Making Media
Episode 42 The Power of a Newsletter
Making Media

Episode 42: The Power of a Newsletter

Making Media

Episode 42

The Power of a Newsletter

Lenny Rachitsky is the founder and author of Lenny’s Newsletter. We cover the strategy behind his media offerings, why he doesn't want any employees, and how he's built an audience of 500,000 people.

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(00:01:13) - (First question) - How he tackles challenges through research, delivering actionable insights
(00:04:24) - Juggling weekly and long-term posts, correlating effort to engagement
(00:07:21) - How his varied experiences shaped his online content journey
(00:11:14) - Maintaining relevance by advising companies, addressing problems, and drawing from a variety of lessons
(00:12:54) - How he aims to sustain his content creation without corporatizing
(00:16:13) - Quantifying podcast success monetarily and by growth; emphasizing quality content to overcome growth plateaus
(00:19:03) - Evaluating post quality and striving for non-obvious, surprising connections while maintaining brevity
(00:22:57) - Emphasizing stakes to underscore a topic's relevance
(00:23:59) - Maintaining simplicity by avoiding empire-building, utilizing contractors, and focusing on core offerings
(00:26:48) - Starting small and curating members while maintaining quality controls for community growth
(00:29:07) - Engaging active supporters and notable individuals for a self-sustaining community
(00:32:36) - Utilizing the 'Jobs to be Done' framework to better serve readers
(00:37:57) - Why some topics resonate more than others
(00:40:27) - How Lenny’s Newsletter drives engagement and distribution across platforms due to its shareability
(00:43:46) - Appreciating Substack's simplicity and audience growth
(00:47:20) - Debrief

 

The Power of a Newsletter

Introduction

Dom
Welcome back to Making Media. I am delighted to be back, and I'm really excited to bring you this conversation with Lenny Rachitsky. Lenny has built the biggest business publication on Substack with well over 500,000 readers, that is 0.5 million readers, is called Lenny's Newsletter and was started in 2019 as an advice column after he had left Airbnb, where he had been for the previous 7 years.

Since starting the newsletter, Lenny has built a thriving podcast community and job boards go with it. And there really isn't hyperbole to say that Lenny’s world has become the destination for product and growth people at companies big and small across the world. Matt and I 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 and stick around at the end for my debrief with Matt.

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