Problems with Newsletters

Hello,

Welcome to What's The Problem, your briefing on high-value problems waiting for a solution.

As a newsletter creator, I’m somewhat close to this topic and understand deeply the challenges newsletters face with growth, engagement, deliverability and monetisation.

So I’ve done a deep dive on this industry and picked the 5 biggest issues and come up with some potential solutions.

If I had to pick one of these problems, I’d pick the last one.

1. The Content Treadmill

Problem

Creators are caught on a relentless "content treadmill", forced to publish on a demanding schedule to stay relevant.

This pressure often leads to creator burnout, a decline in content quality, or both.

The core conflict is between the need for consistency, which audiences expect, and the time required to produce high-quality, original work.

Why

Inbox saturation is at an all-time high. Audiences have become ruthless in unsubscribing from newsletters that are inconsistent or fail to deliver exceptional value in every edition (really hope you’re liking this one).

Furthermore, the rise of AI-generated content risks commoditising generic advice, making a unique, high-quality human voice more valuable and harder to maintain.

Scale

A solo creator can easily spend over 30 hours a month researching, writing, and producing a single high-quality newsletter.

With hundreds of thousands of active creators on major platforms, this equates to millions of hours spent on strenuous, repetitive labour. This time cost represents a massive drag on productivity and scalability.

Current Solutions

• AI Writing Assistants: Tools like Jasper or Copy.ai can generate ideas or drafts, but they often produce generic content that lacks the creator's unique voice and perspective.

• Hiring Freelancers: Outsourcing is effective for delegating tasks but is prohibitively expensive for most independent creators and introduces new management overhead.

• Content Calendars & Templates: These tools help with organisation but do not solve the fundamental problem of creating the content itself. They simply provide a structure for the work.

Opportunity

There is a clear need for a tool that serves as an AI-powered co-writer, not an AI ghostwriter.

A product that can deeply analyse a creator's existing body of work to learn their specific style, tone, and knowledge base.

It could then assist in drafting new content that is genuinely on-brand, suggest unique angles based on past popular topics, and help synthesise research into the creator's voice, significantly cutting down on production time without sacrificing quality.

2. Ineffective Monetization Models

Problem

The dominant monetization models for newsletters - sponsorships and premium content - are fundamentally inefficient.

Conversion rates from free to paid subscribers are notoriously low (typically 1-5%), and platforms offer little flexibility beyond this binary model.

Creators are leaving significant revenue on the table.

Why

As the creator economy professionalises, relying on a small number of paying subscribers is not a sustainable business model.

Economic pressures and the declining effectiveness of ad-based revenue mean creators must build more resilient, diversified income streams to transition from a side-hustle to a viable business.

Scale

While the top 1% of creators earn millions, the "long tail" of the creator economy struggles to earn a living wage.

The issue is not necessarily a lack of value, but a lack of tools to capture that value effectively.

A creator with 10,000 free subscribers and a 2% conversion rate has only 200 paying customers, a difficult base from which to build a full-time business.

Current Solutions

• Sponsorships: Finding and managing sponsors requires manual outreach and negotiation, a time-consuming sales process that distracts from content creation.

• Affiliate Marketing: This provides a revenue stream but often has a low return on investment unless the newsletter has a massive, highly engaged audience in a specific product-heavy niche.

• Selling Separate Digital Products: Creators often bundle posts into an e-book or create a course, but this requires a significant upfront time investment and often involves using clunky, disconnected platforms for sales and delivery.

Opportunity

The opportunity lies in building a flexible monetization layer for newsletters.

Imagine a tool that integrates with platforms like Substack, Beehiiv, or Ghost and allows creators to implement dynamic revenue models.

This could include pay-per-article access for non-subscribers, the ability to sell themed content bundles directly from the newsletter, or even an automated system that analyses subscriber engagement and triggers personalised upgrade offers at the optimal time.

3. The Untapped Value in Back Catalogues

Problem

Established newsletters are sitting on a goldmine of content—their archives—that generates zero ongoing revenue.

Under the standard subscription model, a new subscriber pays a single month's fee and gets access to potentially years of valuable work, fundamentally devaluing the entire back catalogue.

Why

This problem compounds over time. The more a creator writes, the more value they are giving away for free.

They are building a massive, depreciating asset when it should be a appreciating, revenue-generating one. This prevents them from capturing the full value of their expertise and hard work.

