A behind-the-scenes interview with Lenny Rachitsky on building his newsletter and podcast

Lenny Rachitsky (00:00:00): I just sat down on this rock on a substance of some sort. This was as I was starting the newsletter, and this phrase of, I have wisdom to share, coming through me over and over and over. I was just watching this crazy visualization of some kind of sitting Buddha thing, and that was for three hours. It gave me the confidence that like, okay, maybe I do have things to share.

Michelle Rial (00:00:19): What do you want to say to our mothers right now? Do you want to take this back?

Lenny Rachitsky (00:00:19): My mom doesn’t know.

Michelle Rial (00:00:23): Do you want to take that back?

(00:00:24): You started your newsletter 2019, and it now has over a million subscribers.

Lenny Rachitsky (00:00:30): 1.2 million.

Michelle Rial (00:00:30): 1.2.

Lenny Rachitsky (00:00:31): Something that we’ve talked about a few times is the best stuff comes from the actual experience.

Michelle Rial (00:00:36): People always say if you want to write, read.

Lenny Rachitsky (00:00:37): The source of the best advice is from practitioners doing the thing for real. At this point, most of my posts are guest posts, where somebody sharing the best thing they’ve learned in their career.

Michelle Rial (00:00:45): What do you think you’d be doing right now if you hadn’t started that newsletter?

Lenny Rachitsky (00:00:49): On the struggle bus of startup life probably. And then probably after that failed, I would’ve joined at some company as a PM.

Michelle Rial (00:00:54): Do you still like it?

Lenny Rachitsky (00:00:55): I can’t imagine doing something more fulfilling and interesting, but the visual I always have is the Indiana Jones boulder is chasing me constantly. It’s like this treadmill that you’re on.

Michelle Rial (00:01:03): Tell me about a time you’ve been really stressed in your business.

Lenny Rachitsky (00:01:07): Well, here’s something I’ve never shared.

(00:01:11): Today, my guest is my brilliant, incredible wife, Michelle Rial, who turns the table and interviews me. I’ve had so many people over the years want me to be interviewed on this podcast, and what could be more fun than doing this with my wife? I share things during this conversation that I’ve never shared anywhere else, including some of the hardest moments from this journey. I get a lot more personal than I’ve ever been on this podcast.

(00:01:35): Also, the day this podcast comes out just happens to be my wife’s birthday. And she is also about to publish her third book, a children’s book, called Charts for Babies, which we chat briefly about. Definitely pre-order it. This was so fun and so special. I hope you love it. Let’s get into it.

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(00:04:11): Michelle Rial, thank you so much for being here. Welcome to the podcast.

Michelle Rial (00:04:14): Thanks for having me.

Lenny Rachitsky (00:04:16): So what are we doing here? People constantly ask me to get interviewed myself. People are like, “Why don’t you sit on the other side of the microphone and get interviewed?” I’m just like, “Nah, I like interviewing.” But you have a book coming out, and we thought this would be a fun opportunity to have you interview me. And so this is going to be your show. I’m just going to be here asking you whatever you want. I have no idea what you’re going to ask me, and we’ll see where it goes. I’m going to ask you some questions about your book, too.

(00:04:46): I’ll turn that over to you, Michelle. What do you got for me?

Michelle Rial (00:04:48): Well, Lenny. Okay, babe. Yeah. Yeah, so you started your newsletter 2019 and it now has over a million subscribers.

Lenny Rachitsky (00:05:05): 1.2 million.

Michelle Rial (00:05:05): 1.2, sorry. Your podcast is very frequently one of the top 10, is that right?

Lenny Rachitsky (00:05:14): Yeah, it’s top 10 tech podcast. Yes, hell yeah.

Michelle Rial (00:05:20): I love it. When I met you, I think you were something called a product engineer.

Lenny Rachitsky (00:05:24): I was a software engineer. Let’s see when you met me. No, I think I was still a software engineer. Yeah.

Michelle Rial (00:05:30): I think you went from software engineer to product engineer to product manager.

Lenny Rachitsky (00:05:35): Yeah. Yeah, I think that’s right.

Michelle Rial (00:05:37): I’m wondering, what do you think you’d be doing right now if you hadn’t started that newsletter?

Lenny Rachitsky (00:05:41): If I stayed in my job?

Michelle Rial (00:05:43): Yeah. I mean, I’ll get to another question about what do you think is the one moment that led you to your newsletter. But you can answer either one.

Lenny Rachitsky (00:05:53): So is the question after I left Airbnb, what would I be doing? Or is it like if I didn’t-

Michelle Rial (00:05:57): Just if you hadn’t, or if you had gotten a different job. Do you think you would’ve gotten a different job, stayed there?

Lenny Rachitsky (00:06:03): When I left my job, I was at Airbnb for seven years. I had plan A, start a company again. Plan B, join a startup as their first PM. Plan C, join a big company as a PM. Plan D, advise companies, become a consultant kind of person. Nowhere in that plan was do this crazy thing that I do now.

(00:06:23): I had a lot of startup ideas. As I was exploring the startup ideas, as you remember, I was just tinkering and prototyping and building stuff. And then on the side I was writing things that I learned and things I wanted to share. You were just like, “Why are you writing? You can’t make money on the internet writing. You should be doing this thing that you’re good at, startups and building and tech and stuff like that.” I’m just like, “I don’t know. It seems like there’s a pull here, so I’m just going to keep doing this.”

Michelle Rial (00:06:51): I don’t know if I say things that you’re good at. I just said, as a person-

Lenny Rachitsky (00:06:55): There’s no money in this.

Michelle Rial (00:06:58): … putting writing on the internet, I don’t make any money unless people buy my book. Plug.

Lenny Rachitsky (00:07:02): Yeah. Yeah, so I guess to answer your question, I’d probably find another company to start and I probably would’ve failed considering most startups fail. I’d probably be in this like, “Oh no, it was this thing I should be doing?” I’d be on the struggle bus of startup life probably. And then probably after that failed, I would’ve joined some company as a PM.

Michelle Rial (00:07:21): So then I guess going back to that question of what do you think, do you think there’s a moment or a collection of moments that led you to go full in on the newsletter? Or even start the newsletter, start the Medium post that led to the newsletter?

Lenny Rachitsky (00:07:32): Yeah, it was definitely a collection of moments. It’s this little journey that I just followed pull that was starting to work. I’m just like, “Huh, maybe there’s something here.”

(00:07:41): A few moments along that journey. One was the first thing I wrote on the… This is the first thing I wrote on the internet, did very well. It was this post on what I learned at Airbnb. Medium featured it. It went all over the place. Brian Chesky shared it with the whole company, so proud of what I shared. That was a nice moment of like, maybe I have something to share. And then I wrote a few more things on Medium at this point. There’s more of just like, this is working. People seem to like it.

(00:08:07): Then I had a conversation with a friend, Lee Jacobs, who’s a VC now, because I was telling him, “I don’t know why I’m doing this. Why am I writing? This is not a future. I should be focusing on the startup.” He’s just like, “You seem to be enjoying it. People seem to be liking it.” Which was very rare, that Venn diagram of things. Just like, how often do you enjoy something and people value it and maybe there’s a way to make money in the future? His advice is just maybe pursue that and double down on that and maybe it’ll go somewhere. That was a moment.

(00:08:38): Another maybe big moment was nine months of doing the newsletter, so I decided I’m going to move to Substack. I’m going to write every week. I tweeted I’m going to experiment with a newsletter, weekly newsletter, see how it goes. And so I did that every week for nine months. I just remember this moment nine months in where I was like, “Huh, I’ve been doing this every week for nine months, which means I could probably do this for nine more months.”

(00:09:03): There’s this Lindy effect. I don’t know if you know this, but there’s this concept of something being Lindy, which is as long as it’s been going for, it will most likely last at least that long in the future. I thought that, “Okay, I could do this for at least probably another year. I have all these ideas and things I want to write about, so let me just keep doing this.” That’s when I decided to add the paywall and start charging and to see if I could make money doing this thing.

(00:09:27): Also in parallel, as you know, I was doing this based on the assumption that my Airbnb stock was going to be worth something and I could take this time to explore. And then COVID hit, and Airbnb was over. RIP Airbnb all over Twitter, and I was like, “Huh, maybe I need to get a job for real.” And so I’m like, “I got to make money on this thing. Let me try.” That’s when I started the paywall, and it worked. That’s like the other moment I think I launched the paywall and it worked. I made meaningful dollars a month in.

Michelle Rial (00:09:59): Speaking of Venn diagram, you said, “I’m good at it and people like it.”

Lenny Rachitsky (00:10:03): And people like it.

Michelle Rial (00:10:04): Oh, and I like doing it. You like doing it.

Lenny Rachitsky (00:10:06): That’s a really good because I didn’t mention that. That’s so true that it’s like-

Michelle Rial (00:10:10): Oh, that Ikigai, right? Yeah.

Lenny Rachitsky (00:10:12): Yeah, I think Ikigai is like five things, right? It’s like a whole bunch of stuff. Yeah, but that’s like a checkup point because it was just like people like it and I’m good at it, but without that, I actually enjoy it.

Michelle Rial (00:10:21): I think you said, “And I liked doing it.”

Lenny Rachitsky (00:10:23): I liked it. Okay, cool.

Michelle Rial (00:10:25): Do you still like it?

