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Lenny Rachitsky: How psychedelics led to a 1.2M newsletter

Through dozens of drafts, practitioner guests, and a COVID-era paywall pivot; the weekly treadmill behind a top 10 tech podcast and a 1.2M reader list.

Lenny RachitskyhostMichelle Rialguest
Mar 12, 20261h 6mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 4:06

    Introduction and role reversal

    1. LR

      I just sat down on this rock on a substance of some sort. And 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. And I was just watching this crazy visualization of some kind of sitting Buddha thing, and that was for three hours. [laughs] It gave me the confidence that, like, "Okay, maybe I do have things to share."

    2. MR

      What do you want to say to our mothers right now?

    3. LR

      [laughs] Oh, no.

    4. MR

      Do you want to take this back?

    5. LR

      My mom doesn't- My mom doesn't know.

    6. MR

      Do you wanna take that back? You started your newsletter 2019, and it now has over a million subscribers.

    7. LR

      1.2 million.

    8. MR

      1.2.

    9. LR

      Something that we've talked about a few times is the best stuff comes from actual experience.

    10. MR

      People always say if you wanna write, read.

    11. LR

      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's sharing the best thing they've learned in their career.

    12. MR

      What do you think you'd be doing right now if you hadn't started that newsletter?

    13. LR

      On the struggle bus of startup life probably, and then probably after that failed, I would've joined some company as a PM.

    14. MR

      Do you still like it?

    15. LR

      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.

    16. MR

      Tell me about a time you've been really stressed in your business.

    17. LR

      Here's something I've never shared. 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. 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. Here's a puzzle for you. What do OpenAI, Cursor, Perplexity, Vercel, Plat, and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises, you've probably felt the pain of integrating single sign-on, SCIM, RBAC, audit logs, and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed-stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise-ready and unlocking growth. They're essentially Stripe for enterprise features. Visit WorkOS.com to get started, or just hit up their Slack support, where they have real engineers in there who answer your questions super fast. WorkOS allows you to build like the best with delightful APIs, comprehensive docs, and a smooth developer experience. Go to WorkOS.com to make your app enterprise-ready today. Who says hiring has to be fair? Every founder and hiring manager I've been speaking with these days is feeling the same pressure. Hire the best people as fast as possible. But recruiting is time-consuming, alignment is hard, and competition for great talent keeps getting tighter. That's why teams like Eleven Labs, Brex, Replit, Deal, and 5,000 other organizations use Metaview, the AI company giving high-performance teams a real unfair advantage in hiring. They give you a suite of AI agents that behave like recruiting coworkers. They find candidates for you based on your exact criteria, take interview notes automatically, gather insights across your hiring process, and help you identify the best candidates in your pipeline. AI handles the recruiting toil and gives you a real source of truth. That means hours saved per hire and a team focused on what matters most, winning the right candidates. Don't let your competitors outhire you. Metaview customers close roles 30% faster. Try Metaview today for free and get an extra month of sourcing at metaview.ai/lenny. That's M-E-T-A

  2. 4:06 – 7:20

    What would Lenny be doing without the newsletter?

    1. LR

      view.ai/lenny. Michelle Rial, thank you so much for being here. Welcome to the podcast.

    2. MR

      Thanks for having me.

    3. LR

      [laughs] So what are we doing here? Uh, 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?" And I'm just like, "Nah, I like interviewing." Uh, but you have a book coming out, ta-da, and we thought this would be a fun opportunity to, uh, have you interview me. And so this is gonna be your show. I'm just gonna be here. Ask me whatever you want. I have no idea what you're gonna ask me. And, uh, we'll see where it goes. And I'm gonna ask you some questions about your book too. So I'll turn it over to you, Michelle. What do you got? What do you got for me?

    4. MR

      Well, Lenny. Okay. Babe.

    5. LR

      [laughs]

    6. MR

      [laughs] Yeah. Um, yeah. So your... You started your newsletter 2019, and it now has over a million subscribers.

    7. LR

      1.2 million.

    8. MR

      1.2, sorry.

    9. LR

      Mm-hmm.

    10. MR

      Uh, and your podcast is, uh, y- very frequently one of the top 10, is that right?

    11. LR

      Yep. It's, like, right around... Yeah.

    12. MR

      Yeah.

    13. LR

      It's top 10 tech podcasts.

    14. MR

      Yeah.

    15. LR

      Yes. Hell yeah.

    16. MR

      [laughs] I love it. When I met you, I think you were something called a product engineer.

    17. LR

      I was a software engineer. Let's see, when you met me... No, I think it was a... I think it was still a software engineer, yeah.

    18. MR

      I think you went from software engineer to product engineer to product manager.

    19. LR

      Yeah. Yeah.

    20. MR

      And I'm-

    21. LR

      I think that's right

    22. MR

      ... wondering what do you, what do you think you'd be doing right now if you hadn't started that newsletter?

    23. LR

      If I, like, stayed at my job?

    24. MR

      Yeah. If you hadn't... And then that... I mean, I'll get to another question about what do you think is the one moment that led you to your newsletter.

    25. LR

      Mm.

    26. MR

      But you can answer either one.

    27. LR

      So is the question after I left Airbnb, what would I be doing, or is it, like, if I didn't quit?

    28. MR

      Just if you, if you hadn't or if you had gotten a different job.

    29. LR

      Yeah.

    30. MR

      Do you think you would've gotten a different job-

  3. 7:20 – 9:58

    The moments that led to starting the newsletter

    1. LR

      I guess, as a PM.

    2. MR

      So then I guess going back to that question of what, 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-

    3. LR

      Yeah

    4. MR

      ... or even start the newsletter, start the Medium post that led to the newsletter?

    5. LR

      Yeah. It was definitely a collection of moments. It's kind of this like little journey that I just followed pull that was starting to work, and I'm just like, "Huh, maybe there's something here." So a few moments along that journey. One was the first thing I wrote on the in- uh, this is like the first thing I wrote on the internet. Did very well. It was this post on what I learned at Airbnb. Like Medium featured it. It went all over the place. Francesca shared it with the whole company, so proud of what I shared. So 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, and there was more of just like, "Hmm, this is working. People seem to like it." Then I had a conversation with this, with a friend, Lee Jacobs, who's a VC now, 'cause I was telling him, "I don't know what I'm... I don't know why I'm doing this. Why am I writing? This is like not a future. I should be focusing on the startup." And 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, in the future. So his advice is just maybe pursue that and double down on that and maybe it'll go somewhere. So that was a moment. Another maybe big moment was nine months of doing the newsletter. So I decided I'm gonna move to Substack. I'm gonna write every week. I tweeted, "I'm gonna experiment with a newsletter, a weekly newsletter, see how it goes." Uh, and so I did that every week for nine months, and 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." There's this, uh, Lindy effect. I don't know if you know this, but there's this concept of a thing, something being Lindy, which is, uh, as long as it's been going for, it will most likely last at least that long in the future. So I thought that, "Okay, I could do this for at least probably another year. I have all these ideas and things I wanna write about, so let me just keep doing this." So that's when I decided to add the paywall and start charging and to see if I could make money doing this thing. Also in parallel, as you know, uh, I was doing this based on the assumption that my Airbnb stock was gonna be worth something, and I could take this time to explore, and then COVID hit, and Airbnb might have... was like over. [laughs] 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 gotta make money on this thing. Let me try." So that's when I started the paywall. And so, and the, and it worked. That's like the other moment I think I launched the paywall, and it worked. You know, I made meaningful dollars like a month

  4. 9:58 – 12:42

    Does Lenny still enjoy the work?

