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Chanel
Lenny Ricciski, he just hit 1 million subscribers. He's like, I don't think anybody's going to read it, but I'll put it out on medium. Six years later, he has a million subscribers.
Dylan
Newsletters are essentially the new blogs. They're just hitting people's inboxes. Right. So you need to stand out, you need to be different. You need to have content that resonates and that is well written and well researched and even has a little bit of personality. So you don't sound like, you know, an AI bot.
Chanel
I'm just curious, like, where this goes from here because he's just been steadily growing, like, does he hit 2 million? And the next year. All right, so today we are going to talk about Lenny Ricky. Now, Lenny is. If you've been in the newsletter space at all for any length of time, you probably know about his newsletter. Lenny's newsletter, he just hit 1 million subscribers. And I thought this was fascinating and I kind of wanted to go back and break down some of his growth journey, what he's been doing since I wrote the Deep dive on him his. And yeah, just kind of riff on what we think is the future or the next steps in his journey. So, Dylan, are you excited for this one?
Dylan
I'm excited. I'm excited. I've been following Lenny's from a bit of a distance. I haven't done as much deep dive research as you on him, but he kind of came on married R probably about 3ish years ago, and I think that's kind of when his growth was really accelerating. So, yeah, I'm excited to get into this.
Chanel
Awesome. So for just a little bit of back background on Lenny, he worked at Airbnb. He was like a product years. So from 2012 until March of 2019 when he left Airbnb, he was there just working in the product space, making the product better. Learned a bunch and was like, you know what? I'm going to start a newsletter. Because he wanted to actually start a different company. And he was like, I want to synthesize, like, what I've learned and just like, share this. He's like, I don't think anybody's going to read it, but I'll put it out on medium and medium.com and see what happens. And now we'll was that six years later he has a million subscribers and he is one of the top voices in the newsletter space and just in the product space in general, he's definitely got the world's largest newsletter on product and growth. So very Very interesting.
Dylan
It's. It's really impressive. And I think he has a quote in one of his posts about hitting one of these big milestones. He did another one of these when he hit 500,000 subscribers. And I can't remember if it was in this 1,000,001 or the 500,000 run, but he basically said, like, growth. I've tried everything. Like paid ads, this, that. And he's like, none of that. None of that really works. Like biz dev. Like, he's tried all this stuff and he's like, paid ads, SEO referrals, bd, and none of them have done a damn thing. And so I thought that was really funny and interesting. Uses the term growth levers, too. He's like, I've tried them all. None of them done a damn thing. And he goes basically to say that word of mouth has been kind of. Kind of his biggest lover for growth, which I think you could probably resonate with.
Chanel
I actually wrote two deep dives on him because I was so fascinated about the story. So I published the first one in April of 2023, and then the next one was the following week. That second one, I just focused on the paid newsletter. So I was like, how do you even grow one of these things? It's so interesting. And I hadn't really done a deep dive into that, so thought it would be a good time to do that. So the first one was all just. Just about his growth. And at that time in april, he had 377,000 subscribers. So that was only a third about two years ago, right? Yeah.
Dylan
Just shy of two years. Yeah. Okay.
Chanel
Pretty wild. That's like some insane growth.
Dylan
Yeah, it's nuts. And it's. It's. It's one of those things where I think just the size of your audience starts to flywheel into your growing because of how big you are, and that just kind of compounds. But that's not to say that he was just growing because he was already big. And we'll get into this a bit more, but I think you. You have to start with equality. Product that people. That people enjoy reading, that is providing them value that is consistent and all those sorts of things. So he wouldn't have gotten there if he hadn't been doing those things, those foundational things to begin with. So, yeah, that's. That's kind of my. My main takeaway when I was. When I was looking at his story.
Chanel
And I think practically every piece of Lenny's that I've ever read is just. It's good. It's so good. It's so in depth. And he's doing. We're going to talk about this again, but he's doing a lot of exclusives as well. And in the sense of even just taking data that might be available elsewhere, creating his own charts, synthesizing it differently. He also goes out and one of his favorite. His things that he does, that's one of my favorites, is he goes out to actual product leads and people working at different companies and actually gathers data from them. So, like, in the beginning, I remember one of his early growth levers was a series on how to build a marketplace. And so if you're not familiar, marketplace is kind of. Well, I'm not even super sure, but it's something like an Airbnb would be a marketplace. Um. Cause you have both customers and people, buyers and sellers. Listings, buyers and sellers. Yes. That was so much simple. Thank you. Um, but he did a whole series on them, and he went out to these companies and asked them, like, how are you growing? What's your biggest growth lover? And he took all that data and he wrote a whole series of articles. He said that that was like one of the turning points for his newsletter. I think I actually had a.
Dylan
You had a chart.
Chanel
A chart, yeah.
Dylan
We'll put that on screen.
Chanel
Growth timeline before that, and then his growth time, like, after that. And you can just see it was like chugging along, chugging along. And then those. Those articles went live and it was like, yeah, it was like, wow. Yeah, people really like that. And I think that made him stand out because he wasn't just, like, writing these thought pieces. He was gathering data from other places.
Dylan
Absolutely. And that's. Again, I'm going to harp on this over and over and over, and it's worth harping on. You. You talked about this at the newsletter summit in your talk about IV content. Insanely valuable content that people want to read. And with the proliferation of newsletters and content everywhere, we're kind of in, like, I guess, the blog 2.0 sort of space. Well, it's probably beyond that now, but just like newsletters are essentially the new blogs, they're just hitting people's inboxes. Right. So you need to stand out. You need to be different. You need to have content that resonates and that is well written and well researched and even has a little bit of personality. So you don't sound like, you know, an AI bot. Yeah. It all comes down to this quality and consistency that he. That he mentions.
