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Either the Kids Suck or the Parents Suck | Caleb Avery (Dad of 3, Founder of Tilled)

Caleb Avery is the Founder and CEO of Tilled . He started his first company at 19 and has spent the last seven years building Tilled while raising three kids with his wife, Kelsey. In this episode, Caleb shares what it really...

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Either the Kids Suck or the Parents Suck | Caleb Avery (Dad of 3, Founder of Tilled)
April 16, 2026

Either the Kids Suck or the Parents Suck | Caleb Avery (Dad of 3, Fou…

Caleb Avery is the Founder and CEO of Tilled . He started his first company at 19 and has spent the last seven years building Tilled while raising three kids with his wife, Kelsey. In this episode, Caleb shares what it really...

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How to Not Raise Entitled Kids | Sam Yagan (Dad of 3, OkCupid & Match Group)
April 9, 2026

How to Not Raise Entitled Kids | Sam Yagan (Dad of 3, OkCupid & Match…

Sam Yagan is the founder of OKCupid and former CEO of Match Group . He’s also an investor, board member, married to a CEO, and a dad of three kids ages 12 to 18. In this episode, Sam shares how he and his wife think about rai...

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New Dads: Stop Fighting The Change | Rex Gelb (Dad of 1, Summit Chase)
April 2, 2026

New Dads: Stop Fighting The Change | Rex Gelb (Dad of 1, Summit Chase)

Rex Gelb is the Founder/CEO of Summit Chase , a paid media agency serving B2B, SaaS, and professional services companies. Before starting Summit Chase, Rex spent more than 11 years at HubSpot, where he became the company’s He...

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Family First Is Harder Than It Sounds | Jesse Rendall (Dad of 5, Sweater Ventures)
March 26, 2026

Family First Is Harder Than It Sounds | Jesse Rendall (Dad of 5, Swea…

Jesse Randall is the founder and CEO of Sweater , a company making venture investing accessible to anyone with a smartphone. He is also a husband and father of five kids, ranging from 7 to 17 years old. In this conversation, ...

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Parenting Through Projectile Vomit | Mike Rome (Dad of 3, moonwater)
March 19, 2026

Parenting Through Projectile Vomit | Mike Rome (Dad of 3, moonwater)

Mike Rome is the founder of moonwater , a performance marketing studio that helps startups grow, and a longtime operator in growth stage tech where he previously served as a CMO and growth leader. Before starting his own firm...

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This Working Mom and Stay-At-Home Dad Flipped The Script on Parenting | Amy and Chris Winther (Parents of 3, Square, Stay-at-home Dad)
March 12, 2026

This Working Mom and Stay-At-Home Dad Flipped The Script on Parenting…

Amy Winther is the Head of Product Design for Core Products at Square and the writer behind Motherboard, a Substack sharing honest stories about senior women in big tech. Chris Winther is a former financial planner turned sta...

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