    1. LR

      in.

    2. MR

      So speaking of Venn diagram, you said, "I'm good at it, and I, and I-

    3. LR

      And

    4. MR

      ... people like it."

    5. LR

      And people like it.

    6. MR

      Oh, and I like doing it. You like doing it.

    7. LR

      That's a really good... 'cause I didn't mention that.

    8. MR

      Okay.

    9. LR

      That's so, that's so true that it's like-

    10. MR

      Well, that's that Ikigai, right?

    11. LR

      ... that's so important.

    12. MR

      Yeah.

    13. LR

      Yeah. I think Ikigai is like five things, right? It's like a whole bunch of stuff. Yeah, but that's like a trigger point 'cause it was just like people like it and I'm good at it.

    14. MR

      Mm-hmm.

    15. LR

      But without the I actually enjoy it.

    16. MR

      I think you said, "I li-" and I liked it. Maybe-

    17. LR

      I like it. Okay, cool.

    18. MR

      Do you still like it?

    19. LR

      I do in almost every way. Like I can't imagine doing something more fulfilling and interesting. Just basically, um, 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 like so interesting. It's my own thing, which makes it extra interesting. But I think a lot about, uh, this artist Finch wrote this blog post, How to Become an Artist, and at the top of his post, he's just like, "You pro- you should not become a professional artist most likely-"

    20. MR

      Right.

    21. LR

      "... because," [laughs] yeah, "because once it's a thing you have to do, it changes it. You have, you know, you have to do it." So now I'm on this... Like this is the downside, but I just wanna preface with saying this is incredible, and I can't imagine doing anything else that I enjoy more. But, uh, having to write a post or put out a post every single week and a podcast episode every week, you know, it's like this treadmill that you're on, so you have to kind of get used to that. That part is no fun. But again, I can't think of anything better that I could be doing. And, and it kinda goes up and down. Sometimes like 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, you know? 'Cause otherwise you can't do this. You can't, you can't survive in this way if you're not doing something consistently and making it awesome every week. So it's a part of it. So the visual I always have is the Indiana Jones, uh, boulder is chasing me constantly [laughs] 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 I'm... It's like, what's next week? All right, that's done. All that work you put into it, over. What's coming out next week? And it's like every week. So the big question I, I don't have an answer to is where this all goes long term 'cause somedayWhether it's at, uh, seven years old or a hundred years old or sixty years old, I don't know. Like, maybe I won't be able to do this every single week. So I think about where does this all go? I don't think there's a answer to, like, Substack writer podcast life long term. Like, what do you do? I don't know.

    22. MR

      Like, according to the Lindy, right?

    23. LR

      There you go. Yeah.

    24. MR

      So twenty nineteen-

    25. LR

      So six more years

    26. MR

      ... to now is s-

    27. LR

      Seven years

    28. MR

      ... seven more years.

    29. LR

      Seven years since the newsletter. Yeah.

    30. MR

      Seven years.

  5. 12:42 – 14:00

    Stress management and misophonia

    1. MR

      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. [laughs]

    2. LR

      [laughs]

    3. MR

      Um, sleep, the toddler or baby sleep stuff.

    4. LR

      Yeah.

    5. MR

      I don't see you as a stressed out person. Uh, do you think there's anything behind that? Do you think that's just you?

    6. LR

      Mm.

    7. MR

      And, or are you just stressed and-

    8. LR

      [laughs]

    9. MR

      ... doesn't... you don't show it?

    10. LR

      I think there's an element of I'm more stressed than I come across as and even recognize with myself. Like, I get these headaches sometimes. I'm like, "What is going on there? Is that stress, or is that something else?" So 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. I think part of it is genetics, and then part of it is I, I work on it. Like, I just have learned to adjust the way I think to reduce stress and to not take things seriously. But I think I, I think honestly, it's probably, like, seventy percent genetics. I'm just like, "Yeah, it'll be all right. It'll be all right," as you know, something we argue about. [laughs] "That'll be all right. That's some, like, raw chicken. That'll be fine."

    11. MR

      Oh.

    12. LR

      "That's fine." Yeah.

    13. MR

      [laughs] Uh, so okay. Do you have any tools or any kind of like... I know you've done med- different types of meditation. We've done breathing courses-

    14. LR

      Yeah

    15. MR

      ... together.

    16. LR

      Yeah.

    17. MR

      You... What...

  6. 14:00 – 15:45

    The psychedelic trip that changed everything

    1. MR

      Do you have a favorite? Do you-

    2. LR

      Oh, to, like, calm down and de-stress and things like that?

    3. MR

      And you did, you did a, oh, ten-day m- silent meditation right before you ended up writing the post.

    4. LR

      Mm. Oh, that's true.

    5. MR

      The newsletter post.

    6. LR

      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. So I went on a, a bachelor party trip with some friends. This isn't where you think it's going. [laughs]

    7. MR

      I hope not.

    8. LR

      [laughs] So it was a trip to Joshua Tree with a friend, and, uh, there was psychedelics involved on this trip. Uh, and I just remember... So we went to Joshua Tree. I just sat down on this rock on a substance of some sort. Uh, and, and this was as I was starting the newsletter, and I just remember sitting there for probably three hours in this one spot, and I was just having this deep breathing happening and this, like, phrase of "I have wisdom to share" coming through me over and over and over. And I was just watching this crazy visualization of some kind of sitting Buddha thing. [laughs] And it's just like, "I have wisdom to share." And that was for three hours. [laughs]

    9. MR

      [laughs] That made you write the post?

    10. LR

      That made me feel like I can do this. Like, 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, give me confidence that there's something inside me that's like, oh yeah, maybe I c- I could do this thing. So that was a big moment. Drugs.

    11. MR

      What do you wanna say, what do you wanna say to our mothers right now?

    12. LR

      [laughs] Oh, no.

    13. MR

      Do you wanna take this back?

    14. LR

      My mom's gonna... No.

    15. MR

      Do you wanna take that back?

    16. LR

      No. No.

    17. MR

      Do you wanna crop it out?

    18. LR

      This is, um... Okay, Mom, I did, I did-

    19. MR

      Anyway, uh-

    20. LR

      ... I did some-

    21. MR

      Next

    22. LR

      ... I did some stuff. [laughs] It's okay.

