Mic'd and Medicated: Unfiltered, Unafraid, and UnExpert

How to Raise a Jack Not a Jackass with David Roberts | Ep 15

• Eva Heyman & Caroline Leventhal • Episode 15

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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.

We’re two New York City women talking candidly about the chaos of modern life, from relationships, parenting, working in and out of the home, to what it takes to stay semi-sane in a world that expects you to hold it all together and be #blessed.

We couldn’t find an honest and vulnerable conversation — so we started one! If you need a laugh, a cry, or just want to hear someone else admit their flaws and validate your crazy, you’re in the right place. Be ready to be… Unfiltered, Unafraid, and UnExpert.

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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