How I Improved My Product Management Skills Using Lenny Rachitsky's Newsletter + Adviserry

I've been subscribed to Lenny's Newsletter for over two years. It's probably the best product management newsletter in existence. Incredible guest interviews, detailed frameworks, real numbers from real companies.

I've also forgotten approximately 95% of what I've read.

I remember vibes. "That episode with the Figma guy was good." "Lenny had a guest who talked about onboarding metrics, I think." Vibes don't help when you're staring at your own product's onboarding funnel trying to figure out why people drop off at step three.

So I ran an experiment. I loaded Lenny's entire newsletter archive (plus his YouTube podcast episodes) into an Adviserry Board and spent a week using it as my product management advisor. Here's what happened.

The setup took five minutes. Created a "Product Management" board, added Lenny's newsletter from my Gmail scan, added his YouTube channel. Imported historical issues to get the full archive. After processing, I had something like 200+ newsletter issues and hundreds of video transcripts, all searchable and chat-enabled.

Day 1: I asked about onboarding. "What does Lenny say about improving onboarding for SaaS products?" The response pulled from four different newsletter issues and two podcast episodes, each covering a different angle on onboarding. Specific metrics to track (activation rate, time-to-value), frameworks from guest experts, and real examples from companies like Notion and Figma. In one query, I had more actionable onboarding advice than I'd gathered from months of vaguely remembering "that good onboarding episode."

Day 3: I asked about user retention. "What frameworks from Lenny's content apply to improving retention for a subscription product?" This is where cross-referencing gets interesting. The AI pulled together Sarah Tavel's hierarchy of engagement framework, Casey Winters' take on retention curves, and Lenny's own writing about measuring and improving retention. Each from different issues, synthesized into one answer. I would never have connected those three pieces on my own because I read them months apart.

Day 5: I asked about feature prioritization. "How should I prioritize what to build next? What do Lenny's guests recommend?" This pulled from episodes with product leaders at Airbnb, Spotify, and Replit, each sharing different prioritization frameworks. The RICE framework, the "what would make users love this?" approach, and the "solve one problem really well before expanding" philosophy. Having multiple perspectives on the same question, all from credible sources, made me think about prioritization differently than I had been.

What changed in my product thinking:

I stopped making product decisions based on instinct and started making them based on referenced frameworks. Not because my instinct was bad, but because "let me check what the experts say about this specific problem" takes 30 seconds and often reveals angles I hadn't considered.

I started noticing patterns across multiple experts. When three different product leaders all say the same thing about activation metrics, you pay attention differently than when you read it once and forget it.

I got more specific in my product analysis. Instead of "our onboarding needs work," I started saying "our time-to-value is too long and we're losing people before they hit the activation event, which based on Lenny's framework should be [specific action]." Same problem, much better framing.

The meta-lesson:

I was subscribed to one of the best product management resources on the internet for two years. The knowledge was already in my inbox. I just couldn't access it when I needed it.

The gap between subscribing to great content and being able to use that content is massive. Adviserry closed that gap for me, not by replacing Lenny's newsletter (I still read it when I can), but by making the entire archive available on demand.

If you're a founder or PM who subscribes to product content and finds yourself thinking "I know someone smart wrote about this exact problem but I can't remember the details," that's the gap this fills.

The advice is already in your inbox. You just need a way to find it.