Chanel
And it kind of reminds me, I know you were starting to mention Akash Gupta before we started recording and I was like, stop, we're just going to hit record. We have to start just going. Cuz we're just going to talk about too many things. We're, we'll have to double dip back on. But Akash Gupta always talks about creating content for the internal share. So like, what is that? One piece of content that somebody in an organization is going to share with all of their team and people in other organizations in the same kind of team. And so I think Lenny has done that super well with the space in terms of just the marketplaces. Like anyone who works at any of those companies on the product teams or even growth or anything really would probably read that. And so I'm sure that just like catapulted his success in terms of paid subscribers too.
Dylan
Yeah, totally. I think the, the interesting thing he says is, wow, I can't believe there's a million product managers. Kind of goes on to say like, you know, my, my audience is actually made up of much wider now, roughly half our product managers, but over a quarter of founders and the rest are a mix of adjacent functions like engineers, designers, growth marketers, et cetera. So it is interesting that, you know, he took this somewhat niche kind of area or category of product marketing and product managers and has kind of spun that off into this sort of larger ethos. And he even talks about a little bit about that, how he's like, I can't just write about product management for the rest of my life. So he, you know, he kind of touches on subjects sort of all around that and in doing so, he mentions as well that he's basically found his icky guy, which is like doing something that he's passionate about, that the world needs, that he can get paid to do and that he's good at. And so like, it's like this combination, this Venn diagram where he's right in the middle and he's publishing about that and that's kind of like, damn, that's the ideal, right?
Chanel
100%. And honestly, if you can write 36 posts about one topic, I think you're onto something. Because most people quit or get bored after 5, 10, 15, and then they're like, I'm gonna jump ship and move on. But he even said, I forget where it was in this piece. But somewhere along the line he realized like, I don't want to just write about product the entire time. Like he knew he had the forethought to think like, I might get bored of Just writing about product and, like, these very technical topics. He's like, so I'd love to expand it a little bit. Still have product as like, the base, but product touches so many, so many pieces of every business. So, like, it makes sense to talk about all of these other things as well. And his audience is interested in that. And after a while, I think he's written about so many things that, like, he can just expand to other topics and when someone asks him about something foundational, he can just link back to those old pieces.
Dylan
Yeah, yeah, it really helps. I mean, he's. He started the podcast too, in summer of 2022, I believe it was, or June of 2022. And so just doing that, building the relationships and building out your network as well. Talking to interesting people in the product space, the tech space, but then even just more so, talking like, he's got. He's had people who've, like, talked about mindset and, you know, just these things again, that sort of surround what you would need to do to be a successful product manager, but aren't actually, like, necessarily directly about being a product, a successful product manager. So position himself really nicely to kind of be like, yes, I'm an expert on this, but, you know, I'm also going to share all this other information that's going to help people in this space.
Chanel
I remember when I did research for CJ Gustafson recently of mostly Metrics, he actually was talking about how Lenny was somebody he looked up to, and he linked out to this piece where Lenny was talking about. He thinks of his content like a puzzle. And so he tries to fill in the gaps every week so he'll think of like, the holistically as a puzzle, fill in the gaps. And then over time, like, he's gonna have to go back and like, rework that puzzle piece and maybe make the edges sharper, you know, rework it a little bit, but it's still part of a bigger puzzle. And so he said, my job is to slowly but surely fill this board in and help you through every challenge, decision and opportunity you'll. I love that. It's just such a straightforward thing. It actually reminds me of the roast we did for Darren Smith. Right. So Darren has a live glossary of all the topics he's going to write about, and he's just, like, linking to them as he writes them. And this just reminds me of the same concept.
Dylan
Yeah, it's really cool. You're filling in the spaces as you go. So it's like this, like Darren said, it's like this living document and really going back and refining that, it takes a lot of diligent, like, not diligence, but like, you have to be pretty dedicated to go back, refine articles, make them better. Um, but it's all just part of creating this really high quality product. And that's what, again, that's what Lenny has done and that he's earned every right to get this 100 or 1 million subscriber count. And again, going back to the quality consistency can harp on it, but it, it all revolves around that.
Chanel
Yeah, totally. All right, should we do like a abbreviated version of how he got to 1 million?
Dylan
Yeah.
Chanel
Or how we think he did?
Dylan
Yeah, let's do. Well, I mean, he's outright said it. Like he's shared. See, I've got an image right here from his 500k post and I'm assuming that the stuff he did to get to 500k is going to be pretty in line with what he did to get to a million. People always ask how I got the newsletter got going with the newsletter. So here it is. And he's got like, first 100 subscribers, next 1,000, next 10,000 and so on. And so we can go over what you wrote about. We can go over this because he's not. He doesn't go into, into a ton of detail with this, but he says he mentions a few things that you talk about, like the first round review article, his Medium post on Andrew Chen's blog or his Medium post and posting on Andrew Chen's blog and stuff.
Chanel
Yeah, I mean, the first couple, the first few thousand is pretty straightforward. My research and his corroborates the same thing. Like, I think what he did was just, you know, he wrote that first piece on Medium. He got, I think he said he got his first hundred subscribers from that. And if I remember correctly, he didn't have an email capture at first, and then he realized he needed one and he added it later.
Dylan
That's right. And Eddie Schlanger did the same thing.
Chanel
Yep.
Dylan
These two, these two guys who've like grown these massive audiences and businesses, but everybody's got to learn. You got to learn.
Chanel
You got to learn. I don't think he thought it was going to take off. It was probably more of him just synthesizing the last seven or nine years of his career. So.
