Sam Doesn't Know How to Be Rich

Summary

Proxy with Yowei Shaw — “Sam Doesn't Know How to Be Rich” (June 16, 2026)

Episode Overview

This episode tackles the rarely discussed complexities of suddenly becoming wealthy—particularly for those who have progressive, anti-wealth politics. Listener “Sam” finds himself with $17 million after selling his company, and is struggling with guilt, evolving relationships, and a deep ambivalence about wealth and status. Host Yowei Shaw brings in a “proxy”—David Steeley, who also became rich but then gave most of it away—to share hard-won perspectives. Their candid conversation explores identity, shame, charity, and the ethics of giving, all with vulnerability, humor, and honesty.

---

Key Discussion Points & Insights

The Birkin Bag Effect: How Wealth Shifts Perspective

• Yowei Shaw sets the stage with musings about Birkin bags and the ways wealth can warp what seems normal—even to well-intentioned people ([04:00]).
• Quote: “Would my need to belong overpower my distaste for gaudy luxury items?...Would I squeal with delight at my very first Birkin?” — Yowei ([05:37])

Sam’s Dilemma: Wealth vs. Values

• Sam is uncomfortable being called "rich," though he’s objectively wealthy after selling his company for ~$17 million ([07:05]).
• He is left-leaning politically (“left of the Democratic Party”), believes wealth inequality is morally wrong, and is unsettled by now being “the 1%.”
• He feels isolated—he hasn’t told most people in his life about his wealth, worrying they’ll react with annoyance or envy ([05:45], [07:00]).
• Quote: “I like having the money, but I don’t know that I want my identity to be a rich guy.” — Sam ([06:24])

Strained Relationships & Guilt

• Everyday conversations about childcare or summer camp become fraught; Sam doesn’t want to be the out-of-touch rich friend ([08:00]-[08:44]).
• Giving to charity seems morally necessary to him, but it doesn’t erase guilt or answer the question of “how much is enough?”

The Anxiety Spiral

• Sam is anxious about how much to share, how much to give away, and the changes wealth brings ([09:23]-[11:46]).
• He worries about becoming detached from “normal” people or adopting the “insulated” mindset of the ultra-wealthy ([09:48]-[10:58]).

Enter the Proxy: David’s Path from Riches to Giving

• David Steeley matches Sam’s profile (self-made, didn’t grow up rich, progressive, became wealthy via a cheerleading business) ([15:16]).
• David also felt an aversion to being “that kind of rich person” ([16:13]).
• His wealth changed his relationship dynamics, habits, and sense of home—gradually eroding his feeling of belonging ([17:27]-[18:50]).

Class Transition & Loss of Belonging

• Traveling for work and increased status led to a sense of rootlessness and a shrinking friend group ([17:27]).

Guilt and the Question of “Deserving”

• Both Sam and David wrestle with whether they “earned” their wealth (“I worked hard...but there’s still a piece of me...that felt like I didn’t really earn this.” — Sam [20:19])

Resource Generation & Anti-Shame Wealth Conversations

• David’s friend brings him into Resource Generation, a group for young progressive wealthy people, to discuss wealth guilt and strategies for giving ([19:17]-[20:19]).
• David finds relief and community in confronting these issues together, and emphasizes the importance of talking about money, not hiding it.

Deciding How Much Is Enough—and Giving it Away

• David wanted to be below the top 10% in wealth, aiming for a sense of “enough” while intentionally rejecting wealth hoarding ([27:24]).
• He and his partner distributed money to family, a donor-advised fund, and to charitable causes, then split up, leaving each with about $1 million and a paid-off house ([27:49]-[28:54]).
• Quote: “I wanted to be out of the top 10%. Firmly out of, like, the top 10% of wealth holders.” — David ([27:24])

The Emotional, Not Mathematical, Nature of “Enough”

• They discuss studies suggesting that above ~$30 million, wealth no longer increases quality of life, but both agree that enoughness is rooted in emotion, not numbers ([31:58]-[33:10]).
• Quote: “If a million didn’t feel like enough, and 5 million and 10 million, then there’s no number.” — Sam ([33:29])

Giving, Receiving, and the Dynamics of Power

• David emphasizes the two-way nature of giving and receiving; consent and agency are critical ([49:10]-[50:08]).
• They discuss how always paying for others, even in small acts like dinner, can disempower friends and subtly shift relationship dynamics ([49:50]-[50:21]).

Shame, Transparency, and Relationship Health

• Transparency with family/kids about money, at an age-appropriate level, is crucial (hiding wealth until adulthood is often counterproductive) ([38:23]-[39:50]).
• Both Sam and David discuss how shame is isolating—whether about money or other identities (David is also gay and draws a parallel to coming out) ([47:03]-[47:44]).

Parenting and Inheritance Ethics

• Sam is conflicted about how much to give to his children: “I want them to build their own life,” but wants them to be safe ([37:31]-[39:50]).
• David suggests requiring kids to engage with class and wealth critically as part of inheritance ([40:45]).

Can Wealth Not Change You?

• David, drawing on many proxies, thinks that worrying about becoming an asshole is a good safeguard ([42:18]).
• However, both he and Sam acknowledge that wealth inevitably alters outlooks, opportunities, and behaviors, if only subtly ([44:12]-[44:51]).

The Paradox of Agency vs. Fragility

• Having wealth brings agency and freedom, but also a sense of fragility (“I don't want to mess this up,” “It feels fragile; don’t break it.” — Sam [21:52]-[22:57]).
• The possibility of “wrong” choices or losing optionality looms—having resources means having more to lose ([53:18]).

The Search for Purpose After Wealth

• Both Sam (semi-retired) and David (post-business) describe feeling lost once the collective drive and external purpose of work falls away. Wealth gives time and freedom, but also space for self-doubt ([54:42]-[55:05]).
• Quote: “I really miss the sense of shared purpose...feels a little lost, honestly.” — Sam ([54:42])

Using Power for Good without Shame

• David: “It’s bad advice to tell somebody to lean away from the power you have...shying away from it, it’s almost the most awkward choice you could make.” ([51:17]-[51:39])
• Accepting and thoughtfully leveraging new power and networks is more productive (and less awkward) than pretending wealth doesn’t exist.

