Jess Mah is Worth $500M. She Flies Her Own Private Jets to Visit Billionaires.

What happens when you place a $100,000 bounty for your future husband on the front page of The Wall Street Journal? How do you handle layoffs when employees know you just bought your second private aircraft? Welcome to a day in the life of Jess Mah.

At just 34, Jess has shattered every conventional playbook. She founded inDinero at 19, built a business empire worth $1.5 billion, and now she's done with the wealth-hiding games that most successful people play. In a world where the ultra-wealthy hire PR teams to downplay their fortunes, Jess has chosen radical transparency—about everything.

Like all Moneywise episodes, Jess breaks down her net worth, income, portfolio, and monthly expenses—and I, your humble host, pick it all apart.

But unlike most guests, she goes places few dare to tread: the awkward prenup conversation with her boyfriend, why she can't date "broke" guys, and the surprising lessons she's learning from "hippy dippy woo-woo LA people."

By the way...this podcast, the concept of it came from Hampton, which is a community of CEOs and business owners that I founded. We realized that in our private conversations, members were discussing money in a way that wasn't happening publicly. They were sharing intimate details about their spending, investing, and all of the complex issues that come with having money. And we realized there was a massive opportunity to have those same conversations publicly, for the benefit of everyone. If you're a CEO, founder, or business owner, check this out. New Moneywise episodes come out weekly.

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

The Numbers

• Net Worth: $500 million (paper wealth)
• Liquid Assets: "Low eight figures"
• Annual Cash Flow: Seven figures that gets immediately reinvested
• Total Enterprise Value: Just shy of $1.5 billion (with her ownership stake at about $500 million)
• Business Holdings:
  • Ownership stakes in over a dozen companies (eight-figure+ stakes)
  • Nine-figure ownership stakes in four companies
• Monthly Expenses: Approximately $100,000/month
• Income: Pays herself only enough to cover expenses (~$2 million annually)
• Housing: Rents for $16,500/month in LA
• Car: Lamborghini worth $320K with $20K in modifications (on a lease with $100K in equity)
• Aircraft:
  • First jet: $4 million (would be $5.5M new)
  • Second jet: $7.7 million all-in (would be $12M new)

From Startup Founder to $500 Million Net Worth

Jess Mah's journey to wealth began with ambition instilled by her mother, who immigrated from Hong Kong, worked her way up from being a secretary to VP at a public company, and later succeeded as an entrepreneur. "I had aspirations of being wealthy since I was a kid, because my parents had that aspiration for themselves," she explains.

At 19, while still in college, Jess co-founded inDinero, an accounting software startup that got into Y Combinator. Despite the company's early success, her personal wealth grew slowly at first. "I was not paying myself anything until really my late 20s," she shares. "Throughout my early and mid-20s, I paid myself somewhere between 30 and $60,000 a year as a CEO."

Her wealth trajectory shifted dramatically in her late 20s: "By the time I got to 30, I was able to cash flow personally millions of dollars a year and get my paper net worth to maybe 100 something million. And then the next few hundred million in paper came only over the past five years."

Rather than cashing out for liquidity, Jess prefers maintaining ownership in her companies and the steady cash flow they provide: "Having really solid personal cash flow, that's more important, and then having the ability to start new companies or invest in what you want to do, that is ultimately what matters."

Beyond Money: Redefining Wealth Through Balance

A profound shift in Jess's perspective came from two sources: observing successful but unfulfilled billionaires and experiencing personal tragedy.

"I've spent the past decade trying to catch up and do as well as my peers," she admits. "And now I'm coming around full circle and realizing that the real winners are the ones who at one point played this wealth generation, business generation game and are able to exit the game and realize this is actually a stupid game."

Jess regularly meets with ultra-wealthy individuals to learn from their regrets: "The biggest regrets from them were always very similar. A lot of it was 'I wasn't present for my kids growing up, and my relationship with them is tenuous at best.'"

Personal loss further transformed her outlook: "My last boyfriend passed away very suddenly, and it really put things into perspective for me. I spend a lot more time doing vacations. I spend a lot of time with my family."

Today, Jess sees wealth as multidimensional: "Wealth is not just about money. I think we need to have a balanced scorecard for wealth, where money is only one out of like five things on the scorecard." Her personal scorecard includes health, family relationships, friendships, and work satisfaction.

When asked if she wants to join the "billionaire club," she responds: "It'd be cool to get to the B club. But right now, I don't care that much, because that's not really the point. And wealth comes and wealth goes. As long as I've got good, steady cash flow that covers all of my life and my health is good, what does it matter if on paper I have 100 or 500 or a billion?"

Living With Radical Transparency

Jess's most distinctive philosophy is her commitment to radical honesty about her wealth and lifestyle—a stark contrast to many wealthy individuals who hide their success.

"What I recognized is that it's hard to be authentic and transparent. But to hide who I am and what my life is like felt like living in a prison. And I wasn't willing to accept that," she explains.

This transparency extends to all aspects of her life:

• With employees: "I bring them to my house. I fly them around on my jet. I show my Lambo to them. I'm very transparent about all of this."
• With dating prospects: "I was super honest with him about my whole situation from day one."
• With the public: She placed a front-page Wall Street Journal article announcing a "$100,000 bounty for anyone who found me my husband" and has been open about personal experiences like "how I OD'd on something and puked at Burning Man."

Her approach occasionally backfires, particularly in business contexts: "It's not a good look when I'm going around flying private and meanwhile we're laying off people." But rather than hiding her wealth, she stepped back from CEO roles: "I fired myself as CEO... and then I could be more authentic and just do what I want."

Jess doesn't mind criticism: "What's the worst case scenario if a million people on Twitter said Jess was the worst person ever? I would find it very amusing and very entertaining. My close friends wouldn't see me any different. They would still love me."

