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
- 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
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.
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.
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.
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
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.
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?
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 start a company now. And so I did that and it just kept growing.
And eventually, this year actually around COVID beginnings of COVID, it was like a year since I left my job. I had no income. I didn’t know what I was going to do. All my stock is down. I didn’t know how I was going to make money again. And so I decided, let me try this pate version of the newsletter and.
And that kind of took things to the next level. And now we’re here where I’m making a lot more than I made it Airbnb. And I don’t have any future plans beyond this.
Yeah. So did you, figure out what the start-up was going to be, or was it still, you were playing around with ideas and the newsletter was a playground to try out or to like think through some of the things you were considering.
Newsletter is more of a playground of collecting things that I’ve learned that I wanted to crystallize, you know, as they say, I don’t know what I think until I’ve written it down. And I was, it was an excuse to crystallize things that I’ve learned over the past. but in terms of the startup, I had, I had a spreadsheet of 50 ideas that I was working through one by one prototyping, asking friends, trying to research them.
So as, as, as I went through like 10 of them, by the time I stopped. And, none of them, none of them really stuck. That was part of it is I didn’t find anything that was, “Oh shit! I really need to stop everything and do this thing.” if I, maybe if I had it, it would have been some different, but startups are hard.
It’s like a hard life to pursue. And so I’m happy not to do that right now.
They are. They’re very hard. And especially that, I don’t know those first two years or three years, you know, before it gets a team in moment it. It just it’s really hard. So, so at that initial traction, that point where you’re like, Hey, this is working.
What were those signs that you look for? How was it a nber of subscribers or was it just moment a rate of growth? What was it?
I’d say early on, it was very qualitative. I just kept getting these really nice messages from people about how valuable some of the stuff I’d written had been. So is that plus continued growth.
People just continue to subscribe and come back and not unsubscribe. That was a good sign. and then, yeah, I guess it was those two things, qualitative feedback and just growth continue to happen, even when I wasn’t doing anything. And also the feedback was coming from really smart, successful people that I really respected, so that added to it.
So those things, I think what’s interesting about that is that. It has you focusing on the quality of the content rather than the results.
Absolutely. That’s what I find over and over again. Anything that I do, that’s not just create high quality content does very little for the success of the newsletter.
I find there’s any time not spent creating high quality content is not time well spent. I just keep finding it over and over. I tried like Twitter ads. I tried a referral program. I tried, cross-promotion across newsletters and none of that really did anything. Although initially there were some things that, that I did that were really impactful to help jpstart it, which we could talk about.
But, but over the long run, it’s all about just valuable content. And, you know, it’s like if you provide value to people, they’re going to want it and they’re gonna subscribe and follow and pay. So the more you could just provide value, the more successful you’ll be. And that’s what I keep finding.
When I think another thing in that is.
The type of people that you’re writing to. So you’re looking at a lot of that qualitative feedback was from people that you really respected, you know, whether it’s industry peers or others. And I find that when I’m writing to someone, who’s one of my peers, the quality of my writing is so much better. If I even have this in mind of like, okay, this didn’t happen, but let’s say this person asked me for advice on how to get your startup to your first 5 million ARR.
You know, then if I write to them, it’s just better. Right. And then I think like reading a lot of your early stuff and even the way that you write today, I get that feeling from it of like, Oh, this feels like it’s written to Lenny’s peers and his friends rather than from the place on high, where Lenny that, you know, Yeah, the startup expert is writing to the masses because it just, it comes through in your writing in a different way.
Yeah. And I think a lot of that comes from, I don’t know if insecurity is the right word, but I just, I don’t feel like I have the answers and I’m not the smartest, most successful person. And so my lens is how do I just give you on arguably correct advice that either comes from successful, smart people or a bunch of analysis over what’s worked or.
Or something like that. So, so the lens I use isn’t I know a lot of people and I like your framework of just like pick a person and a specific person in my end, right. To them. I use it more like a broad lens of if I’m like a founder reading, this is this like actually useful to me or is this just like a bunch of fluffy stuff?
That sounds nice that I can, I’m going to just forget immediately. And so I always come back to you as, as concretely. Actionably valuable immediately to somebody. And if it’s not, then I refine it further and cut out stuff. That’s not actually useful.
Yep. That makes sense. What were some of those things that worked for the early on that you were talking about to get the initial growth?
So, so I started, I started at zero is everyone starts with, and what I, the way I first launched the newsletter was actually on Twitter and kind of like, it kind of created this interesting back and forth between medi and Twitter and sub stack. So I wrote that first piece on medi and it got like featured by medi.
The, it was about Airbnb. What I learned at Airbnb, the CEO of Airbnb sent it out to the entire company and it got into this collection. So it just got a ton of use. And that led to some Twitter following. Somehow, they kind of found me on Twitter. And then as I was reading, you have much of a Twitter following.
Not really. I had, I had like a few thousand followers, something like that, which is not from
being on Twitter for
years and yeah, exactly. Yeah. Yep. Which is, you know, some people have less than a thousand, so that’s a different place to start. And I’ll also add, I’ve never like focused on Twitter followers.
I was just like, how do I share valuable things with people? Cause I just want to get it out of my head. And so that was, as I was writing these medi posts, I was also tweeting little nuggets of things that either were in that post or just couldn’t make it into a whole post. So I started just kind of doing both things, tweeting and medi posting and that built up the Twitter audience just because some of the stuff was proved to be really valuable.
And then when I launched the sub stack, I basically just tweeted out, Hey, I’m launching a sub stack newsletter. You should subscribe. I don’t know what it’s going to be at, but it don’t miss it. And so that got me to my first few hundred subscribers, just like tweeting about it. And I had maybe like 10,000 followers at that point, something like that.