Lenny Rachitsky (00:10:26): I do in almost every way. I can’t imagine doing something more fulfilling and interesting. Just basically my job is to write about things that are interesting and share people’s interesting insights and experiences and interview people and extract wisdom. It’s just so interesting. It’s my own thing, which makes it extra interesting.

(00:10:48): But I think a lot about this artist Finch wrote this blog post, “How to Become an Artist.” At the top of his post, he’s just like, “You should not become a professional artist, most likely.” Because once it’s a thing you have to do, it changes it, you have to do it. This is the downside, but I just want to preface with saying this is incredible. I can’t imagine doing anything else that I enjoy more. But having to write a post or put out a post every single week and a podcast episode every week, it’s like this treadmill that you’re on. You have to get used to that. That part is no fun.

(00:11:28): But again, I can’t think of anything better that I could be doing, and it goes up and down. Sometimes I love it. I’m so happy I get to write a thing every single week, and then some weeks I’m like, “It’d be cool not to do it this week.” But that’s part of this life because otherwise you can’t do this. You can’t survive in this way if you’re not doing something consistently and making it awesome every week. It’s a part of it.

(00:11:50): The visual I always have is the Indiana Jones boulder is chasing me constantly. Because you put out something, like I have a post come out… What’s today? We’re recording on Wednesday. I had a post come out yesterday and then it’s like, what’s next week? All right, that’s done. All the work you put into it, over. It’s coming out next week and it’s every week. The big question I don’t have an answer to is where this all goes long term. Because someday, whether it’s at a seven years old or 100 years old or 60 years old, I don’t know, maybe I won’t be able to do this every single week. I think about where does this all go. I don’t think there’s an answer to Substack writer podcast life long term. What do you do?

Michelle Rial (00:12:30): According to the Lindy, right?

Lenny Rachitsky (00:12:32): Yeah, six more years.

Michelle Rial (00:12:32): Okay, so 2019, seven more years.

Lenny Rachitsky (00:12:34): Seven years since the newsletter, yeah.

Michelle Rial (00:12:34): Seven years.

Lenny Rachitsky (00:12:34): I think-

Michelle Rial (00:12:34): Good luck.

Lenny Rachitsky (00:12:34): Seven more years.

Michelle Rial (00:12:39): Hope you don’t run out of ideas.

Lenny Rachitsky (00:12:39): Okay, so we got seven years. I could do that.

Michelle Rial (00:12:42): Yeah. Okay, so speaking of the boulder, you don’t seem like a stressed out person and I don’t see you as a stressed out person, only like potty training, or baby sleep stuff. I don’t see you as a stressed out person. Do you think there’s anything behind that? Do you think that’s just you? And/or are you just stressed and you don’t show it?

Lenny Rachitsky (00:13:07): I think there is an element of I’m more stressed than I come across as and even recognize with myself. I get these headaches sometimes. I’m like, “What is going on there? Is that stress or is that something else?” I think there’s a bit of I’m probably more stressed than it looks like and that I even feel, but I think I’m probably less stressed than the average person.

(00:13:25): I think part of it is genetics, and then part of it is I work on it. I just have learned to adjust the way I think to reduce stress and to not take things seriously. But I think honestly it’s probably like 70% genetics. I’m just like, “Eh, it’ll be all right. It’ll be all right.” As you know, something we argue out, but that’ll be all right. It’s some raw chicken, that’ll be fine. It’s fine.

Michelle Rial (00:13:55): I know you’ve done different types of meditation. We’ve done breathing courses together. Do you have a favorite? Do you-

Lenny Rachitsky (00:14:01): Oh, to calm down and de-stress and stuff?

Michelle Rial (00:14:03): You did a 10-day silent meditation right before you ended up writing a Medium post.

Lenny Rachitsky (00:14:10): That’s true, that’s true. That was a big wisdom. Oh, here’s something I’ve never shared. Okay, you asked about going back to the moments that led me to this life. I went on a bachelor party trip with some friends.

(00:14:22): This isn’t where you think it’s going.

Michelle Rial (00:14:24): I hope not.

Lenny Rachitsky (00:14:27): It was a trip to Joshua Tree with a friend, and there was psychedelics involved on this trip. I just remember, so we went to Joshua Tree. I just sat down on this rock on a substance of some sort, and this was as I was starting the newsletter. I just remember sitting there for probably three hours in this one spot, and I was just having this deep breathing happening and this phrase of, I have wisdom to share, coming through me over and over and over.

(00:15:00): I was just watching this crazy visualization of some kind of sitting Buddha thing, and it’s just like I have wisdom to share. That was for three hours.

Michelle Rial (00:15:12): That made you write the post?

Lenny Rachitsky (00:15:14): That made me feel like I can do this. It gave me the confidence that like, okay, maybe I do have things to share. Yeah, that was a really powerful moment just to give me confidence that there’s something inside me that’s like, “Oh yeah, maybe I could do this thing.” So that was a big moment.

Michelle Rial (00:15:28): What do you want to say to our mothers right now? Do you want to take this back?

Lenny Rachitsky (00:15:28): My mom doesn’t know.

Michelle Rial (00:15:28): Do you want to take that back?

Lenny Rachitsky (00:15:28): No, no.

Michelle Rial (00:15:34): Do you want to crop it out?

Lenny Rachitsky (00:15:38): Okay, mom.

Michelle Rial (00:15:39): Anyway, next-

Lenny Rachitsky (00:15:40): I did some stuff. It’s okay. It’s okay, it’s time to share.

Michelle Rial (00:15:43): And then you did 10-day meditation. You did a specific type of meditation that seemed to me to affect you in physical ways. And then you told me once about a happiness course you took.

Lenny Rachitsky (00:15:58): Yeah, that was actually pretty transformative. I took this online course at University of Pennsylvania about the psychology of happiness, and it was basically all the science of what makes you happier and how to be happier. That really had a big impact on me because it showed you you can increase your baseline level of happiness by doing a few things. One of the things is just thinking more positively, thinking more optimistically. There’s also gratitude stuff that I didn’t find as useful, but there’s just something about…

(00:16:27): Everyone’s got this baseline. That was actually a big learning from that course is everyone’s just this baseline level of happiness. You could be at 100, you could be at zero, probably most people are in between somewhere. Something amazing happen. You go, oh yeah, way up in happiness, and then you come back to that baseline. Something terrible happens, you go back to that baseline. The main thing you can do is work on improving that baseline so that you come back to a higher place.

(00:16:50): That’s what a lot of the work is and what you learn in that class. One of the thing is just be optimistic. Just have a positive outlook and don’t let your mind spiral into these like, “It’s going to be terrible.” It was a lot of just think more positively, and I feel like my baseline of level of happiness has gone up. Yeah, that helps.

Michelle Rial (00:17:11): I think you told me exercise, too. Used to run.

Lenny Rachitsky (00:17:14): Yes, that was a really good insight, so exercise, the science… This was like 15 years ago, I’m guessing there’s new research, but the interesting thing there is exercise doesn’t make you happier, but it brings you out of the negative. You’re negative one without exercise, and exercise brings you to zero so that you’re not depressed basically.

Michelle Rial (00:17:32): Speaking of stress-

Lenny Rachitsky (00:17:34): Okay, then I have a question for you.

Michelle Rial (00:17:35): Oh, okay. Let’s do this. Let’s do this because I know on your podcast you have a lightning round. We’re going to do a thunder round.

Lenny Rachitsky (00:17:46): Is that extra faster, or what does that mean?

Michelle Rial (00:17:46): No, it’s sound. Your one thing that I think stresses you out the most at times is your misophonia, which is… You want to explain what it is?

Lenny Rachitsky (00:17:56): Yeah, it’s funny to talk about it, but it’s like this disorder. It’s like a real thing in the brain where I get bothered by certain sounds. And so I get very bothered by people eating with their mouth-

Michelle Rial (00:18:11): Okay, thunder round is going to be top five worst sounds, or you can rank these sounds.

Lenny Rachitsky (00:18:17): Okay. You’re going to give me the five?

Michelle Rial (00:18:21): Best sound to worst sound, so 10 is worst. 10 is best. I don’t know.

Lenny Rachitsky (00:18:26): What are the best sounds?

Michelle Rial (00:18:27): Okay, okay. Okay, let’s say chewing, chewing one to 10.

Lenny Rachitsky (00:18:30): Chewing with the mouth open, just like-

Michelle Rial (00:18:33): Chewing with the worst, yeah.

Lenny Rachitsky (00:18:34): I hate it. 10 is the worst?

Michelle Rial (00:18:36): 10 is the worst.

Lenny Rachitsky (00:18:39): Yeah. It’s 10, nine or 10.

Michelle Rial (00:18:40): Or nails on a chalkboard, what’s that?

Lenny Rachitsky (00:18:42): That’s less bad for me.

Michelle Rial (00:18:43): Right, what’s the number?

Lenny Rachitsky (00:18:44): If it’s someone sitting right next to me just chomping away and it’s so awkward to ask anyone to stop. I hate doing that.

Michelle Rial (00:18:50): It’s so weird. You’re sweet.

Lenny Rachitsky (00:18:52): But it’s just like, what? I’m just sitting here eating. Leave me alone.

Michelle Rial (00:18:56): Yeah, that’s how I feel whenever I do by accident near you.

