When your side project becomes your full-time job: Lenny Rachitsky on making a living from a newsletter

In late 2020, we hosted a lively with Lenny Rachitsky, creator of the wildly popular Lenny’s Newsletter. Once a product lead at Airbnb, Lenny now makes a living off his Substack — and he joined us to share what he's learned about building an independent business through content, audience trust, and staying curious. While many attendees were senior operators considering newsletters of their own, this session offered universally relevant wisdom on creating value, setting boundaries, and doing work that lasts.

If you’d been there, here’s what you’d still be thinking about:

It’s easy to start a newsletter. It’s hard to keep going.
Starting is a few clicks — what matters is sustaining it. Lenny stressed the importance of writing about what you are genuinely curious about. That’s the only way you’ll stay engaged week after week. “If it feels like a job, you’ll quit,” he said.

You’re probably underestimating how much you know.
After leaving Airbnb, Lenny worried he had nothing unique to say — but quickly realized even “basic” insights were novel to many readers. “Don’t take for granted what you’ve learned,” he urged. It turns out your lived experience is valuable content, especially if it’s honest and practical.

Newsletters are startups. Start with product-market fit.
Writing is like building a company: you’re testing hypotheses, delivering value, and adapting fast. But the bar for “value” is high — Lenny classifies it into five types: entertain, inform, help people make money, make them smarter, or make them feel part of something bigger.

There’s still so much room.
Despite the boom, the newsletter market is far from saturated. “There’s almost no competition for many high-quality topics,” Lenny said. “There are a thousand niches, languages, and interests that no one is covering well yet.”

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