Startup Dad

Jonathan Stull, President and COO of Handshake and father of four, juggles scaling an AI-focused company with school drop-offs, Little League, and family adventures. He talks about building a village of support, staying mentally present amid startup demands, parenting principles like agency and resilience, and how fatherhood sharpened his leadership.

Ashish Kundra, founder and CEO of Conceptual and dad of a four-year-old, talks parenting, building companies, and life design. He explains how being married to a pediatrician shapes everyday choices. He shares why he started a company with a young child, why small falls build resilience, how he avoids over-parenting to preserve agency, and why he journals to track happiness.

Robert Whitney, Co-founder and CTO of Hapiko (creator of Stickerbox) and dad to a young son, talks about how parenthood reshaped his priorities and product work. He explains why most AI for kids is failing, how Stickerbox started from a rainy-day play moment, and why safety, simplicity, and play-first design matter for children's tech.

Caleb Avery, founder and CEO of Tilled who started his first company at 19 and raises three kids, shares candid stories about building a startup while parenting. He talks trade-offs of time and energy, paternity leave regrets and course corrections, why bedtime became a non-negotiable, the struggle of making parent friends, coaching T‑ball, screen time rules, and choosing boundaries over balance.

Sam Yagan, founder of OKCupid, former Match Group CEO, investor, and dad of three. He talks about raising kind, grounded kids amid wealth and ambition. He covers family systems like weekly meetings and annual reviews. He explains introducing philanthropy early, managing startup-era trade-offs, and shaping a home that draws kids and friends together.

A new dad shares why he and his partner quit stable jobs right after parental leave and how that leap reshaped their priorities. They discuss letting go of old identities, fighting perfection pressure, and practical household systems that reduce friction. They also talk about using AI for monthly milestone alerts, email threads for big family decisions, and intentionally letting kids face small struggles to build resilience.

Jesse Randall, founder and CEO of Sweater and father of five, shares candid takes on balancing ambition, marriage, and parenthood. He recounts moving his family to Puerto Rico, why prioritizing career can cost joy, and how fathers should lead with care. He explains a no-hint-dropping rule for better marriage communication and how he uses AI to reinvent his kids’ education and teach critical thinking.

Mike Rome, founder of moonwater and father of three, blends startup grit with parenting reality. He talks about launching a company later in life, designing real schedule flexibility, and building through his son’s heart crisis. He shares using startup frameworks for parenting, choosing presence over proximity, and the chaotic comedy of parenting moments like a projectile-vomit dinner.

Chris Winther, a former financial planner who became the primary caregiver for their three kids, and Amy Winther, Head of Product Design at Square and author of Motherboard. They recount a one-hour childcare pivot that flipped roles. They discuss shared finances and power, navigating being the lone dad in parent spaces, school and doctor defaults, and their yearly family planning system.

Jacob Bank, founder and CEO of Relay.app and former Google product leader, is a dad of three who built his company around flexibility and trust. He explains why small, async teams can be better for parents. He shares his three-part decision framework for leaving big tech, how he turns chores into bonding time, and a parenting trick called "Imagine if I Did That."