022: Lenny Rachitsky - The Dark Side of Paid Newsletters Nobody Talks About

The Nathan Barry Show

Lenny Rachitsky sold his company to Airbnb years ago and he spent a bunch of time there as a product manager, working on growth.

Now Lenny’s full-time job is his simply-titled “Lenny’s Newsletter”, where he shares everything he’s learned about building products and teams. With over 3,200 paying subscribers, Lenny’s Newsletter brings him a larger income than he had at his tech job!

In this fun interview, Lenny shares his journey—how he went from wanting to found another startup to being a one-man newsletter business, and the lessons he’s learned along the way.

You’ll learn the “value-add” for a paid newsletter that’s been a great success for Lenny, and how he’s avoiding the trap of workaholism as he builds his business.

Lenny also shares how he never runs out of topics, and how he stays interested and curious so he can enjoy running his newsletter for years to come.

Plus, as popular as paid newsletters are, they come with some important downsides! Lenny reports from the trenches on what they are and how to deal with them.

Links & Resources

• Airbnb
• Coda - A new doc for teams.
• Why a Paid Newsletter Won’t Be Enough Money for Most Writers (And That’s Fine): The Multi-SKU Creator - Hunter Walk

Lenny Rachitsky’s Links

• Sign up for Lenny’s Newsletter
• Twitter: @LennySan
• LinkedIn: Lenny Rachitsky

Episode Transcript

Lenny: [00:00:00]
I find there’s any time not spent creating high quality content is not time well spent over the long run. It’s all about just valuable content. You know, if you provide value to people, they’re going to want it and they’re going to subscribe and follow and pay.

Nathan: [00:00:18]
Today’s interview is with Lenny Rachitsky. Lenny’s company was acquired by Airbnb more than seven years ago. He spent a bunch of time at Airbnb as a product manager, working on growth, where he became fascinated with things like, how do you manage a team? How do you grow a company? What are the product management best practices?

All of these things after leaving Airbnb, he started a newsletter just called Lenny’s Newsletter, and it now has over 3,200 paying subscribers. he’s now earning more from his newsletter than he was at his tech job. Quite a bit more actually. And we get into so many things, but how to keep writing newsletter really fun, how to grow and scale your audience using guest posts to get those first subscribers so much good stuff.

Let’s dive in. Lenny. Thanks for joining me today. Thanks for having me. So you actually kicked off our call and kind of a fun spot. So I want to start the interview there. And that was, you just said, so did you read the New Yorker article, you know, and, the New Yorker just did another article about newsletters.

Why don’t you give us a high level? Cause it kind of takes us into the state of newsletters, you know, on the web right now.

Lenny: [00:01:28]
Oh, so I find, I generally try to avoid pontificating on the state of media and newsletters, because I feel like that’s not my depth. There’s a lot of newsletter writers that like come from media, I’ve thought about, you know, this whole space of newsletters for a long time.

And it’s fun to think about it and talk about, and, and tweet about sometimes. But yeah, I don’t have the most thorough opinions of the whole industry, but. What I find is when people do this kind of like overview of what’s happening, it’s always this interesting combination of like, Oh, here’s all the good elements.

People can write whatever they want. And they have freedom. They’re running their own business and creating their own kind of life. And then there’s like, Oh, but all these dangers, what are they, what’s going to happen? They need health insurance. And how do we moderate all these folks? And who’s going to win.

And how do you, how do you not create this? Just like 1% that does well. And so, so the post is kind of essentially going through a bunch of stories of all those things happening. And I think the conclusion as always, as it’s complicated and there’s good and bad end, we’ll see where it all goes.

Nathan: [00:02:32]
Yeah.

It’s been fascinating to watch how the landscape has changed over the last, you know, seven or eight years since I’ve been working in this space. But you know, particularly the last say 18 months as Substack has gained a ton of traction. I think a lot of people, this is kinda what I want to talk about next.

Who maybe in the past would look at newsletters and go, that’s an interesting business. Like that’s a thing. Maybe that’s your lifestyle business. I don’t know I’m going to go do a startup, you know? that was all the mindset. And now

Lenny: [00:03:05]
that’s exactly what I did. That was my whole plan is start a company.

And then I started this newsletter on the side just to like play around with something and magically, it turned around and the newsletter became the main thing that I do.

Nathan: [00:03:16]
Yeah. So let’s talk about that more. Cause you spent what? Seven, eight years at Airbnb working on, on growth and product management. and so I’d love to hear, well, let’s see, let’s talk about just the transition out of Airbnb and then what was next?

Lenny: [00:03:34]
Yeah, so I left Airbnb about a year and a half ago. Last March. I was there for seven years, sold my company to them and. My plan a, when I left, first of all, I had no real plan. I was just like, I need to, I need to do something different. I need to move on to some new, and so plan a was, likely start a company again.

Plan B was maybe do some advising consulting plan C was maybe join a startup plan. D was maybe join a big company. And now are on those lists of plans that I have make a living off writing a newsletter. But what started happening is I first started collecting my thoughts of what I learned at Airbnb and things I’ve done in the past, just so that I don’t have to relearn them.

When I start a company is I put out medi posts and that did shockingly well, and then I put out a few more medi posts and those did well. And then somebody suggested I switched to sub stack to, you know, to the classic reasons to have your newsletter it’s own your audience, to not give all the benefits and medi and those kinds of things, which we can talk about.

And that just kept going well. And it was always a side project that everyone around me was like, okay, stop this writing thing you’re doing. And you really want to do a startup. You should really focus on that. And just spending so much time writing, what are you doing? But I just kept doing it cause it was interesting and fun and people seem to value it.

And I had a good conversation with a friend, maybe six months into it. And his advice was okay, this seems to be working well. People seem to value it. You seem to enjoy it. Maybe just try that for a little while longer. And don’t put all this pressure on yourself to st...