    23. MR

      We... Okay.

    24. LR

      It's okay.

    25. MR

      So-

    26. LR

      It's time to,

  7. 15:45 – 17:30

    Online happiness course and baseline optimization

    1. LR

      time to share

    2. MR

      ... and then, yeah, you've done medita- you did ten-day meditation. You did a specific type of meditation that, that seemed to me to, to affect you in, like, physical ways.

    3. LR

      Yeah.

    4. MR

      And then you told me once about a happiness course you took?

    5. LR

      Yeah. That was actually pretty transformative. I took this online course at University of Pennsylvania about, uh, the psychology of happiness, and it was basically all the science of what makes you happier and how to be happier. And 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, and one of the things is just, like, thinking more positively, like, thinking more optimistically. There's also, like, gratitude stuff that I didn't find as useful, but there's just something about you can... Everyone's got this baseline. That was actually a big learning from that course is everyone's just kind of at this baseline level of happiness, and you could be, like, at a hundred, you could be at zero, probably more... most people are in between somewhere, and, like, something amazing happens, you go all the way up in happiness, and then you come back to that baseline. Something terrible happens, you go back to that baseline. And the main thing you can do is work on improving that baseline so that you come back to a higher place. So that's what a lot of the work is and what you learn in that class. And one of the things is just be optimistic, just kind of have a positive outlook, and don't let your mind kind of spiral into these, like, "It's gonna be terrible" and... So it was a lot of just, like, think more positively, and I feel like my baseline of level of happiness has gone up. And I think that it... Yeah, that helps.

    6. MR

      I think you told me exercise too. Like-

    7. LR

      Yes

    8. MR

      ... you used to run.

    9. LR

      Yes. That was a really good insight. So exercise, the, the science. This was, like, I don't know, fifteen years ago. I'm guessing there's new research, but the interesting thing there is, uh, exercise doesn't make you happier, but it brings you out of the negative. So you're negative one without exercise, and exercise brings you to zero

  8. 17:30 – 20:20

    Thunder round: Lenny’s misophonia worst sounds

    1. LR

      so that you're not depressed, basically.

    2. MR

      Speaking of stress-

    3. LR

      Okay, then I have a question for you.

    4. MR

      Oh, okay. Let's do this. [laughs] Let's do this, uh, because I know on your podcast you have a lightning round.

    5. LR

      Okay.

    6. MR

      Um, we're gonna do a thunder round.

    7. LR

      [laughs] Is that extra faster?

    8. MR

      Because-

    9. LR

      What does that mean?

    10. MR

      No, it's sound. Your one thing that I think stresses you out the most at times is, uh, your misophonia, which is... Do you wanna explain what it is?

    11. LR

      Yeah. It's like [laughs] it's funny to talk about it, but it's this... I th- 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-

    12. MR

      Okay. Thunder round is gonna be top five worst soundsOr you can rank these sounds.

    13. LR

      Okay. [laughs] You're gonna give me the five-

    14. MR

      Number... Like, like best, best sound to worst sound.

    15. LR

      Okay.

    16. MR

      Right? So, like ten is worst, let's say.

    17. LR

      Okay. What are like-

    18. MR

      One is best. I don't know. [laughs]

    19. LR

      What are the best sounds?

    20. MR

      Okay, what's... Okay. Okay, let's say chewing. Chewing, one to ten.

    21. LR

      Chewing, like with the mouth open, just like-

    22. MR

      Chewing with-

    23. LR

      Yeah

    24. MR

      ... the worst. Yeah.

    25. LR

      I hate it. Uh, ten is the worst?

    26. MR

      Ten is the worst.

    27. LR

      Yeah. It's, you know, it's probably... It's in, yeah, it's ten. Nine or ten.

    28. MR

      Or like, like nails on a chalkboard. What's that?

    29. LR

      That's like less bad for me.

    30. MR

      Right. What's the number?

  9. 20:20 – 23:55

    What makes Michelle’s charts so shareable

    1. LR

      uh, so you make these incredible, genius, funny charts. There's one example in this book. So you have this first book here called Am I Overthinking This?, which a lot of people identify with, has sold many copies. Uh, so you're, you create all these charts that try to synthesize things in life, things people experience, things people feel. 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 like 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 o- over the years. [laughs] What makes your charts so shareable so widely? How, why do they go so viral so often?

    2. MR

      Mm. By the way, I stopped looking at that 'cause it doesn't help me. Anyway, um-

    3. LR

      [laughs] That's good. I think that's for the best.

    4. MR

      Well, I think like-

    5. LR

      Like that's the good, yeah

    6. MR

      ... I think as, as your thing has gotten more successful, it's like not as important to me. [laughs] I do think it's interesting that they are often like detached from me, which is, I don't know why. But, um-

    7. LR

      Yeah, people want to get credit

    8. MR

      ... when they do, when they do, um, and it's... I, I think I can figure out, 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 other, some like moment happens, or I'm like, "Oh, no, this is what it needs," and then I'm like, "Now it's, now I can feel that's really good." And usually it's like it's something that makes me laugh or cackle even though I made it. It's like, like it's like, "Oh, I've already seen this in my own brain," and it's still funny to me or makes me kind of like tear up. Then I feel like, "Okay, I think people are gonna like this." I am often wrong. [laughs] And sometimes too, like there are things, there's something from that book that I didn't share at all, but someone took a photo of it. That's how it went viral is like just a photo of a page of a book that people loved.

    9. LR

      Like it wasn't even like a digital high quality picture. It was just like some random photo.

    10. MR

      Mm-hmm.

    11. LR

      Yeah.

    12. MR

      Yeah, which is interesting as well. But, and also people's attention spans, uh, sometimes they're just... What I, what I like to make is things that are really simple, um, 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, and if it makes them feel something is another thing. And it's also nice to make something that's, that isn't a lot of like physical labor, [laughs] because some things you can make and it can take you forever to draw out because my brain does work in this like overthinking kind of way of like this, but then, oh, this, and then this. People like it when it's really simple.

    13. LR

      Yeah. I, I love your point about like the way you know a chart is done is intrinsically you feeling like this is hilarious. This is, makes you laugh, makes you feel something, and that's similar to the way I think about my newsletter post. And yeah, more, more the newsletter than the podcast is it just, to me, it feels like this is like really interesting and really good. It's very like not waiting for other people to give you, you know, approval or feedback. It's like I feel this is good, and I think that's really interesting that that's similar to the way I approach my stuff. I find that when you work on your charts, uh, you're like, you think so many levels deep. They're like, they're like so, they're like too clever sometimes, and I have to like pull... 'Cause 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," and I have to like, "Hmm, that's a little much." You have to like simplify it a little bit. Yeah.

    14. MR

      Yeah. You're my editor sometimes as well.

    15. LR

      I try, but you're like, "No." You're like, "I don't care. I don't, I don't care about your feedback." You're like-

    16. MR

      [laughs] No, you're pro- you're

  10. 23:55 – 26:59

    Where chart ideas come from (and why meditation helps)

    1. MR

      usually probably right.