And then, and then I did a couple of guest posts, one on Andrew Chen’s blog and one on the first round review. And that it’s a tweet Twitter. Plus those two got me to the first thousand, essentially. Plus in that time, maybe like 20 actual posts that were valuable enough for people, right?
Yeah. Is guest posting something that you would recommend for someone I’d
Yeah, I’d say initially when it’s early, for sure. Because if you think about just marketing anything, you just want to go to where your audience is. And if you can write something that in a place somebody already has that whole audience and. Show how awesome you are. They’re going to come follow you wherever you are.
So I find it, I found it to be super valuable, but you have to just pick the right blogs and newsletters and do a great job.
Yeah. That’s I mean, in the early days of my newsletter, maybe after I had it with 2000 subscribers, a thousand, 2000, somewhere in there, I started doing guest posting pretty heavily.
And it’s exactly what you said. Like some people think about guest posting as like, Oh yeah. Here’s this thing that. I wouldn’t put it on my blog, but sure. I’ll try to see if you want to run it. It’s not an effective strategy instead of you’re like, here’s the best content that I wrote, like, et cetera, writing one, an article versus specialty magazine, which is a web design
My wife’s been in that. Oh,
nice. Yeah, she’s a designer. Yup. and I read them a lot and so I wrote a post on product launches. That was 4,000 words, long, all kinds of detail, everything, you know, I tried to put as many real nbers in there as possible. And just try and be like, this is everything I’ve got, you know, and that post, I think got me, well, had a great call to action for like sign up for a free email course at the end that I had, like, here’s a ton of great value.
And then if you want even more like in the weeds, nerdy stuff, he, you know, he here’s even more. And that picked up like 2000 email subscribers from a single post, which at the time, you know, we’re like, 50% ground, you know, it’s, it’s pretty amazing to thousands of them a lot. Yeah. But even if at that stage, if you’re getting a hundred or, or 300, like that’s totally worth it.
Yeah. Similarly to the one I did with Andrew, I worked on it for like months. It was a 28 ways to grow supply in the marketplace. And I had like all these examples and, and quotes and all these things and I showed it to him cause we got to know each other a little bit on Twitter and he’s just like, and I republish this on my blog.
I’m like, Well, can I also publish it of mine? It’s like, let’s do a 24 hour exclusive. And it was a really tough call cause I was really proud of it as the best thing I’d written up to that point. But again, it, I think that’s why it worked because it was high quality.
Th the exclusive is interesting because it still gets out to your audience, but it leads over there.
yeah, they’re not, they’re not as into that. They don’t want you to republish it at any point.
Yeah. And the, I mean, they’ve got quite a content strategy and
yeah, they’re amazing. I’ll give you an editor. It’s amazing.
Yeah. So it’s guest posting something that you’ve continued to do, or is that more for initial traction and then just focus on your own property?
that a couple of times. I did a couple more first round pieces actually, now that I think about it, but it was more just, it felt good. It wasn’t. It didn’t really do much honestly directly, but you know, all these things add up. But what I find now is that now that I have a meaningful audience, I can promote other people through guest posts, which one people come to me to try to do that, which is really funny.
And then on the other hand, it saves me work because I get this amazing content from someone. Great. for a week because with a paid newsletter after right every week forever, and the more amazing pieces of content I can create that I don’t have to write myself the better. So, Oh, it was a balance obviously, but what I try to do is collect just like the best people in each field and have them write and definitive answer on a topic that people are asking me about.
And so it’s kind of flipped now, which is kind of interesting
when I think having the. Well, you, you basically set the bar for the content and then you’ve said, If anyone in the industry who’s really experienced can meet that bar or exceed that bar. Then I would love to have you. And then it’s, it’s not a like, Oh man, this article is not from lending this week.
It’s from some random person it’s instead like, Whoa, I can’t believe Lenny got this person to come on and share this level of detail.
Yeah. And here’s a rule of thb I’ll share is if someone reaches out to me to try to do a guest post. That automatically means they’re not going to do a guest post. I have to go reach out to them because I find that the people that I want to do the guest poster, often the ones that aren’t interested in doing one.
Right. Have you ever had, I had someone who reached out to you do a guest post that like met the bar for quality and was really good?
Not yet. Okay. I’m sure it’ll happen, but I wonder.
So I’m just spit balling here. I wonder, like I’m saying, if I were to pitch you on a guest post, like if I was listening to this and heard like Lenny doesn’t take outside pitches, if I were to be like, yes, but he hasn’t seen my content.
What I would do is I would pitch you with the entire article pre-written and I would say, okay, but. You know, what about this? Do you think that
would work? Oh, that would definitely work better because I find that once I get started with someone, it’s hard to just, if I find that it’s not great, it’s hard to be like, no, nevermind.
So yeah, the more I can see where you’re going to land, the more likely it is to work out. And what I find is often with even the most amazing people, there’s a bunch of back and forth, right. Push them to make it more concrete and more actionable. And more tactical. So, so I, I love seeing the draft cause then I can see how far it is from something that’s going to be amazing.
Right. And you can see immediately if, if this is an idea that’s been played out and done plenty of times before, or if you’re like, it’s not good yet, but I bet if you change it. Exactly.
Yeah. It could be. Yeah. There you go. There’s a, there’s a good
trick. And so, I mean, we can carry that forward, right. If even someone who, doesn’t often take guest, I mean, it’s, it’s basically.