Dylan
Well, like you said, he. He wanted. He'd quit or had left. I'm not sure if he quit on his own volition, but he had left Airbnb and wanted to start his own Company. And so he thought, man, what did I learn It. I should probably, like, synthesize, like you said, what I learned while seven years as a product manager at Airbnb. And so he's like, I guess I'll just write it down and, like, flesh it out. And then I have nowhere to post it. I don't have a website, so I'm just gonna post on Medium. And sure enough, he did that. And obviously the Medium algorithm picked that up, and it got quite popular and did really well. And one thing he wrote about, too, was that was, like, signal. He's like, oh, people are interested in this. Maybe I should go. You know, maybe should go down this rabbit hole a little bit more and write about it a little bit more. And, you know, he, like you mentioned, he guest posted on First Round Review, which is Andrew Chen's blog. And Andrew Chen, I think, was a friend of his as well, or an acquaintance who was kind of encouraging him to do so. Um, and it just kind of snowballed from there. That's how he got to kind of his first a thousand subscribers, I believe. Roughly.
Chanel
Yeah. So he wrote two guest posts. He wrote one on First Round and then one on Andrew Chen's blog. Right.
Dylan
Sorry. They're two separate things. Yeah, my mistake.
Chanel
Yeah. And those together, those got him to a thousand. I only remember this because it was in my talk.
Dylan
Yes. Okay.
Chanel
So I, like, had been going back through it. Yeah, I thought that was interesting. And it's. It's just another reminder of, like, guest posts work. Like, you don't have to know an Andrew Chen or know this larger VC outlet. Like, you can keep going with, like, getting 50 subscribers, a hundred subscribers. Like, that's good enough. Like, just keep getting your writing out there in front of other audiences. It's so important. I think it's such a great way to get started.
Dylan
Yeah, it is. And, I mean, CJ did that, too. Who you discovered, right? Yes, and exactly. And he got paid to do it. So, like, there's. There's perks, too, to writing good quality content and sharing it with other people and guest posting. So. So that was the first 1,000.
Chanel
Those were the two ones. Yep. First 1,000, and then after that next 10,000, he said writing useful stuff every week for nine months and tweeting summaries of it and word of mouth. Okay, Lenny, that's, like, way too simple. Right?
Dylan
So, like, that. That's. I mean, but in the gist of it is that's what he did. Right. Writing useful stuff comes down to that. Quality consistency, because it was for every week for nine months. So he's like, okay, I'm doing this and tweeting summaries of it. So that's like publish or publish. Broadcasting it, like, to an audience. That he's actually writing this stuff. He's not just relying on people in substack to find it. So he's sharing it and then he's leveraging word of mouth. So he's. The useful stuff, creates the word of mouth. Because people like, wow, this is really good. I'm going to share it.
Chanel
I found his, like, Twitter Flywheel, essentially. So he used to write multiple threads all the time. Some days I found he wrote two threads in a single day. So, like, he was not just going lightly on Twitter. He was going hard, like, trying to make this work after a certain point. So he would take his longer form pieces and he would turn them into threads, which is how I grew in the beginning, too. It works, or it did work. I'm sure you have to do it somewhere else now. But, I mean, he was. There are screenshots on the. The deep dive, if you want to go see them. But there are just like, his threads were getting like 500 plus likes, 200, 300 bookmarks, like, retweets all over the place. Yeah. And at the end of it, he would just link back to that newsletter piece. And so this is obviously at a time when Twitter wasn't like, playing links and like, letting you get reach, even if you had something in there, which they don't really do anymore. But he was taking advantage of that opportunity at the time, and it clearly worked.
Dylan
Yeah, yeah, no, it worked very well. So he's downplaying when he says, you know, write useful stuff and tweet about it. And it's like, yes, to sum it up, that's what he was doing. Um, but he was. Yeah, he was really leveraging the viral nature of what he was writing about and of the Twitter algorithm. So, yeah, whether or not you could do that now is probably debatable. Um, but there's still other platforms that will surface this stuff that much more, whether you're using LinkedIn, which is still probably an okay algorithm to. To go viral and grow an audience. But I think the whole point of this is reading consistently and, like, sharing it consistently all the time. And so people were finding out about it.
Chanel
And so even we were just talking about those pieces where he would go get data from other folks that worked at these companies. And so not only published that post on his newsletter, he would then write a thread about it. And in the thread he would tag every single person that gave him data. And of course those people were like, I look great because I gave him this awesome information. Let me retweet this.
Dylan
Yeah.
Chanel
And so it just kept going and going and then of course at the end it linked back to that piece and it was just like a great flywheel, especially if you can get quality data from people who have experience in the space. So super smart what he's done. I don't think you can do that with every single newsletter necessarily, but I think he stumbled into something really smart.
Dylan
And, and then when he got to his next 100,000, in his words, he continued to write useful stuff every week for years. And he tweeted about it and leveraged word of mouth. So again, not, not crazy, insightful, but he just basically, this is his way of saying, I found something that worked and I just kept doing it. And sure enough, it was working for him. So I guess why reinvent the wheel? If it ain't broke, don't fix it. Throw every cliche at the book at him here. He, he's, he was doing something and it was working, so he kept doing it.
Chanel
Yep, 100%.
Dylan
But then there was an inflection point.
Chanel
Are you referring to his paid newsletter?
Dylan
No, we can talk about that. That was an inflection point.
Chanel
Revenue recommendations.
Dylan
But yes, yeah, yes. In 2022, Substack launched this lovely feature, Substack Recommendations.
Chanel
Well, let's be honest, it was like, honestly revolutionary at the time because newsletters are notoriously hard to discover unless you are out there on these other places, like social platforms. So recommendations were just like incredible. I think over time it's getting watered down a little bit because they're just so overdone. Still works, still can be a good growth lover. But I think you have to be a little bit smarter about, you know, cleaning up your list after using them. But yes, he has no shame in telling people that as soon as Substack launched their recommendations, he had hundreds of people recommending him. And then he just started growing from there.
Dylan
Yeah. I think he's even said he's got over a thousand people recommending his newsletter.
Chanel
So I could, we could probably go see it. Right?