    2. LR

      Yeah. 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 had a children's, now you have a children's book. Uh, you're working on like charts for parents. You have all this other stuff going on. Where do your ideas come from, Michelle?

    3. MR

      The ideas come from just living life and noticing, noticing a lot of things, and then also kind of, um, observing-A lot, I, I know that I've been really prolific when I've been meditating. And in meditation, you learn to kind of observe your own thinking. And if you're anxious about something, like, oh, I'm... That's funny that I was anxious about that random thing that I ha- I've never thought about it that way before, and which is interesting because it is kind of like overthinking every moment, which it, meditation shouldn't be teaching you to do, but that's what happens. But I, I've noticed if I focus too much on my work, I stop living life, and then I stop having ideas. And it's a little different with children's books, which is what I'm working on right now, because the, it's not like relatable things. A little bit, but it's, um, more children's concepts. But the adult stuff has to be just through living life and-

    4. LR

      Noticing, yeah

    5. MR

      ... yeah, noticing.

    6. LR

      Makes me think about, I think David Sedaris had this story where he's just has to say yes to everything he's invited to just 'cause he needs to have experiences 'cause he just has to keep pumping out stories. So he's just like, "Sure, let's go to Vegas right now. Let's do it." [laughs] So I feel like that's a lot of the work here is just to live real life. You can't just kinda sit there and come up with ideas. You have to try stuff and do crazy things.

    7. MR

      Yeah, so at the first... So my first children's book, which is, is out soon, um, that one actually came out of kind of observing parenthood and early new parenthood moments. That's how I started. I started at the beginning of the notebook writing, kind of like trying to make charts for new parents. But we'd been reading so many kids books together that I just had this like da-da-da-da-da-da [laughs] like rhythm in my head of children's books. And so what it... I just turned to the back of the notebook and started writing more like children's book rhymes involving charts.

    8. LR

      This is the back of a notebook 'cause you're working on a different book, and you're just like-

    9. MR

      Actually, that note- this notebook, I-

    10. LR

      Oh, this is the notebook?

    11. MR

      ... I picked it up to put my questions in for you.

    12. LR

      What?

    13. MR

      Yeah, and so I started-

    14. LR

      Oh, wow

    15. MR

      ... off in the front. Um, I'm not gonna show you. [laughs]

    16. LR

      So you started in the front on a different idea.

    17. MR

      I started off in the front, charts for new parents, and then I was like, got, you know, a few in. You know, like a good amount in. And then I was just in the park writing, and then I kinda was just like, "Yeah, but I, I have always wanted to do these charts for kids or for babies." And I just kept wanting to write that, so I started in the back, and then I filled it up that way.

    18. LR

      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 in. I'm gonna try it and just see where it goes." Look at this. [laughs] What a callback. Okay, back to you, Michelle.

  11. 26:59 – 28:54

    Where does “Lenny” come from?

    1. MR

      [laughs] Back to you.

    2. LR

      Back to me.

    3. MR

      Back to you, Lenny.

    4. LR

      Back to you through me, through you.

    5. MR

      Yeah, exactly. Okay, okay. So, um, tell me about... I, I do wanna ask you this question inspired by a friend who, like, reverse nicknames you and says, like, "Leonard."

    6. LR

      [laughs]

    7. MR

      Is your name, full name Leonard? Where's Lenny come from?

    8. LR

      And by the way, reverse nickname meaning they give you a nickname without you, like, asking them to.

    9. MR

      Rever- Well, there's people who give you a nickname without you asking.

    10. LR

      Yeah.

    11. MR

      That's... Yes.

    12. LR

      Yeah.

    13. MR

      He gives you the full name.

    14. LR

      Oh, I see. Makes it long. [laughs]

    15. MR

      Yeah. It's not a thing. I'm just-

    16. LR

      A nickname

    17. MR

      ... making it up.

    18. LR

      Okay. I like that.

    19. MR

      Yeah.

    20. LR

      Okay. So the question is my na- well, my real name, uh, so 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, big news-

    21. MR

      Odesa

    22. LR

      ... for people. Odesa, 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.

    23. MR

      It's just Lenny.

    24. LR

      No Leonard.

    25. MR

      No, no Leonard.

    26. LR

      No Leo. Yeah.

    27. MR

      No... Yeah, Leonard. No.

    28. LR

      Just Lenny.

    29. MR

      Just Lenny.

    30. LR

      Yeah.

  12. 28:54 – 31:24

    Being recognized in public

    1. MR

      And speaking of strangers, how do you feel when people approach you, and, and is it weird at all? Like, like-

    2. LR

      Oh, yeah

    3. MR

      ... like, does it remind you how big your newsletter has gotten? Or, like, do you like it? Do you like certain ways of approaching it?

    4. LR

      Yeah. So I guess what you're, uh, speaking to is when I walk around the Bay Area in particular, people often recognize me, which is extremely weird, and started with the podcast once it... Like, interestingly, I had the newsletter for four years.

    5. MR

      Yeah, you got to be, like, you got to be stealth.

    6. LR

      Yeah. And, like, my face was tiny in some Twitter profile. But I, once I started the podcast, people just... Yeah, it just... It was, like, very weird the first time it started happening, and then... And now it happens, uh, quite a lot. 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. Uh, it always is very flattering. 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.

    7. MR

      What a... Okay.

    8. LR

      [laughs]

    9. MR

      That's great. That's cool.

    10. LR

      And I often ask people what's their favorite podcast episode or favorite newsletter 'cause I'm just curious. So I always ask just, like, "Are you a founder? Are you a product person?" Like, "What's your story?" Yeah, it's really nice.

    11. MR

      What about if you're in the middle of... If you're, like, at a coffee shop and you have headphones on-

    12. LR

      Oh, yeah

    13. MR

      ... and somebody says, like, "Hey." Or if you're, like, playing with your kid, what do you think? [laughs]

    14. LR

      [laughs] I think you're projecting-

    15. MR

      Right. [laughs]

    16. LR

      ... about what you would want.

    17. MR

      Girl, yeah.

    18. LR

      [laughs] People don't do that. I think people have been generally very conscious. You know, there could be a moment of just like, "We're getting somewhere, and I can't talk for too long, and I don't wanna be rude."

    19. MR

      Or you're, like, in a focus. It's-

    20. LR

      Yeah

    21. MR

      ... but, but then, yeah.

    22. LR

      Yeah. It hasn't been a problem yet.Uh, almost like 99% of people have been very considerate.

    23. MR

      Yeah.

    24. LR

      And I don't want people to feel like they can't just talk to me and say hello.

    25. MR

      Yeah. That's cool.

    26. LR

      Yeah. They're always so cool.

    27. MR

      I like that.

    28. LR

      Yeah.

    29. MR

      Is there any, like, instance of delightful?

