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.

Has life and work changed since we last talked?

Definitely! You all published the first piece in August of 2019. I was CEO of a startup then. I’m now an executive coach to about 15 CEOs. I don’t need Notion as much as a collaborative tool, but more one to make sure any information I need is easily at my fingertips.

Why did you initially start using Notion as an "operating system"?

I started using Notion as a knowledge management platform for my startup, Holloway, back in 2017. I like tinkering with new products, and the more I started using Notion the more I liked it. 

The main feature that grabbed me was how Notion displayed documents in a database view and allowed you to add and edit properties. Before Notion, your documents were stuck in a user interface like Apple Finder or Google Drive, where you have a filename with a bunch of properties in a view that hadn’t meaningfully changed in functionality since I first began using computers in the 1990s.

Are you still keeping up your commitment to using Notion? What's stayed the same? What's changed?

I’ve since left my startup, Holloway, but have expanded my use of Notion personally and for my coaching business in a huge way. Notion is easily the tool I use the most. 

In 2020, I began watching Marie Poulin videos on YouTube—she has an absolutely insane Notion setup. I copied a lot of what she does: databases for meetings, people, a library (any books, notes on books, clipped articles, etc.), quotes, and tags, all with relations between them.