Dylan
Oh, can you?
Chanel
I'll look it up. Keep talking.
Dylan
Yeah, so, so I guess my point is he, he, he refers to, in his write up, when he's kind of reflecting on this, he refers to recommendations as word of mouth. Right. Because, you know, essentially that is what it is. People are recommending you and they're not going to recommend you if you, if you're writing is crap, if you're, if you're, if your newsletter sucks, even if you collab with them, they might recommend it, you might get some subscribers, but you're not going to retain those subscribers. Also if your newsletter sucks, um, the word of mouth is, is really important. But again, if your newsletter sucks and your quality of content is bad news, it doesn't matter. Substack recommend recommendation feature will work, especially in the short term. Lenny was writing really good stuff that people wanted to read and so more and more people were recommending him and it was just again another flywheel where great quality leads to more recommendations, leads to more subscribers, leads to more people recommending him, leads to more, you know, it's just like this constant evolution.
Chanel
So he actually wrote it in his 1 million piece. He said today over 5000 other newsletters recommend my newsletter. I was a little off without it. If you extrapolate from the trajectory beforehand, I'd maybe be at 500,000 subscribers. I would prob, probably say he'd be closer to like 3:50. Like he had good trajectory, but that doesn't always sustain the whole time. So I don't know, could be wrong. I mean he did launch podcasts, which has definitely helped as well. So.
Dylan
Yeah, no, it, yeah it has and I, I mentioned that too as kind of like a sort of a content flywheel where I think this was probably, this probably definitely helped in discovery, especially when he started publishing on YouTube. So you're going to get viewers who are maybe more video aligned or people who prefer to consume content on video like on YouTube. And so in June 2022 when he started publishing his podcast, I don't think he was publishing to YouTube right away, but it wasn't too long after where he started publishing the podcast episodes to YouTube video version. And now he's got 282,000 subscribers on YouTube. And you know that like some people found him there and then, you know, went to subscribe to his newsletter. I can't say exactly how many, but it's just this flywheel effect of like I'm getting big on one channel, therefore I'm kind of growing on another channel. And then they just kind of both feed each other and it's smart and it's. I definitely think the podcast has helped.
Chanel
Him grow oh thousand percent.
Dylan
I'll let you comment on that. But there's one other interesting point about his, his podcast that he mentions too.
Chanel
In terms of revenue well, yeah, that's what I was going to say, because I think he said at some point. I don't know if I have this the right quote, but I remember him saying at some point, the podcast is making more than the newsletter in terms of sponsorships and brand deal. So.
Dylan
And it's about wild. Yes.
Chanel
And he was already making over seven figures at that point when he launched a podcast. From what I gather, he doesn't really, like, talk necessarily about it, but that's crazy. So that means almost overnight, he added, he doubled that.
Dylan
And you know how long it takes him to. He compared the time and effort into. Into these two things. Right. So he puts in way more time and effort into publishing a written piece for his weekly post. And even if he's doing the guest post, which I don't think we've touched. Talked too much about. Well, we talked a little bit about it. But when he does the guest posts, he still works with that guest author to refine the piece to go through five or six different drafts and revisions and stuff. So there's a bit of his time sunk into it. Lots of time spent with the writing. It doesn't make as much money as a podcast. His podcast, he says, takes maybe about five, six hours a week to do, including, like, the research, the recording of it, the post. And yes, he has some contractors and freelancers he works with. But essentially what he's saying is the podcast takes way less time and makes way more money. So it's like a nice little problem to have, I guess, 1,000%.
Chanel
Um, yeah, I. We actually. We didn't talk about the guest post thing. We talked about it on. In terms of him writing a guest post, but not him contracting people to write for him.
Dylan
Okay, yeah.
Chanel
Um, let's talk about. Which is exciting. I actually learned this morning Lex Roman wrote a guest post for him.
Dylan
Oh, sick.
Chanel
Like, in the early, early days.
Dylan
Oh, wow. Really?
Chanel
Yeah. So Lex apparently started the newsletter at the same time as Lenny, and they're like, well, I'm kind of bummed that I stopped writing this, because I could have been, I don't know, like, said that somewhere near there, but.
Dylan
Yeah, yeah, yeah, that's. That's true. Oh, that's funny. Okay.
Chanel
But anyway, I thought that was funny.
Dylan
That is funny. Did we mention about. So the guest posting, in terms of why Lenny does guest posts?
Chanel
No, go for it.
Dylan
Okay. Well, he. He basically, like, realized pretty early on that he's going to publish this once a week, which is 52 editions a year, and he's like, I can't come up with like 52, you know, high quality, unique insights and lessons on, you know, product management or whatever in a year. Right. For forever in perpetuity. So he basically was like, I need to bring in other voices. And so Lex being one of them that he's brought in. And, and so now he says that he brings in guest posts. He didn't really say how often he brings them in, and I should have checked, but whenever he brings in a guest post, a guest author, they go through about five or six drafts, like I mentioned, to refine the content to, like, the level of quality that Lenny's readers would expect. And now he says that his guest posts are mostly the most popular posts that are on his, that are on his blog. They usually get the most response and that sort of thing. So it's kind of like another sort of win win for Wendy. Lenny, just like the podcast was guest post less work, more popular, probably drives a little bit more growth and virality and stuff like that. So really smart.
Chanel
If you get to be the person writing the guest post, you get a lot of new subscribers that I've seen at least a handful of people launch a newsletter, or at least they were early on in their journey when they wrote a guest post for Lenny and then they were able to just like, take off from there because they got in front of that audience, right?
Dylan
Yeah, that'd be massive. I mean, getting in front of a million or even like with open rates, say 400,000 people is nothing. Yeah, yeah, that's, that's a decent amount of eyeballs on your stuff. And if you do a good job, which it sounds like, Lenny's not going to let you publish a guest post that isn't. Is bound to drive you some, some new subscribers, grow your audience.
