Sam Doesn't Know How to Be Rich episode artwork

EPISODE · Jun 16, 2026 · 58 MIN

Sam Doesn't Know How to Be Rich

from Proxy with Yowei Shaw · host Yowei Shaw

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 justiceNew 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 @yoweishawVisit — proxypodcast.comGet in touch — [email protected]

Episode metadata supplied by the publisher feed · Published Jun 16, 2026

Embed this episode

NOW PLAYING

Sam Doesn't Know How to Be Rich

0:00 58:25

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of Proxy with Yowei Shaw?

This episode is 58 minutes long.

When was this Proxy with Yowei Shaw episode published?

This episode was published on June 16, 2026.

Can I download this Proxy with Yowei Shaw episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!