Email Newsletters Still Print Money – Run 100 of Them

01 /The Concept

Letterhead describes itself as "the only platform built for scaling newsletters" – where scaling means not growing subscriber counts, but growing the number of distinct newsletters.

As one profile of the company describes it, the typical company runs one newsletter: one editorial team, one platform, one set of processes. But media companies and multi-brand businesses have already blown past that model – many are now running dozens of newsletters, each with its own topic and audience.

As new newsletters launch, each tends to develop its own team, its own workflows, and its own tool stack. The result: multiple parallel editorial operations doing essentially the same work in incompatible ways, on different platforms, with no shared infrastructure.

Scaling newsletters the old way means scaling headcount and tool sprawl proportionally. Letterhead treats newsletters the way sound business practice treats any product: they should be run efficiently, scalably, and with shared resources.

The Letterhead platform is a single environment for managing multiple newsletters, with a shared content library, a unified subscriber database, and integrations with other content platforms and CRM systems. Individual newsletters can have their own editorial workflows – but those workflows are visible and manageable within one roof.

One team can run many newsletters. A single editor can oversee multiple newsletters on the same platform, accessing all company content and drawing from a shared pool of contributors.

Growth – adding more newsletters – no longer requires growing the team proportionally or multiplying tool sprawl. One team can operate 10, 100, even 1,000 newsletters on Letterhead while retaining full tools for content creation, curation, monetization, and per-newsletter performance tracking.

The platform has proven genuinely useful in practice: roughly 2,000 distinct newsletters are currently created and distributed on it, across what appears to be a few hundred client companies.

Letterhead raised $5.3 million at the end of 2023. In late October it closed a new $34 million round – a signal that growth is tracking well.

02 /Why It Matters

As Letterhead's founder correctly observes, most companies treat their email newsletter as a quick-and-dirty marketing tool – something to blast out product announcements or sale alerts.

But a well-run newsletter is a product. It should be treated like one – developed intentionally, managed with clear ownership, and tracked against its own profit and loss.

That also means not every newsletter has to be a click-generation engine. Letterhead has clients building newsletters designed to be read inside the inbox, not to drive traffic. That's fine – if the format serves the audience and builds retention in that vertical. Effectiveness for such a newsletter isn't measured in click-through rates. It's measured in different metrics that need to be defined upfront and tracked accordingly.

Another sharp observation from the founder: build newsletters for the fans, not for the people who unsubscribe.

In other words – stop reflexively changing the newsletter every time someone opts out. Focus on the readers who genuinely open, read, and look forward to each issue. Ask how to make the newsletter even more valuable to them. Then find more people who look like those fans.

This is the same logic as product retention: what's the point of driving new signups if they all churn quickly? It's filling a bucket with a hole in it.

But truly serving a specific audience makes it nearly impossible to serve everyone in a single newsletter. The moment you notice a topic resonating strongly with a subset of readers – that's the signal to spin up a dedicated newsletter for that segment.

Follow that logic consistently and you end up with dozens or hundreds of newsletters covering different topics for different audiences. Which becomes unmanageable – unless you have a platform purpose-built for exactly that. Which, conveniently, is what Letterhead offers.

On the topic of email newsletters: a [recent review](/review/da-prosto-vozmi-i-perenesi) covered Workshop, which has raised $27.7 million (including a $7 million round in March after the original review) by applying the same idea to internal company communications – newsletters for employees rather than customers. The engagement and retention logic applies equally there, and the same multi-newsletter architecture may be just as necessary internally as externally.

03 /Opportunities

The uncomfortable truth is that we've entered an era of content consumption where volume beats quality. Being present everywhere in large quantities is now more effective than surfacing occasionally with something exceptional.

The reason is simple: attention is competed for across an overwhelming volume of content from all directions. Disappearing between posts means being forgotten. Any single piece of content is easy to miss in the flood.

One consequence: the rise of video content factories capable of pumping out advertising at scale. A functional content operation at that level targets 10,000–15,000 pieces per month – counting cross-posting and format variations, but still an enormous number.

Startups are responding with automated content factories.

Extuitive ([related review](/review/kontent-fabriki-reklamy-tolko-pojavilis-no-ih-uzhe-mozhno-ubit)) raised $20 million in September for a platform that connects to a Shopify store, automatically generates ad creative, tests it against AI personas representing the target audience, and launches the best-performing ads across advertising platforms – tracking real-world results continuously.

Reacher ([related review](/review/zarabatyvaj-kak-genri-ford-no-na-svojom)) graduated Y Combinator in September with a platform for automating and scaling influencer ad placements.

Duel ([related review](/review/novyj-samyj-bolshoj-kanal-privlechenija-pokupatelej)) raised $16 million in September for a platform that scales brand promotion through customers rather than influencers – automating the process so efficiently that one employee can manage advocacy across 15,000 active buyers.

Letterhead fits squarely in the same trend – a content-scaling tool, but in the form of newsletters rather than ad creatives or video.

The directional bet: automated content factories that let brands produce 10x, 100x more content for brand building, acquisition, and retention. Those who can't scale content production will fall behind – and eventually every company will realize it. At that point, these platforms stop being competitive differentiators and become table stakes.

It's frightening to imagine what the internet looks like when every brand operates a content factory. But the alternative is irrelevance. If you can't beat the trend, lead it.