do you think that your strategy early on was correct?

[00:29:04] Alex: I think it's been correct. I think it's still my strategy. I don't think it would change much about it. Like, there is always in early dates that urge to like flex a little bit. And so I'm like, try to be very thoughtful about that. Make sure that I'm not like, I'm like, oh yeah, like I sold a company like I never, I never say that. I never say I sold a company. That's like one of the things I tried to avoid.

[00:29:26] Sam Parr: You have to imagine they've all googled you, though. No.

[00:29:29] Alex: Yeah, absolutely. So they can draw conclusions from that. But, yeah, try to, like, draw it out for a while.

[00:29:38] Sam Parr: That's just another check mark about why you're probably just with amazing women. You got the mysterious vibe going. Well, I think women might love that.

[00:29:53] Sam Parr: All right. And that's it. I hope you guys enjoyed this episode. And if you made it this far, I've got a few requests. The first, this podcast is not free when you've listened to more than one episode. You are now in debt to me, and the way that you repay that debt is you just share, money wise with your friends. So post it on Instagram, LinkedIn, Twitter, whatever. That's all I want from you. I put a ton of work into this podcast and all I ask in exchange, if you've listened to more than one episode, just share it with your friends. It would mean the world to me. You can tag me at the Sam Parr. Now the second request if you are listening to this podcast, that means that you probably are a higher net worth person or you want to be. And that means that you likely own or have started a company. And if you have, check out Hampton. That's my company, join Hampton. It's a community of CEOs and founders. We have over a thousand members. And the whole point of this podcast, it was inspired because I would see all these private conversations that we have about money. And I thought, dude, these have to be public. These are so good. No one talks about this stuff publicly and that is where money wise came from.

[00:30:58] Sam Parr: And in fact, most of the guests like Alex, they are members of Hampton, so I've actually met them in Hampton, so check it out. Join Hampton. Com. We have hundreds of events throughout the year. We have a community where you can talk about all this crazy personal private stuff and it is awesome. It has changed my life and changed a lot of our members lives. So again, join Hampton. Com and the third request, if you have an interesting story that you think would be good for money wise, email me. My email is sampah at. You can be anonymous. You cannot be anonymous. It's up to you. But email me sampah at com. And the fourth request. Sorry, this is full of requests. You guys have to check out Lower Street. Lower Street is the company that has made this podcast. If you're a company looking to make a podcast like this, you guys should check them out. Lower Street. They make life so much easier when it comes to making a podcast like this, which by the way, it takes so much work. So check them out. Lower Street Co. All right, we'll see you next week with some more episodes of Money Wise.