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 to have. 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, who also came into a lot of money and had to figure out how to live with it. Together, they talk about secrecy, guilt, redistribution, enoughness, and the lonely, morally complicated question: what are you supposed to do when you have more than you need? **From the episode:** — David Steely — Sam’s proxy, who also came into significant wealth and had to figure out what to do with it — 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. Proxy is an independent show, supported mostly by listeners. Paid members get 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**](mailto:proxythepod@gmail.com)