The Platform Rewriting Digital Media's Playbook To Reboot The Creator Economy
How Substack's writer- and reader-first strategy empowers creators like Lenny Rachitsky to outperform legacy media stars
How does an unemployed product manager with a single viral Medium post to his name go from nothing to over $1 million in yearly revenue?
When Lenny Rachitsky republished that Medium post as his first Substack newsletter in 2019, he was neither a famous journalist nor a bestselling author. Six years later, he earns more from his newsletter and related businesses than multiple New York Times and Wall Street Journal opinion writers combined.
This remarkable transformation isn't just one creator's lucky break.
It demonstrates how Substack's strategic choices have designed a creator economy where value flows directly between creators and their readers, creating a total reset of the digital media playbook.
From Crass to Crafted
By optimizing for pageviews, clicks, and advertising sales, online publishing has made readers the “product,” and turned the online reading experience into a cluttered nightmare.
You could compare the current state of online publishing to an all-you-can-eat Vegas buffet – flashy, overwhelming quantities of mediocrity that leave you at once both stuffed yet unsatisfied.
Amid this wasteland, Substack, by contrast, represents something entirely different: a farm-to-table restaurant where the chef knows your name, serves exactly the kind of food you love, prepared with care. And when the bill arrives, you feel the experience was worth every penny.
Creator-First
By flipping conventional media priorities, Substack is winning by optimizing for engagement, reader advocacy, and two-way, value-based monetization without the need for massive scale.
To understand how Substack's approach enables creator success, let's look at how one burned-out product manager transformed a few long-form pieces into a seven-figure media empire.
It’s a journey that beautifully illustrates what can happen when strategic platform choices align to build a special bond between creators and their readers.
From "Lenny Who?" to Substack's Product Management Superstar
After Airbnb acquired his “Localmind” check-in tech company, Lenny Rachitsky spent seven years at the vacation rental startup as a Product Lead before leaving, exhausted by the grind of startup life.
Lenny distilled the lessons he learned helping to build Airbnb into the world’s biggest hotel chain 2019 in a heartfelt Medium post that gained extraordinary traction with over 30k likes. After writing a few other Medium pieces, Lenny was unsure whether to do another startup or pursue writing.
He moved to Substack in 2020 because regardless of his next move, he knew he'd need to own his email subscribers.
Making the Ask
After his first Substack series on product advice did well, Lenny took a leap of faith and introduced paying subscriptions in April 2020, at the height of the pandemic.
That initial bet on direct monetization turned out to be just the beginning. As his audience grew, Substack's evolving platform capabilities allowed Lenny to gradually transform his simple newsletter into a multi-channel media business that would make traditional publishers jealous.
And he did it all without technical expertise, employees, or massive capital outlay.
Feature-Driven Expansion
Each new platform feature Substack added allowed Lenny to further expand and diversify his media business portfolio:
Podcasting: His podcast featuring product management superstars quickly hit 10 million downloads, ranking on Spotify and Apple's top charts
Video: Repurposed podcast content gained tremendous traction on YouTube
Recommendations: Once Substack launched Recommendations, as much as 80% of Lenny's new subscribers began arriving through it
Community: A Slack community with local meetups and daily engagement grew to over 20,000 people globally
These features, combined with Lenny's unique skill in product management, skyrocketed his subscriber growth from just 6,000 in 2020 to over 1 million today.
I've tracked dozens of creator journeys and have never seen growth curves like this outside of venture-backed startups. What makes this truly extraordinary is that Lenny did it as a "solopreneur" without raising a single dime.
For context, star opinion columnists at major news outlets like Paul Krugman, Maureen Dowd, and Thomas Friedman earn between $250,000 and $500,000+ annually.
Lenny's newsletter alone generates over $1,000,000 yearly, and that represents just part of his seven-figure income.
Substack's Strategic Choices Through the Strategy Choice Cascade
To fully appreciate how Substack is enabling creators like Lenny to succeed, I’ll lay out its contrarian choices using Roger Martin's "Strategy Choice Cascade."
It provides the perfect lens to decode how Substack's decisions create a mutually- reinforcing ecosystem where writers can thrive while readers are delighted to pay for writing crafted exactly for their needs.
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