The Second Brain of a CEO Whisperer

I'm fascinated with how the smartest people in the world get their work done. That's what Superorganizers is about: seeing all of the little habits that make up a great work day and a great life. Artificial intelligence has changed what it means to be productive and efficient at work, so we decided to revisit some of our favorite interview subjects to understand how their routines have changed in the era of AI models. Last week, we spoke to designer Marie Poulin and newsletter writer Polina Pompliano. Today, we’re back with former Holloway CEO Andy Sparks, now using his experience to coach other CEOs—Dan Shipper

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Andy Sparks used to use an “operating system for work.” When the then-CEO of the publishing startup Holloway first spoke with Every in 2019, he had created an intricate and novel organizational system using Notion, inspired by fellow Superorganizers interview subject Marie Poulin. Back then, Sparks used the tool to keep track of weekly agendas, a to-do-list, and even the company's values.

A lot has changed since then. Sparks left Holloway and has spent the past four years as an executive coach. His relationship with Notion has evolved too. While he no longer needs Notion for team collaboration, it's become an even more crucial tool for maintaining what he calls his “second brain.”

We caught up with Andy to explore how his systems have evolved, what he thinks about AI's impact on personal organization, and why he's betting on tools like Perplexity to transform how we learn and retain knowledge.

Sponsored by: Every

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