#57 / The $200 Newsletter That Blew Up Tech Twitter
How Lenny turned a couple of emails into a $16000 AI toolbox
Last week my feed went absolutely feral: Lenny Rachitsky dropped a pay‑once bundle for his newsletter. Fork out $200 and you walk away with a year of Cursor Pro, Notion Plus, V0 and a stack of other top‑shelf AI tools—total sticker price around $15 000.
First reaction across X (formerly Twitter): “This can’t be real, right?”
Second reaction: “Wait—who on earth is Lenny, and how did he negotiate a discount large enough to make Black Friday blush?”
I smashed the subscribe button before my coffee went cold and, predictably, vanished down a research rabbit hole. Here’s what I found—and why it matters if you’re trying to build your own thing.
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Who is Lenny, anyway?
His story starts at Airbnb.
Lenny spent seven years there as a product lead after Airbnb acqui‑hired his own start‑up. In 2019 he left with a plan to found another company, but first gave himself six months of “free‑range exploration”.
The light‑bulb moment? He realised writing energised him far more than corporate product roadmaps. A small, obvious insight—yet it changed everything.
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The Medium post that accidentally went viral
Soon after quitting, Lenny tossed a casual article on Medium: Seven things I learned in seven years at Airbnb. No growth hacks, no SEO wizardry—just honest reflections.
Thirty thousand claps later, Airbnb’s CEO had shared it with the entire company, and Lenny had proof the market liked what he loved creating. VC friend Andrew Chen nudged him: “When passion and demand overlap, double down.” Lenny listened, ditched Medium, and launched his own newsletter. He even retro‑fitted a signup link at the bottom of that old post—one tiny tweak that netted his first hundred die‑hard readers.
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The engine: weekly, reader‑driven content
Every Tuesday, without fail, Lenny publishes one deep‑dive that solves a real reader problem. He keeps a monster question bank and picks the topic he’s personally curious about that week. Result: pieces that feel alive rather than AI‑flavoured porridge.
Then he repurposes. Long‑form essay becomes a Twitter thread; each thread tags the heavyweights mentioned inside—founders, PMs, angels—so amplification happens on autopilot.
But the true rockets are his research specials: months interviewing execs from Uber, Zillow and crew about growth mechanics. When those multi‑chapter investigations land, subscriber counts double in a fortnight. His mantra is brutally simple: ship high‑value work, consistently.
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OK, but how did he wrangle $15 k of software for $200?
Once you’re known for delivering gold week after week, doors open. Founders of V0, Cursor, Superhuman, even OpenAI’s CPO—these are regulars on Lenny’s podcast. At that relationship altitude, cooking up a ludicrous‑sounding bundle suddenly isn’t ludicrous at all.
High‑value network → high‑value deals → snowballing audience. The flywheel turns because the content made the introductions in the first place. Lesson noted.
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Why this hits home for me
I’m basically standing where Lenny stood in 2019: moving on from a tech role, mid‑exploration, wondering what my next chapter looks like. His path reminds me the playbook isn’t mysterious:
1. Start creating now.
2. Publish where people can see you.
3. Let one breakout piece pull you into an entirely new orbit.
None of it happens unless you push that first scrappy draft into the wild.
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Try it yourself
Feeling stuck? Draft something today—an article, a sketch, a two‑minute video—and post it. You genuinely don’t know which “small” piece changes your trajectory.
And if you’re curious how powerful a newsletter can get, check Lenny’s out. While you’re at it, subscribe to mine; one day I’d like to drop a bundle that melts the Internet too.
👉 Lenny's Newsletter：https://lennysnewsletter.com
👉 Bear's Newsletter：https://beardesign.substack.com
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See you in your inbox.
— Bear
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Claude.ai
Hello, I’m Bear—a product designer, UX mentor and an award‑winning bilingual podcast host, currently living in Auckland, New Zealand. I enjoy sharing insights from my work, life, and study, helping all of us grow together.
Bear Academy Newsletter is my weekly email packed with thoughts on technology, design, and productivity—featuring book breakdowns, learning tips, and career reflections.
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