    30. LR

      Like, maybe the first time this happened, uh, we live in Marin, and I was walking over through San Anselmo a- 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!" [laughs] God. And this wasn't even in San Francisco. It was in-

  13. 31:24 – 36:30

    Early projects

    1. MR

      You had just said something. Okay. People coming up to you. Um, okay, you're gonna have to cut this [laughs] because I-

    2. LR

      See, no, we're not gonna cut it 'cause this is what I go through, too, as a podcast interviewer.

    3. MR

      I thought of something. I lost it.

    4. LR

      This is what I am constantly-

    5. MR

      Okay

    6. LR

      ... dealing with.

    7. MR

      Yeah.

    8. LR

      That is a challenge of the interviewer.

    9. MR

      Uh, sucks.

    10. LR

      And I think it's fun for people to see 'cause you're like, "Okay, I have to think about what's... I'm gonna say next," and then you're like... They're stopping, and you're like, "Oh, shit. [laughs] What's it gonna be?" So that's why s- on... when I do the podcast, I'm secretly writing notes to myself constantly.

    11. MR

      Oh. I-

    12. LR

      So-

    13. MR

      Okay

    14. LR

      ... check your notes.

    15. MR

      Yeah. Well, okay, I closed my... Okay.

    16. LR

      Yeah.

    17. MR

      I should've written it down. Let's talk about, like, thinking back to what, what kind of, um, hints that you would start this newsletter or, like, things that you worked on when you were younger that are mildly-

    18. LR

      That helped me with this?

    19. MR

      ... like, a little... or, like, adj- uh, mildly adjacent or, like, you know, 'cause you had some wet- like, some websites. You had Atheist Spot. [laughs] You had... Like, you had some thought-

    20. LR

      Utorials.

    21. MR

      Utorials. That's one.

    22. LR

      So the question is like what are the things I did earlier that helped me with the work I do now?

    23. MR

      Or yeah, just 'cause just looking back, like, anything that, that is kind of, like, makes it obvious that you would've started this newsletter or, like, a little more.

    24. LR

      I don't think there's 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. Uh, 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 kind of stay behind the scenes." So it was a... It's a very unexpected path for me, and part of the reason I think I was able to do it is, uh, 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, like, "Hello, everyone." I could stay, like, in my little hole. But just to, uh, follow through on these things you pointed out that I did earlier, 'cause, uh, I don't think I've ever talked about these things. I had all these different side projects before, uh, like, through college, I guess. Yeah, through college. I was, like, a very, uh, uh, big atheist, and I'm still an atheist, Jewish atheist, [laughs] which is many Jews. But I was, like, very into it before, and now I'm like, "Okay, I don't care, whatever. Believe what you wanna believe." Uh, so I used to run a website called theatheistspot.com, which was Reddit for atheist news, [laughs] which is not a... You know, Reddit is that. It's fine. I don't... You don't need it. But I went to, like... There's, like, conventions that we went to, atheist conventions. [laughs] Uh, so I did that. And the funny thing is that was the... 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, so it was, like, Christian Mingle and, like, all these funny dating sites that didn't make sense for the audience. So I always thought that was funny. And then, uh, I worked with a friend on this other project called Utorials, which was so ahead of its time. The idea was Utorials, tutorials for you by you.

    25. MR

      Nice.

    26. LR

      And so it's people contributing things they've learned and writing a how-to, like how to make eggs, how to take a quick shower, and there's all these-

    27. MR

      That's like TikTok, right?

    28. LR

      It's like TikTok.

    29. MR

      That's like what TikTok is.

    30. LR

      It was before Wikipedia, I think.

  14. 36:30 – 37:49

    Michelle and Lenny’s yin and yang

    1. MR

      Okay, so you were mentioning the, the atheist bot with a bunch of religious dating sites.

    2. LR

      Yeah.

    3. MR

      Reminded me that you were my first online date ever-

    4. LR

      Hell yeah

    5. MR

      ... on a, on a-

    6. LR

      Snatched right up

    7. MR

      ... platform called How About We? And I remember that... I mean, you had had other dates. Um.

    8. LR

      [laughs] Where's this going?

    9. MR

      Anyway, no.

    10. LR

      I like this.

    11. MR

      But I remember you were like, um, had... See, I think you had a thing for designers.

    12. LR

      Yeah.

    13. MR

      And I wonder if you regret that preference. [laughs]

    14. LR

      [laughs]

    15. MR

      Like, designer artists sort of like-

    16. LR

      No, not at all

    17. MR

      ... stereotype. No?

    18. LR

      No, no.

    19. MR

      Like, I'm not... Like, like, you're pretty neat.

    20. LR

      Yeah. Yeah, it's true. You're kind of chaotic, yeah, which is... We can talk about your process, but it's like, it's a messy process. [laughs] It's true. You know, we have a good yin and yang.

    21. MR

      Yeah.

    22. LR

      Yeah, I'm just like-

    23. MR

      Yeah, like you're unstressed, unbothered. I'm bothered. [laughs]

    24. LR

      [laughs] Yeah.

    25. MR

      I'm just, I'm stressed, yeah.

    26. LR

      Just things everywhere.

    27. MR

      Yeah.

    28. LR

      We get cleaners, they help things out.

    29. MR

      Yeah.

    30. LR

      Yeah, it's true. You know?

  15. 37:49 – 39:37

    Missing office culture (but not really)

    1. MR

      home. Um, but yeah. Do you feel, do you ever feel like lonely not ha- 'Cause you were always really social, and then this goes into, too, like even before you were niche famous, or whatever [laughs] we wanna call it-

    2. LR

      Yeah. That's how, that's how I describe it

    3. MR

      ... people were always coming up to you on the street like, "Lenny!" [laughs]

    4. LR

      Oh, from-

    5. MR

      You know?

    6. LR

      Yeah, from Airbnb.

    7. MR

      From Airbnb-

    8. LR

      Yeah

    9. MR

      ... 'cause you're organizing things, and-

    10. LR

      Mm-hmm

    11. MR

      ... um, do you feel like you miss of- office culture?

    12. LR

      Hmm. I have... People ask me that over the years, and I've always like, "No, it's amazing. I don't need that." Like, I just doing my own thing and I don't need people around. But I've kind of started to feel that a little bit, and I'm just like, "Huh, there's no one..." Like, I just sit at home all day and just like... [mimicking typing]

    13. MR

      Our dog likes to be right next to you.

    14. LR

      Yeah. Yeah. He's sweet.

    15. MR

      Yeah.

    16. LR

      Uh, so I do feel like I do miss it now. It's not, like, a huge problem, but it's just like, yeah, it'd be cool to just jam with someone on stuff. And I have a team, and I have you, and Twitter. [laughs] Like...

    17. MR

      Well, you like to go to coffee shops.

    18. LR

      I like to go to coffee... Yeah, but it's-

    19. MR

      What do, what do you get?

    20. LR

      But it's like bowling alone, kind of. I don't know. It's like, if that's a good metaphor. [laughs] Like it's-

    21. MR

      And you have your headph- You put your headphones too.