Chanel
Yeah. And even being a guest on his podcast. So I know Growth in Reverse Pro member Ben Williams actually was on Lenny's podcast.
Dylan
Nice.
Chanel
He's also in the product space and he, he, he knows Lenny just from being in the, in the space. You know, he got on his podcast and that was like a huge win in terms of just like getting the credibility even, even if you get 0 subscribers, just like having that credibility, it's almost like Lenny certified. It's like. Yeah, because he has such a good quality newsletter and people trust it as a good outlet. So if you can get on there and be a guest, I think you're. You're doing good.
Dylan
Yeah. If you can get, you know, verified on Twitter, like back in the day, this is like Lenny's basically. Lenny Seal.
Chanel
Yeah. He should have, like, a little certified seal, get some backlinks from it.
Dylan
That's right.
Chanel
You know, you can put it, like, the bottom of your website.
Dylan
Yeah.
Chanel
Certified by Lenny.
Dylan
Yeah. That's good. That's good. What are the big takeaways, then, from. From Lenny's journey? Like, what. What are the applicable steps that somebody can take out of his journey and what they could do?
Chanel
Yeah, I mean, if. If you ask Lenny, it's just write good content. Keep writing good content, post a couple Twitter threads and take advantage of substack, and you're good.
Dylan
Yada, yada, yada. You got a million subscribers.
Chanel
Do it for six years and. Yeah, yeah. No, but honestly, I think I'm increasingly convinced that the name of this game is just sticking with it. I was talking to Jay Claus recently, and he was like, I don't have a good growth journey. I was like, you absolutely do. You've been doing this for eight years. Like, people don't stick around that long in the same space. Huge. And he's like, you're right. He's like. And now people are just starting to recognize that, and he's starting to hit that growth trajectory of, like, escape velocity, if you will.
Dylan
Yeah, that's the word that was coming to my mind. Who. And Laura used that word a few times when we interviewed her. It's stick with it, Ness. Right. Like, can you stick with this and not just stick with it? Because you can't just be operating with your eyes closed and your blinders on and, you know, not realizing that it's not working. You need those signals that things are working and you need to iterate and. And pivot when something isn't working. That's what Jay's done. Right. Like, he started with, I think, just a newsletter and then turned it into a podcast, and then turned that into a community and then turned it into a YouTube channel. And, like, it's just like, he's gone through this evolution as a creator, and look at him now. He's doing. He's doing awesome. He's busy, but he's really grown quite significantly in the last few years, thanks to, by and large, sticking with it. And Lenny is. Is no different.
Chanel
Yep, exactly. So I think takeaways are, yeah, stick with it for six years.
Dylan
Yeah.
Chanel
I think that's probably the minimum where you hit that point. Unless, I was going to say, unless you're Justin Walsh. But even then, like, he was writing on LinkedIn for three, four years before he even started a newsletter. So yeah, I think there is something to like that five, six year mark, especially for personal brand, solo operator type things and then put your heart and soul into the content. That's the second one. It's just so key and I don't want to keep talking about it but I feel like we need to because people just, they want the growth hacks. But that is the ultimate growth hack is just good content, build relationships, stick with it. What else?
Dylan
Yeah, I think that's important. Kind of like your level of give a shit ness as well. Like how much do you do you care about your content and about your audience and your readers that that kind of matters. That's proven out again in the people we've just discussed is they care and they care about putting out a good quality product. So one of my things that I thought that was sort of insightful, quite insightful I think especially for somebody who's more towards the beginning of this journey as opposed to kind of the middle, you know that Lenny's been on. So Lenny talks a lot about job to be done. So figure out the job to be done for your newsletter is Caitlin Burgoyne's talked about this a lot. Of course they're not the only ones, they didn't coin the term, but Lenny does. It has a great example of essentially what a, what a job to be done for your newsletter looks like. And if you're not familiar with it, I would recommend checking out his 500,000 posts where he basically says like do your job to be done better than anyone else in the world. So you got to figure out what it is. What newsletter? What purpose does your newsletter serve for your audience? He figured that out and then he basically figured out how to do it better than anybody else in the world. And two questions I'll just that he writes here that I'll just share. Answer these two questions. Who exactly is your audience? Think of a specific person, what they what would they find extremely interesting or useful? And number two is what is your concrete job you're doing for them? Is it entertainment, helping them make money, inspiring them, helping them understand the world or something else? So kind of start there. I think you touched on this a little bit too Chanel with your Ivy content talk. Because these kind of buckets are so.
Chanel
When you were right, when you were, when you were reading those off, I was like, oh, are they the same? No, pretty close. Well they are, which is good.
Dylan
I was going to say you'd want to resonate with, with somebody like him being the same mindset So I think you basically had the same gist of those buckets as well when you're writing about insanely valuable content. So figure out your job to be done was one of my big takeaways from, from Lenny, as well as obviously writing quality and consistent content. You know, the stick with it ness. One other thing that I think is pretty important is sharing your work publicly. So he did that and we talked about how much he tweeted, even though he kind of, he kind of dumbed it down a little bit by saying, you know, tweeting summaries. But I think you really need to almost uncomfortably share your work.
Chanel
I like that. I like the jobs to be done. It's such a more tangible way to think about what you're creating and the content you're putting out into the world. But yeah, I mean, it does need to land in one of those buckets, which makes sense. So I don't know, I'm just a big fan of Lenny's like, outlook and even he's just a calm guy. Like, if you listen to his podcast, he's just like, he's like my speed. He's like very chill, but, like super smart, but really chill. And so I resonate with that a lot more than like a, I don't know, hormozy style, like in your face type thing.
