Why I’m leaving my job at Substack

I helped build our Partnerships team, and now I’m going independent

I started my job at Substack in 2020, during the first summer of the pandemic. There were about a dozen of us then and no Partnerships team yet, though Hamish McKenzie and Fiona Monga had been recruiting writers for some time and helping them establish their newfound autonomy. As I joined them, we really just made it up as we went, learning each day, along with our writers, what worked and what didn’t.

It was a charming, almost quaint time in the history of the company. We were a dozen employees strong, the underdogs of the industry. Almost no one had heard of Substack back then, outside of a smattering of media-world obsessives. On each writer call, I would begin by describing the concept in as simple terms as possible: a platform where you could publish whatever you wish, own your work, have a direct line to your audience, be your own boss, and earn revenue through subscriptions.

I rang up friends and former collaborators to pitch them the idea. Patti Smith wondered if she could serialize a memoir. George Saunders thought he might form a community of people who wanted to nerd out on the craft of short fiction. Ted Gioia was sitting on more than a hundred essays, completed or in draft, the ingredients for what would become The Honest Broker. Jeff Tweedy decided to launch his Substack on the first day of a Wilco tour, creating a place where he could share songs, audio memos, and stories. Kareem Abdul-Jabbar had a piece about the 20th anniversary of 9/11 and wanted to publish it independently, rather than hand it over to a media outlet.

Along with those era-defining artists and writers, a crop of homegrown stars began to emerge, such as Caroline Chambers, who arrived with an excess of talent and vision, soon rising from relative obscurity into the biggest food writer on the platform and a legitimate presence in the broader culinary world. Every sort of writer, artist, musician, and creator could soon be found on Substack, doing their thing, from hobbyists to journalists, illustrators to politicians, fashionistas to market analysts, novelists to scientists. The platform evolved to include audio, video, podcasts, community tools, and livestreaming, but everything remained anchored to that same foundational ethos.

As time passed, we hired more people for Partnerships, forming the core of a team that included some of the most gifted and passionate people I’d encountered, colleagues who came from creative backgrounds themselves and truly cared about what we were trying to build. Any one of them could have been successful as a writer or creator on the platform, but instead we banded together to pour our energy and love into serving other writers and artists, helping to forge a new path for independent culture. It was the greatest pleasure to see the model take hold and flourish, to celebrate alongside a creator as they grew their audience and revenue from zero to a hundred thousand to a million and beyond.

That feeling hasn’t gone away for me. The Kool-Aid still courses through my veins. I fully believe in Substack and other platforms that are at the center of this revolution in media, this shift towards ownership and autonomy.

But despite the conviction of my belief, and despite my affection for so many coworkers and for the writers and artists I’ve gotten to work with over five and a half years, I’ve decided to leave the company. Today is my last day.

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A friend of mine recently watched Jerry Maguire on a flight. Over coffee, he reminded me of the basic story. Jerry, a successful sports agent at a large firm, finds himself facing down an identity crisis. In the middle of the night, he dashes off a manifesto, a mission statement. Before he thinks better of it, he drops a copy in the mailbox of each of his colleagues, making a case for fewer clients, less money, more attention. He nervously walks into the office the next morning, and his coworkers stand to applaud his virtue but snicker behind his back. He soon finds himself ousted from the agency.

This is not exactly my Jerry Maguire moment, but I sat down to rewatch the film, and so much in there resonated with me.

One symptom of success, of multiplying in size the way that Substack has, is that some level of intimacy and depth is often sacrificed, by necessity. There was a time in which I would take every call that came my way and would spend long hours dreaming with a writer or artist about what they could build, and then I’d help them do it. But eventually that became impossible. I found myself sprinting from one Zoom to the next, often losing the ability to spend adequate time with each writer or artist. I felt less like a creative partner and more like a sunbaked shepherd overseeing a vast flock.

I guess I’ve reached an age in which I’m susceptible to nostalgia. But I’m also a realist. I understand that success means scaling and that scaling requires a shift of approach. My job had to develop in the way that it did. It’s just no longer the right approach for me. So I’m starting over, dashing off a mission statement and dropping it in all your inboxes. My decision to go independent is less about show me the money and more about help me help you. And hopefully a bit of you had me at hello.

Tomorrow I’m launching a new company, Amplifier, that’ll allow me to dig in with only a handful of clients, to get back to collaborating on making things of value and consequence and putting them out into the world. A lot of that work will happen here on Substack but also across a constellation of other platforms. I’ll partner with media companies, agencies, and brands that are trying to navigate the evolving media world, to find their place and expand their reach. And I’ll work with individual culture stars, to help them figure out how to succeed in this new landscape, how to create something that will resonate and endure.

Fewer clients, more attention. I’m trading scale for depth.

Over the past years, I’ve had relationships and conversations with thousands of you across the platform—writers, artists, thinkers, musicians, podcasters, filmmakers, and of course my wonderful colleagues at Substack. It’s been one of the most fulfilling and rewarding jobs of my life, to build this alongside all of you. Thanks for working with me and helping to make Substack the kindest, smartest, most creative corner of the internet.

This platform is still relatively small, but somehow it has become the red-hot center of cultural energy in our modern world, punching way above its weight. I know there’s much more brilliance to come. I’m so excited to see what you all make next, and I’m thrilled to hop over to the other side to join you.

If you have an idea for how we might work together to make something great, I’d love to hear from you.