Substack doing things that don't scale

In the world of tech startups, conventional wisdom often pushes founders to build products that can scale to millions of users from day one. But some of the most successful platforms began by doing exactly the opposite—focusing intensely on serving just one user exceptionally well. Substack, the newsletter platform that has revolutionized independent publishing, exemplifies this “do things that don’t scale” approach. By initially building their product for a single writer’s specific needs, the founders laid the groundwork for what would become a transformative platform for creators worldwide.

The Genesis: A Problem Worth Solving

Substack’s story begins in 2017 with three founders who shared a concern about the state of media and publishing. Chris Best (former CTO of messaging app Kik), Hamish McKenzie (a former journalist and Tesla communications lead), and Jairaj Sethi (a developer who had also worked at Kik) saw a troubling trend in the media landscape. The advertising-based business model was pushing publishers toward clickbait and sensationalism, while quality journalism and thoughtful writing were being devalued.

“We were worried about the incentives in the media ecosystem,” McKenzie later explained. “Writers and journalists were being pushed to chase pageviews and engagement metrics rather than focusing on quality and truth.”

The founders believed there was a better way—a model where writers could earn a living directly from readers who valued their work, rather than from advertisers who valued clicks and eyeballs. This direct relationship, they theorized, would align incentives properly: writers would be rewarded for creating content that readers found valuable enough to pay for, rather than content that merely generated traffic.

But building a platform to enable this vision would be challenging. Many writers were skeptical about charging for their work, uncertain if readers would pay, and hesitant to abandon established platforms with built-in audiences. The founders needed to prove their model could work, and they needed to do it in a way that would convince skeptical writers to take a chance on their unproven platform.

The Unscalable Approach: Building for One Writer

Rather than building a generic platform and hoping writers would adopt it, the Substack founders took a radically different approach. They decided to build their first product specifically for one writer: Bill Bishop, the author of Sinocism, a highly respected newsletter about China.

“To maximize value creation for each writer from the very early days, they built the first Product for just one person: Bill Bishop, author of Sinocism,” noted one analysis of Substack’s early growth.

This approach was decidedly unscalable. The founders were essentially creating a custom publishing solution for a single writer, investing significant time and resources into understanding and addressing his specific needs. But they believed this intense focus would yield insights that a broader approach might miss.

McKenzie had a pre-existing connection to Bishop through his journalism background, which gave them an entry point. Bishop had been publishing Sinocism as a free newsletter since 2012 and had built a devoted, influential readership that included diplomats, business leaders, journalists, and others with a professional interest in China. Despite the newsletter’s quality and impact, Bishop wasn’t monetizing it directly—a perfect test case for Substack’s model.

The founders approached Bishop with a proposition: relaunch Sinocism on their new platform, introducing paid subscriptions for the first time. They promised to build exactly what he needed to make this transition successful.

Understanding Specific Needs: The Bishop Collaboration

The collaboration with Bishop wasn’t just about convincing him to use Substack—it was about deeply understanding his workflow, challenges, and aspirations as a writer. The founders spent extensive time with Bishop, learning about his content creation process, his relationship with readers, and his concerns about monetization.

Several key insights emerged from this collaboration:

1. Simplicity was crucial: Bishop wanted to focus on writing, not on managing technology or business operations. Any platform would need to be exceptionally easy to use.
2. Reader relationships mattered: Bishop had built trust with his audience over years. The transition to paid subscriptions needed to respect and preserve these relationships.
3. Flexibility was necessary: Bishop wanted to offer both free and paid content, allowing him to maintain his broad readership while monetizing his most valuable insights.
4. Analytics were important: Bishop needed to understand how readers were engaging with his content, which topics resonated most, and how his subscriber base was growing.
5. Independence was non-negotiable: Bishop wanted full ownership of his content and subscriber list, with the freedom to leave the platform if needed.