Dylan
But yeah, I could see that. I, I agree. And it's not for everybody. Some people need the hormozy style in your face, like, pump you up thing, and to each their own. Absolutely. But yeah, Lenny's definitely a little bit more of a laid back guy. He's, he's very, you could just tell by the way he's writing this. Like, very modest and unassuming too. Like, I got a hundred thousand, I got a million subscribers by just writing useful stuff, consistently tweeting about it. You know, people liked it and it's like, that's like, it's totally his vibe too. Right. He's not gonna be like, here's what I did. This is how, this is how I thought about it. And it's like, you have to do this and, and you just kind of like sharing in a very modest way of how he really, like, crushed the newsletter game.
Chanel
It's funny. And I think he's just easy to recommend because he's such. You can tell that he cares. You can tell that he cares about the content, how valuable it is for his readers.
Dylan
Yeah.
Chanel
And he, he listens to feedback, so I think that's pretty cool.
Dylan
Yeah. And it also Helps too. Like, he's got this sort of circle of content, like that's product manager sort of specific, and you'll have those kind of guests on. But then he, he branches out from that so it attract, you know, you could recommend it to just about anybody in a professional setting and they probably will find something useful out of one of his posts or one of his podcast episodes. Not every single one of them, of course, but he just, it has this ability to reach a larger tam, if you will, than just focusing on one thing. And not everybody can do that. And I don't think you probably should do that in the beginning. You should probably pretty be pretty focused and niche down in the beginning so that you know who you're talking to and what you're talking about. But then as you grow, and as Lenny grew, he was able to expand out into these other kind of adjacent categories, if you will, or topics that he knows his readers would be interested in.
Chanel
Totally. It reminds me of Sahil Bloom. When he got started, he was writing about finance.
Dylan
Yeah.
Chanel
And then over time, he started writing about more other things.
Dylan
More other things.
Chanel
More other things.
Dylan
Yes.
Chanel
I can talk really well, can I?
Dylan
You talk good. You talk good.
Chanel
Smrt.
Dylan
Yeah.
Chanel
Yeah.
Dylan
So, yeah, you gotta start. Gotta start focused and then, you know, branch out. Um, in my opinion, it's gonna help, I think.
Chanel
Well, I think it's easier too, when it's just easier mentally to like, wrap your head around what you're creating and how much and what to create next. Otherwise you can be like, I'm just gonna write about the sky tomorrow or like, you know, something random.
Dylan
Yeah.
Chanel
So I think if you can niche down, it just helps you as a writer.
Dylan
And you do that from the kind of, the beginning too. You were just gonna focus on. You kind of had these parameters set. You're going to write about newsletter operators, newsletter creators who had a 50,000 subscriber audience or larger. It really was like, I kind of want to write about this person. But a. They. Maybe they're not a newsletter writer or they hadn't hit 50,000 subscribers. Right. And so you did that for a long time. And then last year you were kind of like, maybe not. And you started writing about people who didn't have 50,000 subscribers because they still had a really powerful growth journey and had a lot of lessons to learn. Or maybe you wrote about somebody who. You're more focused on their audience size, their general, like, online presence, as opposed to just their newsletter size too. So I think it's, it's important to stay. It's just an example. It reminded me of how you stay kind of focused in the beginning is really helpful for you and it's going to be helpful to explain what your newsletter is to people. Kind of strict to some degree on what you're writing about and what you're talking about. And then again, once you gain that steam, gain some traction, write about it for a while, then you can kind of expand out of that realm. And I'm not saying this is a hard rule that everybody has to follow, but it just, I think for the general, the general public this would be a kind of a smart way to go about it.
Chanel
Yeah, totally agree. Well, cool. Well, is there anything else you wanted to talk about in terms of Lenny hitting a million?
Dylan
Yeah, two other really quick takeaways and one won't go harp on these, but one is to obviously leverage network effects. So he was able to leverage Substack's recommendations. I wouldn't even necessarily say that he leveraged it. It's not like he was going out saying, hey, recommend my newsletter. He was on a platform that had this opportunity and these network effects. And so he stayed there. He obviously wasn't going to leave Substack. Even if there was. The grass might have been greener elsewhere. Maybe he could have made more money on subscriptions because Substack takes maybe a larger percentage of your revenue. He stuck with it. He grew rapidly thanks to it. And so I guess keep an eye out for platforms that you're on and where the network effects can be, I guess, leveraged or taken advantage of. So that was kind of one thing that sort of stood out. And the other one, I don't know if. Do you want anything to add to that before I go to the next one?
Chanel
No. I mean, yeah, pretty much just what you said. I think there are always, there's always going to be a new platform that's, you know, you can take advantage of it when it's new and they're not like putting so many ads out or that kind of thing. And you can get more reach on a platform, especially if you're going like the social media route. Um, so yeah, just keep in mind and I think honestly Lenny built his newsletter like a product. So he took all of his learnings and he built a. Just a best selling product essentially how meta based on what he had learned. It's so meta, but it's like you kind of forget it when you read his stuff for a while and then you're like, oh yeah, he's using all of this on the back end.
Dylan
Yeah.
Chanel
So it's pretty interesting.
Dylan
Absolutely. He definitely has taken it as a product, you know, paid subscription model, all of that. It's like. It's kind of like a SaaS knowledge product. The last point I thought we should bring up is just collaborations again. So we talked about this, but I think we harp on this all the time as well. But he knew he couldn't write 52 editions of, you know, a product manage or a. Yeah, a product management newsletter every year, all the time in perpetuity. So we started thinking about guest posting relatively early on and really leveraged that. And he's found success with it as they've been some of his most popular posts. So don't be afraid to collaborate with people and then just make sure you try to find the right people to do that with.