---

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote | |-----------|---------|-------| | 07:13 | Sam | "Did I really earn this? Do I even want it?" | | 09:48 | Sam | "...it was both, for one, very boring...they don't seem like very nice people." (on meeting rich parents at school) | | 14:02 | Sam | "I lost about a million dollars." (matter-of-fact, about market downturn) | | 22:57 | Sam | “It’s like, I don’t want to mess this up. It feels fragile, right? Don’t break it.” | | 31:58 | David | "At $30 million of net financial worth, there is no discernible difference in your quality of life above that." | | 39:50 | David | "Not hiding the fact that there is money...Having it be a surprise at some point in their life—not great." (on parenting & inheritance) | | 42:18 | David | "People who are worried about being an asshole usually do a pretty good job of not being one." | | 47:03 | David | "That’s where shame creeps in...I just don't think anything good comes of shame." | | 54:42 | Sam | "I really miss the sense of shared purpose...feels a little lost, honestly." | | 56:22 | David | "I just aligned my actual values with the work that I'm doing. I feel so grateful to have had those friends and the space that money bought me to be able to do that." | | 53:55 | David | "Constantly planning for the worst case scenario also doesn’t feel like any way to live." | | 51:39 | David | "Shying away from [your power]…is almost the most awkward choice you could make. It's so awkward. Why are you doing that?" |

---

Important Segments & Timestamps

• Sam reveals his net worth & core discomfort: [07:00]–[07:13]
• Strained friendships & “offering to pay” woes: [08:00]–[09:23]
• Proxy introduction & David’s backstory: [15:16]–[17:05]
• Class transition, loss of home, and belonging: [17:05]–[18:50]
• Resource Generation and class guilt: [19:17]–[20:19]
• Giving away wealth: motivations and experiences: [27:24]–[29:02]
• “How much is enough?” emotional & numerical debates: [31:43]–[33:39]
• Consent and the power dynamics of giving: [49:10]–[50:21]
• Parenting and navigating inheritance: [38:23]–[40:45]
• Transparency vs. shame in relationships: [47:03]–[48:37]
• Reorienting to purpose after stepping back from work: [54:42]–[56:22]
• Epiphany on wealth, power, and healthy use of privilege: [51:17]–[51:39]

---

Tone & Takeaways

The episode is frank, warm, and at times self-deprecating. Both Sam and David are deeply introspective, candidly sharing personal insecurities and questioning their motivations. They discuss wealth and class not as political abstractions, but as lived realities—full of complexity, contradiction, and uncertainty.

Key Lessons:

• Having wealth does not magically confer moral clarity or happiness.
• Shame and secrecy breed isolation; transparency and community soften the psychic burden of money.
• “Enough” is more emotional than mathematical; security and agency are feelings, not numbers.
• Mindful, transparent giving—done in community—can bring relief and purpose, though it won’t solve every dilemma.
• Accepting one’s power and privilege, rather than denying it, is a necessary step toward using it responsibly and helpfully.

---

End Credits & Fun Fact

• In an on-air disclosure, Yowei reveals that Sam later donated $25,000 to Proxy after hearing one of her fundraising pitches ([58:07]), underscoring the blurred lines when reporting on real people with real-world stakes.
• As a fun sign-off, David briefly sings in his operatic tenor range ([61:32]), bringing levity to a heady, heartfelt conversation.

---

"Money exists, wealth exists. Pretending it doesn’t isn’t helping anyone."
—Sam ([51:39])

---

This summary was created to help you grasp the tangled emotional, ethical, and practical impacts of sudden wealth—especially when it clashes with your ideals.

Transcript

[A]

So you haven't shared any of these conundrums or questions or anxieties with people in your life besides, like your wife?

[B]

Correct.

[A]

And is the reason because you're afraid people might say something to the effect of like shut the fuck up?

[B]

I think that's part of it, yeah.

[A]

Yo yo, I'm Yowei Shah on proxy. We believe no one is ever alone with their problem because statistically, somewhere out there is somebody who gets it. And through the powers of reporting, we find them. Today's case, the progressive guy who got rich and is trying not to become someone he doesn't like. What do you do when your politics and life stop matching? That's after some ads. As listeners of this program know, pouring your heart out, really confronting your emotions helps you understand yourself and the world better so you can be better. That's what the podcast how to Be a Better Human is all about. Host and comedian Chris Duffy skips the typical self help advice and instead talks to experts unpacking big, relatable questions about how we navigate being human. Somehow I made the cut and was recently on an episode even though I don't identify as an expert and I had so much fun talking to Chris, we got into the weirdness of being laid off to why friendship breakups hit so hard and so much more. Listen to how to Be a Better Human Wherever you get your podcasts, this episode is brought to you in part by Quints. Right now I am sweating in my recording booth because summer is here and this time I am equipped with a Quint swimsuit that I don't have to worry about fading or pilling like my other swimsuits. I just got the Italian V neck bikini in cherry, which is made with recycled materials and has removable padding, adjustable straps and a hook closure for a perfect F. But this is what you can count on Quints for high quality essentials for every season, like soft organic cotton sweaters for layering on cool summer nights and breathable 100% European linen pants, dresses and tops starting at $32. Everything at quints is priced 50 to 80% less than similar brands. They're able to do that because they work directly with ethical factories and cut out the middlemen. So you are paying for quality, not brand markup. And Quint doesn't just do clothing, they've become a destination for elevated essentials across the home, kitchen, bedding and beyond. Elevate your summer wardrobe. Go to quince.com proxy for free shipping on your order and 365 day returns now available in Canada too. That's Q-U-I-N-C-E.com proxy. This show is supported by Odoo. When you buy business software from lots of vendors, the costs add up and it gets complicated and confusing.

[C]

Odoo solves this.

[A]

It's a single company that sells a suite of enterprise apps that handles everything

[C]

from accounting to inventory to sales.

[A]

Odoo is all connected on a single platform.

[C]

In a simple and affordable way.

[A]

You can save money without missing out

[B]

on the features you need.

[C]

Check out Odoo at O D O O dot com. That's O D O O dot com.

[A]

I try to see the humanity in people. It's kind of what the show is all about. But there is a type of person who I genuinely worry if they have a brain virus. People who own Birkin bags. I only know about Birkin bags because I watch too much Real Housewives. They're absurd, expensive luxury tote bags that the women on the show covet and cherish and sometimes fight about. A Birkin will cost you 15k up to 200 or 300k. And how do I say this? They look dumb. They're exceedingly boring. I wouldn't want a Birkin even if it were a steal. But on Real Housewives, nobody ever objects to spending this much money on such a mediocre looking bag. They egg each other on. They say it's an investment. These are, for the most part, savvy and intelligent and extremely likable women. And it makes me wonder, what is going on with rich people. Does the world of incredible wealth just warp your sense of what feels reasonable and necessary? Could it happen to anyone? Could it happen to me? If I were suddenly to become a real housewife? Would my need to belong overpower my distaste for gaudy luxury items? Would I squeal with delight at my very first Birkin? Anyway, a proxy listener got in touch because ever since he got rich, he's been struggling with a version of this question.

[B]

I'll be honest, you've described me as rich. I was like, oh, yeah. No, I mean, sure. Like that's, that's what we're talking about is that I'm rich. It's not wrong, but it's not a descriptor I use for myself.

[A]

This is Sam. Well, in the story he's going by Sam. Recently, after selling a company he started over a decade ago, Sam got rich. Like really rich. Richer than anyone in his middle class, friend and family group. And he has feelings about it. Do you not want to see yourself as a rich person?

