Big things start small: How Substack sparked its early community of writers

From a laser-sharp focus on the first writers to scaling through building with writers, not for them.

Downloading what we learned from an extraordinary community.

Issue #3

Substack 📧

Today, we’re bringing you the story behind Substack, a community-driven platform that should sound familiar. Our email made its way to your inbox because of Substack’s remarkable product. 😜

Substack is just three years old and growing quickly. About a week ago, they reported that over 250,000 readers were paying for at least one Substack newsletter.

But that’s not why we’re sharing Substack’s story with you. We’re digging into their history and strategy because we believe that if you’re running a budding creator platform, Substack offers a masterclass on how to spark, stoke, and scale a vibrant community.

How Substack works

Substack’s founders came together to solve a problem: helping writers earn a living directly from their readers.

When readers pay writers directly, the founders realized, writers can focus on doing the work they care about most, not what editors, algorithms, or advertisers deem valuable. The small team built Substack to make that independence feasible.

Today, Substack resembles the email newsletter tools you’re familiar with, but with a crucial twist. When readers like me subscribe to a Substack (like Lindsay Gibbs’ newsletter “Power Plays” covering women’s sports or Kimberly Rose Drew’s “Something I Saw,” a one-a-day artwork spotlight), I may have the chance to pay them for their work. Maybe I’ll pay $5 a month, maybe $10. With economies of scale, these paying subscribers can really add up for writers and for Substack, which takes a 10% cut of the revenue writers earn. Some writers have turned Substack into their full-time gig and earn into the six figures, while others are using Substack as a reliable anchor of income. (Note: we offer this “Get Together” Substack for free).

Recently, we interviewed Fiona Monga and Nadia Eghbal from Substack’s Writer team to learn about how they help new writers through the challenges of changing platforms and going independent. Tune in here.

Writers helping writers 📬 Fiona Monga & Nadia Eghbal, Substack | Get  Together

Tune in on our podcast 🎙

In this case study, we’ll cover how Substack went about kickstarting their community. Who were their first creators, and why? Then we’ll dig into how the team continues to support new writers transitioning to Substack, and explore how that work may scale as their growth accelerates.

Who Substack focused on to seed the community

Whereas other email newsletter tools serve broad use cases (everyone from e-commerce to media to personal blogs), the Substack founders focused on a small but passionate “Who” at the outset: professional writers

This sharp perspective was informed by one of the co-founders, Hamish McKenzie’s, background as a journalist and writer. Hamish had his finger on the pulse of the ad model-driven industry because he had been personally affected by that world and its challenges.

L to R: Co-founders Chris Best, Hamish McKenzie, and Jairaj Sethi, via Substack.

Nadia Eghbal, who runs the Writer Experience team at Substack and previously worked on the Developer Experience team at GitHub, is also a writer. She just published a book about open source developers (Working in Public: The Making and Maintenance of Open Source Software) and writes regularly on her website and newsletter. She reflected in our interview on how her experience has been different than journalists like Hamish:

“Journalists, as professional writers, feel these challenges–having to write in a certain way or with certain kinds of incentive models–faster than people like me who have the luxury of writing about stuff on the side. Professional writers really feel the pain, and had a need for a publishing alternative that was more independent and more dictated by their own terms.”

So the early Substack team didn’t just focus their email newsletter on writers within the sea of people who need an email tool, they focused on building a tool for professional writers, not amateurs or semi-professionals. 

One of the challenges we see many people face when they attempt to spark a community is a lack of specificity. We try to build a community for everyone.

But by serving everyone, you serve no one. Without a clear focus, efforts get muddled. Substack avoided that trap. They got cognitively clear on who their first early allies would be: professional writers. 

P&C Tip: Craving focus for your “Who”–the people your community building investment will focus on? Ask yourself:

  • Who brings the energy now–who are the people who already engage, contribute, or attend?

  • Assuming that the community flourishes, who will you stick with?

Ask: Who are your Ben Thompsons?

To get a community off the ground, the Substack team also had to take action–to pinpoint the first people they’d invite and do the high-touch work to reach out to those folks. These first publishers would be the kindling that sparked a much bigger fire

In doing so, the Substack founders again had a sharp focus for their outreach. They looked for people who resembled Ben Thompson, who runs a popular one-man publishing operation called Stratechery.

