📌 Inside 2 AI Newsletter Playbooks

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This week, we're switching things up with an overview of two AI newsletter powerhouses - Ben’s Bites and The Rundown AI.

Both are widely recognized names in the AI space, yet they take completely different paths - from content style to growth tactics to monetization.

But one thing is clear: there’s something to learn from both.

This week’s 3 handpicked email gems…

1. Free email course on writing irresistible copy by Sam Parr, founder of The Hustle.

2. A prompt to write a killer subject line (from Brad Wolverton & Mark R. Hinkle)

3. Newsletter examples that generated $1MM in MRR

Backstory

Ben Tossell is no stranger to startups.

A serial entrepreneur, he sold his company to Zapier in 2021. By October 2022, he launched Ben’s Bites, an AI-focused newsletter.

Then, just a month later—ChatGPT exploded.

Right place, right time? Sure. But Ben knew how to capitalize on the momentum.

Meanwhile, across the AI newsletter battlefield, The Rundown AI has been on an even wilder growth trajectory.

• 900,000 subscribers in just over two years

• An average of 1,200 new subscribers per day.

• Rowan Cheung, the founder, is still in his mid-20s.

This isn’t just about numbers—it’s about two completely different styles, visions, and goals.

Both are winning in their own way, but they’re playing different games.

What's in it for you?

1. Learn how content style impacts audience engagement and loyalty.

2. Uncover two winning AI newsletter growth strategies in action.

3. Find the best monetization model for your own newsletter.

Content

While both newsletters deliver daily AI news, their execution reflects two very different priorities.

The Rundown AI: Structured, Scalable, and Straight to the Point

Rowan Cheung’s The Rundown AI follows a media-style approach that prioritizes structure, speed, and efficiency.

• Highly structured format: Every issue follows the same repeatable template - news, AI tools, job listings, and monetization hooks.

• Fast, digestible news: No personal commentary, no humor—just the most important updates in a scannable format.

• Monetization built-in: Seamlessly integrates sponsorships and premium content upsells within the newsletter.

• Designed for scale: The writing style is neutral, fact-based, and mass-audience friendly.

Why This Works

• Allows for rapid production and expansion (Rowan has a team of 12 producing it).

• Ensures high engagement per issue—readers know exactly what they’re getting every day.

• Ideal for readers who want quick, reliable AI news without distractions.

The Trade-Off

• Lacks a personal voice or unique perspective - this is AI news, not AI opinion.

• Feels less like a community - built for scale rather than deep reader relationships.

Ben’s Bites: Casual, Engaging, and Community-Driven

Ben Tossell’s newsletter isn’t just delivering AI news—it’s fostering discussions, sharing insights, and encouraging hands-on experimentation.

• Conversational, informal tone: Written like a casual conversation, often with humor and personal commentary.

• Flexible structure: The content blends news, industry analysis, community updates, and practical AI learning.

• Community-powered content: Highlights discussions happening in Slack, making readers part of the conversation.

• Actionable AI tools & tutorials: Encourages readers to go beyond just consuming news and start applying AI in their work.

Why This Works

• Feels personal and engaging - more like a discussion than a traditional newsletter.

• Encourages active participation - readers contribute to the Slack community, attend workshops, and collaborate.

• Turns AI curiosity into action - helping readers not just learn about AI but use it in real-world projects.

The Trade-Off

• Harder to scale, as Ben is personally involved in writing and community engagement.

• Less structured, more fluid - sometimes feels like a mix of everything, whereas The Rundown AI is more predictable.

Both are successful, but they are playing very different games.

Want to dive deeper into their content approaches?

Find the Ben’s Bites content template here.
Find The Rundown AI content template here.

Growth

Paid Acquisition, But With a Different Endgame

The Rundown AI: Scale First, Optimize Later

Rowan’s growth strategy is aggressive, systematic, and focused on rapid expansion.

• Twitter virality machine
  Grew from 1,000 to 250,000 X followers in just four months by leveraging high-engagement AI content. Every viral post included a call to action directing readers to subscribe.

• Paid ads through multiple platforms
  Invested heavily in paid acquisition, using the Beehiiv Ad Network, Meta, and Twitter/X Ads as key growth levers. The primary goal was simple: acquire as many subscribers as quickly as possible.

• Team expansion
  Built a 12-person team to manage content, sponsorships, partnerships, and technology, ensuring that scaling efforts remained consistent.

Ben’s Bites: Community-Driven Growth with Paid Ads as a Boost

Ben also runs Twitter ads, but his strategy prioritizes engagement over aggressive scaling.

• Twitter Ads, but at a more measured pace
  While Twitter Ads contribute to growth, they are used as a complement rather than the primary driver.

• Slack community as a retention flywheel
  Readers are not just consuming content; they are actively discussing, networking, and sharing knowledge. This engagement fuels organic word-of-mouth growth.

• Live workshops and AI tutorials
  Instead of just delivering news, Ben integrates hands-on education, increasing retention and long-term audience loyalty.

Key Differences

• Rowan focuses on acquiring subscribers rapidly and optimizing engagement later.

• Ben prioritizes engagement and community first, then scales more organically.

Which Approach Works Best?

• If the goal is rapid subscriber growth, The Rundown AI’s model of paid acquisition and viral content is the clear choice.

• If the focus is on long-term engagement and community retention, Ben’s Bites’ interactive, hands-on approach is more effective.

Monetization

Rowan monetizes at multiple touchpoints, ensuring steady revenue growth from both advertising and premium content.

• Sponsorships
  Seamlessly integrated ads that are cleanly placed within the content, making them feel like a natural part of the newsletter.

• AI University ($999/year)
  A premium educational platform with more than 5,000 paying members, offering deep-dive AI courses.

• Exclusive partnerships and interviews
  Rowan’s credibility—boosted by interviews with AI leaders like Mark Zuckerberg—enhances The Rundown AI’s value for sponsors and advertisers.

Ben’s Bites: Knowledge Monetization Over Ads

Ben takes a different approach, prioritizing education and community-driven revenue over heavy advertising.

Rather than turning every relationship into a financial transaction, he offers affordable, one-time payment options that ensure accessibility while building long-term trust.

• Pro Membership ($175/year, often discounted)

• Lifetime Membership ($228, often discounted)

And the results? While The Rundown AI has 5,000 paying members, Ben’s Bites has surpassed 20,000 lifetime and annual paid members.

• AI Tutorial Database (Freemium Model)
  Includes more than 450 tutorials, with a mix of free and paid content, allowing users to try before they buy.

• Minimal sponsorships
  Unlike The Rundown AI, Ben limits ad placements and focuses on product-based revenue.

Key Differences

• The Rundown AI follows a traditional media monetization model, leveraging ads, sponsorships, and high-priced premium content.

• Ben’s Bites operates more like an education business, with affordable one-time or low-cost membership fees, tutorials, and community learning.

Which Model Works Best?

• If your goal is high-scale media revenue through sponsorships, premium content, and partnerships, The Rundown AI is the model to follow.

• If you prefer monetizing through learning, memberships, and deep audience engagement, Ben’s Bites provides a strong alternative.

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