Luxury Spending Without Apology

Unlike many wealthy individuals who downplay their spending, Jess is refreshingly open about her lifestyle choices.

She spends approximately $100,000 monthly, with her two aircraft being her largest expense. Other major expenditures include her Lamborghini ($320K plus $20K in modifications) and her $16,500/month rental home in LA.

When asked why she rents rather than buys, Jess explains: "I thought I would find a boyfriend and then if it got serious, then we'd get a house or build a house together. I wasn't ready to commit to buying a house."

Her aircraft ownership, however, was a more decisive commitment: "I know I'm gonna have an airplane no matter if I have a boyfriend or kids or not. Whereas for a house, I don't know if I'm going to be in this neighborhood long term."

Jess personally flies her jets (with a copilot for safety), having earned her commercial pilot's license. Her favorite expense? "I love spending money on taking my friends on my jet to go somewhere fun for vacation for the weekend."

Dating, Wealth, and Relationship Dynamics

Jess's wealth and success have significantly impacted her dating life, creating both challenges and insights.

"I got feedback from a few friends that they said, 'My friend thinks you're cute and really wants to ask you out. But they're kind of a wussy and didn't want to embarrass themselves because they're not at your level,'" she shares.

Beyond the intimidation factor of her wealth, Jess recognizes how success has changed her personality: "I became more alpha. I became a lot more domineering starting companies. And that creates a difficult dynamic in a relationship."

Regarding wealth disparity in relationships, Jess is candidly honest: "I think that all women, deep down are a little bit gold digger. And I've definitely been that way." She's dated "many billionaires and people you've definitely heard of," but discovered that extreme wealth doesn't guarantee relationship satisfaction.

"I had to learn the hard way that that's not really what matters," she explains. "What matters to me now that I have enough income to basically buy whatever I want is I want a partner who sees me for who I am and accepts me for who I am and can give me their presence."

Her current boyfriend has "an eight-figure net worth," which she describes as "a good middle ground that works for me." Despite her wealth and independence, Jess still desires traditional relationship dynamics: "I absolutely feel a desire to be taken care of. My rule with Nick is if we're traveling together, I don't want to pull out my credit card. And I want to feel like he's in charge."

Jess is also pragmatic about protecting her assets: "My wealth management people and my lawyers told me to not agree to community assets. That was an awkward conversation with my boyfriend because I basically said, 'Even if we got married, if we got divorced, then you're not going to have access to any of this.'"

Learning From Others' Experiences

Throughout the conversation, Jess repeatedly emphasizes how she learns from others' experiences—particularly from those further along life's journey.

She studies successful people's regrets: "I love meeting with successful people and asking them what they would have done differently."

From divorced wealthy women, she learned about relationship dynamics: "These were very brutal divorces... I noticed a few commonalities in these stories. One, the woman was very successful. Two, she was very alpha... and the guy felt like he had no voice."

Jess also values perspectives beyond the wealthy: "I'm realizing that I'm actually learning even more from the hippy dippy woo woo LA people who haven't made that much money, but they seem to have mastered life in a way that I haven't."

Other Key Quotes

"I was penny-wise and pound-foolish back then. And then I spent more time with really wealthy people, and I realized that they paid themselves extremely well, and they were unapologetic about paying themselves well."

"What will make you feel fulfilled? What will make you feel like you're advancing the world and doing interesting things? And you're really passionate about this? For me, I'm funding a lot of this science research."

"When I'm in girlfriend mode, I'm trying to be different. I'm more open to letting him take the lead on stuff and letting him set the tone and not trying to fix his problems the way I do at work."

"It's easy to get sucked away and think, 'Oh, I'm not hitting my goals. Therefore my life sucks.' That's just not the case if I look at my whole balanced scorecard."

"There's always a bigger fish. And I talk to my friends who in their super yachts and they say, 'Yeah, there's always someone else with a bigger superyacht.' That's a vulnerability that we have as human beings."

Links You Might Like

• Permission to Shine - Andrew Namami's podcast (guest interviewer for this episode)
• inDinero - Jess Mah's accounting software company she founded at 19
• Levin Lab - The bioelectricity research lab Jess mentions funding
• Jess Mah on My First Million -- Round 1
• Jess Mah on My First Milion -- Round 2

Full Transcript

[00:00:00] Jess: I have my one car. Lambo. I don't even have a backup car. The first one was a $4 million jet. I had a $100,000 bounty for anyone who found many billionaires. People you've definitely heard of.

[00:00:15] Sam Parr: This is fucking insane. Jess Mah is 34 years old, and she's worth half a billion dollars. And you know what? She's sick of acting like she isn't. And so she's stopped trying to downplay it.

[00:00:30] Jess: What I recognize there is that it's hard to be authentic and transparent. But to hide who I am and what my life is like felt like living in a prison. And I wasn't willing to accept that.

[00:00:45] Sam Parr: Jess has embraced radical honesty, which means she's stopped worrying about other people's opinions. She's stopped hiding how much money she has, what she does with it, and what she wants to do with it. Which, by the way, this is perfect for you, a Moneywise listener. Someone who listens because you want to hear how high net worth people spend, save and invest their money. And truthfully, the impact it's had on her life is very fascinating. It's changed everything. Dating, friendships, work, even her relationship with her parents. And she's here on Moneywise to tell us all about it. My friends, I'm Sam Parr, and this is Moneywise. You could spend just a few minutes on social media, and you're going to see tons and tons of junk out there on how to get rich, but nothing that teaches you how to handle life after you've already made a little bit of money. I'm the co-founder of a company called Hampton. It's a community of CEOs and business owners. Check it out. Join Hampton. Com. Our members range from newish startups with 3 million in revenue, all the way up to publicly traded companies with hundreds of millions in revenue. And so because of this, I'm able to see all types of private conversations about money. And I think a lot of those conversations, they should happen in public.

