How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky

Today my brilliant wife, Michelle Rial, flips the script and interviews me. I go more personal than ever, we talk about her new children’s book, Charts for Babies, and the timing’s perfect because it’s also her birthday—so yes, please pre‑order it; this was special, let’s dive in.

You launched your newsletter in 2019 and now it’s huge. If you hadn’t started it, what do you think you’d be doing?

I’d probably have tried a startup, struggled, then ended up a PM somewhere. When I left Airbnb after seven years my plan had zero writing in it, but I kept feeling pulled to share what I was learning, even when it didn’t make obvious sense.

Was there a single turning point, or a string of moments, that made you go all in?

It was a chain: my first Medium post unexpectedly took off and even got shared internally at Airbnb; a friend told me to lean into the rare overlap of what I enjoy and what people value; after nine straight months of weekly posts on Substack I used the Lindy idea—if I’ve kept it up this long, I can likely keep going—to add a paywall. Then COVID hit, I needed income, turned it on, and it worked.

Do you still love it?

I do—writing about ideas and extracting lessons is deeply fulfilling, but the weekly cadence is a relentless treadmill that always asks, what’s next. Long term is a question mark, yet I can’t imagine work that fits me better right now.

You don’t seem stressed—are you actually calm, or just good at hiding it, and what helps?

I’m calmer than average but feel more stress than I show, and mindset work helps me not escalate everything. A positive‑psychology course taught me you can raise your happiness baseline with optimistic thinking, and exercise helps pull you out of the lows.

A pivotal moment was a Joshua Tree trip where, on psychedelics, a clear mantra surfaced that I did have something worth sharing; that confidence carried me into writing.

Let’s do a quick thunder round on your misophonia—what is it, and what sounds spike it?

It’s a real sensitivity to certain sounds. Close‑up chewing is by far the worst, baby cries can hit hard, and a blaring leaf blower wrecks focus, while nails on a chalkboard oddly bothers me less.

Your charts get shared everywhere, sometimes without credit—why do you think they spread like wildfire?

I stopped chasing credit because it’s not useful; the hits land when they’re simple, instantly clear, and make me laugh or tear up even after I made them. Short attention spans reward quick emotional punches, and sometimes a phone photo of a page goes viral before the polished file ever does.

I feel the same way about my posts—if it’s compelling to me first, it’s usually right—though I sometimes push you to trim layers when an idea gets too clever. Where do your ideas come from?

Living and noticing—meditation helps me observe my thoughts, but if I overwork and stop living, ideas dry up. Children’s concepts are a different lane, yet the raw material still comes from real life.

My first kids’ book started with new‑parent observations; I literally flipped to the back of my notebook and followed the pull toward writing in rhyme.

Following the pull matters. Quick detour—people ask about my name: is it Leonard?

Yeah, give us the origin story, reverse‑nickname and all.

I was born Leonid in Ukraine; when we moved to the U.S., my parents Anglicized it to Lenny. No Leonard, just Lenny.

How do you feel when strangers come up to you now that the podcast is big?

It started after the podcast and still feels surreal, but I love when people say hi and tell me their favorite episode; once a dad literally stopped his red car to shout his love for the show. If you see me, please say hello.

You also have a bit of faceblindness, which makes that tricky.

Names and faces are hard for me, so if I blank, it’s me, not you—thanks for the grace.

Looking back, were there early clues you’d end up a writer?

Not really—I’d never written online and preferred staying behind the scenes. I did build side projects though, like an atheist news aggregator, a user‑made tutorial site, and Localmind, a location Q&A startup we sold to Airbnb.

Do you miss office life now that you work solo?

I love the independence but sometimes miss jamming with someone at the same table, and I’m careful not to scale into a job I’d resent. Keeping a lightweight setup helps me protect the work I enjoy.

Share a time you were truly stressed in business, and one in your personal life.

Business: a Product Pass promo triggered coordinated fraud waves, so we worked with Stripe and Substack to plug exploits while my engineer barely slept; it was a scary, reputation‑at‑risk week. Personal: during our child’s birth the anesthesia went the wrong way and they rushed to intubate you, and I paced the hall repeating it would be okay until I knew you both were safe.

What environment lets your charts flow best? I’ve noticed coffee is part of the ritual.

I need the exact right dose of caffeine—a single shot—and a real but short window, like two hours; good sleep is non‑negotiable. Too much coffee makes the ideas manic instead of clear.

I jot seeds as they come and translate them into the simplest visual I can; my brain likes patterns thanks to a very math‑y upbringing.

The best work comes from lived experience and ruthless iteration. You’ll often park drafts and return with a better angle, while I’ll refine a newsletter dozens of times before it ships.

Okay, define product management in five words—and you can’t say mini‑CEO.

Think impact, collaboration, judgment, and alignment; in plain words, it’s delivering outcomes by choosing and solving the most important problems. Great PMs think like owners of their slice of the business.

Has any of that carried into parenting?

Influence and clear communication help at home too; I’ll set a simple system for bedtime with stars and steps, and I lean on proven playbooks more than gut feel.

Why pivot to children’s books after two adult titles?

Charts teach core early concepts—opposites, size, direction, color mixing, even feelings—so it felt natural once we read a mountain of kids’ books and I was watching our son learn; the first draft poured out, and a feelings book is already finished for next year.

That’s the through‑line today: do the thing, then distill what’s true from experience.

You can find me at michellerial.com and a bit on Instagram. I hope you and your kids enjoy Charts for Babies.

This was an A‑plus—going to do numbers. Thanks for listening; subscribe on your favorite app, drop a rating or review, and find past episodes at lennysPodcast.com.