Lenny Rachitsky launched a paid version of his aptly named Lenny’s Newsletter with Substack in April 2020. In a month, he had 13,000 free and 486 paying subscribers, putting his gross ARR at $56,000. By the end of the year, he had 45,000 and 3,300 paying subscribers — raising his ARR to likely around $360,000.
Lenny’s Newsletter covers a variety of topics, including product, growth, and startup building. As Rachitsky puts it: “It’s an advice column for product and growth, working with humans, and anything else that stresses you out at the office,” Rachitsky said in an interview with Latka.
These are all topics he knows well. A decade ago, Rachitsky founded the startup Localmind with $600,000 raised in capital and sold his company to Airbnb. After spending seven years at Airbnb, Rachitsky quit. He didn’t know what was next, but he gave himself six months to figure it out.
“My initial plan was to start a company. That was plan A. Plan B was to join a company, Plan C was to join a big company,” Rachitsky says.
None of those plans worked out. Instead, Rachitsky gathered his thoughts into an essay — “What Seven Years at Airbnb Taught Me About Building a Business” — and published it on Medium. To his surprise, the post made $1,700.
So Rachitsky kept writing, eventually turning his essays into a Substack newsletter. After nine months, he monetized it. About 200 of his followers paid for his subscription in the first couple of days.
“Partly what gave me confidence to do it is I had kept it up for nine to 10 months every week, which was not obvious to me that I could keep this up for that long, and at that point I was like, I could keep going for years probably doing the same thing. So let’s just give it a shot,” Rachitsky says.
Rachitsky charges $15 a month — more than a standard Netflix subscription — so he knew he needed to add extra value to make it worth subscribers’ dollars: “It all comes down to providing value. If you can provide value to people consistently, they’re going to follow you. They’re going to subscribe.”
To that end, Rachitsky created a subscribers-only Slack group, where members can talk about topics related to the newsletter. Rachitsky only maintains a few channels to create a critical mass around a topic. Current channels include product, growth, and startups, along with a self-promotional channel. He’s also adding value by creating “Lenny Prime” which includes curated guides to the best reads on several topics, such as SEO and product.
Rachitsky regularly chats with the community on Twitter, where he asks questions to flesh out concepts and come up with new ideas for his newsletters.
For now, Rachitsky is sticking with Substack instead of turning back to the start-up route.
“They’ve definitely captured people’s imagination and it’s kind of a cool thing to be on Substack,” he says. “I don’t know how long they’ll last, and for now I’m really happy there.”
What is Lenny’s Newsletter’s annual revenue?
In 2020 Lenny’s Newsletter generated around $360,000 in ARR.
What is Lenny’s Newsletter’s monthly revenue?
In 2020, Lenny’s Newsletter generated around $30,000 in MRR.
Who is the creator of Lenny’s Newsletter?
Lenny Rachitsky, age 39, is the creator of Lenny’s Newsletter.
Transcript Excerpts
How to give yourself a sabbatical
“The key is having that runway. A lot of people aren’t fortunate to have that. So I had savings [and] I just budgeted. Six months, here’s how much it’s going to cost me to live with no income. I’m just going to set that aside and that’s going to be my cost for this time that I’m going to give myself. And that alone made me feel more comfortable.”
Incentivizing people to subscribe ahead of a newsletter launch
“One thing I did is I gave them a discount if they subscribed in the first 48 hours. So I price set at $15 a month, or $150 a year, and if you subscribed in the first 48 hours after I launched, it was $10 a month, or $100 a year, and the call to action was just ‘subscribe now.’ … I think it was two weeks, before when I announced when I was going paid, so I gave people two weeks of more free and the call to action was really simple.”
Adding value by creating a community
“I was thinking, what else can I add as a part of that cost? And so initially I just added it to the pitch: ‘Someday there will be a private community that you’ll have access to.’ And I had no idea what it would be, I just knew I would try that at some point. So I threw it in the pitch and then … three months later, I was like, I guess I should make this thing real.”
Why Rachitsky switched from Medium to Substack
“The pitch was just like, why are you giving Medium all of your content? They’re gaining all of the upside, all of the SEO, all the subscribers, you don’t get any email addresses of your audience. You have no access if you leave. And so that was the benefit of Substack. And it was totally true [at the time].”