[00:01:50] Sam Parr: Hence the creation of this podcast. With Moneywise, we want to provide real advice by speaking to people who have made a lot of money and who are willing to be radically transparent about all their numbers, meaning their monthly expenses, their portfolios, and more importantly, all the personal issues and problems that come with being successful and how they're solving those problems. And so my plug, if you are a CEO of a startup, check it out, join Hamptons.com. You're going to be put into a group of eight people who are similar to you. You'll be able to meet with them in real life once a month, and you're going to have access to thousands of other business owners who are members and frankly, have a lot of conversations, sort of like the ones that we're having on Moneywise. So check it out. Join Hamptons.com. So now, as I said in the intro, Jess is practicing radical transparency, which obviously meshes well with this podcast. But for us, she's upping her transparency game to a new level. Jess is a very popular entrepreneur. She's been on the cover of Inc. and Entrepreneur, and those types of magazines and the numbers that she's going to reveal today, it's the first time that she's ever shared that before. And by the way, they're huge.

[00:02:54] Jess: I have a few close friends I've talked to this about with, but I think it's the first time I'm really being honest on a podcast about this.

[00:03:02] Sam Parr: And we're not going to waste any time getting to those numbers. We're going to tell you them right away at the top of the podcast. Oh, and I got to give a quick shout out to Andrew Nmami. He's the one who did this interview. He's got Jess on the podcast and got her to reveal a lot of crazy and wonderful stuff. And so big shout out to Andrew. Awesome. Awesome interview.

[00:03:19] Sam Parr: Of your $500 million, how much of that is liquid?

[00:03:22] Jess: Low eight figures is liquid. And every year I have seven figures of cash flow that comes back to me that gets immediately reinvested into starting new companies or into growing existing companies or doing acquisitions. So very little of the 500 is liquid.

[00:03:40] Sam Parr: Talk to me about how that's broken down.

[00:03:42] Jess: I have ownership stakes in over a dozen companies that are meaningful, eight figure plus ownership stakes, and I have nine figure ownership stakes And for companies, which means that if any one of those companies went BC, I would still have a few hundred on paper.

[00:04:05] Sam Parr: Do you know the total value of your enterprises?

[00:04:08] Jess: The total value is just shy of 1.5 billion. And my ownership stake in it comes down to about 500.

[00:04:16] Sam Parr: That's really cool. By the age of 34.

[00:04:18] Jess: Yeah. It's cool.

[00:04:20] Sam Parr: Yes, by the age of 34. But let's backtrack here and let's learn how she got to this point at such a young age. It all started when Jess was a kid.

[00:04:30] Jess: I had aspirations of being wealthy since I was a kid, because my parents had that aspiration for themselves. My mom came to the US from Hong Kong. She never went to college, and she was a secretary and worked her way up the corporate ladder at a public company to being a VP, then quit, then became an entrepreneur, and then did really well for herself. Self. So she kind of got me accustomed to going from the family, having no money to the family, then being able to have very nice vacations and she could pay to send me to college, which was very generous. And after that she's like, well, good luck, you're not going to have anything from me. And there's no trust fund. There's no more support. Good luck. But I believe in you, and I think you could make enough money to have a great lifestyle. So that made me think. All right, well, I don't want to lose this lifestyle that I am now able to see that my mom's able to have. So that got me thinking about this from a pretty early age.

[00:05:36] Sam Parr: Jess experimented with a lot of projects when she was young, and then at the age of 19, when she was still in college, her and a few others, they started this company called Indinero, which is an accounting software startup, and it got a ton of attention and she got into Y Combinator. And while the company did really well, really fast. She grew her own wealth relatively slowly.

[00:05:56] Jess: I was not paying myself anything until my really my late 20s. So throughout my early and mid 20s, I paid myself somewhere between 30 and $60,000 a year as a CEO. Even when I got to like 50 plus employees, I was paying myself at that point maybe 70, $80,000 a year in San Francisco. So better than the average American, but not wealthy by any means.

[00:06:26] Sam Parr: And what was revenue?

[00:06:27] Jess: Revenue was in the millions of dollars. So I could have afforded to pay myself more.

[00:06:31] Sam Parr: But I had 10 million. 2 million?

[00:06:33] Jess: No. At that point, you know, we're in my mid 20s. Revenue was maybe in the 5 million range. So what I would have done in hindsight was I would have peed myself a healthy like $250,000 salary because then I'd be sweating less about my personal life. Instead, I was so cheap and I was pinching pennies. I was really penny-wise and pound-foolish back then. And then I spent more time with really wealthy people, and I realized that they paid themselves extremely well, and they were unapologetic about paying themselves well. And so that's when things flipped for me and I thought, wow, I should really be myself a lot more by the time I got to 30. Yeah, I was able to cash flow personally millions of dollars a year and get my paper net worth to maybe 100 something million at 30. And then the next few hundred million in paper came only over the past five years. And I'm happy with that. And a lot of people say, why don't you sell a company and just get like 100 million liquid? And my answer is, well, if I did that, then I'm just going to do what I'm doing now, which is use the cash to start more companies or grow my existing companies or do more acquisitions, which I'm already doing with my cash flow. And I don't want to have to do more of that, because if I had 100 or 200 million freed up liquid, I'd have to use that to then buy companies to replenish, and then it's going to be liquid again. So I don't really, you know, see the point because I have good enough cash flow to cover my personal living expenses.

