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Show Notes

(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