Full Transcript Interviewer : Hey guys, my guest today is Lenny Rachitsky. If you haven’t heard of him, you are not on Substack. He writes one of the most popular newsletters on product and growth coming from Airbnb and his own startup before that. He walks the walk and talks the talk. Lenny, you ready to take us to the top? Lenny Rachitsky: Thanks man. I am. Interviewer : You bet. You’re not good with compliments. I see you rock back and forth when I talk about your success. Lenny Rachitsky: You’re good at reading body language. I’m not. I’m a humble person. Interviewer : Well, I’ll try and stay away from too many compliments, but I do want people to learn from you and listen to the whole episode, so I don’t want to bury the lead. You’ve launched a paid newsletter on Substack. And how many total free readers do you have today? And how many have converted to paid? Lenny Rachitsky: I’m at about 45,000 free and about 3,300 paid at this point. Interviewer : And that equates, I believe, if my math is correct, my research is right, somewhere around $360,000 in terms of annual run rate. Lenny Rachitsky: I don’t share my revenue, but it’s something like that. Interviewer : Lenny stopped May 2020, put a tweet out, 13,000 free, 486 paid, and 56K in gross ARR. Why’d you stop sharing the revenue side? Lenny Rachitsky: Honestly, I feel like there’s a point at which I stopped becoming the guy you’re rooting for and the underdog. And I just like, “Man, why is this guy making so much?” So honestly I try to avoid the dollar figure at this point. Interviewer : Do you think that’s a big advantage? The underdog? Lenny Rachitsky: I think when people are rooting for you, it’s not so much advantage it just kind of feels nice. “Oh, wow, look at this guy go.” Interviewer : Can you be a big newsletter and still manufacture folks rooting for you? Lenny Rachitsky: Absolutely. I don’t know. Ben Thompson, I’m sure people root for that guy. The lady that’s at the top of Substack right now, Heather Cox Richardson, I’m rooting for her. She’s making over a million bucks. Interviewer : Part time. It’s crazy. Lenny Rachitsky: Yeah, part time. Wow. Interviewer : Let me get one question to you on Substack before we go back and get more of your history. Because your business is on top of Substack, if you were leading, if you were the lead PM at Substack, what does the Substack product look like a year from now? Lenny Rachitsky: I’ve been talking with the Substack guys a little bit about this, honestly, and it’s a big challenge. At some point the fees end up being a lot, and I don’t know what the answer is to be honest. They basically have two options. One is drive in and make it such that it’s well worth paying this fee because they’re making more money directly, and the other is make it a lot easier for me to do his job, so provide tons of tooling and support and other things where I just can’t get that anywhere else, and it makes up for the costs. And I honestly don’t know what I would do. It’s a tough place to be. But I’m bullish. I’m a big fan. Interviewer : Do you feel like Substack has a real sort of defensible moat? I mean, can someone else convert [inaudible 00:02:45] launch something and really compete with Substack, or do they have too much of a moat network effects? Lenny Rachitsky: I don’t know if anyone really has a moat. What’s interesting is their pitch is you can come and you can leave anytime you want, which works really well for people like me that joined, because there’s no reason not to try it. But then the downside is people can leave anytime they want, and so nobody really has a moat in theory, but they’ve definitely captured people’s imagination and it’s kind of a cool thing to be on Substack. I don’t know how long they’ll last, and for now I’m really happy there. Interviewer : Guys, you’re going to enjoy the next 10 minutes. You sort of got a sense of where Lenny is today, but it all started really back in 2010, 2011, with one of his first companies called Localmind. Lenny, what was the idea behind Localmind? Lenny Rachitsky: Localmind was built back in the day when check-ins were really cool. Foursquare, and Gowalla, and Facebook, so what we did is we sat on top of their data and allowed you to talk to people that are checked in anywhere in the world to find out what’s happening, where they’re at. So if you’re thinking about going out to a bar, “Hey, is this bar fun right now?’ If you’re thinking about going to a concert, “What’s happening there right now?” Or “What’s the special of the day?” Lenny Rachitsky: It was called Localmind, and the idea was to give you this local mind anywhere you’re thinking about going to. And ran it for about a year and a half, raised some money, moved to San Francisco, and then sold the company to Airbnb, which is how I joined Airbnb. Interviewer : How much did you raise for the company? Lenny Rachitsky: Only about 600K total. Interviewer : Could you have bootstrapped it? Lenny Rachitsky: Yes, but looking back, it’s not the kind of company that would have worked, really. There was no real business model and check-ins kind of died away, and so it wouldn’t have worked no matter what path we took it, I think. Interviewer : Now you’re really going to rock with this question if you rocked on my first compliment I gave you, but was that acquisition with Airbnb sort of more of an acquihire or was it really a freeing financial moment for you where you could really focus on Airbnb, have no financial worries the rest of your life? Lenny Rachitsky: At the time our lead investor thought it was a terrible, terrible deal because it was all stock and the value equated to not that much in their eyes. And our pitch to them was, this is going to be worth a lot more than it is now, and especially a lot more than the 409A valuation is telling you it’s worth. And looking back, we were very right and it worked out well. And I’m very happy we made that decision because, like I said, I don’t think the startup would have worked out. Interviewer : Did the investors hold on to the… It sounds like you held onto the Airbnb [crosstalk 00:00:05:14]. Lenny Rachitsky: Yeah, in a sense that they had to. There’s not much of a secondary market that is allowed. Interviewer : Ask forward to market close today and Airbnb is at an $85 billion market cap, so you saw something they didn’t. How long did you stay at Airbnb? Lenny Rachitsky: Seven years. Interviewer : Seven years. And so what I want to get to now is, it’s very rare, if you were there for seven years, how old were you when you left? Lenny Rachitsky: How old was I? Wow. 36-ish. Interviewer : So you’re like 37, 38 today? Lenny Rachitsky: Interviewer : What happened? Because I assume you see internal metrics, you know you’re sitting on a rocket ship, you’re giving up a big salary, what was the catalyst that got you to say, you know what, the opportunity cost is too high to stay, I need to leave and create space to invent something new? Lenny Rachitsky: Honestly, it was a very visceral, non-rational feeling. I went on sabbatical. I was there seven years, took some time off, came back, and I just felt like the Kool-Aid had worn off and I was just ready for something new. I just came back and I just didn’t have the same energy and drive that I had before that. Lenny Rachitsky: Then I spent another month rationally kind of getting there by talking to other teams and leaders to see if there was a different role or another opportunity, but it just kind of felt like naturally this is the time to go. And I didn’t actually have a plan when I left. I was just, I’m just going to see what happens. I’m going to give myself six months to explore. And it ended up taking me a year to figure out this is the path I want to go down. Interviewer : Lenny, how do we encourage more people to do that? There’s a lot of people that don’t know how to get their mind in a place to just say, I don’t know what I’m going to do, but I have six months of runway in my life to cover my expenses. I’m going just going to go be in an empty space for a while. How do we encourage more of that? Lenny Rachitsky: The key is having that runway. A lot of people aren’t fortunate to have that. So I had savings where the way it did it is I just budgeted. Six months, here’s how much it’s going to cost me to live with no income. I’m just going to set that aside and that’s going to be my cost for this time that I’m going to give myself. And that alone made me feel a lot more comfortable. Lenny Rachitsky: Giving up the salary and investing, that’s a whole different story, but at some point that has to end. It never ends. There’s always going to be more salary investing if you’re at a tech company. So, a lot of it was I was just ready to take a leap. I had savings to give myself a chance, and I never thought I’d be there seven years, so it was kind of this, okay, what the hell am I still doing here seven years later? I probably want to start another company or do something else. Let’s just do it. Interviewer : Lenny, there’s two ways to create runway. One is to live below your means, decrease your expenses. The other is to save more and just build a bigger cash cushion. Which one did you choose? Was there one or the other? Lenny Rachitsky: It was mostly saving enough and just kind of setting this dollar amount. If I spend at the current rate, if I do nothing different, I’m comfortable with that. Interviewer : Can we get a sense, get in your life a little bit, when you were, I guess, 37-ish leaving Airbnb, you’re living in San Francisco, correct? Lenny Rachitsky: Yeah. Interviewer : I mean, are you comfortable sharing a range of what your life expenses were per month back in those days? Lenny Rachitsky: The way I did it is I just set aside 100K. Here’s a 