[00:08:18] Jess: So I think that is also another area that I would challenge people on that selling your company and being fully liquid isn't necessarily the goal. Having really solid personal cash flow, that's more important, and then having the ability to start new companies or invest in what you want to do, that is ultimately what matters. And I learned this from this guy who runs a massive family office. But he said that the one thing he hates hearing about at family office conferences and events is that people say their goal is preservation of wealth, because what is the point of preserving your wealth per se? He says that what you should really do is make sure you have enough money to cover all your personal needs, and then some, which I do through my cash flow. But then after that, the rest of your wealth should be devoted to manifesting what you want to create in your life. What will make you feel fulfilled? What will make you feel like you're advancing the world and doing interesting things? And you're really passionate about this. And for me, I'm funding a lot of this science research. I'm really excited about what Mike Levin is doing at Levin Lab, where he's able to grow, regrow limbs on frogs and use bioelectricity to cure cancer. And animals like, literally cure cancer without having to kill the cancer cells. I think this is just mind blowing stuff. And we're creating companies out of his work. That is what I would use my wealth for, and I'm able to do that today. So I feel really fulfilled.

[00:10:00] Sam Parr: The habit of talking to people who have had more experience than her, and learning about what to do and what not to do based on their own life, is something you'll notice that Jess does a ton. And by the way, this is just such an easy layup for me. But this is exactly why we created Hampton. Now, being in tune with the people around her, it's actually what brought her to her first big epiphany that led her to embracing brutal honesty. It happened while she was still at Y Combinator.

[00:10:25] Jess: I saw so many other successful founders go through, and it was less about wealth from an ego perspective or from a material wealth perspective, but more from a competitive perspective, like, why are all these people winning? I want to win, too. And so I've spent the past decade trying to catch up and do as well as my peers who've for the most part crushed me on the success metric. And now I'm coming around full circle and realizing that the real winners are the ones who at one point played this wealth generation, business generation game and are able to exit the game and realize this is actually a stupid game. Like, there's actually no need to compete on this level. What really matters is the quality of friendships, our relationship with our family, and just how much love we have in our life that matters way more. I think it's really sad that it took me so long to get to that point, but I also learned that from these crusty old billionaires I would meet with, and I would ask them about what's gone well in your life, what hasn't gone well in your life, and the biggest regrets from them were always very similar. A lot of it was I wasn't present for my kids growing up, and my relationship with them is tenuous at best. It's good, but dot dot dot is what I'd hear. And a lot of these people don't have long term loyal friends. A lot of their friends are just other ultra wealthy people, but that means they're not having access to a large part of humanity. That's really sad to me. So I think I'm willing to go out of my way and visit wealthy, successful people anywhere just so I could learn these lessons ahead of time.

[00:12:14] Sam Parr: Jess does these visits a lot, and she does it on her private jet, which she herself flies. And we're gonna get all to that. But first, there was another major traumatic event that changed Jess's perspective on life and what wealthy actually means. We're going to get to that right after a quick ad break.

[00:12:34] Jess: I changed my life considerably over the past few years, partly because of that, partly because my last boyfriend passed away very suddenly, and it really put things into perspective for me, and I spend a lot more time doing vacations. If I'm being candid, I spend a lot of time with my family. I visit them a lot. I have them come out and see me in LA, and I call my parents multiple times a week. I really make time for these people in my life, and I think when I was working super hard, I pushed that off a lot more and now I'm not doing that anymore. And now, even though I am obviously still building and trying to create more value in the world, the tension is a lot less where I'm doing it, more from a place of curiosity, interest, like, is this fun? Am I enjoying it? Versus oh man, I got to keep up with someone else.

[00:13:33] Sam Parr: So this is how just views wealth today.

[00:13:36] Jess: Wealth is a multidimensional thing. It's not just about money. And I learned that also because I saw so many of these crusty old billionaires who had lots of health issues and they weren't working out. They weren't taking care of themselves, and they looked terrible. And I would talk to them about all the biohacking stuff and my workout routine and diet and everything. And I think that we need to have a balanced scorecard for wealth, where money is only one out of like five things on the scorecard, so that we realize that even if you're winning here, it's not everything. And if you're losing here, you could still overall be winning.

[00:14:19] Sam Parr: That's really interesting. What would you have on that scorecard of five things?

[00:14:23] Jess: I would say I'm doing really well. I think I'm extremely wealthy in that my health is top notch. I never get sick. I get eight hours of sleep every night and I'm in really good shape. So health is a plus. Family. I have no conflict with my family. I talk to my parents and my brother all the time. I have an amazing relationship and great boyfriend. I have many, many dozens of inner circle, loyal, devoted friendships. And then I work with great people and I have no one breathing down my neck at work. Like, if you look at the whole picture, it's really good. Now, that's not to say that my life is perfect because I do get stressed out. There are lots of things I do want to improve on and change. And obviously I have more financial goals because everyone has financial goals. But it's easy to get sucked away and think, oh, I'm not hitting my goals. Therefore my life sucks. That's just not the case if I look at my whole balanced scorecard.

[00:15:25] Sam Parr: But that doesn't mean she's not open to the idea of more money.

[00:15:29] Jess: It'd be cool to get to the B club. No.

[00:15:32] Sam Parr: Just promise me you won't be one of those crusty old billionaires.

[00:15:34] Jess: I'm really trying not to. But also, I told one of my best girlfriends a few months ago that I just stopped caring about getting to the V club. The truth is, it oscillates week to week. But right now, as I talk to you, I don't care that much, because that's not really the point. And wealth comes and wealth goes. Like on paper, maybe it'll shrink. And for me, as long as I've got good, steady cash flow that covers all of my life and my health is good, what does it matter if on paper I have 100 or 500 or a billion, you know?

[00:16:14] Sam Parr: Yeah. What would a billion get you? That 500 million can't.

[00:16:18] Jess: Honestly, I don't think there would be any big difference. And my spending power right now is in the tens of millions of dollars. Even if I sold a company for a few hundred million dollars and just made it all liquid, it wouldn't change my lifestyle, like, at all.