It’s similar to what you did with, Andrew of you didn’t pitch him, but you said, Hey, I’m working on this. I don’t know. I don’t know exactly what you said, but I’m working on this. Can you give me feedback? Can you give me ideas? and then he’s like, not only that, but can I run it on my, on my site?
That’s exactly right. And actually the first round, it was the same way I had kind of the outline in a lot of the posts and I showed it to them and that got them excited.
Somebody who did this really well, And I feel bad that I’m spacing on his name right now, but who runs groove, groove, hq.com. they built a really, really popular blog on their journey going to 500 K.
now I’m trying to think of 500. I’m trying to think what the nber is anyway. It’s a lot of subscribers. no, sorry. It was on the, for their software product. Maybe they’re trying to get to 5 million, 5 million ARR or something like that. They had some. It’s was probably 500 K of MRR is what, the nber they’re turning.
Cause I remember looking up to it being like convert your wasn’t at that level. And I was like, Oh, that would be cool to get there. You know? and something that he did really well is have a content like a sort of an advisor group. Where he basically reached out to a bunch of smart people and said, Hey, I’m going to write stuff on these topics.
Would you mind if I sent you a draft of it from time to time for you to look over it? If I think it’s particularly relevant to you? and I think that can work well because, so he looked me in on that and I was like, yeah, you’re writing great stuff. I’d love to see it before it’s published. And maybe you share some tips or insights.
yet he’d been shot plenty of other people. And then what happens is when he would then publish the piece, he would email the same group and it was probably 20 people or something and say, Hey, thanks for your help on this adhere to his life. And then I’d see all those people tweeting about it and sharing about it because they had like a, an emotional, or they had an investment in him and his success.
That’s actually something I forgot to mention that I found really effective when I launched, when I launched the paid plan is I did exactly that with my launch announcement and ran it by folks like Andrew Chan and, and a bunch of other people with a large Twitter following, like generally to get their feedback on how to frame the announcement.
Cause there were supporters along the way and then also led to them, tweeting about it. And that helped a lot. Yeah, that
makes sense. Well, let’s turn to page. What made you choose a paid newsletter as the business model compared to, you know, many of the other ways that you could earn a living in, in startups or from a newsletter
I’ll say that it there’s a lot of downsides to going pay that I didn’t think about until I went paid one being you’re, like I said, you’re stuck writing every week. Some people do it daily. I don’t know how they do that. It’s blows my mind. but you’re basically stuck doing it for I in theory, forever because people are paying you these annual plans and I don’t, I stop unless you just shut it all down and just refund everybody their money, which is hard to do psychologically.
So that’s one is you just kind of have to be ready to do this for a long time. You know, maybe if it’s like a few years and you can just move on, that’s probably fine, but you can’t stop. You know, in a few months. So for me, it took nine months to get from starting the free newsletter to switching, to paid.
And a lot of that was building confidence that I could keep this up. And I had a topic every week that I could write about that I was excited about. So that’s the reason that it’s, it’s something to think about the other is before I wrote every week and it was totally free to everyone. And then once I flipped the switch, I’m doing the same amount of work, but almost all of it is not hidden behind a paywall.
And it just feels really bad. Like just like man doing all this work and no one’s going to see it. Cause initially you have very few paying subscribers and it’s just like, feels like it goes into a black hole. And if, kind of get used to that of just like, well, I’m getting paid, people are paying for it.
That’s the benefit. And that’s the, that’s the cost of writing this and doing all that work. So, but that like, I dunno, like, like it feels like an obvious thing, but feel the feeling of it. It doesn’t feel good, but it all, it all works out.
Yeah. Digging in on that. How have you found, like your writing process and like that showing up really consistently and the pressure of needing to publish could feel like a hamster wheel.
It could also be turned into a system. And so one of I’d love to hear anything that you’ve done to establish your process, to bring it from like hamster wheel to a reliable, you know, productive system or if that’s even happened. Yeah,
totally. And if we want, we can come back to the paid, the launching of paid.
so, so in terms of my process very much the way I describe it, as it feels like a, Boulder’s always chasing me in, as soon as I’m done with one week, there’s just like the next one’s coming. And I have to always plan ahead and it’s a real thing and it’s used to be stressful, but now that I’ve done it long enough, I, I, it’s, again, kind of the confidence where I’m like, okay, I’ve done this for like a year and a half now.
I’m not worried. I’m not going to find something great this week. But what I’ve done now is, I basically have three months of ideas mapped out. So I have a Coda doc where I have every topic kind of on its own page, kind of mapped out for the next three months, roughly just like the topic is the headline.
And then for the more eminent posts, I’ve I basically go in there and just flush out with bullet points initially, just like the things I want to say and thoughts that I have as I think about it. And then as it, and then for the next like month, I go deeper. So it’s kind of this like spectr of depth the next few months, the what’s cool about the format that I happened upon is, is it’s an advice coln.
And so that means people send me questions that they’re tackling in real life. And so I have this large backlog of. Really great questions from founders and product managers and growth people. So I’m finding, I’m never going to run out of things to write about at this point. And if I do, I could just go back and do better on things that have already written up.
So the topics don’t seem to be a problem, but then actually delivering high quality stuff every week for sure is a challenge. What helps one is just thinking a little bit ahead. So. So I’m trying to, I always try to be like a few weeks ahead of like done content, but I never actually get there. So it’s usually like the next post is like 80% done a week ahead of time.
And then the rest are like 20 to 10% done. And then the rest are just headlines. and otherwise it’s just making time to write. I block out my morning site. I have no meetings until 3:00 PM. That’s my new rule that helps a lot. And it’s hard to do if you have a day job and. That just always comes back to, no, you can’t do this.