100K that I can burn through, both life expenses and also business expenses. And that was my investment in myself. Interviewer : So sabbatical, you come back, lower energy, savings of six months, you leave, then what? What prompted you to start writing this first piece of content back in, I guess it was May 2019? Interviewer : How? I didn’t know that was thing either. Lenny Rachitsky: It’s a thing. You put it behind a paywall and they pay you some small amount based on views and based on how many people convert to a paid Medium account. But I moved off to Substack later, which we can also talk about if you want. Interviewer : Lenny Rachitsky: Okay. So, anyway, that did well. I kept going, kept writing, but I kept wanting to come back to the startup stuff, and I had this tension internally of should I spend time writing because this seems to be going well, or should I work on the startup explorations? And I had like 50 ideas of startup ideas I was exploring and intrigued with, and my plan was to work through them one by one. Lenny Rachitsky: There was basically a conversation I had with a friend where he just helped me realize, this writing seems to be going really well. You seem to be enjoying it. People seem to value it. Maybe don’t take that for granted and maybe double down on that and pause the startup stuff. And I did that and seemed to work it out. Interviewer : That’s great. Hey, Lenny, I’m actually here visiting my dad in Virginia because he had a health scare and he’s asking my name real quick. Let me just make sure he’s okay. Give me one second. Hey, dad. [inaudible 00:10:36]. Lenny Rachitsky: All good? Interviewer : Sorry about that, Lenny. [crosstalk 00:10:49]. It’s one of those things. I don’t know what your parents’ situations are, but I never thought I’d be 31, doing my own tech stuff in LA and get a call from my dad, and I’m like, “Dad, I’m going to be there tomorrow.” And so now I have sort of this makeshift office on the floor where I’m doing all my podcast interviews. It’s how it works sometimes. Lenny Rachitsky: Well, thank goodness for remote work [crosstalk 00:11:08]. Interviewer : That’s right. That’s right. Lenny Rachitsky: But it sounds like he’s okay right now? Interviewer : He’s doing better. He’s doing better. Thanks for asking. So, picking up where we left off, just to create a clean edit there, that first Medium post, I just pulled it up. It did extremely well. You’re talking… Does it say here how many claps? [crosstalk 00:11:26]. 28,000. 28,000 claps, from what I can see. This is extremely, extremely well. And so you made some capital off of this and then sort of pick up from there. What happened after this? Lenny Rachitsky: I just kept writing. I wrote five more pieces around how to get into product management. Actually, what Buddhism taught me about product management, because in that three months I took off I actually went on a meditation retreat, and that actually informed a little bit of how I was thinking about life at that point. Lenny Rachitsky: I kept writing, kept doing well, not as well as that first one. And then eventually someone convinced me to switch to Substack because the take was… The pitch was just like, why are you giving Medium all of your content? They’re gaining all of the upside, all of the SEO, all the subscribers, you don’t get any email addresses of your audience. You have no access if you leave. And so that was the benefit of Substack. And it was totally true. Interviewer : Your last post on Medium was February of 2020. Now here’s my question, was this someone from Substack and part of Substack acquisition strategy was go pick people up on Medium? Lenny Rachitsky: It was someone connected to Substack, but it was not a strategy, it was just actually genuinely good advice. Interviewer : I love that. So you move over and so what does it actually mean? You move to Substack, what does that mean? Lenny Rachitsky: I just copied and pasted my posts. So, first I just created a Substack account and I called it Lenny’s Newsletter, because I had no real plan for this thing, it was like, what’s the simplest thing I could start with. And now I’m stuck with that. And so I just copied and pasted them. And that’s my first few posts was those copy and pastes. Interviewer : This is great. And then to pull forward the story, that first post on Substack you remember what month that was Lenny? Lenny Rachitsky: It was June, I believe, June of 2019. Interviewer : By May of 2020, you tweeted out, you had crossed 13,000 free subscribers and 486 had converted to paid, and that was six weeks after you launched the paid subscription. So my question to you is, writing free for 10 months requires incredible discipline, and it also was past your six month window for you making money because you were through your 100K, I think, at that point. So two questions, why didn’t you start scrambling faster