Sam Doesn’t Know How to Be Rich

2026-06-16

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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.In this episode, we find Sam a proxy: David Steely, a former millionaire who has since given most of his money away. Together, they talk about sec...

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.

In this episode, we find Sam a proxy: David Steely, a former millionaire who has since given most of his money away. Together, they talk about secrecy, guilt, redistribution, enoughness, and the morally complicated question: what are you supposed to do when you have more than you need?

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.

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