Chanel
Nice. Yeah, yeah. And a couple of weeks ago on the podcast, we were talking about potentially doing like, a grow without social course, if you will. I got some good feedback on that, so if you're interested. Yeah, people just straight up sending me random emails, being like, I read, I listen to the podcast. I want it nice. So nice. It's a good sign. I think maybe I should set up like a legit landing page for this. Because honestly, every. I feel like every deep dive I do, I'm like, yep, they used collabs, they did cross promos. They were working with other people doing guest posts. Like, I just wish people would optimize this process and do it better. So that's why I kind of want to create that.
Dylan
Well, why don't you throw up a teaser pre sale landing page link?
Chanel
All right, what if we do? I have not made this yet.
Dylan
I know.
Chanel
Reverse dot com. Slash. Oh, boy. Dun, dun, dun. Let's do slash. No social.
Dylan
I put anti Social.
Chanel
Antisocial.
Dylan
Yeah, it's kind of fun, right?
Chanel
Sure, let's do it. All right. Growth in reverse dot com. Antisocial.
Dylan
There we go.
Chanel
I'll just make it a. A form that they fill out.
Dylan
Okay. No pre sale. Like commerce into it at all?
Chanel
No, no, no. Just a waitlist form essentially for now, but eventually, when it's ready to go, we'll redirect that.
Dylan
Awesome. Is my voice is starting to cut out. Cool. Any other. Any other parting thoughts? Words of wisdom about Lenny and his journey? I mean, we could probably go on for a while. Um, but should probably wrap it at some point.
Chanel
Yeah, I mean, I think I'm just curious, like, where this goes from here, because he's just been Steadily growing. Like, does he hit 2 million and the next year?
Dylan
I mean, it's one of those things where you are growing because you're growing kind of thing. I think the size of your audience is just like, oh, this guy's got a million subscribers. He is bound to be writing something that people like and that I should subscribe to. So just by like virtue of the size of your audience alone and subscriber list alone, you're going to grow. I'm, I'm interested in what this looks like. In five years. Is he still going to be publishing? Is he sold? Has he, you know what, what does that, what does that look like?
Chanel
Is there like a Lenny's newsletter for marketing? Is there a Lenny's newsletter for. Does it like, does he take this playbook and like redo it in some other niche and let somebody else, like, run it? Yeah, I don't know.
Dylan
My gut says he probably, he probably doesn't because he seems like more of a. Not that he's not ambitious, but he seems like he values his lifestyle the way it goes. And he even mentions in his post, he's like, yeah, even when I'm writing an article that takes like up to 30 hours of research and writing to publish it, and then I'm spending, you know, maybe six to ten hours on a podcast, that's still just a 40 hour work week. And he's making a good amount of money. He doesn't have any full time employees. He does have contractors and freelancers that he works with to help expedite all this stuff. But at the same time, I think he, he doesn't want to be like, constantly managing people. So my guess is he's going to keep it, I would assume pretty simple in this, in this respect.
Chanel
I'm just wondering like, if somebody approaches him and says, like, all right, Lenny, we're gonna buy this. You have a three year off ramp, right? Teach somebody else how to do this in another vertical. I don't know. It could be interesting. I doubt he would, but we're gonna.
Dylan
Offer Lenny's newsletter and you're no longer the face of it, but it's gonna.
Chanel
The new industry dive, but Lenny's dive, that's the thing.
Dylan
See, that's part of the problem with personal brands, right? And personal newsletters is if you do have an exit plan, you need to kind of pivot that brand from your face and your name. If, if that is the case, if that's what you want to do.
Chanel
Craigslist. Angie's List.
Dylan
Yeah, I think Part of Craig's still.
Chanel
Running, I was gonna say.
Dylan
The difference there, though, is that nobody ever knew what Craig looked like. And no one really cared about Craig. They just cared about, you know, the application. In our day and age, where people have social profiles and they've got YouTube and TikTok and audio podcasts, there's just so much more personality in person with the brand. So it's a personal brand that I think it's just that much harder to kind of exit something that you've really built up based on your face and your name and all your thoughts and opinions and experiences. Right. That stuff is really hard to shoot over to somebody else to take over. So if people are coming for your unique, you know, like, think about, like, a comedian. A comedian isn't just be like, hey, I'm retiring. But this guy over here, he's gonna start doing my bits. He's gonna try to, you know, match my comedy vibe, and he's gonna take over my tour. Hope you're all okay with that. It's like, no. No one's gonna, like, want to hear, Want sign up to go see.
Chanel
Yeah.
Dylan
You know what I mean? Like, it's. It's just. It's something you have to really be thoughtful about. And I don't think it's as easy as just hiring somebody and training them. But some, in some situations, that could be the case.
Chanel
I don't know. It's fun to think about the possibilities. Well, this is fun. Yeah, it's fun going back through his story and seeing what he's doing now.
Dylan
Do you think he would ever join us either on the podcast or in the community?
Chanel
He doesn't do podcasts.
Dylan
He has one, but he doesn't do them. He doesn't.
Chanel
Guess he does not do them anymore.
Dylan
Okay.
Chanel
All right, I'm gonna work on it. We'll see if anybody in the audience knows Lenny. Let me know. I don't know. Gotta work something out.
Dylan
He wasn't at the newsletter marketing summit, was he?
Chanel
I don't think he goes to anything like that.
Dylan
Yeah, yeah, he would probably get accosted and like, lady, you gotta come on the podcast or. Yeah, yeah. Doesn't need the spotlight. Cool. Well, if people have been listening this long, maybe we should give a shout to Growth Reverse Pro Community. And just a quick heads up of, like, what's going on there.
Chanel
Yeah. So the Growth and Reverse Pro Community, if you haven't heard us ramble about this yet, we put together a paid community for people Growing newsletters. It's very Straightforward. But we do things like get on a call and spend an hour talking about sponsorships and nerding out about how to better grow your newsletter or use LinkedIn to grow or swaps or anything like that. Started having some in person events at conferences, which is fun.