The Substack team didn’t just listen to these needs—they built their entire product around them. They created a simple, clean publishing interface that required minimal technical knowledge. They developed a subscription system that allowed for both free and paid tiers. They built analytics tools that provided meaningful insights without overwhelming complexity. And they structured their business model to ensure writers maintained ownership of their content and audience.

This bespoke approach was labor-intensive and time-consuming. The founders were essentially functioning as Bishop’s personal publishing team, addressing his feedback and making adjustments in real-time. But this investment allowed them to create a product that perfectly fit the needs of a serious, professional newsletter writer—exactly the type of creator they hoped to attract to their platform.

The Launch: Proving the Model

On October 16, 2017, Bill Bishop relaunched Sinocism on Substack, introducing paid subscriptions for the first time. The results were immediate and compelling: within the first day, Bishop generated six figures in subscription revenue.

“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,” noted one account of the launch.

This successful launch was significant for several reasons. First, it validated Substack’s core hypothesis that readers would pay directly for content they valued. Second, it demonstrated that established writers could successfully transition from free to paid models without alienating their audience. And third, it provided a powerful case study that the founders could use to attract other writers to the platform.

The success wasn’t just about the technology—it was about the perfect alignment between Substack’s platform and Bishop’s specific needs as a writer. Because the founders had built the product with Bishop’s workflow and audience in mind, the transition was seamless for both the writer and his readers.

This success story became a powerful tool for recruiting other writers. The founders could now approach potential Substack authors with concrete evidence that their model worked, pointing to Bishop’s experience as proof that readers would pay for quality content delivered through their platform.

Expanding the Approach: From One Writer to Many

Having proven their concept with Bishop, the Substack team began to expand their approach, but they maintained their commitment to understanding and addressing the specific needs of individual writers. Rather than pivoting to a mass-market strategy, they continued to work closely with each new writer who joined the platform, particularly in the early days.

“We spent a lot of time with each writer who came onto the platform,” Best explained in a later interview. “We wanted to understand their unique challenges and make sure Substack was solving real problems for them.”

This writer-by-writer approach allowed Substack to refine their product based on diverse needs and use cases. They worked with journalists leaving traditional media, experts in specialized fields, fiction writers, and cultural commentators—each bringing different requirements and expectations to the platform.

For example, when technology journalist Casey Newton decided to leave The Verge and launch his newsletter Platformer on Substack, the founders worked directly with him to ensure the platform could support his specific workflow and content style. When legal scholar Heather Cox Richardson brought her historical perspective to the platform, they made sure her academic approach was well-supported.

This personalized onboarding wasn’t just good customer service—it was a deliberate growth strategy that allowed Substack to continuously improve their product based on real-world feedback from their target users. Each new writer brought new insights that informed product development and refinement.

Building Community Through Individual Relationships

As Substack grew, the founders maintained their focus on individual writer relationships, but they also began to foster connections between writers on the platform. They recognized that building a community of supportive creators would enhance the value of Substack for everyone involved.

They organized writer gatherings, facilitated introductions between authors with complementary interests, and created resources to help writers learn from each other’s experiences. These community-building efforts were still fundamentally about addressing specific needs—now at the collective level as well as the individual level.

“We wanted to create an environment where writers could help each other succeed,” McKenzie noted. “Each writer faces unique challenges, but there’s also tremendous value in shared experiences and collective wisdom.”

This community approach helped Substack attract more writers to the platform. Prospective authors could see not just that individual writers were succeeding, but that they were joining a supportive ecosystem of like-minded creators. This reduced the perceived risk of making the leap to independent publishing and made Substack more attractive compared to going it alone or joining more impersonal platforms.

Scaling Without Losing the Personal Touch

As Substack continued to grow—eventually hosting thousands of newsletters with millions of subscribers—maintaining the same level of personal attention for each writer became increasingly challenging. The founders had to find ways to scale their support without losing the personalized approach that had been key to their early success.

