From Napping Startup to Newsletter Empire

The Story

Raised in Philadelphia and a product of Catholic schools, Packy McCormick graduated from Duke University in 2009 into a job in finance at Merrill Lynch (Source 1).

When he grew bored with the lack of autonomy, he turned to AngelList and went all-in on interviewing with Breather, a startup that gave people in Manhattan spaces to nap. “When I was working in finance, I always knew I wanted to nap, but there was nowhere to sleep,” he said. He wrote his own job description and interviewed nowhere else. “I was like, oh wow, you could just take a network of spaces all over the city where you might go take a nap in, kind of like you had in school. This is great” (Source 1).

Breather had a hard time taking off. It later pivoted into co-working spaces, putting it up against the likes of WeWork. Plus, the big buildings around Manhattan “weren’t just willing to give up their space to some company that would bring in a revolving door of strangers” (Source 1).

Work became rote. McCormick started writing. He went to David Perell’s Write of Passage course. “I’d just be sitting in meetings, and — this isn’t an insult to anyone — would look around and feel like there was no way to remain intellectually curious while I was still there. I’d say, I don’t want to become like these people. I had to write to change that” (Source 1).

He spent six years at Breather before quitting.

Lesson for Creators

Packy’s path from Merrill Lynch to a napping startup to a newsletter empire looks chaotic in hindsight, but each step built something. Finance gave him the analytical framework. Breather gave him six years inside a startup, watching strategy, pivots, and fundraising up close. Writing started as self-preservation, a way to stay intellectually alive in a job that was dulling him. The “career detours” were actually research for the newsletter he didn’t know he’d write.