Raising a Kid in New York City

Robert shares challenges and cultural richness of city parenting, from subway obsession to diverse experiences.

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Robert Whitney is the Co-Founder and CTO of Hapiko, the company that invented Stickerbox, an AI powered product helping kids create and play in more imaginative ways. Before starting Stickerbox, he helped scale New York Times Games, Grailed and spent time at Anthropic thinking deeply about the future of AI and how it will shape the next generation.

He’s also a co-parent to a four-and-a-half-year-old son in New York City. In this conversation, Robert shares how fatherhood changed the way he approaches work, decision-making, discipline, and presence. We also talk about co-parenting as a founder, his shift away from a hard-partying New York lifestyle, the parenting principles he’s developed, and why he believes most AI products are failing kids. We discussed:

Why parenting is the ultimate life experience: How becoming a dad made Robert more grounded and less reactive.
Co-parenting while building a startup: What it looks like to split time as a founder and a parent, and how Robert thinks about being fully present in each mode.
Leaving behind a hard-partying New York lifestyle: Why Robert made a major life change years before becoming a dad, and how sobriety reshaped his priorities, energy, and sense of self.
How loss changed his perspective on fatherhood: What losing his mom shortly after becoming a parent taught him about time and presence.
What most AI products get wrong for kids: Why Robert believes kids need safer, simpler, more thoughtful tools.
How Stickerbox started with his son: The rainy-day moment that turned into a company built around play and creativity.

Where to find Robert Whitney