Scale

A creator with 200 archived articles has the raw material for multiple niche e-books, paid resource hubs, or topical masterclasses.

This represents thousands of pounds in potential product revenue that is currently untapped.

For a single creator, successfully monetizing this archive could be the difference between a hobby and a career.

Current Solutions

• Manually Creating E-books: The process of copying, pasting, formatting, and designing an e-book from old posts is incredibly time-consuming and tedious.

• Setting up a Separate Digital Storefront: Using a platform like Gumroad or Shopify to sell products creates a disjointed user experience, forcing readers to leave the newsletter ecosystem to make a purchase.

• Doing Nothing: This is the most common solution. The perceived effort is too high, so the asset remains untapped.

Opportunity

A product that automatically productises a newsletter's archive. This tool would connect to a creator's account, scan the entire back catalogue, and use AI to identify thematically related posts.

It would then automatically group, format, and package these posts into well-designed digital products (e.g., a PDF "mini-book" on a specific topic).

With one click, a creator could generate a new product, complete with a cover design and a payment link, ready to be sold to their audience.

4. The Spam Folder Black Hole

Problem

A significant percentage of newsletters never reach their intended audience because they land in the spam folder.

The primary cause is the failure of non-technical creators to correctly configure essential email authentication protocols (SPF, DKIM, and DMARC) for their custom domains.

Why

In 2024, inbox providers like Google and Yahoo made these authentication protocols a mandatory requirement for anyone sending bulk email.

Non-compliance is no longer just bad practice; it is a guarantee of poor deliverability. If your emails don't land in the inbox, your business is invisible.

Scale

Industry data suggests that around 20% of legitimate, permission-based emails never reach the primary inbox.

For a newsletter business with a list of 10,000, that could mean 2,000 subscribers are not seeing the content they signed up for.

This directly translates into lost engagement, lost customers, and lost revenue.

Current Solutions

• Following ESP Tutorials: The documentation provided by email service providers is often highly technical, confusing, and difficult for a non-developer to follow, leading to errors.

• Hiring a Consultant: Paying an expert to fix the issue is effective but expensive, especially for what is often a one-time setup task.

• Deliverability Monitoring Tools: Services like GlockApps or Mail-tester are excellent for diagnosing a problem (e.g., "your DMARC record is missing") but do not guide the user on how to fix it.

Opportunity

There is a need for a simple, automated deliverability setup service.

A tool that securely connects to a user's domain registrar and email platform, analyses their current configuration, generates the exact DNS records needed, and provides a simple, copy-paste workflow with verification.

Think of it as a "Lighthouse for email deliverability" that not only identifies the problems but provides a guided, automated fix, turning a complex technical task into a simple 5-minute process.

5. The Unengaged Audience and High Churn

Problem

Newsletters consistently suffer from low engagement (average open rates hover around 20-30%) and high subscriber churn (25-30% annually).

The root cause is a one-size-fits-all approach. Sending the same generic content to an entire list inevitably leads to reader disinterest.

Why

Low engagement is a leading indicator of future churn. More importantly, email providers use engagement as a key signal for sender reputation.

Consistently low open and click rates will cause providers like Gmail to route your emails to the promotions tab or, worse, the spam folder, creating a vicious cycle of declining visibility.

Scale

For a newsletter with a list of 10,000 subscribers, an annual churn rate of 25% means losing 2,500 subscribers who must be replaced through marketing efforts just to maintain the same list size.

This represents a huge, recurring cost in both time and money.

Current Solutions

• Manual Segmentation: Creators can tag subscribers based on sign-up source or survey responses, but this is a time-consuming, manual process that relies on crude data points and is difficult to maintain.

• A/B Testing Subject Lines: This can provide a temporary lift in open rates but does nothing to improve the relevance of the actual content inside the email. It optimises the "wrapper," not the "gift."

• Re-engagement Campaigns: Sending "Are you still there?" emails to inactive subscribers is a reactive measure that is often too little, too late.

Opportunity

The opportunity is for an intelligent personalisation engine that automates segmentation based on actual reader behaviour.

Such a tool would track which links and topics individual subscribers engage with over time.

It could then be used to dynamically curate future newsletters, re-ordering sections or highlighting articles that match a reader's demonstrated interests.

This moves beyond basic "Hi [First Name]" personalisation to true content-level personalisation, done automatically.