If you have a day job, I don’t know how people have a newsletter. That’s good with a job. And that’s the secret is I have time to do this stuff. And most people don’t like, I don’t know how you do it. Newsletter having running a company.
Well, I mean, I do a lot of what you’re talking about of like, yeah, this will totally be done for this week.
And then you were like, wait, I said my newsletter every Tuesday and, yeah, I don’t know with Tuesdays, but it sounded good. Someone
said it, it was the best data send for open rates and
now it’s stuck. I think it’s that I don’t want to be in the Monday morning inbox. and so that, but I don’t also want to be at Friday end of the week.
And so I’m like Tuesday, you
guys, you guys must have data on which day of the week is the highest open rates. It’s
not so much definitive, like it, it’s not like wildly, you know? but, but Tuesdays are good and
shout every, every percentage
we can get. Yes, exactly. And that’s, you know, we send a little over a billion emails a month, so we have a good amount of it can amount of data that
we, you heard it here first Tuesdays.
exactly. So on, let’s see, Oh, with the content coming out, that’s something that I always run into. Like I was actually going to send a year in review posts tomorrow
and that’s what I’m doing.
Yeah. But it’s not done, you know? And I was like, Oh, it’s end of the day, Monday. And that’s not going to happen between now and then.
And so I have basically the same process that you do of like, this is what’s coming. And then here’s the ideas. And, and dripped out from there. something else that you mentioned that I thought is a really good point is the asking. It’s not well asking your audience questions and then asking them to submit your questions.
So one is the generic, like, Hey, if you have any questions about these three topics, like ask why, or even if you said something like, Hey, I’m going to write about freemi a freemi business models in a couple of weeks, like submit your stories, or like you can solicit that kind of thing. Especially once you get past.
Maybe two or 3000 engaged subscribers, then you start to get a good nber of things there. But then the other thing that I love is to ask, Hey, what’s your biggest frustration related to life as a product manager, you know, running a freelance business, like whatever the topic is for your newsletter.
and that can get a lot of good things where, you know, people will come in and say like, You know, here’s my frustration. And you’re like, Oh, let me tell you how to solve that. And that’s the writing prompt that you were looking for to take an idea actually all the way through?
Yeah. I think that I kind of made my newsletter, like I leaned into that even more and it’s just like, this is purely an advice coln.
Same your questions, anything you’re dealing with that, that stresses you out at the office or around product or growth or managing hans. And so at least a lot of really good questions because they’re very, they always end up being very real, like stuff they’re actually dealing with. And I wish I could answer them all, but it just piles up.
And so I have to pick one. And the other thing I have to think about, cause my newsletter has this broad spectr of product management and growth and startup stuff. And people management people join me with different, hopes and dreams for what the newsletter’s going to be. So I have to balance out all these different types of content every week.
So it’s a weekly newsletter, so I kind of have to do. A nice balance. I can’t have like three product posts in a row. Cause then all the growth people are going to leave. And so that’s something I have to think about. Yeah. Do
you see, is that a fear that you have, or is that, does that actually manifest in the nbers as well?
It’s hard to see the nbers. I definitely find people on subscribe, but they’re just like, nah, not what I thought it was going to be I’m out, but I don’t know what the root causes and it’s all anecdotal, but I do. It just feels like that’s probably what’s happening is they’re just like, I don’t care about growth, stop talking about growth,
Yeah. And you get both sides of it where someone comes in from the greatest article they’ve ever read on growth. They’re like, Oh man, this is all he ever talks about. It’s incredible. And then other person comes in from the same side on a product management. Or people management or whatever. And they each think that you talk about something.
Yeah. And that reminds me of something I’ve realized about this whole, newsletter game is that it’s really important that you stick to what you enjoy and are curious about yourself and are interested in writing about versus what people want you to focus on and write about, because coming back to your question about how to keep it up, I find that you’re just not going to keep it up.
Well, if you’re writing for. What people want you to write versus like stuff you really actually are curious about and want, wanna write about. So I try to do like a 80%, what do I actually care about this week? And I’m excited to write about with a 20% of like, well, people care about it this week. And is this a topic that’s top of mind for anyone?
Because otherwise you just, you just like created a job for yourself. You don’t like, and why did you even do that? Right?
Yep. That’s good. And especially because it gives you permission as your interests change over time, right? For me, I started writing about designing iOS apps. Like that’s all I cared about.
And then it was like, what’s the marketing and more general design. And I haven’t designed an iOS app in seven, eight years. I don’t know if those subscribers
are still around
there. There are some of them, you know, and, but if it’s around what you’re interested in, then it’s much easier to let go of those subscribers.
Whereas if you’re like, no, I have to keep everybody on the list. Then you’re going to. You’re trying to force yourself to be interested in things that you’re just
not. Yeah. And it’s just, you’re not going to enjoy it. It’s not going to be good if aren’t going to be like, Oh, this is, this is what I’m here for.
Yeah. And so, so the key is just like just right. Yeah. So I mean, back to your question of process, I have this like list of what I’m going to write about over the next three months, but then I rearrange it constantly based on what I’m drawn to as much as I can. And that, that really helps. Otherwise you just, you just burn out.
Yep. That makes sense.
Okay. Now let’s talk, writing, switching to a paid newsletter. what are some nbers now? As far as how many subscribers you have on the free version and the paid version?
So, so I’m going to share this publicly, in parallel. And so you can see the charts. If you’re curious, by the time this probably comes out, I have to have about 45,000 free subscribers around now.
I have just over 3000 paid subscribers, and then I give a bunch of like comps to various groups. So it’s larger than that in reality, and make it about over 600 years, more and more than I made in my. Nancy tech job, which blows my mind. Like my entire goal in the beginning of this whole endeavor was once I make more than I made it, Airbnb I’m done.