on how to make money at the six month mark instead of the 10 month mark, and what gave you the discipline to go the extra four months before introducing a paywall? Lenny Rachitsky: So the first question, basically I just realized that I hadn’t figured things out yet, and I just talked to my wife and we both agreed. Let’s just do another six months, which I still had budget for. And she was starting to feel like, “Hey, maybe you should get a job. What are you doing with this writing? What are you doing writing? What is this? What are you doing with your time?” Lenny Rachitsky: Because that was not a path that I ever imagined myself going down. And so, we just agreed, let’s just see what happens. Because the writing wasn’t really clicking yet and I hadn’t found a startup idea I was excited about. So it was just a little kind of agreement, let’s just keep going. Lenny Rachitsky: There’s actually a 2019 and 2020 jump. So I actually did 10 months of free, and then into the next year, right as COVID hit, is when I actually decided to start charging. Because at that point it’d been over a year, I had no income for a year, had no job, wasn’t looking for a job. and then all the markets tank, Airbnb stock tanks, I don’t really know how much I have in savings anymore, and so I decided to try the paid route. Interviewer : At 100,000 that you sort of saved a budget over six months, that puts your sort of monthly San Francisco expenses at like 10 to 15 grand a month. Something like that. Lenny Rachitsky: Yeah, something like that. Interviewer : what were you expecting when you launched the paywall? You launch it, you then go to bed, or your developers, maybe you launch at like 2:00 AM, and then you like wake up at 11:00 and what happened? Lenny Rachitsky: No, it lunch at a reasonable hour. I launched it. I got a bunch of help on the way to frame the launch and how to price it and things like that from just various smart friends, and I kind of crafted a whole pitch of why this makes sense and why this is valuable. And yeah, it was like nine months of free every week, up to that point. Partly what gave me confidence to do it is I had kept it up for 9-10 months every week, which was not obvious to me that I could keep this up for that long, and at that point I was like, I could keep going for years probably doing the same thing. So let’s just give it a shot. And so I launched it and I got about 200 paid subscribers in the first couple of days, and then I got up to about 400 something in the first month, and it just kept growing. Interviewer : As you experimented, your first shot at the call to action to convert people from free to paid, what was your first stab at that? Lenny Rachitsky: One thing I did is I gave them a discount if they subscribed in the first 48 hours. So I price set at 15 bucks a month, or 150 a year, and if you subscribed in the first 48 hours after I launched, it was 10 bucks a month, or 100 a year, and the call to action was just subscribe now. I gave them a week. I think it was two weeks, actually, before when I announced to when I was going paid, so I gave people two weeks of more free and the call to action was really simple. Subscribe now. Support this kind of work if you found value in this thing. The way I pitched it essentially was, if you can make one better decision a year through this, that’s worth 150 bucks a year, especially if you can expense it to your company, which some folks do. Interviewer : When you look at what recently happened with Quibi, you start to wonder, and you’ll read Carlota Perez’s book on technological advancement and production capital verses just regular capital. You start to go, wow, maybe capital’s not the scarce resource today, but attention is. And if you believe that, then maybe you also believe that social capital is our precursor to financial capital today. In other words, you can’t buy attention, you have to earn it. And only after you do that can you scale. You’ve essentially earned a ton of attention here, and at some point you decided to launch a Slack group to go even deeper. Walk me through that decision. Lenny Rachitsky: This all connects to kind of a core, I don’t know, thesis I have that it all comes down to providing value. If you can provide value to people consistently, they’re going to follow you. They’re going to subscribe. They’re going to pay you if it’s valuable enough. And so the Slack is essentially, how do I provide more value to my readers? When I first launched it I was like, man, 15 bucks a month, that’s a lot of money. It’s more than Netflix. Interviewer : So it was an upsell. It wasn’t included in the paid subscription. Lenny Rachitsky: It was. And it was basically, I didn’t feel like I was giving enough for $15 a month or 150 a year. So I was thinking, what else can I add as a part of that cost? And so initially it was I just added it to the pitch. Someday