[B]

I mean, maybe not, right? I like having the money, but, yeah, I don't know that I want my identity to be a rich guy.

[A]

After the sale, Sam didn't have a party. He didn't celebrate with friends and family. He didn't tell anyone in his personal life how much money he got, except for his wife. How much money are we talking?

[B]

Oh, man, it's weird. I feel like there's such a stigma around numbers. Like, my mom doesn't know.

[A]

Your mom doesn't know?

[B]

No.

[A]

I feel so privileged. That is, if you're gonna say it in the end.

[B]

Yeah, well, now you built it up. It's probably 17 million.

[A]

Damn.

[B]

And at first, I really did struggle with. Did I really earn this? You know, do I even want it?

[A]

Sam has always been skeptical of wealthy people. He's a progressive. He wanted Elizabeth Warren to become president in 2020, but really, he's left of the Democratic Party. He thinks the wealth gap in this country is horrific and morally disgusting. He wants the 1% to pay a lot more in taxes. So now that he is the 1%, it's weird. And not just for his political identity.

[B]

I'm worried in a lot of ways that the money will change relationships I have with people I care about.

[A]

Do you feel like the money has already caused distance between you and any of your friends and family?

[B]

I mean, there's definitely been times where, you know, someone's talking about childcare, some other problem that's not a problem for me, and I stay silent, you know? Cause it doesn't feel like it's my place to comment on it, because, like,

[A]

if you were to say anything, maybe your friend might have the reaction that I have had where it's like, oh, that's easy for you to say.

[B]

And I think that's a valid reaction. It is easy for me to say,

[A]

but what if Sam did offer to pay? Say he stepped in to help his friend with a few months of childcare? Would that make things awkward? Would people just expect him to start paying for everything and then resent him when he didn't?

[B]

We can make this more personal, too, which is that you had a fundraiser for the show. I think I missed it originally, but, you know, I definitely listened to that episode and thought about sending you a check, but we'd already been talking, so you felt awkward. Would you feel obligated to make an episode to a. To a donor?

[A]

Oh, my God. That's so funny.

[B]

Right?

[A]

Well, I can tell you right now, it does Feel weird. Yeah, I guess this is what they talk about with editorial independence.

[B]

There you go.

[A]

Having more money than friends and family. It's created this dynamic where Sam is constantly making these calculations in his head at every dinner with company, at every beach vacation with the extended family. At the same time, it's not like Sam just wants to hang out with rich people. Now is there a specific person in your head that you are afraid of becoming?

[B]

One of the things I do spend money on is the kids. Right. Youngest was too young to start pre K. She put her in a private school. They had a getting to know the parents night at one of the board members houses. It was like a very beautiful property, like a mansion. They had bartenders and catering and food and stuff set up. Someone rolled a TV out there. There was some kind of football game going on. And it was a bunch of people who, most of them had jobs, high powered lawyers or defense contractors. And talking to these people and I'm like, man, I don't have anything in common with them. Just overhearing some of the conversations. It was both, for one, very boring.

[A]

What were people talking about?

[B]

There was a lengthy talk about the ins and outs of the golf tournament that was coming up and like heady comments about, well, that person picked that partner. I don't know, let's. I don't think it was more a vibe than any particular offensive thing anyone said, but it was just like they don't have a lot going on and also they just don't seem like very nice people.

[A]

Sam doesn't want to become one of those people. And so he's made it a priority to give money to charity. So far he's given away 1.5 million, which is a shit ton of money. But he says he still has too much and it makes him feel guilty. Can I ask, why don't you just give away all your money so that you don't have this dilemma?

[B]

I've asked myself that too. If you'd asked me when I was younger, if you made $10 million, how much would you give to charity? I would have said, oh, give 5 million, I only need 5. But then it happened and like, I didn't. I took the money. I think most people would, but I took the money.

[A]

I think most people would.

[B]

I think so too. But what does that say about the person I thought I would be? You know, am I greedy? Who am I really?

[A]

When we return, I find Sam a proxy to talk to about his rich people problems. All right, I want to take a moment to Tell you about a big year long series from this day, a history podcast here at Radiotopia. If you haven't noticed from all the annoying decor in stores, at least in the US 2026 is America's 250th birthday. And over at this day they are in the middle of a year long series called 50 Weeks that Shaped America. This day is doing deep dives each week on the stories from 250 years of US history that brought us to the very complicated moment today. Some of them are new perspectives on huge moments like the Civil War or Prohibition. Others are lesser discussed stories that still had a massive impact like the Transcontinental railroad or the so called Hard hat riots of the 1970s. This day is also doing a special weekly newsletter, live shows, collaborations, bonus episodes and lots more. So as we head towards the 4th of July and beyond, this is a great time to join in. Go to this day.pod.com or find it wherever you get your podcasts. Uh, how's it going?

[B]

It's going okay. Yeah. How have you been?

[A]

The day of the proxy conversation, Sam is nervous.

[B]

Not so much. I mean, the conversation I. I'm curious about. I guess I'm more nervous how I'm gonna. How I'm gonna end up sounding that I will sound like someone who doesn't have real problems to complain about.

[A]

There's also the fact that he lost just a bit of change since we last spoke.

[B]

It was like, I don't know, lost about a million dollars.

[A]

Oh my God. It's complicated. The short version is that when he sold his company, part of the payment came in stock options in the new company, which is now tanked. You're still wealthy, right?

[B]

Yeah, it was like.

[A]

This episode is taking quite the turn.

[B]

No, I mean it's.

[A]

You lost a million dollars, but you're still wealthy.

[B]

Yeah.

[A]

Damn. Okay, Roxy's here.

[B]

Cool.

[A]

You ready?

[B]

Yes.

[A]

Can I just say, it is very difficult to get rich people to talk on the record about being rich. I had a few people drop out and then I found em a guy who checked all the boxes. Same general wealth range as Sam. Didn't grow up rich, didn't inherit money, jumped classes through his own efforts and similar progressive politics to Sam. Also not an asshole. His name is David. David Steely.

[C]

Sam. It's great to meet you.

[B]

Nice to meet you.

[A]

David is a former millionaire who has since given away most of his money.

[C]

I mean, I grew up in a small farming town in Michigan. It was mostly white. It was mostly kind of like lower Middle class, working class folks. I remember going to college. I was on scholarship. I actually went to college for music. I was an opera singer. But I remember going. And in my class, everybody had gone to private school. Like there was like a dinner of like 20 of us and everyone had gone to private school. And I was like, oh, I couldn't, I couldn't have afforded that. I couldn't have. I wouldn't be able to be here without the scholarship I'm on. You know, there was like this. There's very clear where I sat in the hierarchy of money, which wasn't so clear to me in a small farming town because people were generally in the same boat growing up.

