Today we welcome Lenny Rachitsky to Making Media. Lenny has built the biggest business publication on Substack, "Lenny’s Newsletter," with well over 500,000 readers. It started in 2019 as an advice column and since starting the newsletter, he has built a thriving podcast, community, and job board. Lenny’s world has become the destination for product and growth people at companies big and small across the world.

We explore his journey, the strategy behind his products or SKUs as he calls them, and we delve into his mindset which is particularly unique for someone who has been this successful at building an audience. I hope you enjoy our conversation with Lenny Rachitsky.

For the full show notes, transcript, and links to the best content to learn more, check out the episode page here.

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Show Notes 

(00:01:53) - (First question) - How Lenny tackles challenges through research, delivering actionable insights

(00:05:04) - Juggling weekly and long-term posts, correlating effort to engagement

(00:08:01) - How his varied experiences shaped his online content journey

(00:11:54) - Maintaining relevance by advising companies & addressing problems

(00:13:34) - How he aims to sustain his content creation without corporatizing

(00:16:53) - Quantifying podcast success monetarily and by growth

(00:19:43) - Evaluating post quality and striving for non-obvious, surprising connections while maintaining brevity

(00:23:37) - Emphasizing stakes to underscore a topic's relevance

(00:24:39) - Maintaining simplicity by avoiding empire-building, utilizing contractors, and focusing on core offerings

(00:27:28) - Starting small and curating members while maintaining quality controls for community growth

(00:29:47) - Engaging active supporters and notable individuals for a self-sustaining community

(00:33:16) - Utilizing the 'Jobs to be Done' framework to better serve readers

(00:38:37) - Why some topics resonate more than others

(00:41:17) - How Lenny’s Newsletter drives engagement and distribution across platforms

(00:44:26) - Appreciating Substack's simplicity and audience growth

(00:48:00) - Debrief