there will be a private community that you’ll have access to. And I had no idea what it would be, I just knew I would try that at some point. So I threw it in the pitch and then, I don’t know, three months later I was, all right, I guess I should make this thing real. Lenny Rachitsky: So I started it and invited a few initial set of people and then slowly grew it up. And at this point it’s just basically, if you’re a paid subscriber, or if I think you’re just going to add a lot to the community, you’re a part of it. And what’s interesting is it creates a really nice filter for the people there. If you’re the type of person that’s paying for content, you’re generally going to be helpful and kind and interesting, and so that creates a really cool community. Interviewer : What month was that? When did you launch that? Lenny Rachitsky: That was maybe September of last year. [crosstalk 00:18:44]. 2020, yeah. Interviewer : Very recently. Now the reason I bring that up is I just interviewed, two before you, actually, Rosie from Indie Hackers and I said, “Who are two [inaudible 00:18:54] communities you really respect?” And she said, “Charlie Ward’s Weekend Club and Lenny does a great job.” And so I said, “Well, why do you like Lenny?” And she says, “Well, the way it’s structured and the quality of content is just really, really high.” And at a surface level that sounds like a sort of fluffy duffy compliment, so I’m hoping you can make that real. What are you doing, where when you go on other Slack groups, you go, they’re not doing this thing, we are doing this thing, and that’s why there’s such difference? Lenny Rachitsky: That’s very kind of Rosie. She’s been very helpful with the community also. I’d say it’s nothing revolutionary. Basically, I try to be very detail oriented about the conversation. So I make sure people add a profile photo, I create as few channels as possible that give people, but still focused so people can know where to go and where to look and where to post, to create kind of a critical mass around a topic. Lenny Rachitsky: I have a channel around product and a channel around growth and a channel around just startups, and actually one that has been super successful that I recommend everybody do is a channel called, promote your stuff, because that just contains all of the self promotion that people always want to do, and so it ends up being actually a pretty cool channel, to all to see all the cool stuff people are working on, but it contains it, so all the rest of the channels are high signal to noise. Lenny Rachitsky: Then there’s just a little greet bot that tells people how introduced themselves that I think every Slack has, and then I welcome everyone individually, as much as I can. And then another thing that I’ve done recently is there’s so much good content in the community, that I work now with someone named Connie who pulls together the best threads each week of the community, and then turns it into a new email that we send out every week of the top thread of the week. Interviewer : I love this. And I think one of the interesting things as I was studying for this, my team was, a lot of people can’t because they have nothing to react to, but if you have a way to create something hitting you, then it enables you to react better. And you have such a superpower on your Twitter account to throw out some questions or ask for examples or tag people. And I’m guessing that’s you sort of testing new concepts and based off it you can then react. Is that accurate? And if so, how can other people learn from that? How can they sort of replicate this with no Twitter following? Lenny Rachitsky: It’s interesting because if you actually look at my newsletter, it’s actually the root of it is that concept, which is it’s an advice column. That’s the way I position it. It’s an advice column for product and growth, working with humans and anything else that stresses you out at the office. And so innately every topic is based on a question that I get from a reader, and so I have this huge backlog of hundreds of questions now. And what’s cool is it makes it such that they’re always very real problems that people are having. Lenny Rachitsky: I kind of found that as your Twitter audience grows, you kind of unlock this superpower where you could just ask any question and you get all these incredible answers from people. And so I use it for two things. One is to fill out a concept that I’m thinking about, to kind of make sure I’m not missing anything important. And then two, to test ideas. What’s interesting to people? I had one around consumer subscription businesses and what metrics matter to people. I just ask what people look at, and it ended up getting 1000 likes, which I did not expect, and so I basically prioritized that post and worked on that sooner than I expected. Interviewer : With all these assets you’ve