Their hypothesis was that more professional writers would go independent like Ben Thompson had if writers had the tool stack to support them in doing so (e.g. payment, blog / email publishing, analytics, community tools). As one of Substack’s co-founders, Chris Best, said, “You just have to be a great writer and we can take care of the rest.” Substack’s kindling would be writers who had the potential to replicate Ben Thompson’s model.

In October 2017, the three founders pinpointed a small pool of these writers to try their site. As Ricardo Bilton reported in 2017, the team extended invites to two types of writers: 

  • Creators who had existing free newsletters with large subscriber bases.

  • Writers with large fanbases who had recently been laid off from major publications. 

One of the first writers on Substack was Bill Bishop, a tremendous writer who had very loyal readers of a longstanding newsletter about China. As Fiona Monga shared in our interview, Substack founder Hamish McKenzie had a relationship with Bill from Hamish’s days as a reporter in Hong Kong, and also knew that Bill had dreams of making his newsletter paid. Because Bill’s interests aligned with Substack’s, and because Bill trusted the Substack team, he took a risk and transitioned to the platform before it was proven. 

Bill Bishop, Substack’s first writer, brought in six figures of revenue at launch and helped prove Substack’s model to writers around the world.

At launch, Bill’s newsletter brought in six figures of revenue, and as Fiona told us, that use case “really opened up the door to kind of what might be possible with other writers.” Bill’s launch was soon followed by Kelly Dwyer’s The Second Arrangement and Daniel Mallory Ortberg’s The Shatner Chatner.

Substack’s strategy to create a tool that would specifically enable more Ben Thompsons was an informed bet, but in those early days, it was far from guaranteed to succeed. As Nadia Eghbal reflected in our interview:

“Around the time I was thinking about joining the Substack team, I would hear people say, ‘How many Ben Thompsons are there really?’ Stratechery is seen as this one example of some guy who managed to make this work, but how many other people are really gonna make writing independently work?

It turns out there are actually a lot of undiscovered Ben Thompsons out there. Beyond that, I think we should be creating more Ben Thompsons in the world.”

In fact, there were thousands and thousands of Ben Thompsons. By just the end of its first year in business, Substack reported that 25,000 paying subscribers used the service. In 2019, that number doubled. This year, it has skyrocketed.

In the communities we've studied, the first people who show up are always people who crave or care about the space you’re building more than the average person, as Bill Bishop did with Substack. These people who care are more powerful than the people who don’t. They alone will help you build a community from scratch. Pinpoint them, as Substack did, and who knows how far you will go together.

P&C Tip: Don’t underestimate the power of personal outreach when you’re inviting the first people to join a new community. There’s no cheat code for personal outreach, and we almost always undervalue its potency. 

So, make it real! Jot down your list of names. For more inspiration, tune into Episode 17 of the “Get Together” podcast with Courtland Allen. Courtland wrote 150 personal emails to spark Indie Hackers, a community of 60,000 entrepreneurs.

At the community training I (Bailey) hosted for Substack’s first batch of fellows in San Francisco. Substack gathered their product team and a cadre of experts to train a class of emerging talent on how to go independent.

Building with writers, not for them

Building a community isn’t about what you can do; rather, it’s dependent upon what you and your people can do. Thus, you have to build a community with your members, not just for them.

Substack co-founder Chris Best told Ricardo Bilton, “In the early days, a lot of it is about learning as a community.” The first publishers on Substack pressure tested the team’s assumptions, and also codified best practices that the next wave of writers would learn from. As Chris reflected: “This whole model is so nascent that there’s so much more to be gained by growing the pie and everyone figuring out how to do this together. Getting publications to work together and share notes and promote each other’s stuff will help accelerate this future that we know is coming.”

From their early days through to today, the Substack team has treated writers as essential collaborators and connected publishers so they can to swap best practices. Substack employees Fiona Monga and Nadia Eghbal mention in our interview how part of their role supporting Substack writers is to notice what works, validate it, then codify and share those learnings. 

For example, by observing and speaking with writers Substack’s team learned that successful publications tend to: 

  • Make the best piece of writing free to their readers, not paid, in order to convert more subscribers. 

  • Publish prolifically. Successful writers publish frequently (e.g. once a week, or once every other week) and are able to hold that consistency over time. 

  • Cover niche topics. Writers tend to do better the more specific their beat is. Writers covering niches have more focused audiences gather around their writing than what a big publication would invest in. 