[00:16:35] Sam Parr: The reason we're going to all this before we talk about her transparency and how it's impacted her life, is because this self-realization needs to come first. Saying you don't care what people think is one thing, but actually not caring. It's really hard. That's something that even the best of us struggle with. I know I struggle with that a ton. And the truth is, is that in order to be completely comfortable in how the world sees you, you first have to have a strong sense of self and a sense of pride. And that ties directly into Jess's view on wealth as an all encompassing part of her life. If you're going to be radically honest about yourself and what you're putting out into the world, you need to have a really solid self-assurance as a foundation. But that's not to say you won't have any doubts, by the way, we're all human, and we all have those types of feelings and these types of imposter syndrome and self-confidence issues. Even Jess has those problems.

[00:17:26] Jess: I think it's worth mentioning if we're also going to be really transparent on this podcast, is that no matter what, I still have the challenge of looking at my friends who've done way better than I've done, and there's always that next level, and I'm still working on that. That's a fundamental flaw in how I see the world that I'm hoping to work through over the next year or two. I'll give you an example. You fly your jet somewhere and you're you're feeling like, okay, this is great. I have my own jet. And then you land and you pull up next to a Boeing business jet and you're thinking, oh, man, like this Saudi prince has way more than I do or whatever. There's always a bigger fish. And I talk to my friends who in their super yachts and they say, yeah, there's always someone else with a bigger superyacht. So no matter what. That's a vulnerability that we have as human beings for some reason.

[00:18:31] Sam Parr: I'm not sure if you guys have noticed this, but this is actually the 25th episode of Moneywise. That means that we've spoken to a lot of different people with a lot of different lives, and that ultimately means that we're going to have some opposing opinions on wealth spending, things like that. However, one common sentiment that we've heard a lot from our guests is to avoid appearing flashy due to the anxiety surrounding how others might perceive you or the things that you're showing off. But like we've said, Jess doesn't care about that. And so what does this look like when it comes to spending? To get to that, we first have to have some context as to how much money she's taking home. She told us that's around $2 million a year.

[00:19:13] Jess: I pee myself only enough to cover my spend, and I'm spending roughly $100,000 a month for my total lifestyle. And the most expensive things I spend my money on would be my aircraft. So the two aircraft cost a ton of money to maintain a year. And then I have my one car, Lambo. I don't even have a backup car. Or a, like, a quote unquote daily driver. And then I rent my house for 16,500 dollars a month, and I'm really happy with it. And I have no plans to change that. So, yeah, I'm just gonna pay myself that every year, and maybe I'll pay myself more next year. Obviously, I get a lot more out in distribution selling equity in stock from companies. But as far as what I personally take home and spend money on, it's about $100,000 a month.

[00:20:06] Sam Parr: Okay, so you're paying $16,500 for the house and you're renting, which is interesting. How much does the Lambo cost?

[00:20:11] Jess: The Lambo was 320 K, but I put in another 20 K in underglow lighting and random mods.

[00:20:20] Sam Parr: Is your car paid off?

[00:20:22] Jess: My car is through a lease that I could write it off, so I put in $100,000 in equity and then have a payment on it that I fully write off to one of my companies.

[00:20:33] Sam Parr: Interesting. Okay. And then why do you choose to rent versus buying houses?

[00:20:39] Jess: Because in LA we have the LA mansion tax. And it's been very hard to get out of a house. And actually, I think the real reason is I thought I would find a boyfriend and then if it got serious, then we'd get a house or build a house together, and I wasn't ready to commit to buying a house. And then it'd be awkward if I dated someone like, hey, you want to move into this house I bought? And then you know what I mean? I didn't want that lock in. Whereas with the plane, I get asked, why do you own an airplane? But you don't charter or rent an airplane? And the answer to that, I go into detail there and the My First Million podcast, where a lot of it is tax related, there are tax benefits to acquiring an aircraft that is used for business purposes, which for me it is majority business use case. So that applies. And I know I'm gonna have an airplane no matter if I have a boyfriend or kids or not. Whereas for a house like, I don't know if I'm going to be in this neighborhood long term, you know, I think it's a very millennial thing. And I think that a lot of us believe that we need the status symbol of owning a house in order to feel accomplished. And I didn't have that ego need. And also, I owned two airplanes. I owned two private jets. So I think it's okay.

[00:22:07] Sam Parr: You just purchased your second jet. It's beautiful.

[00:22:09] Jess: Thank you.

[00:22:10] Sam Parr: What were the costs of the first one?

[00:22:12] Jess: The first one was a $4 million jet. New would be five and a half. Got it pre-owned for four. And then the second jet, brand new would be 12 million. Got it pre-owned for seven five, but put in some work, so probably all in. Let's say it's seven seven.

[00:22:29] Sam Parr: And do you care to share that you also fly this airplane?

[00:22:33] Jess: Yeah I personally fly them and I always bring a copilot, so I'm never flying alone. It's just safer to have two pilots than one. But yeah, I've got my commercial pilot license and I operate my own aircraft myself most of the time.

[00:22:48] Sam Parr: What is your favorite thing to spend money on?

[00:22:51] Jess: I love spending money on taking my friends on my jet to go somewhere fun for vacation for the weekend, and we might leave on a Friday and come back on Monday. And it's very expensive to operate the aircraft and and go like even an hour somewhere. So yeah.

[00:23:17] Sam Parr: All right. So Jess is worth half $1 billion and her primary vehicle is a Lamborghini, and she flies private on her own jet. Sorry, I meant that's one of two of her personal jets. Now, this is the part where we have to talk about what dating is like because, well, dating someone like Jess, I think that could be pretty intimidating. So let's talk about it.