[A]

David says he didn't dream of becoming rich. That was never the plan.

[C]

I don't know why, to be honest. Like, I didn't know any rich people who were like jerks. But in my head you get this like, rich people are jerks thing. They have more than they need. They're hoarding it. Like all these like messages that I received from, I literally don't know where but had that. So like really kind of had this aversion to like being really wealthy. It wasn't going to go after it.

[A]

And then David met and fell in love with his ex partner, a well known choreographer in the world of competitive cheerleading. And they started a business together selling camps, uniforms. And the business was everything they lived for. All the money they earned went back into it.

[C]

We were like risking it all the time. There was like, not a lot in our, like personal bank accounts. We like worked our butts off, lived very thinly for a long time, I mean, for years, just with the belief that we could like build something.

[A]

Before long, business was booming. They were traveling all over the world for work. And by most accounts, they were winning. They had more than what they needed. They were building wealth. But over the years, David noticed a slime creeping up from his feet. It was the money. It was changing him.

[C]

Like, I had enough status on the airlines because I was traveling all the time that I was almost always bumped up to first class. And I was like, oh, this is really nice. This is a lot better. And really like, my partner used to make fun of me because I was like, when I didn't get upgrade, I would complain you had upgraded this time. And he's like, who are you? Like, where, how did you get there from. From where you had been. I was also gone all of the time for work. And maybe you ran into this too. But like, there were certain friends that could Roll with that. It's like, okay, we haven't actually seen you in two months, but you're back and let's grab dinner and we're cool. But those became fewer and further between of people who could roll with that kind of friendship. And there was also this like loss of like location, base, feeling of belonging. I remember coming back to my apartment when I hadn't been there for a couple months. I'd spent like a month in New Zealand and then had to do other travel before I came home. And I got home and this was the place where I lived and it felt like a crash pad. Yeah, I was like, I could just be changing out clothes and like from the closet and leaving again and it would feel no different. And I remember I sat down and cried because I felt so attached to my home. And here I was with the only home that I had and I was like, this doesn't feel like a home to me.

[B]

Yeah, I can. I definitely understand why. Why you were my proxy. My business was all online. I didn't travel that much. But it still resonates over time. There was a shift, right? It was gradual of like this feels different, you know, and it feels disconnecting from friends who are not in the same situation.

[A]

In David's case, it was a friend who intervened. She'd been clocking his class transition by some of his behavior and was concerned.

[C]

And I remember her saying, I don't know what your financial situation is right now, but I can tell that it's upwardly mobile. So why don't you come to this organization? Organization, we talk about money.

[A]

The friend had gotten involved with something called Resource Generation, a non profit that organizes young wealthy people to give away their money to social justice orgs. And I have to say, before this story, I had no idea this kind of thing existed. But there's actually a whole movement of groups trying to get rich progressive people to channel their wealth into the causes they care about. David says when he first went to a Resource Generation meeting, he had this funny realization that most of the people in the room had inherited their wealth. So they felt guilty about the money, whereas David did not.

[C]

I didn't have any of the hang ups. Like I didn't actually do anything to earn this money. It's like, well I did, I did do a lot to earn this money.

[B]

Yeah, at first it really did feel like, well, this is, this is mostly luck, right? Lucky me. I won a lottery ticket and. Any more self esteem than that?

[C]

Right?

[B]

Like, no, I worked hard. I applied skills and Worked hard. But, yeah, there's still a piece of me, especially at first, that felt like I didn't really earn this.

[C]

I absolutely felt that, too. I was like, well, why do I deserve this?

[B]

Yes.

[C]

Lots of people work really hard, and some of them worked harder and way crappier jobs than I had.

[B]

Yep.

[C]

And they aren't getting this. Why do I deserve this? I really feel you on that.

[B]

I had the piece, too, of there were people at the company, early employees who stayed with it, and everyone got a fair salary. We weren't trying to make money by underpaying people, but they didn't get millions of dollars at the end. And some of them worked just as hard as I was in that sense. Yeah. I felt undeserving. I felt badly. Felt like, man, if I could go back and do it again, I would have set up stock options and done it this way and given everyone so. So that now it would feel more fair. We did give a bonus to everyone who was working there, and there was a formula and all that stuff, but it's not the same. In many ways, it isn't fair.

[A]

Sam says after they sold the company, his co founder bought a lake house. While Sam just wasn't in that headspace, he didn't want to start acting like the rich person he was. He didn't want to splurge, even though he could.

[C]

Can I ask Sam, what. What made you not splurge?

[B]

To be fair? So I did buy a car. It was a Honda, but it was a new Honda. It's my first new car, you know, so I bought a car. Why didn't I spurge? That's a good question. Honestly, part of it is I got really good at saving money. Right. And that's very different from spending money and investing and saving money and working a business and making money. Part of it, too, was the script sort of flips, right? It's like, we're taking these big chances. I'm starting this company. We're doing all these things. You know, the first year, I didn't take a paycheck. We're making these sacrifices. Big risk, big reward. And then once you have the money, it's like, I don't want to mess this up. Right? It's like, we got to be prudent with this. You know, I don't know if the lightning is going to strike twice. Like, it feels fragile, right? Like, don't break it. I don't want to lose what I have. And I think that was a piece of it, too. So it was Kind of like, well, yeah, the obvious thing is just I give it to a financial advisor and tell them to invest it in broad stock index funds, and I've got decades ahead of me, and we just end up sit on it. Right. And that's pretty much what I did.

[C]

I totally feel you on that. And then the reality, I think, for me, as I look back at that moment is like, I'd probably never been more financially empowered than I had in that moment, and yet it felt frat fragile. Such a great word. I was like, oh, I feel like I could make the wrong move and it would all be gone.

[B]

Yeah.

[C]

Which is wild because you have so much control over it.

[B]

Yeah.

[C]

And I think I have learned or experienced also having a lot of agency over my life and time that I didn't have before. And I'm in this moment of so much empowerment and at the same time feeling so fragile and vulnerable and. And scared. In some danger somehow. Like, maybe actually somebody's going to come after me now that I have money. Maybe I have some danger headed my way. When the reality. Well, I think from the outside, it. It feels clear to folks. It's like, no, you. You won. You won, dude.

[B]

Right? Yeah.

[C]

But, like, that's also a just like this implicit fear if you're wealthy, is that someone's trying to get your money, trying to trick you, trying to get you into their investment so that they can make money off of your money. I see Sam, I see you nodding.

[B]

If you go read online of like, I came into a huge windfall. What should I do? Well, don't tell anyone. Right. That's step one. Don't tell anyone because distant relatives are going to come out of the woodwork. Someone will trip and fall on your sidewalk and sue you. I don't know that I took that to heart, but I definitely was like, I mean, yeah, that makes sense. I wasn't particularly worried about, like, swoop and falls or relatives, but, like, the vibe is real of just, like, a

[C]

vulnerability and I think further isolating. Right. It's like yet another message in your head that it's like you actually can't trust people. You have to protect yourself. You have to protect the money.

