Newsletter & Email Growth: Growth In Reverse

This Newsletter Sold For $150m (And Why It Matters)

31 snips

Oct 15, 2025

This discussion kicks off with Bari Weiss's jaw-dropping $150M newsletter sale, shedding light on the evolving landscape of digital media. Discover how newsletters can act as impressive career portfolios, potentially leading to enticing job offers. Gamification takes center stage with The Assist's innovative engagement game, plus insights on leveraging LinkedIn's competitive features. The hosts dive into effective referral strategies and the importance of mastering one of the Big 3 media platforms. Finally, they explore how video content can dramatically enhance reach for creators.

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ANECDOTE

Game As Engagement Hook

The Assist launched Workle, a Wordle-like game, to drive site visits and brand engagement.
Games like Workle can hook readers and increase regular interactions with a newsletter brand.

INSIGHT

Competition Fuels Retention

Leaderboards and streaks turn casual play into competitive retention loops that boost habit formation.
LinkedIn's puzzles show competition and streaks increase daily engagement and retention.

ADVICE

Use Tiny Interactive Hooks

Be creative with simple engagement mechanics like buttons or prediction games to prompt replies and repeat opens.
Use tiny interactive hooks to drive readers to open future issues and stay involved.

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The Growth Vault is LIVE: Chenell's brand-new offer for newsletter creators is here—filled with newsletter templates, growth strategies, and real examples you can implement at your own pace.

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“If you’re not exceptional at one of the Big 3 — it’s impossible to build a content business.” — Dylan quoting Matt McGarry

We're sharing the biggest stories, trends, and lessons from the newsletter space over the past few weeks.

From Bari Weiss’s $150M Substack newsletter sale to gamified engagement strategies and the rise of YouTube as the new discovery channel, we're unpacking what these moves mean for creators and operators running newsletters today.

KEY TAKEAWAYS

What the $150M acquisition of Bari Weiss's The Free Press proves about newsletters.
How creators can reverse-engineer their dream roles or acquisition partners.
The game that The Assist launched to boost engagement & reader affinity.
What LinkedIn’s games can teach creators about streaks, competition, and retention loops.
A referral program so smart it practically funds itself.
The "Big 3 Media Strategy” that should reshape your content marketing.
The #1 fear that's holding back most newsletter creators.

LINKS MENTIONED

The Free Press by Barri Weiss
News: CBS parent company Paramount Skydance buys The Free Press
Workle by The Assist newsletter
The Dink Deep Dive (via GIR)
The "Big 3 Media Platforms" article via Matt McGarry
Get Chenell's brand-new offering for newsletter creators: The Growth Vault — newsletter templates, growth strategies, and real examples you can implement at your own pace.
Want your newsletter roasted? Submit it here.
Ask us a question or submit a podcast topic idea: growthinreverse.com/questions
Check out past Growth In Reverse Deep Dives: https://growthinreverse.com/archive/

FOLLOW ON SOCIAL

Chenell: Twitter | LinkedIn | Substack
Dylan: LinkedIn | Bluesky

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