Lenny Rachitsky (00:19:00): Yeah, so 10.

Michelle Rial (00:19:02): Okay, so nails on a chalkboard.

Lenny Rachitsky (00:19:03): It’s like six. I don’t know. Five. I don’t mind.

Michelle Rial (00:19:06): What about a baby crying, or what’s a baby crying versus your baby crying?

Lenny Rachitsky (00:19:10): Baby crying, so 10 is the worst?

Michelle Rial (00:19:12): Yeah.

Lenny Rachitsky (00:19:12): So how loud? Very loud baby crying?

Michelle Rial (00:19:16): In newborn phase, didn’t know what to do.

Lenny Rachitsky (00:19:21): Oh, yeah. When Jude was born?

Michelle Rial (00:19:21): Yeah.

Lenny Rachitsky (00:19:22): Oh yeah, that’s pretty hard. Thunder round, okay. Like eight.

Michelle Rial (00:19:31): Okay, okay. What about when Jude says papa?

Lenny Rachitsky (00:19:33): Yeah, one. One is the best, yeah.

Michelle Rial (00:19:36): Is there any other sound you…

Lenny Rachitsky (00:19:38): Jude laughing.

Michelle Rial (00:19:39): Okay, okay. What about another bad sound?

Lenny Rachitsky (00:19:44): I don’t know.

Michelle Rial (00:19:45): Okay, you can ask me now if you want if you’re getting…

Lenny Rachitsky (00:19:51): No, no, no, there’s not that many bad sounds. It’s just very specific bad sounds that-

Michelle Rial (00:19:51): Chewing.

Lenny Rachitsky (00:19:55): … I’m just like-

Michelle Rial (00:19:56): Basketball?

Lenny Rachitsky (00:19:58): If I’m trying to be calm and there’s a bunch of commotion, like okay, like a gas blower when I’m trying to work.

Michelle Rial (00:20:07): That’s I think a notorious one for people. Is that a 10?

Lenny Rachitsky (00:20:10): It’s like if it’s super loud and right in my face, I would say let’s say a seven. That’s about it.

Michelle Rial (00:20:15): You can ask your question now if you want, or I have more for you.

Lenny Rachitsky (00:20:18): I’m going to ask you a question. You make these incredible, genius, funny charts. There’s one example on this book. You have this first book here called Am I Overthinking This, which a lot of people identify with, has sold many copies. You create all these charts that try to synthesize things in life, things people experience, things people feel.

(00:20:40): A lot of these charts get shared on socials by people that steal your charts and just pretend like they made this or just found it and they cut out your attribution. They make pillows and mugs, and there’s all these websites that sell all these charts you’ve made just like on swag that you get no credit for. I know it’s bothered you a lot over the years.

(00:21:01): What makes your charts so shareable so widely? Why do they go so viral so often?

Michelle Rial (00:21:06): By the way, I stopped looking at that because it doesn’t help me. Anyway.

Lenny Rachitsky (00:21:11): That’s good. I think that’s for the best.

Michelle Rial (00:21:12): Well, I think-

Lenny Rachitsky (00:21:13): That’s the good.

Michelle Rial (00:21:14): Yeah, I think as your thing has gotten more successful, it’s not as important to me.

(00:21:19): I do think it’s interesting that they are often detached from me, which is… I don’t know why, but-

Lenny Rachitsky (00:21:25): Yeah, people want to get credit.

Michelle Rial (00:21:26): … when they do. Some of them, it’s clear when I make it, whether it’s like I make it and then I let it sit and then some moment happens. Or I’m like, “Oh no, this is what it needs.” And then I’m like, “Now I can feel that’s really good.” Usually it’s something that makes me laugh or cackle, even though I made it. It’s like, “Oh, I’ve already seen this in my own brain and it’s still funny to me,” or makes me tear up then I feel like, “Okay, I think people are going to like this.”

(00:21:56): I am often wrong. Sometimes too there’s something from that book that I didn’t share at all, but someone took a photo of it. That’s how on viral is just a photo of a page of a book that people loved.

Lenny Rachitsky (00:22:09): It wasn’t even a digital high quality pictures, just like some written photo, yeah.

Michelle Rial (00:22:12): Yeah, which is interesting as well.

(00:22:14): Also, people’s attention spans. Sometimes what I like to make is things that are really simple and quick and show you something you haven’t thought of before and I think that if it’s really easy to digest. People’s attention spans are short these days.

(00:22:32): And if it makes them feel something is another thing.

(00:22:36): It’s also nice to make something that isn’t a lot of physical labor because some things you can make and it can take you forever to draw out because my brain does work in this overthinking kind of way of like this, but then oh this, and then this. People like it when it’s really simple.

Lenny Rachitsky (00:22:54): Yeah, yeah. I love your point about like the way you know a chart is done is intrinsically you feeling like this is hilarious, this makes you laugh, makes you feel something. It’s similar to the way I think about my newsletter post. Yeah, more the newsletter than the podcast is it just, to me it feels like this is really interesting and really good. It’s very like not waiting for other people to give you approval or feedback. It’s like I feel this is good. I think that’s really interesting that that’s similar to the way I approach my stuff.

(00:23:26): I find that when you work on your charts, you think so many levels deep. They’re like too clever sometimes, and I have to like pull… Because to your point, people have a short attention span. Sometimes they’re like too clever and I have to like, okay, this is too many layers you have to understand. I have to like, that’s a little much. You have to simplify it a little bit. Yeah.

Michelle Rial (00:23:48): Yeah, you’re my editor sometimes.

Lenny Rachitsky (00:23:50): I try, but you’re like, “No.” You’re like, “I don’t care. I don’t care about your feedback.”

Michelle Rial (00:23:53): No, you’re usually probably right.

Lenny Rachitsky (00:23:56): Yeah.

(00:23:57): Okay, let me ask you one more question and then we could switch it around again. How do you come up with your ideas for your charts? You have so many, such variety. You had an adult book, you have a children’s book. You’re working on charts for parents. You have all this other stuff going on. Where do your ideas come from, Michelle?

Michelle Rial (00:24:14): The ideas come from just living life and noticing a lot of things, and then also observing a lot. I know that I’ve been really prolific when I’ve been meditating, and in meditation you learn to observe your own thinking. If you’re anxious about something like, oh, that’s funny that I was anxious about that random thing that I’ve never thought about it that way before, which is interesting because it is like overthinking every moment. Which meditation shouldn’t be teaching you to do, but that’s what happens.

(00:24:49): But I’ve noticed if I focus too much on my work, I stop living life and then I stop having ideas. It’s a little different with children’s books, which is what I’m working on right now, because it’s not like relatable things a little bit. But it’s more children’s concepts, but the adult stuff has to be just through living life.

Lenny Rachitsky (00:25:13): Noticing, yeah.

Michelle Rial (00:25:14): Noticing.

Lenny Rachitsky (00:25:15): Makes me think about… I think David Sedaris had this story where he just has to say yes to everything he’s invited to just because he needs to have experiences because he just has to keep pumping out stories. He’s just like, “Sure, let’s go to Vegas right now. Let’s do it.” I feel like that’s a lot of the work here is just to live real life. You can’t just sit there and come up with ideas. You have to try stuff and do crazy things.

Michelle Rial (00:25:37): Yeah, so my first children’s book, which is out soon, that one actually came out of observing parenthood and early new parenthood moments. That’s how I started. I started at the beginning of the notebook writing, trying to make charts for new parents.

(00:25:54): But we’d been reading so many kids’ books together that I just had this rhythm in my head of children’s books. And so I just turned to the back of the notebook and started writing more children’s book rhymes involving chart.

Lenny Rachitsky (00:26:10): Is this the back of a notebook because you’re working on a different book and you’re just like-

Michelle Rial (00:26:13): In this notebook.

Lenny Rachitsky (00:26:13): Oh, this is the notebook?

Michelle Rial (00:26:15): Put my questions in for you.

Lenny Rachitsky (00:26:16): What?

Michelle Rial (00:26:17): Yeah, and so I started off in the front. I’m not going to show you.

Lenny Rachitsky (00:26:20): You started in the front on a different idea?

Michelle Rial (00:26:22): I just started off in the front charts for new parents, and then I was got a few in, a good amount in. And then I was just in the parking and then I was just like, “Yeah, but I have always wanted to do these charts for kids or for babies.” I just kept wanting to write that. I started in the back, and then I filled it up that way.

Lenny Rachitsky (00:26:45): I love that this is another example of just following pull and not just doing the thing that you’re doing. Just like, “Huh, this is pulling me and I’m going to try it and just see where it goes.” Look at this. What a callback.

(00:26:58): Okay, back to you, Michelle.

Michelle Rial (00:26:59): Back to you.

Lenny Rachitsky (00:27:00): Back to me. Back to you through me. Through you.

Michelle Rial (00:27:02): Yeah, exactly.

(00:27:03): Okay, okay, I do want to ask you this question inspired by our friend who reverse nicknames you and says, “Leonard.” Is your full name Leonard? Where’s Lenny come from?

Lenny Rachitsky (00:27:18): By the way, reverse nickname meaning they give you a nickname without you asking them to.

Michelle Rial (00:27:21): Well, there’s people who give you a nickname without you asking. He gives you the full name.