[00:23:39] Jess: I got feedback from a few friends that they said, hey, my friend thinks you're you're cute and really wants to ask you out. But yeah, they're like kind of a wussy and didn't want to embarrass themselves because, you know, they're not at your level. And so I know it definitely hasn't helped. It's definitely filtered out a lot of people. And I think the harder part isn't the money. It's that I became a different person along the way and I became more alpha. I became a bit more domineering. And by a bit I mean a lot more domineering starting companies. And that creates for a difficult dynamic in a relationship. Like you depolarize the relationship when you're acting like a CEO. So when I'm in girlfriend mode, I'm trying to be different. I'm like more open to, like, letting him take the lead on stuff and letting him set the tone and not trying to fix his problems the way I do at work, letting him fix his own problems and like, only helping if I'm directly asked. So it's stuff like that that I've had to learn over the years, and I've only started to figure that out, I'd say, in the past year.

[00:24:58] Sam Parr: You've always had this desire to become rich, right? It's like kind of in your blood from mama ma. And so I would assume that you've always had a desire to date somebody who was rich. Is that safe to say?

[00:25:11] Jess: I think that all women, deep down are a little bit gold digger. And I've definitely been that way. And I'm just gonna be super honest about it, that. Yeah, like, we're all a little bit gold digger.

[00:25:26] Sam Parr: And how has that played out for you? Like, has that been successful? Did it burn you? Tell me about it.

[00:25:33] Jess: I'll be honest. I've dated a lot of extremely wealthy people. I've dated many billionaires and, uh, people you've definitely heard of and have read about in the front page of the newspaper. And I had to learn the hard way that that's not really what matters. That's not what I'm actually looking for, what matters to me now that I have enough income to, like, basically buy whatever I want to buy is I want a partner who sees me for who I am and accepts me for who I am and can give me their presence. And I notice that a lot of these extremely wealthy guys were not that present. They're always thinking about, how do I win the next game? How do I up level, how do I feed my ego? And they're not thinking, what will it take to make just happier. How do I make her more successful? How do I support her and be a better boyfriend? That that wasn't high on their list of priorities. And I think it took me dating a bunch of these guys to realize that that was going to be an issue.

[00:26:45] Sam Parr: How do you find that wealth disparity affects relationships?

[00:26:49] Jess: I have noticed that it's less about the wealth disparity and more about the intellectual and hunger and drive disparity. That's the problem. And I think a lot of guys who haven't demonstrated any success in their life have more insecurity, and that would probably be difficult for me to date. The guy I'm dating now has seen success and has an eight figure net worth, and that really helps. And he's not a billionaire. But you know, I think this is like a good middle ground that works for me. And he doesn't have a chip on his shoulder, and he just loves me for who I am, and he's able to have these difficult conversations. We could sit down and talk about whether or not this is awkward. And you were in the kitchen with me before we started recording. Asking him some of these questions, and he could see that he was actually really open to talking about it. And it's not awkward at all.

[00:27:50] Sam Parr: Yeah, he's like, the money could disappear tomorrow, but I'm still dating Jess Marr. For who? Jess Marr is not for her Lamborghini or for her jet or whatever.

[00:27:58] Jess: Yeah, exactly. Right. So that made me feel really good. And I think the inverse is true, too. If a guy is dating a girl, even if she's a little bit of a gold digger, um, ultimately she will hopefully fall in love with him for who he is at the core and be there no matter what. Even if he went totally bc she'd still be there. And in your heart you'll know if that's true or not.

[00:28:24] Sam Parr: Wow. This podcast is like really fucking good.

[00:28:27] Sam Parr: So with all this wealth and resources, do you still feel a desire to be taken care of?

[00:28:33] Jess: I do. I absolutely feel a desire to be taken care of. So my rule with with Nick is if we're traveling together, I don't want to pull out my credit card. And I want to feel like he's in charge. And so I can just, like, rest and relax and not feel like I'm at work and not feel like I have to put on my CEO hat when I'm done with my work.

[00:28:58] Sam Parr: Have you ever dated somebody who was broke?

[00:29:00] Jess: I've tried. It hasn't worked out very well.

[00:29:03] Sam Parr: How did it go? Tell me about it.

[00:29:04] Jess: Oh, God. I tried this a few times, and it's just, like, very. I could tell it's not going to go anywhere long term because they can't fit in with my friends. They can't fit into my universe in any way. And I don't feel drawn to have deep intellectual conversations with them, and talking about money is awkward and makes them feel uncomfortable. So yeah, it has not worked for me.

[00:29:35] Sam Parr: When did your current boyfriend become aware of your reality?

[00:29:39] Jess: He became aware of it up front because I told him I wasn't looking to date anybody. I just wanted to hang out as friends. And I was super honest with him about my whole situation from day one, and how it's definitely impacted my desire to date. And that's a big reason why I thought, I'm just going to take six, 12 months off from dating. And so we had a few months to just hang out as friends. And then feelings naturally developed from there. But I was up front from day one.

[00:30:07] Sam Parr: And by super honest, she means the first time she met him, she actually showed up in her Lamborghini, which is different because her normal usual routine is. Up. Until then, it's borrowing a friend's car that was less flashy. That story is nothing compared to her front page Wall Street Journal bounty. That's gonna come up in a minute. But before we get there, there's another part of our relationship that requires some upfront honesty. And this isn't just about like saying this is who I am, this is how much money I have. This is the lifestyle I live. A good relationship also means being honest about expectations when it comes to how you view your partner's role in that wealth.

[00:30:48] Jess: I think that it's just easier to have separate marital assets, like why combine 50% once you're married, when you could arbitrarily decide what to put in the community pile on a month by month basis, like it makes no sense that you should agree to the terms upfront, you know? And also, my wealth management people and my lawyers told me to not agree to community assets, so that's part of it. But that was an awkward conversation with my boyfriend because I basically said, hey, like, even if we got married, if we got divorced, Then you're not going to have access to any of this. Hunh? Like, how does that make you feel?

[00:31:29] Sam Parr: What did he say?

[00:31:30] Jess: He said, yeah, it definitely felt weird. And I have to process this.

[00:31:34] Sam Parr: And how has it gone over now that you guys have had some time to mull on it?