[B]

Yes.

[C]

It becomes like this, like, personified thing. I remember really feeling like it was the money is like a character in your life now.

[B]

Yeah. And were there people who you felt like were, I don't know, doing something for the money?

[C]

Yes. And I think my core people. That wasn't true for certainly, like, nobody in my family. They were really Happy and proud, which I, again, I feel like so lucky. I don't think that has to be true for somebody. My, like, close friends there. There was a similar vibe. I think that next circle out there was a little bit of like, hey, I have this opportunity for you.

[A]

Oh, people actually came up to you and asked about opportunities?

[C]

Well, they had an opportunity for me. That was always the funny. Yeah, that was always the funny way to be welcomed into that conversation. And for a long time it was easy to say no because we kind of had a class appearance, like a class status of just flying all over the world, traveling all the time. But, like, actually we didn't have any cash, like, at all.

[A]

David, can you tell us, like, what is the story of how you decided to give away money? And how did you decide how much to keep versus give away?

[C]

Yeah, this is like the irony of this hap. The timing of this. I was on the board of Resource Generation. I really, I got in deep with that organization and still love it and support it. And we as a board were dealing with the question even what is a wealthy person? We organize young people with wealth. Who's that? So we really started to think about what is the top 10% or top 1% of wealth holders in different age brackets and roughly at the same time this document is finished was when the sale of my business actually took place. And for a brief second in time, I was in the top 1% for my age bracket of net financial wealth. In the meantime, I'd been working with this organization and organizing around, hey, that's wealth hoarding. Just like calling that like, if you're in the top 1%, you're. You're hoarding wealth. And it freaked me out.

[A]

David and his ex started planning how to Robin Hood themselves. They had a lot of discussions, beginning with how much money is enough? How much should they give away?

[C]

And for me, I wanted to be out of the top 10%. I wanted to firmly be out of, like, the top 10% of wealth holders. And I wanted a home that was safe, that was kind of the. The stable place that I would build off of.

[B]

Yeah.

[A]

After selling the cheerleading company, they had around 5.5 million, which after attorneys fees and taxes immediately went down to 2.9 million.

[C]

The thing that felt really clear when we had a big pile of money was to give some to my parents who had really supported us, give some to some friends that had really supported us.

[A]

From there, they dropped 250k into a donor advised fund, which is essentially a place to park your money. To give to charity on your own timeline and can also lessen your tax

[C]

burden in the end. I think in the first year, we probably gave away about $500,000. So that put us at like 2.2 million. And then this wasn't ever the intention. But funny enough, we ended up splitting, my partner and I. So by the time we split, we both took about a million dollars. And for me, I mean, I'm sitting at my house in Phoenix right now, which is virtually paid off at, and is worth that. So I have a home that is paid off and I still have to work to you know, make my life work. And that was. Yeah, that was kind of our, our process on giving away that money.

[B]

I guess I want to hear more about how you made the decision to give the money away and then what it felt like afterwards.

[C]

You know, I was around resource generation enough. One of the activities they do is we everybody at the conference. I don't think they actually do this anymore, but they did this for years. So a hundred people would sit down in a room, in a circle and everybody would tell their one minute money story.

[A]

What's a money story?

[C]

Right? What is a, what is a money story? Points you try to hit when you're sharing your money story. Where in the like, class strata you grew up, how you got your money, what impact has that money had on your life? And there came to be some pretty formulaic stories after you hear hundreds of money stories. And a lot of them started with my father, my uncle, my grandfather, my great great grandfather started a business. And usually there was some kind of good investing, some kind of success found. And a generation, two or three in the money has become the biggest problem in the family. It has torn the families apart. We're not allowed to talk to this person in the family or this side of the family. A lot of times it's my, my dad and his brother. Don't speak. This was so common. You know, I want to say, I'm sure there were folks who were there that are like, you know, I have more than I need and I'm really excited to like, do some good with it. There's not a bunch of drama in my family about it. So I don't want to paint only the dark side of that, but. But I will say it happened more often than not. There was this like kind of horrible picture painted of what the money meant in their family and their relationships and in their lives. Sometimes it was. I have so much of it that I don't. There's no point to my life. It's that dramatic for folks. And I was just like, I don't want any of those futures. I don't want this responsibility hanging around my neck of, like, what happens to the money after I die. It was kind of scared me. And also found that people who were actively giving their money away were just, like, in community with people and were excited and felt good about what they were doing with the money they had.

[B]

Yeah. Thank you for that.

[A]

Going back to the what is enough question, how to figure that out?

[B]

Yeah. Could you tell me that? How much is enough? I need, like, a number. It's a tough question for someone else to answer for you. Right. It's how much is enough for you? It feels. Yeah.

[C]

I. I could offer you a data point.

[B]

Sure. I'll take a data point.

[C]

A data point is that at $30 million of net financial worth, there is no discernible difference in your quality of life above that.

[B]

Yep.

[C]

You can buy assets, you can buy. Instead of renting the house, you buy the house, you own it. Or there's a conversation to be had about Legacy. But at $30 million, your quality of life doesn't change. So you could be a billionaire. You could be a 30 millionaire.

[B]

Right.

[C]

That's it. That's what the planet can offer a wealthy person in terms of experience, in terms of. Of life.

[A]

That number is really high. I thought it was gonna be much lower.

[B]

I. I believe it's true. It's the number at which no more money matters anymore. Like, it should be a big number. Right. I don't know. It's like I was doing these silly games of, like, well, if I live for another 50 years and don't work, and it's like, well, is that even the goal, to live 50 years at the same quality of life? I'm sure there is a formulaic way to try and get at this. I actually kind of like the, you know, 1% for the bracket or 10%. Like that. I actually kind of like that approach. But also, it wasn't really a number question. Right. Like, it's like a feelings question. It's an emotional question.

[C]

Yeah, it totally is. It totally is a feeling question. What feels like enough? When am I going to feel secure.

[B]

Yeah.

[C]

Or prepared for things that life will throw at me? And I. I don't think it's necessarily a numbers question. Right. Like, it's not like this amount of money will do it.

[B]

No. And if a million didn't feel like enough, and 5 million and 10 million, then there's no number Right.

[C]

Yeah. Yeah. There's just different entry points to it, and I think that how much is enough is actually the hardest entry point.

[B]

Yeah. Yeah.

[C]

I think it's the most challenging to be like, this number is enough. And it's like, well, what if you gave away the interest? How much would you be giving away every year if you gave away 7%?

[B]

Yeah.

[C]

Another one, too, is how much would you have to give away every year to not like, wealth increases just sitting there. Money makes money. So how much would you have to give away every year to not gain wealth in a year?

