Choosing a Second Child

Lee explains why he and his wife decided on a second daughter, balancing fleeting moments and sibling benefits.

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Lee Robinson is the VP of Developer Education at Cursor, one of the fastest-growing AI developer tools in the world. Before Cursor, he spent five years at Vercel helping define how modern developers learn and build on the web.

He’s also a husband and a dad to a young daughter, with a second daughter on the way. When I first invited Lee on the show, he had a five-month-old baby and felt like he was deep in the trenches of new parenthood. Nearly a year later, we finally sat down to talk about what that first year of fatherhood was really like.

In this episode, Lee shares how becoming a dad changed his perspective on work, ambition, empathy, and priorities. He talks about parenting while working inside hypergrowth startups, navigating family planning with an intense career, setting boundaries, sharing the load at home, and how Lee thinks about AI, education, and raising kids in a rapidly changing world. We discussed:

Becoming a dad inside hypergrowth startups: What it was like navigating new parenthood while working at two of the fastest-growing companies in tech.
Questioning readiness for fatherhood: How uncertainty, self-doubt, and honest conversations with his wife shaped the decision to start a family.
Miscarriage and pregnancy anxiety: The emotional challenges that came before their first daughter and how it changed Lee’s perspective on control and fear.
Setting boundaries without losing ambition: Why prioritizing health and family actually made Lee better at his job, not worse.
Sharing the load at home: How Lee and his wife divide responsibilities, protect evening routines, and make remote work actually work for their family.
Raising kids in an AI-powered world: Lee’s thoughts on education, curiosity, and why he wants his daughters to believe they can build and shape the future.

Where to find Lee Robinson