[00:31:39] Jess: I think it's going really well. I think we're just really good at having honest conversations and just talk about it very openly. And he he's just such a great sport about it.

[00:31:56] Sam Parr: You mentioned that you've seen a lot of divorces because of wealth. And I'm curious what advice you have for people in relationships who are getting ready to have these wealth discussions?

[00:32:08] Jess: I met with many very successful women, typically in their 50s, who got divorced from their husbands, and these were very brutal divorces. Like they would speak negatively about their husband being a deadbeat, being a loser and an asshole. And, you know, usually a terrible absent father. And I noticed a few commonalities in these stories. One, the woman was very successful. Two, she was very alpha, and she was basically wearing the pants in the relationship, and the guy felt like he had no voice and he didn't feel empowered or confident, and that negatively impacted his career. And so he became the loser that she saw in him. And that became a vicious negative spiral. And so I thought, how could I avoid that? I think part of it is in just finding someone who's already confident and already a bit successful. And then two, how do you lift them up and make them feel good about themselves instead of putting them down? I mean, this goes back to what I spoke about earlier, which is I love studying people. I love meeting with successful people and asking them what they would have done differently. And these women, they're brutally honest. They're like, yeah, I would have married someone different. I'm glad I got kids out of that, but I wish I had a better prenup. I wish I kept my assets separately. I wish I had these trusts that were divorced, protected, like a lot of stuff that I'm doing. I learned from these women.

[00:33:44] Sam Parr: Again, we come back to this part, which is part of the reason why Jess is so confident and so upfront about what she wants and does with her life is because she's done the research. She's consistently meeting with people in different stages of life to learn from them. And by the way, that does not mean just meeting with wealthy people.

[00:34:01] Jess: I think it's easy to get stuck with only surrounding oneself with really impressive people. And for a while, that's what I did. And I'm realizing that I'm actually learning even more from the hippy dippy woo woo la people who haven't made that much money, but they seem to have mastered life in a way that I haven't.

[00:34:21] Sam Parr: And that my friend, I think that is great advice and we're also here for the fun stuff. So let's hear about that famous bounty story.

[00:34:28] Jess: I had an article in the Wall Street Journal where I advertised that I had a $100,000 bounty for anyone who found me my husband. I know. Front page of the Wall Street Journal. I'll pull it up for you. And I got, like, 100 calls from people dying, my customer service line and sending me cold emails saying, hey, like, how about my brother or my cousin? Funny, right?

[00:34:56] Sam Parr: I love that.

[00:34:56] Jess: I didn't do it, actually, to try to attract anyone. I did it more because I thought it'd be provocative and because why not? Like, how do we live our life in a way that's more YOLO, where we're not so scared of what other people will think? And that's why I'm so honest and why I'm so transparent here. Like, there's a lot of stuff I'm embarrassed by. And like, who cares if I get a bunch of heat and a bunch of negative comments from this podcast episode? Like, I don't really care at all.

[00:35:27] Sam Parr: Mhm. Well, I think that one, I'm curious how you got that placement on the Wall Street Journal. Is that something that you paid for?

[00:35:33] Jess: No, I didn't pay for it. I just talked to a reporter and I told them a bunch of provocative things, like how I have $100,000 bounty if you find my husband. I told them about how I talked to my employees very openly about going to Burning Man. And oh, yeah, I talked about how I OD'd on something and puked at Burning Man front page of the Wall Street Journal. My mom was horrified. And yeah, like so I just gave them the article. And then also, I remember getting cover placement on Inc. magazine in my mid 20s, and people also asked me, how did you get a cover article? And I gave them the story around how I went to marriage counseling with my business partner, and I think it does help that I am an Asian chick, and they felt like they wanted more representation there. But having a transparent and authentic story really helps, even if it makes me look worse. I'd rather the truth be out there than make myself seem better than I am.

[00:36:43] Sam Parr: And here is another, maybe more controversial take that Jess has. Your transparency shouldn't end with your personal life. We'll talk about that after a really quick sponsor break.

[00:36:56] Sam Parr: How have you brought this transparency and this wealth to your workplace? Are you open with your employees?

[00:37:03] Jess: Yeah, I bring them to my house. I fly them around on my jet. I. I show my Lambo to them. Like I'm very transparent about all of this. I'd say.

[00:37:12] Sam Parr: Has that ever backfired?

[00:37:15] Jess: I think that it backfired earlier on when I was operating a company as CEO, because we were going through layoffs and we were going through tough times. And unfortunately, it's not a good look when I'm going around flying private. And meanwhile we're laying off people. You know, it's a really, really bad luck. And what I recognized there is that it's hard to be authentic and transparent. But to hide who I am and what my life is like felt like living in a prison. And I wasn't willing to accept that. And so my solution, my solutions were one of three things one, just not be honest about it. Two, be honest about it and deal with the consequences. Or three not be a CEO anymore. Also, I was a terrible operating CEO. Like I'm great at strategy, great at putting these things together, but like, I just like, don't want to be a CEO and deal with all the people problems. So I fired myself as CEO and if I was not the majority owner, I probably would have been fired anyway. So whatever, I got fired and then I could be more authentic and just do what I want. And then, yeah, if any company has issues, you know, I make peace with that because I know that we're doing our best and a company needs to be self-sustaining. And if that company can't justify the costs, it can't justify the costs. And it's a bad idea for me to sacrifice my personal life in order to put more money to basically cover up a sinking ship if that sinking ship has to fix itself, you know?

[00:39:08] Sam Parr: We talked a bit at the beginning about how to be able to live this openly, especially when you live a lifestyle like Jess, you need to have a lot of self-assurance because it's essentially guaranteed that there are going to be a bunch of people who disagree with how you live life. Or to put another way, you're going to have a lot of haters. And that's something, by the way, Jess has a ton of experience with.

