Lenny's Time Capsule

The Idea Behind This

Lenny Rachitsky did something cool -- he opened up transcripts from 263 episodes of his podcast and asked people to build something with them. Claire Vo cleaned up all the markdown, and suddenly there was this goldmine of product wisdom sitting in a GitHub repo.

I saw the challenge and had an idea: what if you could describe your situation -- where you are in your career, what you're struggling with -- and get a personalized letter from the leaders who've been there? Not a generic AI summary, but something that feels like advice written specifically for you, grounded in what these people actually said.

How It Works

Describe Your Situation

Complete the sentence: "I'm a [role] who just [situation] and I'm struggling with [challenge]." Be specific. The more honest you are about where you're at, the more relevant the letter. It searches through all 263 episodes to find leaders who've navigated similar moments.

Get a Personalized Letter

The letter pulls from real advice these leaders have shared on the podcast. It's grounded in what people like Shreyas Doshi, Shishir Mehrotra, and Ravi Mehta have actually said about navigating similar challenges — not made-up platitudes.

Wisdom From People Who've Been There

There's something powerful about getting a letter addressed to you from someone who struggled with the same things you're facing. It's a reminder that the people you admire have been exactly where you are.

Why I Built This

Honestly? Lenny's challenge was just too fun to pass up. I'd been listening to his podcast for years and always thought the best moments were when guests got vulnerable about their struggles. Having all those transcripts available made it possible to turn that scattered wisdom into something personalized.

Plus, after years in product, I've had plenty of those "am I even good at this?" moments. Would've been nice to get a letter from someone who made it through.

Privacy

Your situation description is sent to an AI to generate your letter. I don't store your inputs or the letters generated. The tool doesn't require any account or login.