    22. LR

      I have my headphones on, yeah.

    23. MR

      And you're focused, so it's like-

    24. LR

      Yeah. So it'd be fun. Like, I have an awesome team and we jam on stuff, but it's not like... Like, I think there's a... 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, like, this whole thing that's complicated that I'm like, "What have I done?" 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." So I'm trying to be really careful about what I commit to and do. Coming back to your question, I do miss it some, yeah.

    25. MR

      Yeah.

    26. LR

      It's like a new thing I've realized that I miss, is being around other people, like, working

  16. 39:37 – 40:47

    Lenny’s face blindness

    1. LR

      on the same thing.

    2. MR

      Yeah. So speaking of other people, like, coming up to you and being around other people.

    3. LR

      Yeah.

    4. MR

      It... I think it's become harder for you now that, now that people you don't know come up to you, because I think you actually have a little bit of face blindness.

    5. LR

      Absolutely.

    6. MR

      And so people-

    7. LR

      Okay. Yeah

    8. MR

      ... people who do know you come up to you, and you're like, and you're, like, waiting to know if, if they just listened to your podcast or if you-

    9. LR

      Like, I know if I know the-

    10. MR

      Yeah.

    11. LR

      Like... Yeah. This is a big problem for me.

    12. MR

      Yeah.

    13. LR

      It's like a, it's like another brain disorder, [laughs] I guess, where I just don't remember people's names. I'm so bad at it. So 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?"

    14. MR

      Yeah. Sometimes I feel like The Devil Wears Prada, um, assistant, where I'm like, "That's Emily. You worked with her [laughs] at Airbnb" or "That's, uh-"

    15. LR

      Wait, you don't do that. You need to do that.

    16. MR

      I, I do it sometimes.

    17. LR

      You do that sometimes?

    18. MR

      Yeah.

    19. LR

      Okay.

    20. MR

      [laughs]

    21. LR

      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. And yeah, it's, like, gotten worse, 'cause now I know more people through the podcast and the newsletter, and like-

    22. MR

      Right. And you just know a lot of people.

    23. LR

      Yeah. It's like a lot of faces.

    24. MR

      People like you. You're very kind, so people like you.

    25. LR

      I try. I try.

    26. MR

      Yeah.

    27. LR

      I try.

  17. 40:47 – 42:50

    The $100M fraud attack story

    1. MR

      Okay. So going back to the, like, unbothered vibe that you have.

    2. LR

      Mm-hmm.

    3. MR

      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.

    4. LR

      Okay. So on the business side, uh, so I have this product pass. So as a subscriber to my newsletter, you get 23 incredible products, and I used to read them all. Linear, Mobbin, Lovable, Replit, Gamma. [laughs] I stopped doing this 'cause there's too many now. I had that end of my podcast, I just read through them all, and now I can't do it anymore. There's too many. 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, uh, that was way too good an offer. People came for it, bad people. So 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 my... all these free goodies. So they set up all these crazy attacks, and I had to work with Stripe and Substack to just, like, shut them down, and they just found all these little exploits in our API that we built, and like this... So it was, like, such a nightmare, 'cause we're just, like, waking up to... Like, every night it was, like, hard to sleep. And I have, I have this engineer, uh, Este, who's so incredible, and he, like, didn't sleep for a week, stopping, filling all these holes, because all... There's a lot of, lot of smart, clever bad guys out there. So that was extremely stressful. Like, it could trickle down into the whole thing falling apart if everyone's like, "Oh my God, can't trust Lenny anymore." So as you remember, it was very stressful. I didn't sleep too well, and it was like-Very scary. And there's all these... They just kept popping up, and there's all these, like, rings, and it went viral in China too. That's, like, in, in the student network, they just, "Holy shit, you get a year free of Cursor and Lovable and Replit and Bolt and v0," and, uh, so it was very stressful. To answer your question on the personal side...

  18. 42:50 – 47:22

    Michelle’s childbirth emergency

    1. LR

      Okay, so when our baby was born, the birth was very complicated. Uh, you had to get a C-section because the induction wasn't getting it there 'cause, yeah, it was-

    2. MR

      Yeah, it was complicated

    3. LR

      ... complicated. We won't get into that.

    4. MR

      And normally I feel like I would tell the story, but-

    5. LR

      [laughs] You weren't awake

    6. MR

      ... but this is also, like, a When Harry Met Sally, but it's, like, how the, the pregnant person almost died, [laughs] you know? But okay, but it's from your perspective because-

    7. LR

      Yeah

    8. MR

      ... I didn't get to experience it.

    9. LR

      Right.

    10. MR

      So.

    11. LR

      Yeah. So what happened is we had to, you had to do a cesarean. They gave you ane- 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.

    12. MR

      With your scrubs.

    13. LR

      They gave me a whole-

    14. MR

      Your shower cap

    15. LR

      ... bunny suit. Yeah, super sterile, just standing there [laughs] in this bunny suit thing. And the idea is they do the anesthetic, and I can come in and then watch the birth and all that stuff, and five, 10 minutes in, I just hear beep, beep, beep, beep, beep, beep, beep, beep, beep, beep, beep. And the doctor runs out, scrubs her hands, runs back in, and then all of the two other people run from another room [laughs] down the hall into the room. And I'm like, "Uh-oh." Uh, and there was like-

    16. MR

      And you were, and you were scared. You were-

    17. LR

      I was-

    18. MR

      ... scared?

    19. LR

      I was very scared because I had no idea what was going on. That didn't sound good. [laughs]

    20. MR

      Nobody told you anything.

    21. LR

      Nobody was telling me anything.

    22. MR

      You were supposed to be in there.

    23. LR

      I was supposed to be in there. No one's coming out, like, "Here's what's happening." And it was, like, 10 minutes of just nothing.

    24. MR

      Yeah, and you were supposed to be in there after, like, a minute?

    25. LR

      Yeah. It's gonna be quick, yeah. Yeah, it was supposed to be like, "Come on in. We're gonna do the cesarean now." And, like, you're awake during it, you know, in real life. So I just remember pacing down the hall using, going back to the lessons I've learned, just like, "It's gonna be okay. It's gonna be okay." That's what I remember saying to myself. Just kind of trust that they know what they're doing, you know. We're in a hospital. There's a lot of doctors around. And, 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 stopped, it was stopping your heart and lungs, and they had to intubate you and do an emergency intubation and get the baby out, and then took, like, an hour for you to come back. They were, they were gonna put you in ICU to help you come back. So that was very scary 'cause you weren't there. I didn't know what was going on.

    26. MR

      And you got to hold, you got to hold the baby for, like, an hour-

    27. LR

      Yeah

    28. MR

      ... without... So that's why he's, like, a, he's like [laughs] only papa. He's a, he's another person that, that prefers you.

    29. LR

      Who's the other person?

