Substack’s Long Game: How a Newsletter Tool Became the Backbone of an Internet Rebellion

What started as a simple idea to fix online media has grown into a platform with 5 million paid subscriptions. But Substack’s rise wasn’t inevitable—it was hand-built, newsletter by newsletter, often manually in the early days.

Today, it's a full-blown creator economy engine, with writers making multiples of their full-time salaries by publishing in their spare time.

Substack Began with Frustration—And One Perfect First Customer

Chris Best didn’t start Substack as a media veteran. His background was engineering. While still in college, he helped co-found Kik Messenger, a messaging app that exploded from zero to a million users in 14 days and eventually reached hundreds of millions of users—at one point, 40% of U.S. teenagers were on the platform.

But after that hypergrowth ride, Chris took a year off and began writing. He drafted an essay criticizing the internet and the media economy. He sent it to his friend and future co-founder, Hamish McKenzie. Hamish told him bluntly: “You’re not a very good writer. This is boring. Everybody knows all this stuff.”

But he also asked the more important question: “How do you fix it?”

That conversation sparked Substack.

The vision was twofold:

• A grand ambition: Build a new economic engine for culture.

• A practical tool: Let writers easily launch a paid email newsletter.

Their first real user was Bill Bishop, who had been writing about China. His blog had been blocked by the Great Firewall, so he’d shifted to email to reach his audience. He had loyal readers but hadn’t monetized—he didn’t want to wrestle with the technology. Substack offered to do it for him.

The results were instant. Bishop launched on Substack and made six figures on day one.

At the time, Substack hadn’t even built a real product. There was no way for someone to sign up on their own. Chris had to type new newsletters into the database manually. There wasn’t even a feature to email the free list.

But Bishop’s success proved that real value was there—and that monetization could work if the tool got out of the way.

Real Writers, Real Revenue

The platform didn’t grow from influencers or media insiders—it grew from writers with day jobs who had something to say.

Two such users—who also happen to work in venture capital—shared their numbers.

• BC Corner: This newsletter has 69,000 subscribers and adds more than 1,000 per week. It hits 1 million views per month.

• Founders Corner: A second newsletter from the same creator, focused on startup growth, already has 25,000 subscribers.

• Product Market Fit: Another newsletter that has 31,000 subscribers and reaches between 300,000 and 500,000 people monthly.

These newsletters aren’t side hobbies. One creator makes “at least five times more” than in his full-time job—while writing only on weekends.

They didn’t even start with the goal of monetization. They launched on Substack to improve as investors—using the platform to sharpen their thinking, build a brand, and communicate their interests to founders.

The money came later—and it came fast.

The App That Took Years to Build—Now a Growth Engine

Substack’s iOS app is now one of the biggest drivers of growth for the platform. It even surpassed X and Reddit in the App Store’s news category.

But getting there was brutally difficult. As Chris explained, “To start a new app that people download and use—it's not easy to do.” Most users only check a handful of apps daily—WhatsApp, Stripe, Chrome, LinkedIn. Making Substack one of them required patience and long-term investment.

The app brought something crucial: a native environment for discovery. Before it, growth was entirely dependent on external platforms like Twitter or LinkedIn. But those are unreliable. LinkedIn, for example, once shut down one user’s account over a security issue. For creators, that’s not just a technical glitch—it’s losing your top-of-funnel overnight.

The app solves that by offering centralized discovery while retaining decentralized ownership. As Chris put it: “You own your connection with your audience. You have editorial freedom. That’s the part that actually matters.”

Substack lets you own the email addresses of your customers while providing the much needed discovery.

This has allowed a #3 finance writer to make over $1M a year from their newsletter.

Why Substack Content Feels “Real”

Substack’s feed feels different. There are no ads. There’s no push to optimize for clicks. Unlike LinkedIn, where every post is a sales pitch, Substack users post because they want to build a community.

Writers aren’t fighting each other for attention. They’re often recommending each other. “Most of us are not writers,” one user said, “we’re not competing—we’re collaborating.”

That dynamic creates aligned incentives. When one writer grows, others grow too. It’s the kind of network effect that traditional platforms don’t have.

The secret of Substack isn’t just the decentralized nature of ownership. It’s the combination of:

• Decentralized audience ownership

• Centralized discovery and growth

That’s what makes the engine hum.

Adding Video, Live, and AI—Without Becoming YouTube

Substack is not trying to become another video-first platform. It’s simply adapting to how creators already work.

The app now supports live conversations—like FaceTime—that can automatically be turned into podcasts, video clips, and distributed content. That’s especially helpful for creators who don’t want to deal with editing tools or production workflows.

As video becomes the “lingua franca” of online discovery, this feature allows writers to meet audiences where they are—without needing a studio.

Substack is also leaning into AI to support creators. If you record a great conversation, the system helps you repurpose it. It’s about removing the friction between expression and publishing.

The goal is to let one person with evenings and weekends create as much impact as a team at a traditional media company.

A Different Kind of Moderation and Monetization

Substack has rules—but they’re narrow by design. You can’t spam. You can’t do anything illegal. But otherwise, each creator sets the tone for their own community.

There’s no platform-wide rule that says what you can or can’t write about—especially not political content, which platforms like Meta have historically suppressed.

Monetization also operates on different principles. Substack doesn’t allow standard email marketing spam. But companies are using it for deep editorial content—venture firms in Spain, for example, are now running their own newsletters.

Substack is not about pushing more emails. It’s about building trust. That’s why people pay—not because they want content, but because they want a relationship.

As one user put it: “Someone paid me for the founding plan, and then told me, ‘I’m not even going to use your resources—I just wanted to support you.’”

The Cultural Stakes of the Next Decade

Chris Best’s long-term vision isn’t about product features—it’s about shifting the cultural economy.

The question he asks is: “What share of the internet will be built by people trying to maximize engagement, and what share will be built by people making things they actually believe in?”

He believes the creator-supported economy can get much bigger—because the internet is no longer limited by money, but by attention.

In a world with infinite content, the most scarce and valuable thing is trust. Substack lets readers vote on what culture they want to exist—by supporting the creators they believe in.

And that model is likely to matter more as AI floods the internet with slop. “If you thought there was a lot of spam before,” Chris said, “there’s going to be a hundred times as much now.”

Special thanks to Guillermo for his interview with Substack Co-Founder Chris Best.

Top Tweets of the day

1/

2-3 years ago, the sentiment on Substack wasn't as great and Beehiiv was actually ahead.

Then they launched the Substack app and used growth hack after growth hack.

Now they are amazing. If you suck at marketing but are a great writer, Substack is the best place to be. It does need some distribution skills but it is much easier than any other alternative platform. Its giving early Medium vibes.

2/

Most short commitments turn into long commitments if you don't push too much.

3/

Kahneman's insights are terrific if you wanna leave a conversation on a high. Works well as a filmmaker too. Think of every movie you've ever liked, there is one thing it has in common with all other great movies you've liked.

Wrote about it a long time ago.

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3. Somehow, I got access to the new Gemini Text Diffusion model as a "trusted tester." Oops. They shouldn't have trusted me. This thing is insane, and can build an entire app in 1 to 2 seconds. by /r/Bard

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