Dylan
Yeah.
Chanel
And then we have other creators come in. So we've had people like Justin Moore, Dave and his wife Marsden Klein are coming into the community soon.
Dylan
That's right.
Chanel
And yeah, I'm. I'm pumped. I. This is like my favorite place. So if you are looking to grow a newsletter and want some other people around you doing the same thing, bounce questions off each other, get feedback, just see how other people are doing it. You can go to growthinreverse.com pro and check it out. It is application only. So you. Sadly, if you just started your newsletter or don't have a ton of experience, maybe wait a couple months and try again. But yeah, I just wanted to create a place where people who are actively working on these kinds of things are in there talking to each other and able to get ideas. That's the whole premise behind it.
Dylan
Ideas feedback has been huge. Like if you're not sure, you know, updating your landing page or you're tweaking your design or you want to update welcome sequence, like all that stuff people are sharing in the community and getting like almost instant feedback on from a bunch of people who are doing the same thing. So they've got actual experience to share. Right. So. So it's a really a cool place. The vibe is. I'm not just saying that because I'm a part of this, but the vibe is really cool. The people in there are so helpful and so kind and so generous with their feedback and their time. So highly recommend checking it out.
Chanel
Yeah. And when you join, the fun thing you get access to immediately is a link to book a call with me and jump on a call and we have a little welcome call. See if I can give you some quick wins.
Dylan
Yeah.
Chanel
And. Or just walk you through how to best use community. Yeah, that's pretty much it. So I'm excited and hope you'll consider joining.
Dylan
Yeah. Come hang out with us.
Chanel
All right. Until next time. See you.
Dylan
We'll see you soon.
Growth In Reverse Podcast Summary: "One Man. One Newsletter. One Million Subscribers: How Lenny Rachitsky Did It"
Release Date: March 26, 2025
In this episode of the Growth In Reverse podcast, hosts Chenell Basilio and Dylan Redekop delve into the remarkable journey of Lenny Rachitsky, who successfully scaled his newsletter to over one million subscribers. Drawing from Chenell's extensive research and deep dives into Lenny's strategies, the hosts unpack the key elements that fueled his unprecedented growth.
[00:00]
Chenell opens the discussion by highlighting Lenny's surprising ascent:
"Lenny Ricciski, he just hit 1 million subscribers. He's like, I don't think anybody's going to read it, but I'll put it out on Medium. Six years later, he has a million subscribers."
[00:08]
Dylan contextualizes newsletters in the modern content landscape:
"Newsletters are essentially the new blogs. They're just hitting people's inboxes. Right. So you need to stand out, you need to be different."
[01:20] – [02:09]
Chenell provides Lenny's professional background:
Notable Quote:
"I'm just synthesizing what I've learned to share it." – Lenny Rachitsky (Chenell paraphrasing)
[02:09] – [05:09]
Dylan reflects on Lenny's growth milestones:
Notable Quote:
"Growth I've tried everything... none of that really works." – Lenny Rachitsky (02:22)
Key Strategies Identified:
[06:08] – [09:21]
Chenell and Dylan emphasize the importance of insanely valuable content:
Notable Quote:
"It's just good content, consistent content." – Dylan (03:58)
Example Highlight:
[14:44] – [19:26]
The hosts discuss how Lenny capitalized on platform features:
Twitter Flywheel:
Substack Recommendations:
Notable Quote:
"Great quality leads to more recommendations, leads to more subscribers, leads to more people recommending him." – Dylan (18:27)
[19:49] – [22:08]
Lenny diversified his content distribution:
Notable Quote:
"The podcast is making more than the newsletter in terms of sponsorships and brand deals." – Chenell (20:51)
[25:29] – [30:10]
Dylan introduces the Job to Be Done (JTBD) concept as explained by Lenny:
Key Takeaway:
"Figure out the job to be done for your newsletter and do it better than anyone else in the world." – Lenny Rachitsky (Dylan paraphrasing)
[32:21] – [36:34]
Lenny recognized the importance of collaboration to maintain content quality:
Guest Posts:
Podcast Guests: Featuring industry experts further enhances credibility and attracts diverse audiences.
Notable Quote:
"Don't be afraid to collaborate with people and then just make sure you try to find the right people to do that with." – Chenell (35:51)
[21:04] – [25:42]
The conversation touches on monetization:
Notable Quote:
"The podcast takes way less time and makes way more money." – Dylan (21:06)
[25:29] – [27:52]
Chenell and Dylan distill Lenny's journey into actionable insights:
Consistency is Crucial:
Focus on Quality:
Leverage Platform Features:
Collaborate and Network:
Define Your Purpose:
Notable Quote:
"The ultimate growth hack is just good content, build relationships, stick with it." – Chenell (26:22)
[37:58] – [41:35]
Speculations on Lenny's future growth include:
Notable Quote:
"The size of your audience is just like, oh, this guy's got a million subscribers. He is bound to be writing something that people like and that I should subscribe to." – Dylan (38:05)
[43:09] – [44:03]
As the episode wraps up, Chenell and Dylan encourage listeners to engage with their own Growth In Reverse Pro Community for support in growing newsletters. They highlight the benefits of collaborative learning, feedback, and access to expert insights.
Final Notable Quote:
"If you are looking to grow a newsletter and want some other people around you doing the same thing, bounce questions off each other, get feedback, just see how other people are doing it." – Chenell (42:23)
Lenny Rachitsky's journey to one million subscribers exemplifies the power of consistent, high-quality content, strategic platform utilization, and meaningful collaborations. By adhering to a clear purpose and relentlessly focusing on delivering value, Lenny has set a benchmark for newsletter creators aiming for substantial growth.
Listeners are encouraged to apply these insights, remain dedicated, and prioritize genuine engagement to emulate Lenny's success in their own newsletter endeavors.