Lenny Rachitsky (00:27:27): Oh, I see. Makes it long.

Michelle Rial (00:27:28): Yeah, it’s not a thing. I’m just making it up.

Lenny Rachitsky (00:27:32): Okay, I like that.

(00:27:33): Okay, so the question is my real name. When I moved to the US from the Ukraine, which we recently chatted about on a podcast with Boris, which turned out to be a big news.

Michelle Rial (00:27:44): Odessa.

Lenny Rachitsky (00:27:45): Odessa, yeah. My parents named me Leonid was my real official first name in the US, but they called me Lenny. Everyone called me Lenny. And so when we became citizens, you could change your name. And so my parents just changed it to Lenny, so it’s my real name.

Michelle Rial (00:28:01): It’s just Lenny. No, no Leonard.

Lenny Rachitsky (00:28:03): Leo, yeah.

Michelle Rial (00:28:04): Oh yeah, Leonardo.

Lenny Rachitsky (00:28:05): Just Lenny.

Michelle Rial (00:28:06): Just Lenny. I love it. Leonid as in it’s a Russian name, or there’s also the star constellation.

Lenny Rachitsky (00:28:15): Oh, the Leonids? I don’t know. I think they just asked their friends just like, what is … My Russian name is Lonya. And so I think they just like, “What’s the English version of that?” I’m guessing some of their friends are just like, “Leonid.” I don’t know if they named it after anything specific.

Michelle Rial (00:28:29): Can I share any of your nicknames? I’m going to assume no.

Lenny Rachitsky (00:28:32): What are my nicknames? Okay, go for it. I don’t know how they are.

Michelle Rial (00:28:32): Like Lyonchik?

Lenny Rachitsky (00:28:37): Okay, sure.

Michelle Rial (00:28:38): I could share that?

Lenny Rachitsky (00:28:39): Sure.

Michelle Rial (00:28:40): Do you like it?

Lenny Rachitsky (00:28:41): Yeah.

Michelle Rial (00:28:41): Do people call you that?

Lenny Rachitsky (00:28:42): Well, it’s like my family calls me that. It’s like a Russian little nickname, Lyonchik.

Michelle Rial (00:28:47): Yeah. Okay, but strangers, can they call you that?

Lenny Rachitsky (00:28:52): No, don’t call me that.

Michelle Rial (00:28:54): Okay, and speaking of strangers, how do you feel when people approach you? Is it weird at all? Does it remind you how big your newsletter has gotten, or do you like it? Do you like certain ways of approaching it?

Lenny Rachitsky (00:29:07): Yeah, so I guess what you’re speaking to is when I walk around the Bay Area in particular, people often recognize me, which is extremely weird and started with the podcasts. Interestingly, I had the newsletter for four years.

Michelle Rial (00:29:20): Yeah, you got to be stealth.

Lenny Rachitsky (00:29:21): Yeah, my face was tiny in some Twitter profile, but once I started the podcast, people just… Yeah, it was very weird the first time it started happening, and then now it happens quite a lot.

(00:29:33): I like it a lot. It’s very cool. I really appreciate it. It makes me feel really nice. I’m not bothered by it in any way. It always is very flattering, and people are always so nice and just have endless nice things to say. I’ve never had a bad experience someone just trying to say hi to me, so please say hi.

Michelle Rial (00:29:51): Okay, that’s great. That’s cool.

Lenny Rachitsky (00:29:52): I often ask people what’s their favorite podcast episode or favorite newsletter, because I’m just curious. I always ask just like you a founder, you a product person? What’s your story? Yeah, it’s nice.

Michelle Rial (00:30:02): What about if you’re at a coffee shop, you have headphones on and somebody says like, “Hey”? Or if you’re playing with your kid, what do you think?

Lenny Rachitsky (00:30:08): I think you’re projecting about what you wouldn’t want.

Michelle Rial (00:30:11): Right, girl.

Lenny Rachitsky (00:30:11): Yeah. People don’t do that. I think people have been generally very conscious. There could be a moment of just like, “We’re getting somewhere and I can’t talk for too long and I don’t want to be rude.”

Michelle Rial (00:30:21): Or you’re in a focus, but then… Yeah.

Lenny Rachitsky (00:30:25): It hasn’t been a problem yet. Almost like 99% of people have been very considerate, and I don’t want people to feel like they can’t just talk to me and say hi.

Michelle Rial (00:30:33): Yeah, that’s cool.

Lenny Rachitsky (00:30:34): Yeah, they’re always so cool.

Michelle Rial (00:30:35): I like that.

(00:30:35): Yeah, is there any instance of delightful?

Lenny Rachitsky (00:30:39): Maybe the first time this happened, we live in Marin. I was walking over through San Anselmo with you as you remember, and there’s this guy in a little red car driving by with his son. He’s driving by and we’re on the sidewalk. And then he just yells, “Lenny, I love your podcast.” God.

(00:31:01): This wasn’t even in San Francisco. I was in San Anselmo, and I was shocked. And then he held up traffic just to say hello. I’m like, “Oh, my God.”

Michelle Rial (00:31:10): Yeah, I wouldn’t do that.

Lenny Rachitsky (00:31:11): Yeah, probably wouldn’t do that. And then I met him later. He runs a hamburger club in Marin. He’s very cool because I saw him again at another coffee shop, so that was quite delightful.

Michelle Rial (00:31:21): I love that.

(00:31:23): Okay, you just said something. Okay, people coming up to you. Okay, you’re going to have to cut this.

Lenny Rachitsky (00:31:32): See, no, we’re not going to cut it because this is what I go through too as a podcast interviewer.

Michelle Rial (00:31:38): I thought of something. I lost it.

Lenny Rachitsky (00:31:38): This is what I am constantly dealing with. That is a challenge of the interviewer. I think it’s fun for people to see because you’re like, “Okay, I have to think about what I’m going to say next.” And then there’s stop and then you’re like, “Oh, what’s it going to be?” That’s why when I do the podcast, I’m secretly writing notes to myself constantly. Check your notes.

Michelle Rial (00:31:56): Yeah. Okay, I should have written it down.

(00:32:00): Let’s talk about, thinking back to what kind of hints that you would start this newsletter or things that you worked on when you were younger that are-

Lenny Rachitsky (00:32:12): That helped me to-

Michelle Rial (00:32:13): Or mildly adjacent because you had some websites, you had Atheist Spot, you had some-

Lenny Rachitsky (00:32:13): Youtorials.

Michelle Rial (00:32:22): Youtorials, that’s one.

Lenny Rachitsky (00:32:25): So the question is what are the things I did earlier that helped me with the work I do now?

Michelle Rial (00:32:30): Or yeah, because just looking back, anything that makes it obvious that you would’ve started this newsletter, or a little more…

Lenny Rachitsky (00:32:37): I don’t think there was anything that would’ve pointed me or anybody to this being the thing that I do now. It’s completely unexpected personally, and I don’t think anyone saw it coming. I had never written anything online before I started writing. I was always not like, “Hey, look at me. I’ve got all the answers and I have all this wisdom to share.” I was always like, “I’m an introvert. I’d like to stay behind the scenes.” It’s a very unexpected path for me.

(00:33:03): Part of the reason I think I was able to do it is the newsletter started during COVID, so I could just sit there and type and put stuff out online. I didn’t have to go anywhere and tell everyone. I could stay in my little hole. But just to follow through on these things you pointed out that I did earlier, because I don’t think I’ve ever talked about these things, I had all these different side projects before, like through college, I guess. Yeah, through college.

(00:33:26): I was like a very big atheist and I’m still an atheist. Jewish atheist, which is many Jews. But I was very into it before and now I’m like, okay, I don’t care, whatever. Believe your own belief. I used to run a website called theatheistspot.com, which was Reddit for atheist news, which is not a… Reddit is that. It’s fine, and you don’t need it. But there’s like conventions. We went to atheist conventions. I did that.

(00:33:55): The funny thing is that was during AdWords when Google AdWords was a way to monetize your site. And so all the ads on the site, because most of the articles were about religion, were all these religious dating sites. It was like Christian Mingle and all these funny dating sites that didn’t make sense for the audience. I always thought that was funny.

(00:34:16): And then I worked with a friend on this other project called Youtorials, which was so ahead of its time. The idea was Youtorials, tutorials for you by you. And so it was people contributing things they’ve learned and writing a how-to, like how to make eggs, how to take a quick shower. It was all these-

Michelle Rial (00:34:31): That’s like TikTok, right?

Lenny Rachitsky (00:34:32): It’s like TikTok. It was before Wikipedia, I think.

Michelle Rial (00:34:32): No, I know. Yeah.

Lenny Rachitsky (00:34:32): Yeah, it’s like YouTube.

Michelle Rial (00:34:32): That’s what I watch TikTok for is watching people make-

Lenny Rachitsky (00:34:42): Yeah, and parenting advice and things to be afraid of and dance videos.

Michelle Rial (00:34:47): That’s what your thing was or that’s what TikTok is?

Lenny Rachitsky (00:34:50): That’s what TikTok is, right? Yeah. Yeah, I was really proud of that.

Michelle Rial (00:34:53): Yeah, it sounds like it was ahead of people. And Localmind was ahead of its time.

Lenny Rachitsky (00:34:57): And Localmind, so that was my startup. We sold it to Airbnb. That’s how I got there. Localmind, amazing idea and not something anyone needs, really.

