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Three years of building community at Substack

Bailey says farewell

Eight years ago,

, and I started a business called People & Company. Our goal was to create a methodology for building a community—a process that could be repeated by community builders around the world, no matter if they’re starting a run club or forging a new online network. 

Three years ago, we sold People & Company to Substack. Kev,

and I went in-house to help the fast-growing start-up and the community of writers rallying around it. (Kai became an advisor to the company.)

And two weeks ago, I decided to take a new opportunity, bringing my chapter at Substack to a close. 

Over the three years I spent at Substack, I got to focus my time on being of service to those writers, big and small, working closely with Katie and the fantastic team at HQ. 

You might know some of the celebrated writers and creators who have joined Substack over the years–

, , , , , and . But there are also beloved homegrown stars. There’s , who has been cooking through 1970s cookbooks from her 1970s kitchen in Chicago. is making new music from the Pacific Northwest in a new key every month. has been eating through every country’s cuisine A-Z in NYC, and chronicling her findings. While , I believe, is writing as beautifully as a human being can about the moon each month. And there are so many more. 

We got to help thousands and thousands of these writers navigate this new platform and its subscription business model—learning about best practices from our team and data, yes, but also learning directly from each other. 

Doing this work was an absolute privilege. Together, we previewed big new products like the Substack app and Notes to writers, and adjusted with their feedback. We gathered for huge courses, weekly office hours, meetups, and small fellowships to advance our collective understanding of how to succeed on Substack. We queried the data, interviewed successful writers for insights, and created new guidance and resources. And then we took every support article and resource we’ve ever created and fed it into an AI brain so any writer in any language could access the very best help whenever they needed it. 

By regularly sharing learnings with a community of writers as partners, and evolving the software to fit their needs, I believe Substack has made it more possible to be an independent creative person today. People advancing big ideas and culture can use Substack to do so with a stable income funded by the people who love and appreciate their work most. This is a radical feat and a shift I didn’t believe I would see in my lifetime. It means that writing online is no longer on the decline—quite the contrary. There are more than 35 million active subscriptions on Substack, including more than 3 million paid subscriptions. Those subscriptions did not exist before Substack and the writer community willed them into reality. And I believe the magic over there is just getting started. 

Katie, Kevin, and the Substack team will continue to advance this mission while I cast off for my next adventure. 

But in today’s special episode of the podcast, we took some time together to reflect on the journey so far and share learnings from the last three years of building community at Substack. 

I hope you enjoy the show. 

Listen wherever you get your podcasts.


Some favorite shots with writers and the team over the years