I don’t need anything more. I’m just going to stop thinking about growth. I’m just going to write, but it just keeps going on its own. I’m not doing anything and it’s pretty bonkers.
Yeah. So what was, first that’s incredible. Like once you build that flywheel, it just. It
keeps working. It’s all, it’s all word of mouth.
I L I love seeing that. What, when you make the switch to pay, did you have a nber in mind of like, this is what I’m, I’m launching this paid version. We’ll say, you know, I don’t know how confident you were going into it. I’m always the one, like, this will probably never work, but here it goes anyway. but I always have a nber of like, okay, if I get a hundred people to pay for this, then it’s working.
Like, what was that first nber for you?
I had like getting, getting a thousand subscribers, I’d say paid subscribers. Cause that roughly equated to about a hundred K after all the fees and. And discounts and things like that. So initially it was a thousand, which is, I think it was Kevin Kelly. You talked about and true fans.
And it was very real. It was like exactly. When I get to a thousand subscribers, I was making a hundred K a year, which is very livable wage in San Francisco, you know, borderline San Francisco. Right. And so that was, that was the goal. Initially it was like, you know, 500 and then wow. It’s thousand. That’d be amazing.
Cause if you do the math, that’s up pretty quickly with, The subscription newsletter, right?
Yeah. So what have you seen on free to paid conversion rates? you know, any in particular driving, more paid subscribers?
So, so if you do the math of about 45,000 free and about 3000 pays, so it’s less than 10% convert, which is an interesting stat.
Initially it was like 2% when I first launched. So I had like 10,000. Three subscribers when I went to pay it. And, and I had about 200 to 300 initially paid subscribers. So it was a very low percentage initially. And then over time it grows, was what was the other question?
So, well, I guess, digging in on that, did you put more content behind the paywall?
or did it just take take time, but what actually drove that conversion rate up? Cause you’re, you know, you’re pushing the eight, 9% now.
So the way, the way I do it is I, I send an email once a week. If you pay you, get it every week, if you don’t pay it, you get it once a month. And so that monthly email basically has to be really, really good because that’s your yoursel.
And sometimes I do these, like here’s a peak at this week’s paid post and give them a glimpse of what they’re missing. And then in the fridge post I share, here’s the three things you missed. So essentially it’s that free posts convert it to people, less Twitter. Just kind of sharing what’s going on in the pave land, but otherwise it’s all hidden behind a paywall.
Yeah. So about having more of those more time for those, here’s what you missed. Here’s the free post to kick it.
It just comes back to just providing value to people and they either find out about it or they want to access it and then they end up subscribing and stick around or leaving. How do you think
about pricing of what price point you set and then how do you think about that changing over time or not?
I definitely spend a lot of time thinking about it. I don’t know if my price is the right price at all. I experimented with various price points, but where I landed is advice I got is priced higher than you think you should. Everybody always wants to start at five bucks a month because that’s the lowest you can go.
And no one ever thinks their stuff is worth it. So they’re just like, Oh, five bucks a month. That’s that’s so much money already. So, so I looked at the leaderboard. And if you think there’s like these various categories of newsletters, there’s news, there’s entertainment. And then there’s broadly just like analysis and make me smarter and better at what I do category and those charged like 20 bucks a month.
So I just picked the middle and went with it. And initially when I launched, I did it, you had a display, there was a big discount. It was 10 bucks a month for a year. And then I increased or lowered the discount. It’s 12 bucks a month or 120 a year. And then I went to the. 15 bucks a month for 150 a year.
And I still don’t know if it’s the right price. There’s probably some curve someone could do for me. That’s like the ideal place. Although I will say when I ran a deal, it’s like interesting learning. I ran a holiday deal and that drove the most subscribers I’ve ever had. And on one day when I discounted it by 25%, so that’s probably the right answers price, a little higher, and then discounted on occasion.
a run a black Friday or,
yeah, that’s what it was. It was, it was a cyber Monday holiday newsletter.
Yeah. And I think that’s interesting. What are you thinking about bping up to the $20 a month or going off from there? You think it’s at the
right? It feels so expensive. And I have this interesting.
Too much pressure. Yeah. And, and I find that I have this interesting combination of people working at a tech company that it can, can expense it and the price doesn’t really matter. And then there’s like a lot of product managers in like India that email me and students in India. That’s like the most common source of emails that I get of just like, this is a crazy price for someone in my shoes.
Is there any like alternative price for folks in India, for example, and I don’t know how to deal with that because. I want to devalue it, but it’s also a crazy expensive price. So that’s a struggle I have. I don’t know. It’d be interesting.
I’m trying to think who said this or a bunch of people probably have, but of being like full price or free.
And they always have that sort of methodology of like, yeah. I, I think it was someone doing agency work, honestly, of like, no, there’s no friends and family discount. There’s no, there’s nothing like that. I like these are my rates. Except for the times where I think it would really benefit you or like I’m going to do this for free.
And it’s very clear that this is what I’m giving you. And there’s none of that. Like you’re paying for it. So you feel like you deserve things, but you’re paying half of the list price or a quarter of it. And so I feel like you can’t be demanding, you know, and there’s sort of that weird demographic. And so you could say like, look, I do full price and then I do full scholarships under.
These criteria and I give out a hundred scholarships a month or 10 scholarships a month or whatever.
I don’t, I don’t know we’ll do that, but that’s an interesting strategy. I do discounts of various amounts and I don’t know if that’s a good idea or not, but yeah, I do. I ended up doing like a 50% discount for students.
and, and then I just give occasional steep discounts for folks that just feel like they, they, they would value it highly and they just can’t
it. I do like the, the students angle. Cause then it’s just like, Hey, this is what it is. And people are paying for it. Right? The nber of people that are saying like, Oh, this will totally change everything.
