Bright Lights

(Or, Zen and The Art of the Exit After Five Years at Amazon)

I’m a sucker for story structure — my therapist might say I need it. Like a subconscious survival instinct. A warm security blanket. Some people find comfort in a well-executed rom-com; in the same primal way, I find it in making sense of things.

So, it’s no shock to me that my five years at Amazon have wrapped up with a tidy little bookend — my own story demanding structure as much as everything else in my life. And that bookend? The easiest, most obvious plot twist: chasing the bright lights of a new opportunity, and a bet.

A Note of Thanks

In February 2020, I got a text from my former colleague Morgan Jones. Audible had just shuttered its San Francisco offices, and while they offered roles in Newark (HQ life, baby), most of the team was looking for an exit. I was already ahead of them on that front — working at a scrappy little Silicon Valley startup called OZY Media. If you’ve read anything about OZY in the past three years, you know how that went.

Morgan and I spent the next few weeks circling the same meetings, the same interviews. Then, he landed. A new team. A top-secret division at Amazon Music. (Side note: while Audible and Amazon Music are technically under the same roof, at the time they might as well have been distant cousins who never spoke.) Morgan, an absolute machine at Audible, had leveraged his status into something big. By April, he was pulling me in, too. By July, I was in the building.

People asked what excited me about Amazon (once the NDA came off), and I always pictured it like this: PODCASTS in big, bright Broadway lights. What I was doing at OZY felt doomed, but beyond that, the whole industry felt small. We were hovering around $500 million — a rounding error in the grand scheme of things. But with Amazon’s resources?

Five Years, What a Surprise

The other thing I told myself back then, besides betting on those big, bright lights, was that I needed some fucking stability. After two years of missing my wife and kids' lives — and probably shaving a few years off my own in the process — I needed to steady the ship. I used to joke, “I think I’m the only person in San Francisco looking for comfortable middle management.” I’d follow that up with: “Maybe in five years, I’ll be ready for a startup again. Maybe even my own thing.”

Turns out, I was right.

I always assumed leaving Amazon would feel bigger — like some seismic shift. But honestly? It doesn’t. I learned a ton. About my work, about people, about myself. And despite what people say about Amazon in the headlines, there are some brilliant, funny, deeply thoughtful folks inside that machine.

And credit where it’s due: Amazon’s internal processes and its writing culture are so damn original, people way smarter than me have written books about it. The way Ford revolutionized the assembly line, Amazon did the same for how ideas are built and pitched. Case in point: I, no joke, once wrote an OP2 about my life.

That said, I’m not losing sleep over no longer relying on this particular corporate giant to put food on my table. And here we are. Five years later. The industry closing in on $2 billion. The bright lights and big cities did in fact show up for our little cottage industry. I made a bet, and I was right.

The Messy Middle

So, what now?

In case you missed it, for the first time in a while, I’m a free agent, and I’m leaving Amazon with some solid projects to keep me moving in the near term. Beyond that, I’m doing two things.

One, I’m leaning into what my therapist calls The Messy Middle — letting go of structure, of certainty, of the need to shape the story before it’s ready to be told. And two, I’m betting again, this time on something else.

And funny enough? That same feeling is creeping in again. The one where I see something in big, bright lights.