In 2020, Lenny Rachitsky made a move that, in hindsight, was the signal. He had been running Lenny’s Newsletter on Mailchimp for over a year, according to his own newsletter post. It worked fine. Mailchimp was reliable, feature-rich, and cheaper than most alternatives. But Rachitsky switched to Substack anyway, and his explanation was telling: Mailchimp was built for marketers, and he was a writer, as he wrote in his newsletter. The tool, however capable, projected an identity he did not want to wear.
That moment captured something larger. Mailchimp did not lose the operator newsletter market on price or features. It lost on identity. The platforms that won, Substack, Beehiiv, and Buttondown, each understood that operators building newsletters wanted to feel like writers running a business, not marketers running a campaign. They won by giving that feeling a home.
The Mailchimp-era assumption and why it broke
Mailchimp was originally designed for marketing emails and e-commerce, according to general industry analysis. It was built for the person who sends a monthly newsletter because their boss told them to. Its language was the language of campaigns, segments, and click-through rates. For an operator building a newsletter as their primary product, that framing was a constant, low-grade insult.
The problem was never that Mailchimp lacked features. It had plenty. The problem was that every interaction with the tool reminded the operator that they were being treated as a marketer. The dashboard was optimized for e-commerce metrics. The templates were designed for promotional blasts. The entire product assumed the newsletter was a means to an end, not the end itself.
Rachitsky’s switch was not an outlier, as he documented in his newsletter. It was the leading edge of a migration that defined the next several years of the newsletter market. Operators wanted a tool that said “you are a writer” every time they logged in. Mailchimp could not say that, because it was not built to believe it.
Substack’s founder-publishing positioning
Substack was founded in 2017 by Chris Best, Hamish McKenzie, and Jairaj Sethi, according to Crunchbase. Its positioning was precise from the start: writers should own their relationship with their audience and run a business directly, rather than relying on ad-driven platforms, as stated on Substack’s blog. That framing was exactly what operators wanted to hear. It elevated the newsletter from a marketing channel to a publishing business.
The model worked spectacularly for a certain kind of operator. Substack’s Top 25 list of paid newsletters shows a concentration in categories like politics, culture, and technology, with top earners making over $1 million annually, according to Substack’s blog. For a writer with a large audience in a high-traffic category, Substack was the obvious choice.
But the same model revealed a ceiling for niche operators. If you were writing about, say, industrial supply chains or municipal zoning, the Substack ecosystem did not offer much help. The platform’s discovery features and social layer worked best for topics that already had large audiences. For the operator building a small, loyal readership in a narrow domain, Substack’s writer-as-business framing was aspirational but not always practical. The platform gave you the identity of a publisher without always giving you the tools to reach one.
The problem was never that Mailchimp lacked features. It was that every interaction with the tool reminded the operator they were being treated as a marketer.
Beehiiv’s growth-tool positioning
Beehiiv was founded in 2021 by Tyler Denk, Benjamin Hargett, and Graham McNicoll, and raised $2.8 million in seed funding led by Greycroft, according to TechCrunch. Its positioning was the inverse of Substack’s. Where Substack said “you are a writer,” Beehiiv said “you are a business that happens to use a newsletter.”
The platform’s growth-tool suite included referral programs, an ad network, and analytics, according to Beehiiv’s features page. These features were not afterthoughts. They were the product. Beehiiv explicitly targeted the operator who wanted to grow fast, who saw the newsletter as a scalable distribution channel, and who was comfortable thinking in terms of subscriber acquisition cost and conversion funnels.
This positioning filled the gap Substack left open. For operators who prioritized growth over writer identity, Beehiiv was the better fit. The platform’s referral programs turned subscribers into a distribution channel. Its ad network monetized attention without requiring the operator to build a sales pipeline. Its analytics gave operators the numbers they needed to optimize.
Beehiiv won by being honest about what it was. It did not pretend the newsletter was a literary endeavor. It treated it as a growth engine, and operators who wanted a growth engine chose it.
Buttondown’s quiet text-first positioning
Buttondown was founded by Justin Duke in 2016 as a side project, focusing on a simple, text-first email newsletter tool with Markdown support, according to Buttondown’s about page. Its founding story emphasized a quiet approach, with no venture capital funding and a focus on simplicity and reliability over rapid growth, as stated in the Buttondown Manifesto.
Buttondown’s positioning was the anti-thesis of Beehiiv and the complement to Substack. It rejected the growth-at-all-costs framing entirely. Its manifesto explicitly stated that it was not trying to be a platform, not trying to raise money, and not trying to become the default for everyone, according to the Buttondown Manifesto. It was a tool for people who wanted to write and send email, nothing more and nothing less.
This anti-growth stance was itself a growth strategy. It attracted operators who felt alienated by the business-framing of Substack and the growth-framing of Beehiiv. For the operator who wanted to write a weekly newsletter to 500 people without thinking about referral programs or ad networks, Buttondown was the obvious choice. Its Markdown support made writing feel like writing. Its simplicity meant the tool got out of the way.
Buttondown won a loyal niche by being willing to stay small. It proved that there was a market for operators who valued writing over metrics, and that a platform could serve that market without chasing venture capital.
The platform that does not exist yet
Three platforms, three distinct positions. Substack gave operators a writer’s identity. Beehiiv gave them growth tools. Buttondown gave them simplicity. Each made a trade-off, and each trade-off attracted a specific kind of operator.
The platform that does not exist yet would combine all three without forcing the trade-offs. It would give the operator the writer identity of Substack, the growth tools of Beehiiv, and the simplicity of Buttondown. It would treat the newsletter as both a creative endeavor and a scalable business, and it would not ask the operator to choose between the two.
That platform would be hard to build. The three positions are in tension. Writer identity often resists growth optimization. Simplicity often resists feature expansion. But the tension is not unresolvable. A platform that started with simplicity, added growth tools as optional modules, and maintained a writer-first identity throughout would cover the full spectrum of operator needs.
The gap is real. Someone will fill it. The question is whether they will be a new entrant or one of the existing three, willing to expand beyond their original positioning.