Rebecca Matchett — A Day In Her Life

Rebecca Matchett co-founded Alice and Olivia at 23 with zero fashion experience, now she's building Synchrony, a social platform for neurodivergent adults, and navigating life as a mom of three in downtown Manhattan — including sending her oldest to college in California this fall.

In this honest conversation, Rebecca opens up about the pattern that's defined her career: jumping into industries she knows little about and figuring it out as she goes. She talks about what it's really like to run a startup while managing three kids' travel hockey schedules (they're apart most weekends), why she sets five alarms every morning just to remember to check her calendar, and the bittersweet reality of watching her firstborn choose a school 3,000 miles away.

What We Cover:

How a dinner with a fellow mom turned into a tech startup addressing the gap in social services for neurodivergent adults
The Alice and Olivia origin story — and what happens when you make pants out of upholstery fabric (spoiler: they chafe)
Why Rebecca deliberately chose sports-heavy childhoods to push back against the "Manhattan private school kid" stereotype
Running a three-founder startup where communication happens across text, Slack, and email at all hours (there is no end time)
The college application process with a Division I-level hockey player — and why visiting schools changed everything
Her 13-year nanny who's transitioned from childcare to home management (and why they'll never let her go)
Using AI to plan a last-minute Portugal trip, review legal documents, and pressure-test business partnerships
The joy of watching three kids speak fluent Chinese to each other — while their parents have zero idea what they're saying

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