Can you give it to me for free? And then, you know, they’re not invested who knows if they’re going to read it or whatever else. Yeah,
exactly. The other thing I’ve been trying to do really hard is to offer the content to folks that are just like, and afforded, or don’t even know it exists. I’ve been giving out a bunch of free subscriptions to like, women in product and like the black product managers group and, Latin X VC and things like that.
And that’s been really helpful. Right?
Yeah. That’s great. And it, it spreads the, you know, grows the community and everything else as well. Yeah, exactly. when you’re looking to, what are you looking to now for growth as far as is it just continually writing or, do you have specific goals in mind and, specific things as you look to, you know, to pass the 50,000 subscriber Mark or go from there?
I, I try really hard not to. I think I mentioned this anytime we do anything, that’s not just create high quality content that creates value for people. It doesn’t do much. So 90% of my thought is always, how do I write great stuff, ongoing and sustainably. And it’s really easy to do more work and find more work for myself like in a podcast and write a book and create a course and all the things.
And so I’m trying really hard to avoid as much of this as I can so I can stay and create just a really good newsletter. That’s hard enough. But the thing. So a couple of things have happened since I started it. One is, as I was launching the paid plan, I was like, man, 15 bucks a month is so much money to ask.
What else can I offer people? And I suggested I was going to have a private community that you have access to as a paid member. And eventually I had to do it because I promised it. And that’s proven to be the most amazing thing that I’ve done maybe this year beyond the newsletter, because it’s turned into this amazing place of.
peer support and help where people are just helping each other all day. And there’s about 2,500 people in there and just asking questions, answering questions. And I turned that into its own newsletter with the best conversations from the community each week. And so that ended up providing a lot of people.
That’s the reason they subscribe. They don’t even hear about the newsletter. They just want to access to the community. And so that’s proving to be really interesting and valuable. And I will say I’m working on a product management course next year. That’s something I’ve decided to do to see where that goes.
But I could see that there being a lot of demand for that. And one thing that’s interesting, there is a lot of people talk about a newsletter or like a paid newsletter as the business model, right. Or you can choose to do courses or books or sponsorships or a paid newsletter. And there. separate things and really, I mean, exactly what you’re pointing is like, they can, they can, co-exist just fine.
You can do a paid newsletter and then do a course for this
direction. Yeah. Yeah. Hunter Walker had this great post about how a lot of creators are. They have this one skew, which initially is the newsletter. And then over time you can add more skews, like of course, and I don’t know a book or something like that.
And so. That makes sense, but it’s, yeah, again, it’s really easy to do more work and I’m trying really hard, not to just add more work to my plate, but this course felt like just, it felt like the right thing to do next. And so I’m going to experiment with that. Yeah, that makes sense.
and I’m, I’ll just say I’m a huge fan of it because who I’ve seen, I’ve been doing that kind of thing for a long time of selling multiple products, multiple courses, and just seeing how one section of the audience really gravitates towards.
Buying one thing. And another section is like, Oh, but we’ll happily pay you in aggregate $50,000 or a hundred thousand dollars for content on this, this specific area. And so being the, the multiple skew creator, really lets your audience choose how they want to support you and what they want to learn from you.
I’m happy to hear this.
Yeah, I think it’s a great direction. so let’s talk platforms for a little bit. Obviously sub stack is, are you started on medi moved to sub stack, sub stack is growing like crazy. They’re getting all kinds of press in the new Yorker, New York times, et cetera. I’d love your thoughts on just where the market is going, you know, and we’re, we’re kind of back on this topic, but, so I guess where the market’s going and then, what are the decisions for you on, you know, When to start on sub stack versus could consider something like a MailChimp or I’d ghost or convert kit.
So what’s interesting about setup stack is I never would have been doing this with my life, if not for something like a sub stack existing, because I had no intention of ever one charging for a newsletter to even doing like a regular newsletter. I just started with a few posts and. The kind of the, the, the chemistry, that stuff stuck kind of discovered, I think, and went all in on was, let’s just make it, it’s really easy to create a newsletter and a blog, and then eventually it could charge for it if you want.
And so I just followed the, I feel like I was exactly there, like in-store user journey that they mapped out in their initial pitch of like, I just play around, sign up, create a sub stack. Do if you posts it’s going well. Okay. Maybe I shouldn’t bet on this. Yeah. Maybe I should charge. And so, so we never would have been doing this if not for a platform like that, but in the end, it’s not a complicated set of features.
And so there’s going to be more and more competition. and as, as you will know, and so I don’t know what’s going to happen there longterm. I will say the fees at scale are very painful and, and so the bet is that they provide. Enough services and benefits and maybe customers that make it worth it.
But, and for now I’m just super loyal to them and just really enjoy that the platform is just because it allowed for me to live this life. so, so I’m happy.
Yeah. I think from a, you know, both you and I working in product management and growth, and all of that, it’s fascinating to look at it from a case study of this is something that plenty of people have tried many times before.
Yeah. And I’m configured. We’ve been working on it for, in, in various farms and for a different market and for a long time and I study it and I’m like, okay, what, what did they get? Right. And it really is that they just made it effortless to go from, I have this one post, this thing that I want to write about to like, Oh, there’s a place for it.
Oh yeah, of course you can subscribe. Whereas the industry for so long was, Oh, you want to start a newsletter? Like. Let’s glue together. 12 different things. Oh, you paid, Oh God paid. Oh man. Okay. You gotta, you gotta set to have so much stuff, you know,
even like that first step of like, you want to start a newsletter.
