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Artwork for Proxy with Yowei Shaw
Proxy with Yowei Shaw · June 16 · 57 min

Sam Doesn't Know How to Be Rich

The case of the progressive rich guy who doesn’t know what to do with his money. Sam grew up middle class, built a company, sold it, and suddenly found himself with more money than he ever expected. But instead of feeling free, Sam feels stuck. He doesn’t want to become the kind of rich person he used to judge. He doesn’t want money to change his relationships. He doesn’t want to hoard it. He doesn’t even want to talk about it. We find him a proxy who became a millionaire and then gave most of his money away. In this episode: wealth guilt, the awkwardness of talking about money, how getting rich changes your relationships, and the question of how much is enough. From the episode: — Resource Generation — an organization for young people with wealth and class privilege working toward wealth redistribution — Showing Up for Racial Justice (SURJ) — a group that organizes white people for racial and economic justice New to Proxy? Try Bisexual Wife Guy for a classic case, or Mic Chooses the Wrong Life, a story about regret, comparison, and the fantasy of the unlived life. For episode liner notes, show gossip, and dispatches from the emotions beat, get our free newsletter File Under Feelings at proxyhq.org — just click "Join for free." Proxy is an independent show, supported mostly by listeners. Become a paid member at proxyhq.org for bonus episodes, ad-free listening, live Proxy hangs, and the satisfaction of keeping emotional investigative journalism alive 🍏 Follow us on Instagram — @proxypodcast @yoweishaw Visit — proxypodcast.com Get in touch — proxythepod@gmail.com

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transcript

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show notes

The case of the progressive rich guy who doesn’t know what to do with his money.

Sam grew up middle class, built a company, sold it, and suddenly found himself with more money than he ever expected. But instead of feeling free, Sam feels stuck. He doesn’t want to become the kind of rich person he used to judge. He doesn’t want money to change his relationships. He doesn’t want to hoard it. He doesn’t even want to talk about it. 

We find him a proxy who became a millionaire and then gave most of his money away.

In this episode: wealth guilt, the awkwardness of talking about money, how getting rich changes your relationships, and the question of how much is enough.


From the episode:

— Resource Generation — an organization for young people with wealth and class privilege working toward wealth redistribution

— Showing Up for Racial Justice (SURJ) — a group that organizes white people for racial and economic justice


New to Proxy? Try Bisexual Wife Guy for a classic case, or Mic Chooses the Wrong Life, a story about regret, comparison, and the fantasy of the unlived life.


For episode liner notes, show gossip, and dispatches from the emotions beat, get our free newsletter File Under Feelings at proxyhq.org — just click "Join for free." 

Proxy is an independent show, supported mostly by listeners. Become a paid member at proxyhq.org for bonus episodes, ad-free listening, live Proxy hangs, and the satisfaction of keeping emotional investigative journalism alive 🍏


Follow us on Instagram — @proxypodcast @yoweishaw

Visit — proxypodcast.com

Get in touch — proxythepod@gmail.com

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