built. It’s fascinating for me to read in your 2020 summary posts, what you think you’re going to sort of, well, what you are going to test in 2021 and it sort of gives me insight into how you’re thinking about leveraging what you’ve built, where you’re adding value to the community, but also leveraging this great asset. And one of the ideas you put out there was this deals thread, specifically to subscribers, and immediately I think of the interviews I’ve done with Noah and how he grew AppSumo, and Drew recently launched in trends the same sort of deals concept. There’s a lot of people sort of trying this. And so I’m curious, what angle are you taking? Is it going to be exclusive to B2B SaaS, or different? And what advantage do you think you have over an AppSumo or a Drew at trends, if any? Lenny Rachitsky: Honestly, this again comes back to just, how do I provide more value to readers? I want it to become such an obvious, 15 bucks a month, of course. So if I could do, if you save hundreds of dollars a year from some deal that I can give you, that’s amazing. So it’s as simple as that. Lenny Rachitsky: I went on Twitter, put it really well that I’m trying to create a Lenny Prime, where you pay 15 bucks a month and you get all these incredible resources, a Slack community, the deals thing, I’m working on a curated guide and resources of just like the best reads on any topic, so you’re not just filtering through millions of articles, it’s like, what’s the best read on SEO? What’s the best read on getting into product? I’m just trying to bundle more and more value. That’s it. Interviewer : I love this. I can’t wait to see how red you blush when someone posts on Twitter the first Lenny Prime tattoo like these [inaudible 00:23:41] folks do. Lenny Rachitsky: I hope not. I’m working on a new logo actually, so don’t tattoo [crosstalk 00:23:48]. Interviewer : I love that. Lenny, this has been great. I guess last question here, what do you think your… A lot of people that build this sort of audience, it’s very powerful and you have to be super careful with it because you can lose trust as fast as you gain it. What are some things that you’ve said no to? Because maybe you entertain them, but you just felt they were too close to the edge. Lenny Rachitsky: In terms of content or in terms of projects? Anything? Interviewer : However you interpret it. It might’ve been a sponsor that really wanted to do you a sponsorship somehow, or a project, or anything. Lenny Rachitsky: Got it. I’ve gotten really good at saying no, because I find that I get constant requests to do sponsorships, to do talks, to write things, to guest post, and all these things. So basically I’ve tried to turn down everything I can because creating something of value is hard enough, and I’m trying really hard to keep this newsletter high quality and consistently valuable. So generally I’m trying to turn down books and podcasts and doing my own podcast, for example. I am going to work on a course. That’s something that I’ve been saying no to for a long time, but I’m going to take a shot at that and we’ll see how that goes. But otherwise I’m just trying to say no to everything, so that [crosstalk 00:24:57]. Interviewer : Selfishly, why’d you say yes to this podcast? What are you hoping to get out of it? Lenny Rachitsky: It’s 15 minutes. I love the style. They just go, boom, boom. You’re done. And obviously, I’m a huge fan of what you’re doing [crosstalk 00:25:09]. Interviewer : Well, I appreciate that. And I learned a ton from you and speaking of 15 minutes, we are over. We got a lot of value from you. Where can people, Lenny, where can they find you online if they want to learn more? Lenny Rachitsky: Lennysnewsletter.com. Interviewer : Guys, lennysnewsletter.com. Again, went to Airbnb after he sold his startup to the company, stayed there for seven years, went on a three month sabbatical and said, you know what, this doesn’t give me the same energy anymore, I’m going to save up a 100,000 bucks, give myself six months to just be an empty space and explore. Interviewer : He started with a Medium post, seven things he learned, it did really well, 28,000 claps. Eventually was convinced in February 2020 to move over to Substack. He launched quickly and grew a following of about 13,000 people before launching a paid option. Grew that to about 480 subs at $56,000 in AR. Lenny, soon, 486,000 paying subscribers, right? Lenny Rachitsky: Soon how many? [crosstalk 00:25:58]. Maybe end of the year. Interviewer : Soon. But guys, he’s scaling nicely. Really, I asked him, I hit him hard many times, and he came back to the same answer, it shows me it’s a key part of how he’s thinking, does it add more value to the community? Am I helping with better discussion and is it more curated? Lenny, thanks for taking us to the top. Lenny Rachitsky: Thanks man. I love that life story. That was great.