Michelle Rial (00:35:07): I still need it. I still need it.

Lenny Rachitsky (00:35:09): But you need it once in a while.

(00:35:11): Just to briefly explain what that is, it was an app that sat on top of forScore and Goalo when that was very cool and allowed you to ask questions of people checked in anywhere in the world. If you’re like, “If they’re a long line at The Mill,” which is near here, “should I go? Is there a long line? What’s the special?”

Michelle Rial (00:35:25): We just used that basically.

Lenny Rachitsky (00:35:27): Yeah, so Google does it with their is it busy. Yeah, all these other ways that you could solve this problem. It was very cool. It was amazing. Nobody needs it, really.

Michelle Rial (00:35:36): If there’s still things you want to ask-

Lenny Rachitsky (00:35:38): You need once in a while. You need once a quarter and it’s holy shit, that’s so good. But you can’t make a business out of that, so I’m glad that we exited.

(00:35:48): Today’s episode is brought to you by DX, the developer intelligence platform designed by leading researchers. To thrive in the AI era, organizations need to adapt quickly, but many organization leaders struggle to answer pressing questions, like which tools are working? How are they being used? What’s actually driving value? DX provides the data and insights that leaders need to navigate this shift. With DX, companies like Dropbox, booking.com, Adyen, and Intercom get a deep understanding of how AI is providing value to their developers and what impact AI is having on engineering productivity.

(00:36:23): To learn more, visit DX’s website at getdx.com/lenny. That’s getdx.com/lenny.

Michelle Rial (00:36:31): Okay, so you’re mentioning the atheist bot with bunch of religious dating sites. Reminded me that you were my first online date ever.

Lenny Rachitsky (00:36:40): Hell yeah. Snatched right up.

Michelle Rial (00:36:42): Platform called HowAboutWe? I mean, you had had other dates.

Lenny Rachitsky (00:36:49): Where’s this going?

Michelle Rial (00:36:50): Anyway, no. See, I think you had a thing for designers, and I wonder if you regret that preference. Designer artists-

Lenny Rachitsky (00:37:02): No, not at all.

Michelle Rial (00:37:04): … stereotype.

Lenny Rachitsky (00:37:05): No, no.

Michelle Rial (00:37:06): I’m not. You’re pretty neat.

Lenny Rachitsky (00:37:08): Yeah, yeah. It’s true. You’re chaotic. Yeah. Which is, we could talk about your process, but it’s a messy process. It’s true. We have a good yin/yang.

Michelle Rial (00:37:17): Yeah. Yeah, I’m just like you’re unstressed, unbothered. I’m bothered. I’m stressed.

Lenny Rachitsky (00:37:23): You stress things everywhere. We get cleaners. They help things out. Yeah, it’s true.

Michelle Rial (00:37:24): I know. Privilege.

Lenny Rachitsky (00:37:30): It’s worth it.

Michelle Rial (00:37:31): Okay, so you’re okay with designers still. Good. And then-

Lenny Rachitsky (00:37:35): As a wife.

Michelle Rial (00:37:37): Yeah, right, right.

Lenny Rachitsky (00:37:37): Highly recommend.

Michelle Rial (00:37:38): Okay.

Lenny Rachitsky (00:37:39): Yeah.

Michelle Rial (00:37:39): Oh, great. Yeah, I was going to ask, do you have any tips for… Because there’s something you said recently, which is you don’t have any coworkers. I was like, “I’m your coworker. We work at home.”

(00:37:50): Yeah, do you ever feel lonely because you were always really social? And then this goes into too even before you were niche famous, or whatever we want to call it-

Lenny Rachitsky (00:38:01): Yeah, that’s how I describe it.

Michelle Rial (00:38:01): People were always coming up to you on the street like, “Lenny.”

Lenny Rachitsky (00:38:04): Yeah, from Airbnb.

Michelle Rial (00:38:06): From Airbnb because you’re organizing things. Do you feel like you miss office culture?

Lenny Rachitsky (00:38:13): People ask me that over the years and I’ve always like, “No, it’s amazing. I don’t need that. I just do my own thing and I don’t need people around.” But I’ve started to feel that a little bit of just like, huh, there’s no one. I just sit at home all day and just like…

Michelle Rial (00:38:25): Our dog likes to be right next to you.

Lenny Rachitsky (00:38:27): Yeah. Yeah, he’s sweet. I do feel like I do miss it now. It’s not like a huge problem, but it’s just like it’d be cool to just jam with someone on stuff. I have a team and I have you and Twitter.

Michelle Rial (00:38:42): Well, you like to go to coffee shops.

Lenny Rachitsky (00:38:44): I like to go to coffee.

Michelle Rial (00:38:44): What do you get?

Lenny Rachitsky (00:38:46): But it’s like bowling alone. I don’t know if that’s the good metaphor.

Michelle Rial (00:38:48): And you have your headphones. You put your headphones, too.

Lenny Rachitsky (00:38:50): And my headphones on, yeah.

Michelle Rial (00:38:51): And you’re focused.

Lenny Rachitsky (00:38:52): Yeah, so it would be fun. I have an awesome team and we jam on stuff, but it’s not like… I think I do miss having someone next to me that I’m just working with on the same thing. But I also am trying very hard to never have full-time employees. I’m trying to keep things really simple because it’s so easy to build this thing into this whole thing that’s complicated that I’m like, “What have I done?”

(00:39:13): One of the challenges with this life is you can create a job for yourself that you hate by doing things that people want you to do or by following opportunities that feel big and then you’re like, “I hate this.” I’m trying to be really careful about what I commit to and do.

(00:39:30): Coming back to your question, I do miss it some. Yeah, it’s like a new thing I’ve realized that I miss is being around other people, like working on the same thing.

Michelle Rial (00:39:38): Yeah, so speaking of other people coming up to you and being around other people, I think it’s become harder for you now that people you don’t know come up to you because I think you actually have a little bit of face blindness. People who do know you come up to you and you’re waiting to know if they just listen to your podcast or if you-

Lenny Rachitsky (00:39:59): I know if I know them. Yeah, this is a big problem for me. It’s like another brain disorder, where I just don’t remember people’s names. I’m so bad at it. I just like, “I know you. Who are you?” It’s like people texting you from a new number, “I’m like, who is this?”

Michelle Rial (00:40:15): Yeah, sometimes I feel like the Devil Wears Prada assistant where I’m like, “That’s Emily. You worked with her on Airbnb,” or that’s-

Lenny Rachitsky (00:40:24): Wait, you don’t do that. You need to do that.

Michelle Rial (00:40:25): I do it sometimes.

Lenny Rachitsky (00:40:26): You do that sometimes? Okay. Yeah, so bad at that. Okay, so if you come up to me and you say hello and I don’t recognize you, please, I’m sorry. I’m really bad at it. Yeah, it’s gotten worse because now I know more people through the podcast and the newsletter and like-

Michelle Rial (00:40:39): Right, and you just know a lot of people.

Lenny Rachitsky (00:40:41): Yeah, it’s like a lot of faces.

Michelle Rial (00:40:43): You’re very kind with people like you.

Lenny Rachitsky (00:40:44): I try, I try, I try.

Michelle Rial (00:40:48): Okay, so going back to the unbothered vibe that you have, tell me about a time you’ve been really stressed in your business and then a time you’ve been really stressed in your personal life.

Lenny Rachitsky (00:41:02): Okay, so on the business side, so I have this product pass. As a subscriber to my newsletter, you get 23 incredible products. I used to read them all: Linear, Mobb and Lovable, Replit, Gamma. I stopped doing this because there’s too many now I had that end of my podcast. I just read through all, and now I can’t do it anymore. There’s too many.

(00:41:19): I had a launch about a year ago, it’s about a year actually where I launched… You get a free year of Cursor and Lovable and Bolt and Replit and v0. I think that’s five. And so that was way too good an offer. People came for it, bad people. I just had so many fraudsters, mostly in China it turned out. Just like all these fraud rings in China trying to find ways to steal all these free goodies. They set up all these crazy attacks, and I had to work with Stripe and Substack to just shut them down. They just found all these little exploits in our API that we built. It was such a nightmare because we’re just waking up to like every night. It was hard to sleep.

(00:42:06): I have this engineer, Este, who’s so incredible. He didn’t sleep for a week stopping, filling all these holes because there’s a lot of smart, clever, bad guys out there. That was extremely stressful. It could trickle down into the whole thing falling apart if everyone’s like, “Oh my God, can’t trust Lenny anymore.” As you remember, it was very stressful. I didn’t sleep too well, and it was very scary.

(00:42:34): They just kept popping up, and there’s all these rings. It went viral in China, too. That’s like in the student network, they just, “Holy shit, you get a year free of Cursor and Lovable and Replit and Bolt and v0?” It was very stressful.

(00:42:48): To answer your question on the personal side, okay, so when our baby was born, the birth was very complicated. You had to get a C-section because the induction wasn’t getting it there because it was-

Michelle Rial (00:43:04): Complicated.

Lenny Rachitsky (00:43:05): It’s complicated. We won’t get into it.

Michelle Rial (00:43:06): Normally I feel like I would tell this story, but-

Lenny Rachitsky (00:43:07): You weren’t awake.