Like I wasn’t even in that mindset, I was just like, Oh, this is a better place to do a blog because I can capture email addresses. So yeah. So they just made it like a trick, almost that like, Oh, okay. I see where this could go.
And it guided you into a six figure business. So I think that’s. I mean, that’s something that’s so important to have like finding a place to start because none of this matters, like people get so obsessed over platform or, you know, any of this, like what’s the fees.
Exactly. And like, if you never get past a thousand subscribers, which a thousand subscribers is hard, like that is a meaningful bar, you get to that point, you have moment. but if you never get past that, like the platform that you choose. Does not matter. And so we’re exactly, you know, as newsletter creators, we often obsess over the wrong decision to start.
Whereas the correct decision is, am I going to do this every day for a year to see if I’m, if I like it?
Yeah, yeah, exactly. How do I, how do I figure that out as soon as possible and as easily as possible before I overthink all the different variables that come into play. And I totally agree, like in the end, it just, again, comes to, can I create value for people consistently?
And then do I enjoy it? That’s, that’s a really important piece because. Cause like, you’re not gonna, you’re not gonna last if you’re not enjoying it enough, at least, you know, writing is hard. also, so there’s not going to be fully enjoying it.
Yes. Yep. That makes sense. Okay. So something that I want to talk about a little bit more, is this idea of keeping the newsletters simple.
So being in the online marketing space for a long time, I’ve seen people scale a newsletter or a content business, and they get to the point where it’s a little, you know, maybe they’re making 200,000 a year and they’re like, I should hire an assistant. I should hire an editor. You know, you get some of that help.
and then it starts to go from there, right? Maybe they’re 500,000 a year, maybe a million a year, and they’re starting to be a team. I’d love your thoughts on that because. That’s a path that you could take. You could turn this into the definitive, like the definitive forget newsletter, the definitive news source for product management.
You know, this could be something, in that way. What, what are your thinking about your approach and keeping it, keeping it simple?
Well, I’ve worked really hard for many years and I know what that’s like. And. I feel like I have this opportunity to create a pretty balanced lifestyle where I don’t need to work 80 hours a week.
And, and you quickly get there by just doing more and trying to add to it and accelerated and build more. And so I’m trying really hard not to do that. And I feel like there’s like, I could just do exactly this for a long time. And when it feels like it will keep growing, even if I do nothing. And I feel like I could make more just keeping it on my own thing.
Not hiring anyone. Full-time not trying to, you know, add more business units to it. Maybe it’s wrong. But yeah, most of it comes from just like a, I could easily become a workaholic again and do a lot more work. And I’m trying hard to avoid that as much as I can while delivering consistent value.
Yeah. I think that’s really important that you touched on of.
But just a little bit of the actual take home of, you can keep driving that top line revenue nber, but this isn’t a, in this right now, a traditional startup. You’re not trying to make it that. And so actually the profit is what really matters. And so if we fast forward and we’re like, okay, this business is going to be.
At $3 million a year, X nber of years from now. And it’s going to have in order to hit that revenue nber and provide that value for that many people, it’s going to need a team of 10 people. It’s going to, you know, it has all of these needs and before you know it, you’re managing payroll again and yeah.
All this stuff. and that’s like, I think a lot of people get to that position, chasing the growth and then look back and say like, Oh man, I liked it when it was simple, when it was recurring revenue, serving a single audience in just showing up in a consistent way.
Yeah, that’s, that’s my current philosophy, but I will say I’m, I have like a designer I’m contracting with, to like kind of level up that feel.
I have a, a PM. I work with that, like hourly, where she helps curate this weekly newsletter. So there’s a few folks that are helping out and there’s a community events friend that’s helping out run events and things like that. So I think what I’m trying to do is yeah, just keep it really simple. Maybe that’s the philosophy.
Just keep it simple. And you ended up making more and being happier. And so far it’s working out, we’ll see where it all goes.
Yeah. I have a good friend, Josh Kaufman, who wrote the book, the personal MBA, and he’s done this really well of sticking to a really simple business. He’s gotten to the point.
He’s always looked for channels where someone else is handling customer support. So like he likes to sell on Amazon audible and stuff like that. So he’s as the author, he’s one step removed. And that’s just one example. If he’s said, no, I want a simple business. and he, you know, that doesn’t mean you can’t work with a lot of freelancers, and have a team he loves to employ editors because they make his writing so much better.
And that’s actually something that I’d recommend for anyone writing a newsletter where you want the content really good. Having someone that you pay to go. Yeah, I see where you’re going with this. What is going on in this section, like, you know, rework that yeah.
If you have anyone you can recommend, that would be awesome.
but I will say there’s like, I, maybe I’m just like, I don’t, I’m not in the, like the ambitious phase of my life. I feel like it’s totally cool to be super ambitious and try to make something huge also. And maybe there’s a venture scale return somewhere in this space, as a creator. And I think it’s totally fine to try.
I just, I think for me personally, I’m just, I’m happy just making a meaningful income and not trying to turn this into like a billion dollar enterprise.
One other thing on that is wherever, let’s say at some point down the road two years from now, three years from now that in that list of the 50 startup ideas, right.
Maybe one of them does start to stand out and then you’re like, I think I want to pursue this. then you have this list of. 30 40, a hundred thousand, maybe it’s 200,000 people by then who you’re like you have your own audience and your own platform to launch to as well as all of these connections.
Super true. Yeah. I could always turn in some new and I could just, okay. Newsletter is done moving off.