    30. MR

      Our dog. [laughs]

  19. 47:22 – 51:58

    Michelle’s creative process

    1. LR

      Yeah. Okay, I wanna ask you a question-

    2. MR

      Okay

    3. LR

      ... but unless you have something we wanna follow up with.

    4. MR

      No, no.

    5. LR

      Okay. So you come up with these incredible charts. They're just, like, you know, it's like the kind of charts you see on the internet that are like, "Oh my God, that's so genius." And watching you come up with it is so wild 'cause you just c- you just, like, it pops out of nowhere, and then there's, like, a little bit of iteration and, like, that's it. What's the process for you coming up with a chart, and what's, like, the environment that you need to create your best work? I feel like coffee is a big part of it.

    6. MR

      Coffee is, like, it's, like, not too mu- There, there's one I have that it's, like, I mean, it has to be the perfect amount of coffee, so I actually s- usually get a single shot latte.

    7. LR

      Do you know about a b- the Ballmer Peak, by the way? Quick tangent.

    8. MR

      Okay.

    9. LR

      Okay. So there's a concept called the Ballmer Peak-

    10. MR

      Yeah

    11. LR

      ... [laughs] 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 don't know. I forget why this is Steve Ballmer related, but okay.

    12. MR

      Yeah.

    13. LR

      So the Ballmer Peak of coffee-

    14. MR

      I have one like that about coffee, but it's not. It's made out of a little coffee straw, and it's like-

    15. LR

      We're gonna show this on YouTube if you're watching this, so you can see the chart

    16. MR

      ... it's like, "I'm a genius," and then I'm having a panic attack. And so that's me is, is like, is like, yeah, I'll get to this point where I feel like... I mean, coffee is a drug, right? So if I have too much, it is like a drug, and I'm-I feel like a genius, and I'm like having all these ideas, but then I think it's, it's too... Like, 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-"

    17. LR

      Right

    18. MR

      ... this. I don't, I'm-

    19. LR

      LSD and stuff in coffee

    20. MR

      ... I don't know. Yeah. And then this is a sp- that had co- spider that had coffee, and it's like instead of a regular web, it's like a web that goes like this. [laughs] Like, it's like just erratic and tangential, and I have some, some really good i- some really good like seeds of ideas in those moments. Then I have to go like scream into a pillow [laughs] or something.

    21. LR

      Was that when you have too much coffee, or is that like-

    22. MR

      That's when I have too much coffee.

    23. LR

      Okay, when you have too much, yeah.

    24. MR

      But, but if... Uh, there's a point like-

    25. LR

      Okay

    26. MR

      ... right before that.

    27. LR

      So single shot latte.

    28. MR

      Single shot is what I get. Single shot latte. S- at least an hour. Sometimes it's good to have, uh, like a somewhere I have to be. It's a time limit, and then I'm kind of like a f- it... I feel like a machine, [laughs] uh, and it's like trying really hard to get somewhere. And, and then the other thing is just like a lot of it is writing something down as I'm out in the world, like writing and then putting it... trying to put it on paper in a way that visualizes it because I'm not strong at drawing. So, and yeah, when I was a kid, my dad did a lot of math with me and a lot of like, you know, fractals and visualization and patterns, and so I sort of think that way, um, like mathematically kind of. [laughs] And, um, yeah, so it helps me to visualize an idea, uh, that in the simplest way possible.

    29. LR

      Let me just say this is very cool that we're doing this. This is like really fun. [laughs] So sweet.

    30. MR

      Oh.

  20. 51:58 – 54:00

    Lenny’s favorite children’s books

    1. LR

      Back to you, Michelle Rial.

    2. MR

      Oh, to back to me, to you?

    3. LR

      Yeah.

    4. MR

      Yeah. Okay. So we did the Thunder round. We did the, the, the worst things to hear. Okay. And the best sounds, which your son's-

    5. LR

      Yeah

    6. MR

      ... laugh.

    7. LR

      Yeah.

    8. MR

      Yeah. Agree.

    9. LR

      It's so great.

    10. MR

      Do you... Okay, we probably know your favorite like product management books. Do you have a favorite children's book other than mine? [laughs] To read to-

    11. LR

      Charts for Babies

    12. MR

      ... to read to... A- and also like-

    13. LR

      Coming out in April

    14. MR

      ... and also maybe you could, you could do more than one because the, you know, they like... Maybe there's one when he was a baby.

    15. LR

      Like I feel like a chart is... And you never take my ideas 'cause I feel like you don't want to-

    16. MR

      I don't wanna get-

    17. LR

      You want it to be your ideas.

    18. MR

      Yeah. [laughs]

    19. LR

      But I feel like there's a books you love that are children's books-

    20. MR

      Yeah, exactly

    21. LR

      ... and books your kid loves.

    22. MR

      Yeah.

    23. LR

      Right? And it's like, I hate reading this one, but he loves it.

    24. MR

      Uh-huh.

    25. LR

      So we're gonna do it.

    26. MR

      Yeah.

    27. LR

      So it's like he decides what his favorite are. I love Jon Klassen books. They're so like beautiful and just like sweet. So those have been really great.

    28. MR

      Are they sweet?

    29. LR

      They're like actually not sweet. You're right. There's like death in all of them.

    30. MR

      There's... Yeah.

  21. 54:00 – 55:31

    Product management lessons in parenting

    1. MR

      yeah, I mean, anything you wanna say about like, I don't know, is there any sort of like product p- anything you've learned in product management or like growth that has translated to parenting?

    2. LR

      You know, like product management is all about influence, and that's basically parenting.

    3. MR

      That's why he likes you better. [laughs]

    4. LR

      Why? 'Cause I give influence? But you also have to make him do stuff, you know?

    5. MR

      Yeah. Yeah.

    6. LR

      So like you do have authority, you know. Uh, all the responsibility without the authority, but you do have authority, so it's easier.

    7. MR

      They have the au- I feel like toddlers don't call the authority.

    8. LR

      They have authority. It's true. It's trueJust like, "Nope. Here's the... You sit there." [chuckles]

    9. MR

      Yeah. I feel like I see your product management in that, like, you make him... Like, I should be the one making him a chart, but you make, you make him, like, the, like, "Here's how..." If bedtime gets too long, you're like, "Here's how bedtime's gonna go. We're gonna read you three books, and you get a star." You know, it's like [laughs] you... And then also I'm answering for you. Sorry.

    10. LR

      Go on.

    11. MR

      Other things where-

    12. LR

      It's good

    13. MR

      ... it's, like, things where it, it's where I'm kinda 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" [laughs] "and this is how we're gonna do it, and, and that's... And it's gonna work." Sometimes it works. Sometimes it doesn't.

    14. LR

      Right. Yeah. I'm not, like, 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.

    15. MR

      Right. Shorten bedtime, sleep through the night.

    16. LR

      Right.

    17. MR

      Yeah.

    18. LR

      Yeah. There's, like... Yeah. There's, like, smart people that have tried this stuff before, you know [laughs] and can tell me what they've done.

