She Retired at 32. Then Came Guilt—and a Moral Crossroads.

The Money with Katie Show

Money with Katie

Investing, How To, Self-improvement, Business, Education

4.8 • 1.3K Ratings

🗓️ 10 December 2025

⏱️ 71 minutes

🔗️ Recording | iTunes | RSS

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Summary

Rebecca Herbst reached financial independence at age 32 during the tenuous early days of the pandemic, and volunteered shortly thereafter to be furloughed from her job in commercial real estate—and so began her (extremely) early retirement. But spending her days exactly as she wanted featured an unexpected side effect: guilt. What do you owe to others when you’ve gotten everything you wanted? Rebecca alchemized her sense of duty and founded Yield & Spread. In detail, we cover: What the “FI-lanthropy” pledge entails How she squares the desire to retire early with the idea of “hoarding money” Where Rebecca gives for the highest impact Who donor-advised funds might make sense for, and how they work How to donate appreciated stock, and why it might be preferable to giving cash Subscribe to my weekly newsletter: ⁠⁠⁠⁠⁠⁠https://moneywithkatie.com/newsletter⁠⁠⁠⁠⁠⁠ Get your copy of Rich Girl Nation, one of Barnes & Noble's Best Business Books of 2025:⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.moneywithkatie.com/rich-girl-nation⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Transcripts, show notes, resources, and credits at: https://moneywithkatie.com/the_mwk_show/the-filanthropy-pledge/ — Money with Katie’s mission is to be the intersection where the economic, cultural, and political meet the tactical, practical, personal finance education everyone needs. Learn more about your ad choices. Visit megaphone.fm/adchoices

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0:23.3	like you sign up for your one dollar a month trial at shopify dot com slash setup
0:32.6	the financial independence community and just like the personal finance world in general is just growing big time.
0:39.5	Like 10 years ago, if I told someone that I was into financial independence, they'd be like, what are you talking about?
0:44.8	And now it's super mainstream.
0:46.6	There's freaks like us everywhere.
0:48.6	And they know what financial independence is, at least in abstract.
0:52.6	So I think the real question is, like, what are we going to do as a community with all this wealth once we built it?
0:58.5	My guest today is Rebecca Herbst, the founder of Yield and Spread, which might sound
1:09.3	familiar to you if you heard it discussed on a recent episode.
1:13.1	Rebecca reached Financial Independence by age 32 after a career in commercial real estate,
1:18.6	and I'm excited to talk to her about the excitement, the freedom, the guilt, and the questions
1:25.7	of purpose that come up in the pursuit of financial freedom
1:29.1	in a very unfair world, and ultimately, where those questions led her.
1:35.5	Rebecca exists at the nexus of two communities of optimizers, the financial independence
1:41.1	community and the effective giving community. So both groups whose
1:45.6	mantras I would consider could be summed up as work smarter, not harder. Welcome back to The
1:52.3	Money with Katie Show. I'm Katie Yaddy Tossin. This felt like, I don't know, just the most
1:57.8	appropriate conversation that we could be having right now midway through the holiday season.
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