Well, you don’t even have to necessarily give up the newsletter. Yeah,
that’s true. If I can find a more efficient way of doing it every week while running a company, maybe. Right.
what are some. Yeah.
What are some interesting doors that have opened from writing the newsletter or opportunities that have come up where people that you’ve met that came about purely because you’re Twitter famous now, certain circle,
speaking of Twitter, like there’s this amazing, super power that gets unlocked. Once you have enough followers, where any question you have, you could just ask it and you get all these amazing answers from people that are just.
You know, very curious to see what everyone else says and they share their insight. So I find that whenever I focus on a topic and I want to get a more complete picture of how people are thinking about it, I just ask the question on Twitter and it turns into this really amazing resource. So I try to leverage that more and more because I find it it’s like helpful to everybody else.
Also. It’s not just, Oh, here’s a bunch of answers I’m going to, I’m going to take it all from you. It’s like now this public thread of all these interesting. answers to a really interesting question. That’s one amazing thing that I didn’t see coming. And then two, I also angel invest and I find like 80% of founders are subscribed to the newsletter or have heard of it.
And. As, as we know in investing, it’s it, it’s on the investor to get into great deals now because there’s so many VCs and angels out there. And so the more you people can see the value you can provide the easier it is for you to get into the deal. And now they can see, Oh, he’s smart about these things.
We should let them invest. And so it’s been really helpful letting me get into it early. Interesting startup deals.
Yeah. That makes sense. On the note of Twitter, what are some of the things that have worked as specifically grow your Twitter
following. It’s exactly the same thing. Just providing value for people.
Anytime I think of something either from a post that I’ve done or just that isn’t enough for posts. I just find a way to share it very succinctly on Twitter. Like, you know, how to do performance reviews or, or even just like smarizing a post that’s long into a Twitter thread. it’s just always that just provide value to people and the vole will retweet it.
They’ll like it and all those things, and it just kinda builds on itself.
That makes sense. And I mean, it just goes back to an everything that you’re doing of there aren’t, even though we work in growth and startups, There aren’t really growth hacks in the same way. It’s like, it’s show up consistently.
That’s the hack show consistently and high quality.
Yeah. Consistent quality. Exactly. Just provide consistent value to people. I know for like morning brew, a referrals program worked really well and there’s like, you know, cases where something like that’s not pure content helped significantly, but I find in the end, if your newsletter just isn’t growing significantly, I would just think about how do I provide more value to the readers.
Again, and again and again, and it’s not going to happen overnight. And that seems to work.
Yeah. Okay. Last question I realized, I was thinking about on the pricing side, you have this, this split that you talked about between individuals paying for it and companies paying for it. And I think that’s relatively new in the newsletter space of a company like a B2B newsletter.
Yeah, exactly. And so if someone was starting out and they’re trying to hone in on their topic and maybe there’s an option for them to write. Something that could be expensed. how would you think about that? Do you think that’s happening a lot? Is that important or does it matter?
I don’t actually know what percentage of my newsletter is expensed.
If I had to guess it’s like 20% expensive, something like that. And so that’s not like a game changer and it’s hard to like, if, if you listened to my advice of stick to things you’re interested in, it’s hard to like Frankenstein on. Oh, I’m also going to have this thing that just happens to be interesting for companies.
But, but it’s, it’s a helpful thing. And I’ve tried to do a little bit of proactive B2B kind of sales, and it doesn’t really do much. I find that it just, I have to wait for people to come to me and ask for like both discounts for their company. And that works well. I also find VCs are offering it as a perk to their portfolio companies occasionally, but all that just comes to me anytime I pitched them on it, doesn’t give anywhere.
So, but it’s an interesting new trend and, I don’t know where it’s going to go. I don’t know if it’ll ever be like 50% of, of my readers. but yeah, if obviously, if you can create value for a company, they have more money. Right. And so you’ll have some sales there. Yeah.
On that note, it just made me think of advice I’ve given in the past.
when people are trying to hone in on a topic and it’s like, well, if you’re trying to make money yourself through, through teaching, right. Which the newsletter, of course, any of that. W we’re teaching in one form or another. If you’re trying to make money yourself, then teach a skill that makes money to people who have money.
And so we’re not talking about, you know, knitting to teenagers, right? We’re talking about product management, growth strategies to startup founders, PMs companies who have money. And so it’s probably not like canvas be expensed or not that you’re thinking about. It’s. Okay. Am I delivering value, a level of value that people can, are now living with, you know, and it, and it will level up their career.
Yeah. Those are definitely the easiest newsletters to monetize. There’s also just like helping make money directly. Like there’s like Bitcoin newsletters and, there’s one around like a distressed asset investing that does it really well. But then there’s also just like, if you look at the subset leader board, like the first two are all just news, like politics analysis, like a really unique perspective on politics.
So you can definitely make money just through news and analysis. And also just like entertainment, like the browser is this awesome newsletter. It’s just beautiful pieces of writing everyday and people pay for that. So there’s a lot of different approaches.
Do you have any newsletters beyond what you’ve just mentioned that you particularly love?
I always worried about answering this question cause I have so many newsletter friends in that one. I always worry. They’re going to get upset at me. You single somebody out. Exactly. So how about, I’m going to tweet my favorites and then go follow, go. Find me on Twitter.
That sounds good. Well, that’s a good place to wrap up.
So on that note, where should people follow you on Twitter and then subscribe to the newsletter?
LennysNewsletter.com, which just redirects to my Substack and then just Lenny-san, S-A-N, @lennysan on Twitter.
Perfect. Well, thanks so much for joining me. This is a really funny conversation and, we’ll, we’ll talk soon.
Thanks for having me.