How the 3 P.M. Rule Forever Changed my Leadership

Every weekday at 3 p.m., I'm sitting in the carpool line at my son Seth's elementary school in Port Washington, New York. No exceptions. No "just this once for the investor call." No "I'll send the nanny because the deal is closing." Three p.m., every day, I'm in the line."

I've co-founded seven companies. I sold Likeable Media to 10Pearls in 2021 for an eight-figure sum. I sold Apprentice in December 2025. I'm running Remembering Live and Kerpen Ventures right now. I have written before that work-life balance is a lie for founders, and that the loneliness of being a founder is one of the most underdiscussed problems in business. The 3 p.m. rule is the single biggest reason I've avoided both issues.

Seth is in fifth grade — his last year of elementary school. Once he hits middle school, the bus comes and he doesn't need a pickup. The clock on the carpool line is running out. So, I’m protecting it like it is the only thing on my calendar that matters, because in a way, it is. Here's what the rule has done for me as a CEO.

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