Michelle Rial (00:43:08): But this is also like when Harry Met Sally, but it’s like how the pregnant person almost died. But it’s from your perspective because I didn’t get to experience it.

Lenny Rachitsky (00:43:20): Right. Yeah, so what happened is you had to do a cesarean, and so the idea is they bring you into the operating room, they do the anesthetic, the epidural or whatever it’s called, and then they let the husband and the partner in. And so I was waiting in the hall waiting for them to do the anesthetic.

Michelle Rial (00:43:41): With your scrubs.

Lenny Rachitsky (00:43:42): They gave me a whole bunny suit. Yeah, super sterile, just standing there in this bunny suit thing. The idea is they do the anesthetic, and I can come in and then watch the birth and all that stuff.

(00:43:52): Five, 10 minutes in, I just hear beep, beep, beep, beep, beep, beep, beep, beep, beep, beep, beep. The doctor runs out, scrubs her hands, runs back in. And then two other people run from another room down the hall into the room. They’re like, “Uh-oh.” I was like-

Michelle Rial (00:44:13): You were scared?

Lenny Rachitsky (00:44:13): I was very scared because I had no idea what was going on. That didn’t sound good.

Michelle Rial (00:44:17): Nobody told you anything.

Lenny Rachitsky (00:44:18): Nobody was telling me anything.

Michelle Rial (00:44:20): You were supposed to be in there.

Lenny Rachitsky (00:44:20): I was supposed to be in there. No one’s coming out like, “Here’s what’s happening.” It was like 10 minutes of just nothing.

Michelle Rial (00:44:20): Yeah, and you were supposed to be in there after a minute?

Lenny Rachitsky (00:44:28): Yeah, it was going to be quick, yeah. Yeah, I was supposed to be like, “Come on in. We’re going to do this here.” You’re awake during it in real life.

(00:44:35): I just remember pacing down the hall, coming back to the lessons I’ve learned, just like, “It’s going to be okay. It’s going to be okay.” That’s what I remember saying to myself, “Just trust that they know what they’re doing. We’re in a hospital. There’s a lot of doctors around.”

(00:44:52): And then eventually they came back and they just said that the epidural went the wrong direction. And so instead of going down, it went up your body and so it was stopping your heart and lungs. They had to intubate you and do an emergency intubation and get the baby out. And then took an hour for you to come back. They were going to put you in the ICU to help you come back. That was very scary because you weren’t there. I don’t know what’s going on.

Michelle Rial (00:45:17): You got to hold the baby for an hour without… That’s why he’s like only papa. He’s another person that prefers you.

Lenny Rachitsky (00:45:30): Who’s the other person?

Michelle Rial (00:45:30): Our dog.

Lenny Rachitsky (00:45:30): For now, for now, for now.

Michelle Rial (00:45:33): Because you’re a sweet guy. But yeah, it’s…

Lenny Rachitsky (00:45:38): Yeah, that was really scary.

Michelle Rial (00:45:39): Stressful. You told yourself I was going to be okay.

Lenny Rachitsky (00:45:42): Yeah, that was the thing that helped, but it was very scary because it’s just like life could be completely different now.

(00:45:51): The anesthesiologist said it was a one in 50,000 chance, and it’s the worst scenario that is very rare and very dangerous. And so it was extremely scary. Luckily he did a great job and everyone’s like, “He killed it.” He knew exactly what to do. He handled it really well.

Michelle Rial (00:46:11): Yeah, and I don’t have any memory of this.

Lenny Rachitsky (00:46:13): You don’t remember this, yeah.

Michelle Rial (00:46:14): It numbed my-

Lenny Rachitsky (00:46:15): Just came back.

Michelle Rial (00:46:15): Numbed my lungs and I was like, “I can’t breathe.” And then I numbed my spinal… What is it? Brainstem, and then I passed out.

Lenny Rachitsky (00:46:24): How about that?

Michelle Rial (00:46:25): How about that? I didn’t have to get to have any…

Lenny Rachitsky (00:46:28): Looking back, are you-

Michelle Rial (00:46:29): We don’t have to talk about it. No, that’s what you said, but it’s interesting to not have an experience around it. The experience was the live experience is more-

Lenny Rachitsky (00:46:40): Yeah, it’s probably the scariest moment in my life.

Michelle Rial (00:46:45): Yeah, and I didn’t know anything about it because they put me under general anesthesia, and then I was all loopy and then I didn’t even know really what… And then later I read the report, months later I read it. I actually had someone else read it who was in the field. It was your cousin Lois and she moved her thick glasses like, “Wow.”

Lenny Rachitsky (00:47:03): Yeah, she’s like a nurse back in the day. Yeah.

Michelle Rial (00:47:05): Anyway, stressful moment. Yeah, so you used your tools.

Lenny Rachitsky (00:47:10): Yeah, I used my tools. Otherwise, that’s a good point because it could have been spiral. Oh, my God.

Michelle Rial (00:47:15): We had a doula, but she had left.

Lenny Rachitsky (00:47:18): The doula was going to be there.

Michelle Rial (00:47:18): She could have helped.

Lenny Rachitsky (00:47:19): But for cesarean, she’s like, “I can’t be here.” Yeah.

(00:47:22): Okay, I want to ask you a question, but unless you have something we want to follow up with.

Michelle Rial (00:47:25): No, no.

Lenny Rachitsky (00:47:26): Okay, so you come up with these incredible charts. It’s like the kind of charts you see on the internet that are like, “Oh my God, that’s so genius.” Watching you come up with it is so wild because it pops out of nowhere and then there’s a little bit of iteration. That’s it. What’s the process for you coming up with a chart, and what’s the environment that you need to create your best work?

(00:47:49): I feel like coffee is a big part of it.

Michelle Rial (00:47:50): Coffee is. Not too much. There’s one I have that’s like, I mean… It has to be the perfect amount of coffee, so I actually usually get a single shot.

Lenny Rachitsky (00:47:57): Do you know about the Bomber Peak, by the way, quick tangent?

Michelle Rial (00:47:57): Okay.

Lenny Rachitsky (00:48:00): Okay, so there’s a concept called the Ballmer Peak from xkcd, which is just the right amount of alcohol where you’re the most insightful and creative. And then it falls down, which is like… I forget why this is Steve Ballmer related, but okay, so the Ballmer Peak of coffee.

Michelle Rial (00:48:14): I have one like that about coffee, but it’s not. It’s made out of a little coffee straw, and it’s like-

Lenny Rachitsky (00:48:18): We’re going to show this on YouTube if you’re watching this so you could see the chart.

Michelle Rial (00:48:21): It’s like I’m a genius and then I’m having a panic attack. And so that’s me is like, “Yeah, I’ll get to this point where I feel like…”

(00:48:29): I mean, coffee is a drug, right? If I have too much, it is like a drug. I feel like a genius and I’m having all these ideas, but then I think it’s too… I don’t know if this was a real image, but there was an image of spiderwebs and it’s like, this is a spiderweb that ingested some-

Lenny Rachitsky (00:48:44): Right, LSD and stuff and coffee.

Michelle Rial (00:48:47): And then this is spider that had coffee, and it’s like instead of a regular web, it’s like a web that goes like this. It’s just erratic and tangential. I have some really good seeds of ideas in those moments, then I have to go scream into a pillow or something.

Lenny Rachitsky (00:49:04): Was that when you have too much coffee, or is that when-

Michelle Rial (00:49:06): When I have too much coffee.

Lenny Rachitsky (00:49:06): Okay, too much.

Michelle Rial (00:49:07): But if there’s a point right before that.

Lenny Rachitsky (00:49:10): Single shot latte.

Michelle Rial (00:49:12): Single shot is what I get. Single shot latte, at least an hour. Sometimes it’s good to have somewhere I have to be to a time limit, and then I feel like a machine. It’s like trying really hard to get somewhere.

(00:49:28): And then the other thing is just a lot of it is writing something down as I’m out in the world, writing and then trying to put it on paper in a way that visualizes it because I’m not strong at drawing. Yeah, when I was a kid, my dad did a lot of math with me and a lot of fractals and visualization and patterns. And so I think that way mathematically kind of. Yeah, so it helps me to visualize an idea that in the simplest way possible.

Lenny Rachitsky (00:49:59): Let me just say, this is very cool that we’re doing this. This is really fun, so sweet.

Michelle Rial (00:50:04): Oh.

Lenny Rachitsky (00:50:05): Yeah, and this was really nice.

Michelle Rial (00:50:07): Yeah, this is our Odessa moment. Yeah.

Lenny Rachitsky (00:50:11): You’re born in Odessa, too?

Michelle Rial (00:50:13): No, no, but one of my questions was like… This would be like if I were in the audience, it would be more like a comment versus a question.

Lenny Rachitsky (00:50:21): We’re going to pretend it’s a big question.

Michelle Rial (00:50:23): Yeah, our families are both from countries that like… Mine from Venezuela, you’re from Ukraine, where people are always like, “Oh,” just that… We didn’t just arrive from Venezuela or Ukraine, so it’s not the same. We have to almost make them be okay. It’s okay. I mean, my family still lives in Venezuela, but…

Lenny Rachitsky (00:50:44): Okay, so I asked you a question. Okay. Oh, that’s back to you.

Michelle Rial (00:50:48): Okay, great.