They addressed this challenge through several strategies:

1. Documentation and resources: They created comprehensive guides, case studies, and best practices based on their accumulated knowledge of what worked for different types of writers.
2. Writer success team: They built a dedicated team focused specifically on helping writers succeed on the platform, providing personalized guidance and support.
3. Community-powered support: They facilitated peer-to-peer assistance, allowing experienced Substack writers to share insights with newcomers.
4. Targeted features: They continued to develop features based on specific writer needs, but now with an eye toward solutions that could benefit multiple authors with similar requirements.
5. Writer programs: They launched initiatives like Substack Fellowships and Substack Pro to provide additional support and resources to selected writers, maintaining the high-touch approach for strategic relationships.

These approaches allowed Substack to grow while staying true to their founding philosophy of building for specific writers’ needs. Rather than shifting to a one-size-fits-all model, they found ways to maintain personalization at scale.

The Results: A Platform Built on Specificity

By 2021, just four years after launching with a single writer, Substack had become home to thousands of newsletters, with the top writers earning hundreds of thousands or even millions of dollars annually from subscriptions. The company had raised over $82 million in venture funding and was valued at approximately $650 million.

This remarkable growth stemmed directly from the founders’ initial decision to build for specific writers’ needs rather than for maximum scalability. By deeply understanding what writers like Bill Bishop required to succeed, they created a platform that genuinely solved problems for their target users, rather than one designed primarily for rapid user acquisition.

The specificity of their approach also helped Substack differentiate itself in an increasingly crowded market. While other platforms offered newsletter tools as one feature among many, Substack’s laser focus on serving writers’ specific needs created a product that serious creators preferred, even as alternatives emerged.

“We didn’t build Substack for everyone,” Best explained in a 2020 interview. “We built it for writers who want to have a direct relationship with their readers. That focus has been our strength.”

Lessons for Entrepreneurs: The Power of Specific Focus

Substack’s journey from building for a single writer to creating a platform used by thousands offers several valuable lessons for entrepreneurs:

1. Start with one perfect user: Rather than trying to appeal to everyone immediately, focus intensely on solving the problems of one ideal user. This approach can yield deeper insights and stronger product-market fit than broader strategies.
2. Do things that don’t scale: The founders’ willingness to work closely with individual writers, starting with Bill Bishop, wasn’t efficient in the short term but created tremendous value in the long run. Sometimes the most unscalable approaches lead to the most scalable businesses.
3. Let early users shape the product: By building their platform around the specific needs of writers like Bishop, Substack created a product that genuinely solved problems rather than one based on the founders’ assumptions about what users might want.
4. Use early successes as proof points: Bishop’s immediate success on the platform became a powerful recruiting tool for attracting other writers. Early wins, even if small in scale, can demonstrate your concept’s viability to potential users and investors.
5. Scale the philosophy, not just the product: As Substack grew, they found ways to maintain their writer-centric approach even as direct founder involvement with each user became impossible. The specific implementation changed, but the underlying philosophy remained consistent.

The Legacy of Substack’s Writer-Specific Approach

Today, Substack continues to evolve, but their founding approach of building for specific writers’ needs remains central to their identity and strategy. The platform has expanded to include additional features like podcasts and community tools, but each new development is still guided by the question: “How does this help writers connect directly with their readers?”

This consistent focus has allowed Substack to weather challenges from larger competitors and changing market conditions. By maintaining their commitment to serving writers’ specific needs, they’ve built not just a product but a community of loyal creators who see the platform as a partner in their success rather than just a tool.

As co-founder Hamish McKenzie reflected in 2022, on the fifth anniversary of Bill Bishop launching Sinocism on the platform: “We started by building for one writer’s specific needs, and that approach has guided us ever since. Every feature, every policy, every decision still comes back to the question: ‘Does this help writers succeed on their own terms?'”

In a tech ecosystem often obsessed with rapid scaling and maximum user acquisition, Su
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