How to Raise a Jack Not a Jackass | Ep 15 - podcast episode cover

How to Raise a Jack Not a Jackass | Ep 15

Jun 19, 20251 hr 20 minEp. 15
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Episode description

Can you still have scrappy kids if you grow up with $? Former financier turned Substack writer David Roberts sits with Eva and Caroline to talk about the social faux paus no one wants to admit — like the awkward realities of generational wealth and getting into school through the back door. David hilariously discusses his trek moving from the UES to the wild West (side, not Wyoming!). How do you teach your kids to appreciate the grit of their Eastern Europe ancestors when they think a $50 sushi roll is normal? Can NYC kids grow up to be game changers or are we destined to raise Bonfire of the Vanities' masters of the universe who will feel broke making $5 million a year? We don’t have all the answers, but we promise a really fun and cheeky episode.

David's Substack is Sparks From Culture where he writes weekly essays focused on aspects of wealth and status. Beauty, Class, and Wealth was a recent essay.

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Surgeon General Warning Disclaimer: We are self-prescribed unexperts, so if you have any real questions or need real advice, please call your nearest doctor.

© 2025 Eva Heyman & Caroline Leventhal

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