Lenny Rachitsky (00:50:48): Yeah. Well, no. Okay. Let me reflect back what you said because this is really interesting. A single shot, so it’s like some kind of neuro stimulation. Single shot, just enough. I like this deadline piece. That was really interesting.

Michelle Rial (00:51:02): It’s like not too much time, not 30 minute. Although that can be why I’m late often is I’m like, “I’ve almost got it.” I’m a time optimist, as you know, that I’m like, “Oh, I think I have it.” But a good time is two hours, and then I have to be somewhere in two hours.

Lenny Rachitsky (00:51:24): Interesting.

(00:51:25): Okay, so those are two elements. And then was there another for optimal creativity?

Michelle Rial (00:51:30): Oh, a good night of sleep. The bad night of sleep plus too much caffeine, then you have no ideas. You just have the frantic piece of the caffeine, the mental energy.

Lenny Rachitsky (00:51:44): Anything else? This is really interesting, I think, just the idea of what creates creativity.

Michelle Rial (00:51:49): Just experiences. Experiences and thinking and almost like thinking too much about them.

Lenny Rachitsky (00:51:55): I like that. Maybe overthinking.

Michelle Rial (00:51:56): Yeah, right. Yeah.

Lenny Rachitsky (00:51:58): Back to you, Michelle Rial.

Michelle Rial (00:51:59): Oh, back to me, to you?

Lenny Rachitsky (00:51:59): Yeah.

Michelle Rial (00:52:01): Yeah. Okay, so we did the thunder round. We did the worst things to hear. Okay. And the best sounds, which your son’s laugh.

Lenny Rachitsky (00:52:11): Yeah.

Michelle Rial (00:52:11): Yeah, agreed.

Lenny Rachitsky (00:52:12): So great.

Michelle Rial (00:52:14): Okay, we probably know your favorite product management books. Do you have a favorite children’s book other than mine? To read to-

Lenny Rachitsky (00:52:22): Charts for Babies.

Michelle Rial (00:52:23): To read to.

Lenny Rachitsky (00:52:23): Coming out in April.

Michelle Rial (00:52:26): Also, maybe you could do more than one because maybe there’s one when it’s a baby.

Lenny Rachitsky (00:52:34): You never take my ideas because I feel like you don’t want to.

Michelle Rial (00:52:34): I don’t want to.

Lenny Rachitsky (00:52:38): You want it to be your ideas. But I feel like there’s books you love that are children’s books and books your kid loves. It’s like, I hate reading this one, but he loves it, so we’re going to do it. It’s like he decides what his favorite are.

(00:52:49): I love John Klassen books. They’re so beautiful and just sweet, so those have been really great.

Michelle Rial (00:52:57): Are they sweet?

Lenny Rachitsky (00:52:58): They’re actually not sweet. You’re right. There’s death in all of them. They all end in death.

Michelle Rial (00:53:04): Yeah, Jude’s new thing, he’s like, “He ate the bunny?”

Lenny Rachitsky (00:53:07): Is it the bear book?

Michelle Rial (00:53:09): Yeah.

Lenny Rachitsky (00:53:09): He stole my hat. Yeah, we started the book and he’s like, “He ate the bunny? Where’s the bunny?” In his belly.

Michelle Rial (00:53:18): Yeah, is there any overlap? You think there’s a favorite that one that’s his favorite that you now love because that you didn’t love initially?

Lenny Rachitsky (00:53:27): Yeah, Dr. Seuss, I think we similarly feel it’s way too long is one because there’s 50 pages, 60 pages. Come on.

Michelle Rial (00:53:37): A lot of words to say.

Lenny Rachitsky (00:53:37): Yeah, it’s a lot of words. And there’s just all these made up animals and he’s like, “What’s a zong?” I’m like, “That’s a zong.”

Michelle Rial (00:53:44): You’re trying to teach them real things in the world, and then he’s like, “What was a tale of zongs? What?”

Lenny Rachitsky (00:53:48): Vipper from Vipp. Yeah, I don’t know. I don’t like that.

Michelle Rial (00:53:53): But we like reading them.

Lenny Rachitsky (00:53:55): Yeah, there’s a rhythm.

Michelle Rial (00:53:56): Well, anything in Spanish I read to him, obviously. Yeah, I mean, anything you want to say about… Is there anything you’ve learned in product management or growth that has translated to parenting?

Lenny Rachitsky (00:54:15): Product management is all about influence, and that’s basically parenting.

Michelle Rial (00:54:20): That’s why he likes you better.

Lenny Rachitsky (00:54:22): Why? Because I can influence? But you also have to make them do stuff. You do have authority. All the responsibility without the authority, but you do have authority, so it’s easier.

Michelle Rial (00:54:33): I feel like toddlers have all the authority.

Lenny Rachitsky (00:54:35): That’s true. Just like, nope, you sit there.

Michelle Rial (00:54:39): Yeah, I feel like I see your product management in that you make him… I should be the one making him a chart, but you make him the… If bedtime gets too long, you’re like, “Here’s how bedtime’s going to go. We’re going to read you three books and you get a star.” And then also I’m answering for you. Sorry.

Lenny Rachitsky (00:54:57): Go on.

Michelle Rial (00:54:57): Other things, where I’m like, “Yeah, it just happens the way it’s happening.” You’re like, “No, I read a book on it. I read three books on it, and this is how we’re going to do it. It’s going to work.” Sometimes it works. Sometimes it doesn’t.

Lenny Rachitsky (00:55:09): Right. Yeah, I’m not an intuition guy. I’m just like, “What have the smartest people figured out about this?” This isn’t the first time somebody has tried to shorten bedtime.

Michelle Rial (00:55:19): Right, shorten bedtime, sleep through the night.

Lenny Rachitsky (00:55:21): Yeah. Yeah, there’s smart people that have tried this stuff before. Kids tell me what they’ve done.

Michelle Rial (00:55:29): Small eye roll.

(00:55:32): Okay, so I guess this is, I think, my last question for you, and I don’t know if you want to answer it, but I, as your wife of however many years, like 10, still… I don’t think I know what product management is. Can you tell me in five words?

Lenny Rachitsky (00:55:49): It’s hilarious. Okay, my words are impact, collaboration, judgment, alignment, and… This is a really good question. It’s almost like the order is how you think about product management. It’s like the word you put them in.

(00:56:09): What else? I’ll just say some stuff because it’s really interesting. Coordination.

Michelle Rial (00:56:15): I think that’s five.

Lenny Rachitsky (00:56:16): Organizing, planning, outcomes.

Michelle Rial (00:56:22): I have tuned out.

Lenny Rachitsky (00:56:23): There’s so many. You’re like, “Shut up. So boring.” I’m just like, “What should I have I said?” That’s what I’m going to think about now. Yeah, it’s like a crazy, weird job, all these different things. Yeah, I’m just like sniped. I want to keep thinking.

(00:56:36): I’ll give you my definition of product management.

Michelle Rial (00:56:38): Yeah, but you can’t say mini CEO.

Lenny Rachitsky (00:56:40): No, I’m a no mini CEO. That’s not cool, although I actually do think PM is a mini CEO. I think people keep saying you’re not, but I think you are.

Michelle Rial (00:56:47): Yeah, you can’t say not a project manager.

Lenny Rachitsky (00:56:51): Yeah, not a project manager. That’s right. I think the way I describe it is your job as a product manager is to deliver business impact by prioritizing and solving the most impactful business problems. Something like that. That’s many words. You’re like, “This is why I never know what it is. It’s so boring. What are you even talking about?”

(00:57:14): This comes back to the mini CEO thing, just to close that thread. I feel like the PM on the team basically should be thinking the way the CEO thinks. Their job is to think, what would the CEO do on this specific product or feature? Because the CEO’s job is to make this successful, make this business grow. And so your job as a PM is to channel that. What will allow this team and product to help the business be more successful?

Michelle Rial (00:57:38): Do you feel like you’re doing that as the… I guess you are.

Lenny Rachitsky (00:57:42): I’m everything in my current world, right?

Michelle Rial (00:57:44): You’re editor-in-chief too.

Lenny Rachitsky (00:57:46): Editor-in-chief, yeah. Yeah, but I have a copyeditor. I have an editor, so I’ve helped.

Michelle Rial (00:57:50): Oh, right. Yeah.

Lenny Rachitsky (00:57:51): Yeah. People ask me what about product management helped me do the job I do now. I don’t think there’s anything, to be honest, except just things I was already into, which is just being very organized, having a very high bar for quality, communicating. I think communication maybe is just how to succinctly communicate points so that people grasp them.

Michelle Rial (00:58:11): That’s like…

Lenny Rachitsky (00:58:14): Whoa, look at this. We’re the same. Introducing.

Michelle Rial (00:58:18): The key is just communicating something simply.

Lenny Rachitsky (00:58:22): Wow.

(00:58:24): Well, let me ask you one more question, so maybe it’s a close. You wrote two adult books. You now did a children’s book. Why the pivot to children’s books? Why’d you decide to do a children’s book?

Michelle Rial (00:58:36): I wanted to do a children’s book based on the first adult book because I thought that charts are so… They’re a ton of early learning concepts put together. If you look at children’s books, the themes are often opposites, colors, shapes, feelings. And then I was thinking you can really teach a lot from a chart and it’s so simple. It’s a lot of opposites. It’s big and small. You’ve got going up and going down. You’ve got overlapping colors becoming another color. You can make a lot of feelings with charts. That’s the second book in this series that I’m-

Lenny Rachitsky (00:59:22): It’s coming out next year.