[B]

But, yeah, no, I. Last year, I made more an interest than my wife, and I earned working. Right. So doing nothing made more money than working.

[C]

Yeah.

[B]

Which is weird.

[C]

Yeah, no, that. That happens pretty quickly with money.

[B]

Do you think the people who. They were doing really well, really happy giving away their money, is that because the kind of people who would sign up to do that are the ones who have the right attitude, or is it because actually it lessens some burden? Right.

[C]

I think. I think it's both, for sure.

[B]

Yeah.

[C]

I do think it takes a certain temperament and personality to do that. And I. Everybody who did it, at any level, I could see a sense of relief.

[B]

Yeah.

[C]

It's like, oh, my gosh, I can. I can do this. And I think the. The other thing they really focus on to. To fight that isolation is don't do it alone.

[B]

Yeah.

[C]

Don't. Don't give your money away alone. Do that with people, and it becomes really powerful in connecting both to the people who you give to and also, you know, that you're connected with them, but also the people you're giving with. It was. Yeah, it was. Honestly, it was a really, like, beautiful kind of sense of community that came from that.

[A]

After the break, the surprisingly complicated ethics of buying your friend dinner. Hello. Hi, it's yoe with a quick thing. If you have a friend who is struggling with enoughness or class guilt or a change in identity, that's isolating, be a good friend and send them this episode. Also, Roxy is an independent show, and we mostly grow by word of mouth, so that would also be nice for us. All right, Ads. Welcome back to the show. So when David told us the story of choosing to give away his money, he said this thing about it being clear to him that he didn't want to be in the top 10% anymore, and I wanted to know why.

[C]

I was really uncomfortable with the idea of being in the top 10% of wealth holders in the wealthiest country in the world. It Felt like wealth hoarding to me. It felt like I didn't need that much to be okay. Yeah, it felt. It felt kind of icky to be honest. What does me having that much mean that someone else doesn't have? There's no direct line like Sam, obviously to like money you have that someone else doesn't. But there is an implicit line that I was really feeling of. Like there's lots of people who don't have enough. And what does it mean that I have that much more than I need. There was like a repelling feeling, I guess that I was like, I gotta. I gotta do something about that. I also don't have kids, Sam, so I feel. I feel a little protective of you in this conversation because I. It's. Everybody's on their own journey and I hope you don't hear judgment in that feeling that I was having.

[B]

No, I appreciate. Look, these are all options I considered. I almost feel like I haven't made any decisions yet. I'm sure there are people who gave nothing to charity in similar situations. And I gave. It's a chunk and I. I don't know what's in the future. Right. Yeah. The kids is a piece of it. The family. You know, it's not just myself, but also I don't think I want my kids to have too much money. Right. It just intuitively feels like a bad idea. But if there's things they need. Kid needs braces. I bought her braces. Right. Like that's not a question. There's no scenario where they're not. Like they're not going to be homeless. Right. Like I'm going to make sure that they are safe. But millions of dollars, I don't know. I want them to build their own life. Right. So I don't know. I guess I'm curious what you've seen other people do that's worked really well.

[C]

I will say based tons of conversations. Right. Resource Generation is an organization of young people who have wealth. I would say things that worked really well. Not hiding the fact that there is money.

[B]

Yeah.

[C]

Having it be a surprise at some point in their life. Not great.

[B]

Yeah.

[C]

What happens when that. When that is the strategy? It's usually like right before or right after college. So these are people who are like just starting their like steps on their like own. Like I am stabilizing my own life. I am responsible for myself and the disruption that happens when it's a surprise. Number one, there feels like a little bit of betrayal. You saw me stressing, you saw me trying to Figure this out. So I think that's tricky. And also I think what I see later on is people who have either grown up with that or, like, have that process interrupted, they feel like they can never take care of themselves. This feeling of, like, I will be able to provide safety and get my needs met for myself that we as adults have to face, and the resilience that comes from that and the pride that actually ends up coming from that gets taken away. You get robbed of that. And it. It gets to the point where, oh, my gosh, you're well educated, you're smart, you're well spoken, you have access and you have no idea how to navigate the world.

[B]

Yeah, I don't want that. I wanna. I mean, enough. We've tried. Like, we talk about, you know, let's help pick the charities together. And like, we as a family, that's one of our values. We give money to charity and we help people. Right. But I don't know. My eldest is nine and said something. I don't even remember the context. We were getting out of the car a few weeks ago, said something like, we don't have a million dollars. I was like, it's like.

[A]

I mean, it's like, wait, what did you tell her?

[B]

Something else happened and it didn't. We were like, going somewhere. It wasn't really, but, like, I probably need to, you know, it's tricky though, also, because I. It's an age where I also don't want. I don't want, like, getting a fight with some kid at school and be like, well, you know, my dad has a million dollars. That's not good either.

[C]

Yeah. Like, how do you determine what is the age appropriate conversation to have about money? That is so hard.

[B]

Yeah.

[C]

But I always thought, hey, the one thing I will require of your inheritance is to. I mean, in my case, it was go to Resource Generations national conference, think and talk about wealth and class. You have to do that, and then you can do what you want. Then I trust you as a person and as my child that I. You know, there was a time where I was really thinking about having kids and I was like, I would at least make them do something that made them think about it. Like, pause to think about what it means to have money and what it means to not. You know, it's a little controlling, I guess, but it also could be a real love letter from you to them at that point in their life too. Kind of depends on who they are and how they receive that.

[B]

They're good kids.

[C]

I have no Doubt. Sam,

[A]

I talked to a few people as potential proxies for this story besides you, David. And something I noticed, not with you, but with other people, was this insistence that money hasn't changed them, that they're still good people. Rich people are people too, which of course they are, but sort of this idea that like, no, no, no, people have it wrong about us. The money hasn't changed me. David, in your experience working with a lot of rich people, do you think it's possible for the money to not change you? And this goes to like one of your. The things we talked about, Sam, is to not become a little bit of an asshole. Like, you know, to not become someone you don't like.

[C]

I think typically people who are worried about being usually do a pretty good job of not being an. Why are you worried about being an?

[B]

I don't. I'm not sure. I'm worried that I will be an. I think it's. I guess it just goes to identity, right, that like my self conception is not like this person with wealth and means that makes things happen and the world bends to their will. It's just not how I think of myself. And I want to be mindful there's a way in which you can be an asshole by taking vast wealth, different things you have for granted. I think that could happen. I don't think for me, I hope not for me. I feel like I'm pretty conscientious. But I guess it depends what you do with the money. There's a way you can use it to insulate yourself from problems and from people with problems and from the world, you know, we could build a big security fence around the house and like, side note, the person I bought this house from, it's like a very nice house. A newish construction moved in and we're looking and there's like all these little boxes up near the ceiling in all the rooms that I thought were like some kind of hardwired smoke detector. No, they did not have smoke detectors in the bedroom. They did have glass break sensors for all the windows for someone breaking in and a gun safe hidden behind a mirror in the bedroom. And we're in like the safest neighborhood in the whole city, you know, and just the mindset of like I'm more worried about like an armed intruder climbing through the third floor window than a house fire. A thing that really happens. It's just like, is that person an asshole? They might also be, but it's just like that mindset of just divorced from reality, I guess. Is more what the concern is.

