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Marketplace All-in-One

Sam doesn't know how to be rich, from “Proxy with Yowei Shaw”

Marketplace All-in-One

Marketplace

News, Business

4.51.4K Ratings

🗓️ 2 July 2026

⏱️ 60 minutes

🧾️ Download transcript

Summary

This week, we’re sharing an episode of “Proxy,” a podcast about the emotional questions that make people feel alone — and the conversation that unfolds when you find someone who gets it.


Sam is a progressive person who suddenly has more money than friends and family — and he doesn’t know how to feel about it. He wants to be generous. He wants to be responsible. He wants to stop feeling guilty and secretive and afraid. But the more he thinks about what money can do, the less clear it becomes what having “enough” is supposed to mean.


In this episode, host Yowei Shaw connects Sam with David Steely, a man who has spent years wrestling with the same questions — and has given away most of his money.



We’ll be back with a new episode of “This Is Uncomfortable” next week! If you want to answer our “Uncomfortable Questions” see more info here.


Follow us on Instagram and Tiktok!


Support This Is Uncomfortable with your donation today: https://bit.ly/mkp_tiu_pod



Transcript

Click on a timestamp to play from that location

0:00.0

Hey everyone, it's Rima. So this week we're sharing an episode from another show we think you'll like.

0:06.8

It's called Proxy, hosted by Yo-Wei Shah, who you might know from NPR's Invisibilia.

0:12.1

Proxy is built around a simple idea. No one is ever completely alone with their problem,

0:17.3

because somewhere out there, there's someone who gets it. In each episode, Yo-Wei takes a very

0:21.9

specific emotional conundrum, the kind of problem that can make you feel isolated, ashamed, or

0:26.4

confused, and she finds someone who's lived through something close enough to talk it through.

0:31.6

In the episode you're about to hear, is very much in that this is uncomfortable universe. It's

0:35.6

about Sam, a progressive person who suddenly has more money than his friends and family,

0:40.1

and he has a lot of feelings about it.

0:42.1

Sam wants to be generous.

0:43.5

He wants to be responsible.

0:45.0

He wants to stop feeling guilty and secretive and afraid.

0:48.1

But the more you think about what money can do, the less clear becomes about what having

0:52.4

enough is supposed to mean.

0:55.5

Just a heads up, this episode includes some swearing.

0:58.2

Okay, I hope you all enjoy it, and I'll catch you all next week with a new episode of

1:01.7

This Is Uncomfortable.

1:03.0

Here's Proxy with Yo-A Shaw.

1:06.9

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

1:17.0

Correct.

1:18.5

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

1:27.4

I think that's part of it. Yeah. Yeah. something to the effect of like shut the fuck up?

...

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