Michelle Rial (00:59:24): Yeah. But yeah, I finished it, but it still takes about a year to come out after that. I wanted to work on it in abstract. I had the thought of wanting to work on it, but it didn’t come until I started trying to work on another adult book that I really just had all these rhymes in my head.

(00:59:44): It was more like a cadence. I had just this in my head. Yeah, I just tried it and it came really quickly, the first draft. Yeah, I always wanted to make one because as a little girl, my dad wanted me to… He was a geophysicist. He wanted me to be strong at math because at the time it was like girls weren’t encouraged necessarily to be good at math. He from just a young age he was always showing me… I do the same with our son too always showing him patterns and like, “Oh, if you flip it, it’s like that.” It’s just really fun for me.

(01:00:20): It’s cool too writing the first one with our son growing up. Learning from experience, like I was saying, having the experiences of him as a baby and how I’m learning how to teach him things. Then he gets a little older and then that helped me work on the feelings. I’ve also learned how to speak to kids as well when I didn’t have any. I was like, “I don’t know what to say to you.” And now it feels more natural. And so I had a children’s book that I tried to write before I had kids. For me that one wasn’t as good, and so I feel like I gained a little bit of just how to talk to a child.

Lenny Rachitsky (01:00:59): That’s a really connection to something that we’ve talked about a few times is the best stuff comes from actual experience. Because you had a children’s book like you just said that you wrote before you had food, and then it wasn’t good. And now having the experience, you can actually make something great.

Michelle Rial (01:01:15): Yeah. And then also another thing I thought about was just reading so many children’s books. People always say if you want to write, read. Yeah, we read a lot. We read still a lot, a lot of books. It just got me in that zone, too.

Lenny Rachitsky (01:01:30): Yeah. It just makes me think about something I think has been key to my newsletter success is it is based on real life doing the thing.

(01:01:39): At this point, most of my posts are guest posts where somebody sharing the best thing they’ve learned in their career, like the one thing they want to share, which I love. It all comes from something I focus a lot on is from people on the ground doing the thing, not just floating in the clouds pontificating. That’s the source of the best advice is from practitioners doing the thing for real, not just pontificating. It’s just I think that’s a really good maybe one takeaway is just the best stuff comes from doing the thing and then sharing your advice versus just thinking you know what you’re doing and then just-

Michelle Rial (01:02:11): Communicating it simply.

Lenny Rachitsky (01:02:13): Simply and just refining. I don’t even get into just all the work that goes into refining.

Michelle Rial (01:02:22): It’s stressful because I make things and I am not sure if they’re good enough yet, and I put them to the side. And then I come back. I might have an idea. Knowing that it’s already in my head, I might have an idea like, “Oh yeah, that’s what’s going to make that better.” Or I go to work on it again, and some other thing adds to it.

(01:02:37): But then as you’ve set it aside, then you see something else. You see something in the world like, “Oh shoot, somebody beat me to that thing I didn’t ever do anything with,” so that’s stressful-

Lenny Rachitsky (01:02:46): Yeah, I go through myself.

Michelle Rial (01:02:48): … to have something sitting might be with your podcast.

Lenny Rachitsky (01:02:52): Yeah. Well, let me ask you this and I’ll answer for myself. How many iterations do you do on a chart on average? How many times do you edit it and refine it?

Michelle Rial (01:02:59): It depends. It could be just-

Lenny Rachitsky (01:03:03): What’s the median?

Michelle Rial (01:03:04): At least five.

Lenny Rachitsky (01:03:08): Okay. For me, I think it’s like 60.

Michelle Rial (01:03:09): I was going to say 100.

Lenny Rachitsky (01:03:11): Okay, that’s probably the real answer.

Michelle Rial (01:03:13): How many times do we through it? I can’t even physically do that.

Lenny Rachitsky (01:03:16): Yeah, it’s just like-

Michelle Rial (01:03:17): Well, what do you mean by-

Lenny Rachitsky (01:03:18): When I write a newsletter post, I go through it probably, let’s say, 50 times making it better. I start, there’s something that’s the beginnings, and then read through it and add to it. Read through it, add to it, read through it, add to it, improve, improve, improve, improve 50 times. And then I have my editor go through it and I have a copyeditor go through it and the designer help me.

Michelle Rial (01:03:36): You don’t do that with your emails, though.

Lenny Rachitsky (01:03:39): No. I should.

Michelle Rial (01:03:41): I do do that with my emails, which should be. I shouldn’t be doing that. I read them over and over again.

Lenny Rachitsky (01:03:46): You do? Okay. I used to. I used to.

Michelle Rial (01:03:49): But no, I do. Yeah.

Lenny Rachitsky (01:03:49): Anyway, anything else?

Michelle Rial (01:03:51): Do you want to plug?

Lenny Rachitsky (01:03:55): Absolutely. When is it coming out?

Michelle Rial (01:03:57): April 7th.

Lenny Rachitsky (01:03:58): April 7th.

Michelle Rial (01:03:58): April 7th.

Lenny Rachitsky (01:03:59): It’s a few weeks, I think, from when this comes out. Assuming this comes out, we’ll see how it turns out.

Michelle Rial (01:04:03): We’re going to check it out.

Lenny Rachitsky (01:04:04): We’ll check it out. If you’re seeing this, we checked it out. It was a success.

Michelle Rial (01:04:08): It was okay.

Lenny Rachitsky (01:04:09): Charts for Babies coming out April 7th.

Michelle Rial (01:04:12): April 7th.

Lenny Rachitsky (01:04:12): April 7th. All your favorite retailers.

Michelle Rial (01:04:15): Yep, local bookstore.

Lenny Rachitsky (01:04:16): Local bookstores.

Michelle Rial (01:04:18): Wherever you buy your book.

Lenny Rachitsky (01:04:19): What’s the age range of kids?

Michelle Rial (01:04:20): It’s two to four. It’s called for babies. I did do a chart recently about how long is your baby a baby? Infant is one to two, and then it’s your baby infinity. Yeah, so I’ve noticed we still call him the… We’re not really anymore the baby.

Lenny Rachitsky (01:04:40): Oh, for sure.

Michelle Rial (01:04:40): Yeah, but he’s almost three. And so yeah, it could be, I would say, zero to four.

(01:04:47): Yeah, you know what? Should I grab it?

Lenny Rachitsky (01:04:49): Yeah, let’s grab it. Let’s just break the frame.

Michelle Rial (01:04:52): People on the recording hit, but the first, the end paper is what this is called. It shows all the things you could learn: sizes, shapes, lines, numbers, directions, feelings, colors, mounts, sharing concepts, relationships, opposites. Anyway, I’m not good at self-emotion clearly, so I’ll stop it. Yeah, it’s a lot of learning.

Lenny Rachitsky (01:05:12): It’s beautiful. It’s hilarious. It’s clever. It’s-

Michelle Rial (01:05:15): Early learning concepts.

Lenny Rachitsky (01:05:16): Funny. Anyway.

Michelle Rial (01:05:17): It’s simply illustrated.

Lenny Rachitsky (01:05:18): Check it out.

Michelle Rial (01:05:18): Rhyming.

Lenny Rachitsky (01:05:21): We’ll link to it. Congrats on releasing this book.

Michelle Rial (01:05:22): Thank you.

Lenny Rachitsky (01:05:23): I know it was a lot of work.

Michelle Rial (01:05:23): Thanks. It was a lot of work. I did have a lot of iterations.

Lenny Rachitsky (01:05:27): The secret to success: iteration, editing.

Michelle Rial (01:05:31): Editing. Spending more time is what your old boss used to say.

Lenny Rachitsky (01:05:34): Spend more time on it.

Michelle Rial (01:05:35): Spend more time.

Lenny Rachitsky (01:05:35): I’m glad.

Michelle Rial (01:05:36): Yeah.

Lenny Rachitsky (01:05:37): Anyway.

Michelle Rial (01:05:37): Okay. All good? We done?

Lenny Rachitsky (01:05:40): Michelle, thank you so much for being here.

Michelle Rial (01:05:42): Thank you for having me.

Lenny Rachitsky (01:05:43): I’ll ask you my typical questions that ask at the end. Where do people find you online? How can listeners be useful to you?

Michelle Rial (01:05:49): My website, michellerial.com, R-I-A-L. Or I’m also on Instagram. Not too much these days, but still a little bit. You can look for the book, Charts for Babies. Yeah, I don’t know when this will be out, you can either pre-order it or order it.

Lenny Rachitsky (01:06:07): Parentheses pre, but order. Michelle, thanks for being here.

Michelle Rial (01:06:14): Yeah, and I hope you like it and thank you. Thanks for having me.

Lenny Rachitsky (01:06:15): My pleasure.

Michelle Rial (01:06:15): I know you have a high bar.

Lenny Rachitsky (01:06:17): Absolutely. You hit it.

Michelle Rial (01:06:18): Okay, great. Yeah, I hope you were okay with the interview.

Lenny Rachitsky (01:06:23): A+. It’s going to do numbers. All right, let’s get out of here. Okay, bye everyone.

(01:06:30): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com.

(01:06:50): See you in the next episode.