[C]

Yeah. There was nothing. Nothing ever, like, dramatic happened where I was, like, super rude to somebody or, you know, But I recognize that I leaned into my path smoothing. So, like, if I go into the bank and have to get something done, I. I know how to, like, hey, can I just check the balance on this account? Great. And then can you help me with this? Right. So they. They saw. They saw that. They saw how much money I had in the bank. And then I asked for a request that I would have asked for anyway that almost anybody could have come into the bank and asked for. But I know my path is going to be smoother because I did that thing at the front of. End of it. Am I being an. Maybe a little bit, like, maybe that's a crappy thing. Is it wrong for me to want my path a little smoother through the world? I don't think so. But there's like a. Like, a piece of, like, ego or attitude that also is carried in that. That I think I recognized in myself. Yeah. I hate saying this out loud, but I think. I think it's honest. And I think it's probably one of the reasons that I didn't want to hold on to the money. Maybe I'm not. Maybe I'm not the one who's suited to hold onto that money.

[B]

I don't think there's anything to be embarrassed about. I mean, I get it, but it's. You know, I think it's admirable, right, that you recognize that that's something that made you uncomfortable. I think it'd be easy to go the other way and say, like, well, my life is so much easier now. I'm gonna do this for everything all the time. I'm sure many people choose that path.

[A]

Sam, it does feel like one of your fears. Not so much about becoming an asshole, but how to not let the money change your relationships in ways that you don't want.

[B]

And it's funny, too, because it's not even anything that actually happened. Right? Is. Is like, oh, well, my goddaughter's going to college, and maybe I could pay some of the tuition. But, like, now other friends, are they going to want money for their kids? And, like, have I changed the dynamic, right, of a friendship that's really important? I am worried about that. I've been very worried about, like,

[A]

I

[B]

gave a chunk of money to charity. I didn't really give anything to people I know or family. Luckily, my family's doing fine. Right. If they needed money, I'm Sure, I would have. No one asked. But it's tough. It's a piece of it that feels alienating, too. You know, I have friends that talk about, like, oh, yeah, we're signing up for summer camp and, you know, but so expensive. And we. So instead of that one, we're going to do this one. And I don't know what to say because it's just not an issue for me. We're gonna do the fancy one. Why wouldn't we? The kids love it, and it's really nice and clean and, you know, it's just tough.

[C]

I just think that's where the shame creeps in. Like right there in that moment, that's where shame creeps in. And I just don't think anything good comes of shame. I think that's why I'm so bought into this idea of transparency. And I think it can lead to some also hard conversations around, like, no's.

[B]

Right.

[C]

Maybe somebody then comes to you and asks and it's like, no, I'm actually not willing to do that.

[B]

Yeah. Yeah.

[C]

But I think that shame is so isolating, you know, and it's. As a gay man, you know, coming out, I know all about shame. I know all about how isolating that can be. And it's different. But that shame shows up around wealth, too.

[A]

Yeah.

[C]

Especially if the folks around you don't share the same access that you do.

[B]

It almost feels harder just because they're all doing fine. I mean, someone was really struggling. Like, it'd be easier, right? It'd be an easy call to say, like, well, I'm not gonna let my friend struggle, but everyone's doing fine, you know, so it's like, well, what? I could help things be easier for them. But like, I don't know. Now what am I doing? I'm just raining money on people. I don't know. And I'll admit, too, it's also much easier to not do anything. It's definitely a cop out on some level because I think intellectually, I think you're right. Transparency, of course, is going to be better, especially with friends and family. If they love and care for you, then they're going to love and care for you. And if they don't, then there you go. But it's still hard. It's easier to not.

[C]

And Sam, who do you become when you become the person who's helping them? Right? Like, who do you become to them and who do you. It just. It. It can change the dynamic of the relationship.

[A]

David, did you have to navigate any of These situations.

[C]

I don't know how else to say it, except I'm incredibly lucky with my family. That just wasn't an issue. You know, they were doing okay. I mean, I set up college funds. That was another thing I did for my nephews, and gave money to my parents, which they didn't expect, and were, like, a little awkward about receiving.

[A]

What do you mean they were awkward?

[C]

They were just like, we don't need this from you. You don't have to do this. And it was like, but I can. And I feel so glad that I can. And I know you're okay already, but I know it will help you. I think one of the things I've learned both going through resource generation and then also working as a fundraiser, is that giving and receiving are two acts. It's not a wealthy person giving. It is also you receiving. And there could, for instance, be strings on money that mean, like, the act of receiving isn't going to happen. I'm not going to actually take this from you. And so I'm a big person for consent and talking actively about consent. And I think that's one of the things that I've really learned and don't always navigate gracefully, but can say, is it okay if I buy you a meal? Is it okay if I buy you this meal? Is it okay if I do these things?

[B]

Yeah.

[C]

Because actually, it can be a crappy thing if somebody's always paying and you're like, I would actually like to pay for you. Like that. That can be a gesture that actually has nothing to do with who has more money, but that I'm just. I'm doing this one.

[B]

Yeah.

[C]

And to take that from somebody all of the time is actually, like, pretty disempowering and can feel pretty crappy. And just being aware of that dynamic that Sam I just like. The more I talk to you more, I'm like. And you are someone who is aware. There's no. No world in my mind where you aren't aware of that dynamic. And I love that you're asking these questions and feel so confident and lucky to be talking to you, because it feels like you are somebody who's really giving this, like, the deep thought that it deserves. I don't think you're going to be an asshole.

[A]

We can all agree that Sam is not going to be coming out.

[B]

All right. We can pack it up. That's all I wanted.

[C]

You know, the. The other thing I'll throw out there is that, you know, in. In my work. But I think this is true. In life too, we're often encouraging people with wealth because they have access to money, because they have access to networks, because doors are opening for them left and right. They can actually leverage that for other people too. Right?

[B]

Yeah.

[C]

I think it's bad advice to ever tell somebody, lean away from the power that you have.

[B]

Right.

[C]

It's shame based. I don't think anything good comes from that. And I think navigating thoughtfully the power you have is important, but shying away from it, it's almost the most awkward choice you could make. It's like, it's so awkward. Why are you doing that?

[B]

It's like, well, I don't see color talking about race. Like, no, it exists. Money exists, wealth exists. And pretending it doesn't, it isn't helping anyone.

[A]

Any last questions?

[B]

Do you have any regrets for the path you chose?

