Lenny Rachitsky - The Dark Side of Paid Newsletters Nobody Talks About - The Nathan Barry Show 022

Lenny Rachitsky, who sold his company to Airbnb and later worked there as a product manager, discusses his transition to becoming a successful newsletter writer with over 3,200 paying subscribers. Rachitsky shares how he started his newsletter, "Lenny's Newsletter," as a side project while planning to launch a startup, and how it eventually surpassed his tech job income. He emphasizes the importance of creating high-quality, valuable content, noting that efforts like Twitter ads and referral programs had minimal impact compared to providing consistent value. Guest posting on established blogs like Andrew Chen's and First Round Review initially helped him gain subscribers. He also highlights his writing process, which involves mapping out ideas three months in advance and balancing different content types to cater to a broad audience.