  • Publish in long form: Although there are exceptions, Substack is a place for thoughtful, long-form writing and rewards deeper thought and reflection on specific topics.  

To make sure as many writers as possible can absorb these crucial learnings, the Substack Writers Team shares best practices through their podcast and their own Substack publication

When we work with clients who are starting communities, we try to instill within them this practice of “building with, not for” your people. You may have to start this community but it doesn’t mean you already know or will know what works for all community members. If you’re building a community of creators like Substack, you may start by sharing best practices from your own experience about how to be a great creator but that only works for so long as you grow. From the moment you gain traction, your challenge is to progressively collaborate–doing more with your people every step of the way.

P&C Tip: We get into the same theme of noticing and nurturing with Lisa Cifuentes and Kyle Baptista from CreativeMornings in Episode 16 of our podcast.

What now? Investing in writers helping writers

Substack has proven its model works, and the platform is starting to take flight. Last month, the team reported that over 250,000 readers were paying for at least one Substack newsletter.

But ask the team at Substack and they’ll be transparent with you that the work is not done. For writers who go independent, the move to Substack’s platform can be challenging. As Fiona Monga told us: “From working with writers before they launch on Substack or before they introduce paid subscriptions and ask for money for the first time, we know these are hard decisions and it’s a challenge. One day you’re writing, and then all of a sudden you’re also an entrepreneur.” Building a paying audience takes savvy and discipline. Writing independently can feel isolating.

As the number of writers on Substack continues to grow, the limiting factor to helping writers navigate the transition to independence will be the Substack team’s bandwidth. “How do we help writers help themselves when we can’t always get on the phone with every single person? Even though I would absolutely love to, at some point it’s just not possible,” Nadia told us. This bottleneck will only get worse as the platform’s growth accelerates, unless the team expands their capacity to support writers.

So Substack is exploring community programs that will empower writers to help each other directly and to do so at scale. As Nadia and Fiona shared, they’re asking questions like: 

  • What are different ways that we can help writers help themselves? Help each other? 

  • How do we balance continuing to work one-on-one with writers when we can, while also creating a knowledge base that writers can use to share and support each other in a successful way? 

  • How can we increase the serendipity that two writers are going to run into each other and want to take their conversation somewhere else?

Today, the team is actively experimenting on programs to tackle these challenges. Since the pandemic, they’ve produced online workshops on Crowdcast, which has a presenter view and a side live chat. “Writers are there to watch someone speak, but also talk to each other on the side, discover one another’s Substacks, and talk about similar problems.” Nadia has observed that sub-communities of writers have popped up through these side chats, and other new writers have found out about existing micro-communities they’d like to join.

Before the pandemic, Substack invited Emily Atkin, author of Heated, to talk to an audience of Substack writers in New York about how she successfully launched paid subscriptions. Then, the Substack team recapped the takeaways on their own Substack here for more writers to access. 

The team has also hosted online discussion threads through their own Substack newsletter. Subscribers can join in the comment thread and talk to each other directly. “That’s helpful because every commenter’s name is linked directly to their own Substack,” Nadia shared. “I remember someone was writing about old watches and posted: ‘Is there anyone else out there that’s a watch writer?’ And quickly someone answered: ‘I write about watches, too!’ We see these great moments of people in the comments finding each other.”

To empower writers to connect and help each other like this at scale, Substack’s team knows they will have to increasingly get out of the way. “We’re the excuse for people to get to go in the same room and find other like-minded people,” Nadia told us. “There’s a temptation to be the center point of these events and control the conversation, to have a Substack writer community that’s our community run by Substack, but we’re more of the lubricant or the accelerant.”

Sounds logical, but trusting others to take over like this can be a challenge. Many of us can get protective, controlling, even paranoid. We worry about people “not having the same standards” or “misrepresenting the brand.”

If you want to scale, you can’t bend to those fears of losing control. If a community is dependent on a lone leader or brand, it’s more at risk of collapse in the face of uncertainty and a changing world. 

Substack’s long term reach and vibrancy will be determined by their ability to go beyond helping writers 1:1. Substack’s founders came together to help writers earn a living from readers. And to realize that mission, they must embrace new ways to help writers help each other.

Want more case studies and inspiring community stories like this one? This “Get Together” newsletter has you covered.

More on all things People & Company and Get Together here.

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