[00:39:32] Jess: I wrote on LinkedIn something about how even though I have, I think the exact words were like, I've dated celebrities, I fly my own jet around, I drive my Lambo around, and life is still hard. And I think thousands of people on Twitter are like, boo hoo. Like, like you're so out of touch with reality. Like, there are people starving in Africa. And here you are complaining about how hard your life is. And it's like, well, look, read the rest of the blog post. Like, it actually gets more interesting. It talks about how rich people have problems. Like, I lost my boyfriend and that was really, really shitty. Like he committed suicide after having severe combat related PTSD like this is serious stuff, but no one was patient enough to read that far. It's just easy to blast me because of my catchy hook. So yeah, I've gotten blasted for it, but but that was part of the idea. I wanted it to be controversial and I wanted to invite lots of comments. So yeah, I don't really care.

[00:40:34] Sam Parr: I love that.

[00:40:35] Jess: I mean, that's true wealth. I think when you stop caring about what other people think and when the only people who matter are my close friends and my family. Even that I would question, like, to what extent does your family's opinions matter? And I've just made peace with the fact that I go to sleep at night knowing I've done my best. And that's really what matters.

[00:41:00] Sam Parr: And I'm curious if you've ever gotten feedback that people find your authenticity or transparency to be off putting?

[00:41:08] Jess: I have not received that feedback. I have gotten negative feedback, mostly from my mom, about how I should be less showy and how it's better for people to not know me at all, or how much wealth I have, or any details about me. And that's why she yells at me every time a Google alert comes in her inbox saying something about me. She's like, just stay quiet, stay under the radar. So that way no one can take you down. She's worried that people on the internet will heat on me, try to, like, rip me apart in a public way or they're going to root for my failure, is what she says. And she may be right. But if I don't really care about my success or failure, if all of this is not even something that registers to me as something that's that important, then it doesn't matter. You know.

[00:42:06] Sam Parr: I think it's quite a generational difference, too, in mindsets.

[00:42:09] Jess: Yeah. Like let's say, what's the worst case scenario if a million people on Twitter said Jess was the worst person ever? What an obnoxious, arrogant douchebag. Would that impact me? And the answer is, I think about that is I would find it very amusing and very entertaining. I'm a bit of a troll and my close friends wouldn't see me any different. They would still love me so, and my mom would still love me and my dog would still love me. So yeah, I'd be fine. And that's that's how I kind of overcame her criticism.

[00:42:45] Sam Parr: Mhm. You have such good character and I think that's why you can sleep so well at night.

[00:42:49] Jess: Yeah. But I question it too because I make mistakes, I do things that are off putting and I have to apologize for mistakes. But I think the difference is I'm willing to look at those mistakes and I'm willing to apologize and try to do better. And as long as I do that, then I can sleep well at night.

[00:43:08] Sam Parr: When did you first start to realize the value of being brutally honest? Has that always been in Jess Moore's character?

[00:43:15] Jess: No. Sometimes it's better to not be honest, too. I would argue like I'm I'm brutally honest with people I care about, and I'm really honest to myself. But I think there's some cases where I'm not as brutally honest because I am still scared of what someone else will think. And because in the times I've been brutally honest, it hasn't come out the right way. I've come off as being an asshole or like, not really caring about other person's feelings. So now I really take a lot of time to figure out how to communicate better. There's a way to be direct with respect versus just being candid and being brutally honest. So I like being direct with respect, then brutally honest. I swear you're the gold I've been running for on it. Like I woke up in one the top row.

[00:44:10] Sam Parr: So I'm sitting here doing this voiceover, and it's taken much longer to do this voiceover because I'm rereading the transcript and I think that this is thrilling. This was a thrilling podcast to listen to. Jess's transparency, for one. That's amazing. Number two, her attitude. Absolutely amazing. I love how confident she is. I love how like in a positive way. And I mean this in a compliment. She's weird in the best possible way. The world wants you to be vanilla. They want to put you in this box. They want to back you in this corner. And Jess is very unique. She's very different and I love people like that. And then of course, three. I mean, she's a baller. Like she's built a lot of amazing things and she's very inspiring to me. If you're listening to this, I hope you are inspired and I hope that you have this one major takeaway, which is what Jess does. It's something that I've done a lot, and a lot of my friends do this, which is they reach out to people and they start conversations and they listen a ton. The way she talked about meeting old wealthy people, I think that's awesome. And if you don't have wealthy friends, just honestly reaching out to older, experienced people, people who are older than you, it's just the best just to listen, just to have conversations with no agenda other than learning, learning different perspectives. I love that I've done that my entire career. Some of my best friends I've made that way. The co-founder of actually Hampton. And so I'm a big fan of this.

[00:45:38] Sam Parr: I hope you loved this podcast again. I've got to give a huge shout out to Andrew Namamee. His podcast is called Permission to Shine, and he went and did a guest interview for us and he nailed it. So Andrew, we appreciate you. And of course, I've got to give one last plug to Hampton. If you're a CEO, a founder, a business owner, and you want to have conversations like this, you have to check out my community. Hampton. It's Join Hampton. Com I think it will change your life. We have over a thousand members and it's absolutely amazing to have conversations like this in private with people who have been there, done that. It's changed my life and it inspired this podcast. And so if you like this podcast, check it out, join Hamptons.com. And finally, quick shout out to Lower Street. I say all the time that this podcast is very hard to make. Well, it's not hard for me. It's actually easy for me. It's hard for Lower Street, but they've done all of the work to make a podcast like this come to life. They have this new product, it's called Authority by Lower Street, and it's reimagined the whole process of making a podcast just like this, just like Moneywise, if you're a busy founder or a business leader, check it out. Lower Street Authority if you want a podcast like this, which, by the way, has completely changed my business. But if you want a podcast just like this, you guys have to check out Lower Street again. Lower Street authority.