[C]

I mean, not yet. I mean, I have to work now for my retirement. I couldn't retire today. And I think it's such a double edged sword because I like love the work that I'm doing and I feel like a real sense of purpose. And then also it's like, oh, yeah, I got to work for my retirement. That has to happen. And something I think about, I don't. Something that comes up for me where this is so. This is such a like weird little slice. But I, as a wealthy donor, you're like in a community of other wealthy donors and I really liked that community. And I'm not a wealthy donor anymore and I still am in those communities and I'm still like welcomed in those spaces. But it's diff. It feels different. And so again, I don't think it's like necessarily regret, but there's been a few things like that that are like a little double edged. So it's like, oh, there's like an identity shift there. And like, I don't feel like I need to be a wealthy donor, but at the same time, like I knew who I was in that identity.

[B]

Yeah.

[C]

It feels harder and more complicated to be like, I am a former wealthy donor. That. That feels more complicated. And so there's like a lack of simplicity there that I'm like, okay, that's fine. But I notice it for myself.

[B]

If that's the worst of it. That seems pretty positive. I think. I think there's a piece of me that really values optionality. Right. Which obviously money provides a lot of options. But I also think it's partly a lack of security. Right. It's about agency and security, which are feelings more than like what those resources can do because I wasn't planning to give away so much money that we're in trouble. Right. But with any amount, there could be a day where it's like, well, I can't even think of what it would be. But like, well, I wish we could have done that, but we can't. Right. Because of the choices we made. Yeah.

[C]

Constantly planning for the worst case scenario also doesn't feel like any way to live.

[B]

No. A little bit of this is, you know, those anxieties that I have. If anything, having the time and the money and the resources gives them room to breathe. Right. Brings them to the forefront a bit.

[A]

Sam says now that he's not working full time, he has all this free time, which also means a lot more time to be in his head. It's this funny contradiction. The money that gives Sam the freedom of choice also allows him to constantly reevaluate. Am I making the right choice, the right decisions? And it's not just that. The money also gives him a kind of independence, which he's finding is a bit lonely.

[B]

I really miss the sense of shared purpose that was like, we're all working together and we're rowing in the same direction towards something. And some of the things I volunteer with have that too. I've been really looking for, like, purely, like, mission driven. We're just trying to make the world a better place and that feels good and we're all working together on that and I like that a lot. But I don't know, feels a little lost. Honestly,

[C]

I really identify with the kind of feeling lost. I worked for the business that bought ours for two years. That was part of the earn out as we went through. And then I bought a camper van and traveled the US For a year. It wasn't my intention to do that at first. I just wanted the van and was doing some small trips. But I had a friend who really encouraged me to, like, get out of the mindset of the hustle and into a mindset of like, hey, if you need some purpose, great. But like, try to align your purpose with what you really want to do and not this, like, hustle sense that was so deep. Oh my gosh. And it took me four months to relax and I was spending every day outside. I went to, like, most national parks. I like, did these incredible, beautiful things. And most of the time I was like in my head about, am I doing the right thing? Is this enough?

[A]

After his year in the camper van, David started consulting for a business and quickly got swept up in the grind again. It took a friend to point out to David that he was about to get stuck in the same trap. And the friend also mentioned that there was a social justice org looking for a donor organizer, someone to help with raising money.

[C]

So now I work at an organization called Surge Showing up for Racial Justice. It organizes white folks, inoculates them against far right messaging, and tries to move white people into multiracial democracy. I just aligned. I aligned my actual values with the work that I'm doing. I feel so grateful to have had those friends and the space that money bought me to be able to do that. The world we live in right now is not what winning feels like, but it feels like the only thing I could do now.

[B]

Yeah, I mean, that makes sense. I'm going through this identity crisis, change. Also, the world is doing what the world around us is doing. And it's like, hard to separate out, like, how much of what I'm feeling now is because it's actually really bad right now. Like, there's a lot of problems that feel scary and threatening and I need to do something about them. And I can't just sit here. There's some guilt there, too. Of the. Well, I've got the means and the resources where I could buy citizenship in New Zealand and go there. That's the thing rich people do. I don't plan to do that, but there's a bit of guilt of I feel like I even have to do more because this isn't a direct threat to me. I owe it to everyone else to stick up a little bit more for them.

[A]

Thank you both so much for doing this.

[B]

I trust in your listeners. I hope they're not too mean to me in the comments, but I trust them. I really enjoyed this. I wouldn't mind hearing more about Serge and the stuff you're working on too.

[C]

Absolutely.

[A]

Thank you to Sam for being our guest today. And thank you to David Steeley for being our proxy. Okay, I have an important disclosure to make, so I started working on the story in 2024. As you can see, we work on cases for a long time. And three months into the story, Sam told me that he'd heard one of my fundraising pitches on the and that he wanted to support proxy. He offered to donate 25k. I knew I was already making the story, but I really didn't know what to do with this offer. On the one hand, it's weird to take money from someone you are making a story about because they can influence things editorially. They can make you omit unsavory details. There's a number of ways it can go bad. On the other hand, there are other listeners who've appeared on the show who donate every month. And at that point and still today, the show is still not making enough money to support itself. And 25k, that would be enough to keep us going for like three months. And Sam was clear he didn't want anything in return. He just wanted to support Proxy. So I decided to do it and just be upfront with you. For those following along, Sam is the anonymous donor from last fall's membership campaign, the person who offered to give proxy 25k if we reached 1000 paid members. If you would also like to support Proxy, just go to proxyhq.org paid members get ad free listening bonus episodes and live Proxy hangs again. That's ProxyHQ.org that'll take you to our Patreon and a salute to everyone who's already signed up. You are helping keep this strange show alive. Proxy will be back on Tuesday, June 30th with our final episode of the season. Sad. We will be taking a summer break to work on cases for the fall. Follow the show so you don't miss the next case. And if you want liner notes to the episode including a link to the document that helps you figure out what class you actually are. Subscribe to File under Feelings, our free Proxy newsletter. You can also get [e-mail] this episode was edited by Tim Howard, mixed by Kyle Pulley and produced and scored by me. Music in this episode by Tim Howard and our theme music is by Brickmaster Cylinder. Proxy is a proud member of Radiotopia from prx, a network of independent creator owned listener supported podcasts. Audrey Martovic is our executive director and Yuri Lozordo is the director of operations. Discover audio with vision at Radiotopia fm. And remember, if you have a niche emotional conundrum you would like investigated by Proxy. Get in touch atproxy the podmail.com we're taking cases. Okay, thanks for being here guys. Later. Would you be willing to sing us anything? What was your like beat in the opera world?

[C]

Yeah, so I was on my way to being like a helden tenor. So kind of like Wagnerian. There's a lot of, lot of sound, a lot of like dark German sound. Oh, what do we sing? We'll. We'll sing. Radiotopia

[A]

from prison x.