In a culture wired to reward straight A’s and perfectly packed résumés, it’s easy to forget: real success often starts with a messy bedroom, half-finished projects, and a kid who’s more interested in making music than memorizing math facts.

On this episode of Great Mondays Radio, host Josh Levine talks with Margot Machol Bisnow, author of Raising an Entrepreneur, about what it really takes to help kids grow into curious, gritty, and resilient humans. Drawing from interviews with 70+ entrepreneurs and their parents—including her own experience raising two entrepreneurial sons—Margot shares what most report cards miss: the drive to pursue passion, fail forward, and keep going.

This conversation explores why traditional metrics like test scores don’t predict entrepreneurial success, how parents can foster a growth mindset without micromanaging, and what it means to parent more like a founder—spotting sparks and stepping back so kids can find their own way.

Whether you’re raising kids, mentoring young talent, or simply trying to lead with more intention, this episode is a powerful reminder: success isn’t about molding—it’s about listening, trusting, and letting curiosity lead.

About Our Guest:

Margot Machol Bisnow is the author of Raising an Entrepreneur: How to Help Your Children Achieve Their Dreams – 99 Stories from Families Who Did, and a former White House official. She’s a mom, a storyteller, and a passionate believer that success starts not in the classroom, but in the living room. Learn more at raisinganentrepreneur.com/.

About Great Mondays:

→ Think you'd be a great guest on the show? Apply here.

→ Running our show takes a lot of coffee. Support us for just $3/month.

→ Watch Great Mondays Radio episodes on YouTube.

→ Want to learn more about Josh's work at Great Mondays? Visit greatmondays.com.