    19. MR

      Small, small eye roll. [laughs]

  22. 55:31 – 58:23

    Defining product management in five words

    1. MR

      And 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, like, I, as your wife, uh, of however many years, like, 10, still I don't think I know what product management is. Do you... Can you tell me in five words?

    2. LR

      Hmm. That's hilarious. Okay. I will... My words are impact, collaboration, judgment, alignment, and... This is a really good question, and it's almost like the c- the order is, like, how you think about product management. Like, you know, it's like the order you put them in. And what else? I'll just say some stuff 'cause it's really interesting. Coordination.

    3. MR

      I think that's five.

    4. LR

      Organizing.

    5. MR

      [laughs]

    6. LR

      Planning.

    7. MR

      Okay.

    8. LR

      Outcomes.

    9. MR

      I'm just tuned out. [laughs]

    10. LR

      There's so many. [laughs] You're just like, "Shut up. So boring."

    11. MR

      [laughs]

    12. LR

      And I'm just like, "What should have I said?" That's what I'm gonna think about now. But it's... Yeah. It's, like, a crazy, weird job, all these different things. Yeah. Now I'm just, like, sniped. I wanna keep thinking.

    13. MR

      Mm. Yeah. Keep, uh-

    14. LR

      I'll give you my definition of product management.

    15. MR

      Yeah, but you can't say mini CEO.

    16. LR

      No, I mean, no mini CEO. That's, that's not cool.

    17. MR

      Okay. Okay.

    18. LR

      Although I actually do think a PM is a mini CEO. Like, I think people keep saying you're not, but I think you are.

    19. MR

      Yeah. You can't say, like, not a proj- project manager.

    20. LR

      Yeah, not a project manager. [laughs] That's right. I think the way I describe it is, uh, 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.

    21. MR

      Yeah. [laughs]

    22. LR

      You're like, "This is why I never know what it is. It's so boring. What are you even talking about?"

    23. MR

      No, it's, it's, it's cool.

    24. LR

      Like, this comes back to the mini CEO thing, just to close that thread. I feel like the PM on the team is basically... should be thinking the way the CEO thinks, you know? Like, their job is to think, "What would the CEO do on this specific product or feature?" Because the CEO's job is make this successful, make this business grow. And so your job as a PM is to kind of channel that. What will allow this team and product to help the business be more successful?

    25. MR

      Do you feel like you're doing that as, as, uh, the... I guess you are, like, the-

    26. LR

      I'm everything, you know?

    27. MR

      Yeah.

    28. LR

      Like, in my current world, right?

    29. MR

      You're editor-in-chief too.

    30. LR

      Editor-in-chief, yeah.

  23. 58:23 – 1:01:30

    Why Michelle pivoted to children’s books

    1. LR

      Well, let me ask you one more question, so maybe it's to 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?

    2. MR

      I wanted to do a children's book based on the first adult book because I thought that charts are so... They're, like, a ton of early learning concepts put together. So if you look at children's books, they're... You know, the themes are often opposites, colors, shapes, feelings. Um, and then I just, I was thinking, like, you can really, you can really teach a lot from a chart, and it's so simple. So it's a lot, it's a lot of opposites. It's big and small. It's, it's, uh, you've got going up and going down. You've got overlapping colors becoming another color. You've got... You can make a lot of feelings with, with charts. That's the second book in the series that, that I'm-

    3. LR

      It's coming out next year.

    4. MR

      Yeah, but we... But yeah, I'm, I, I finished it, but it's... You know, it still takes about a year to, to come out after that. But yeah, it's, it, it was this, like, uh, I wanted to work on it i- in abstract. Like, I had, 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, like... I had... It was more like a cadence. I had just, like, this, like, da, da, da, da, da, you know, in my head. And, and yeah, I just tried it, and it came really quickly, the first draft. And yeah, and it, it also... Yeah, I, I always wanted to make one because as, as a little girl, my dad wanted me to... He was a geophysicist. He wanted me to be strong at math. He was like, you know... 'Cause at the time it was kinda like girls, um, weren't encouraged necessarily to be good at math, so he, he from just, like, a young age, he was always showing me. I do the same with our son too, like, always showing him patterns, and like, "Oh, if you flip it, it's like that." And it's just really fun for me. And it's, it's cool too, r- uh, writing the first one with, like, our son growing up, learning from experience, like I was saying, like, having the experiences of him as a baby and, like, how I'm learning how to teach him things. Then he gets a little older, and then that helped me work on the, the feelings. And 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." [laughs] And now it feels more natural. And so I, I, I had a, a children's book that I tried to write before I had kids, and for me, that one wasn't as good. And so I feel like I gained a little bit of just, like, how to talk to a child.

    5. LR

      That's a really good, like, segue. Or not segue, I don't know, connection to something that we've talked about a few times is the best stuff comes from, like, actual experience. Like, 'cause you had a children's book, like you just said, that you wrote before you had dude, and then it wasn't good. And now having the experience, you can actually make something great.

    6. MR

      Yeah. And then also, like, another thing I thought about was just reading so many children's books. And people always say, "If you wanna write, read." And [laughs] yeah, we read a lot. We read still a lot, a lot of books. And it, um, it just got me in that zone

  24. 1:01:30 – 1:06:53

    The power of iteration and real experience

    1. MR

      too.

    2. LR

      Yeah. It just makes me think about something I think has been key to my newsletter success is, uh, it is based on, like, real life doing the thing. Like, so at this point, most of my posts are guest posts, where somebody's sharing the best thing they've learned in their career, like the one thing they want to share, which I love. And 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. And that's the source of the best advice is from practitioners doing the thing for real, you know, 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-

    3. MR

      Communicating it simply

    4. LR

      ... simply, and just, like, refining. I don't even get into-

    5. MR

      Yeah, yeah

    6. LR

      ... just all the work that goes into refining.

    7. MR

      Keep... And then, yeah, we always, you always talk about, like, we... Yeah, another thing I do is, like, I often ma- It's, 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, and, and 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 gonna make that better, or I go to work on it again, and some other thing adds to it. 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. Like, so that's-

    8. LR

      Yeah

    9. MR

      ... stressful-

    10. LR

      I go through that myself

    11. MR

      ... to, like, to, like, have something sitting. Like, with, with maybe with your podcast and-

    12. LR

      Yeah. Well, let me ask you this, and I'll answer for my own myself. How many iterations do you do on a chart on average? Like, how many times do you, like, edit it and refine it?

    13. MR

      Uh, it depends.

    14. LR

      Yeah.

    15. MR

      Yeah. It could be just-

    16. LR

      What's, like, what's, like, the median?

    17. MR

      At least five.

    18. LR

      Okay. Like, for me, I think it's, like, 60.

    19. MR

      I was gonna say 100.

    20. LR

      Okay [laughs] . That's probably the real answer.

    21. MR

      But I, but I-

    22. LR

      It's how many times do you do it?

    23. MR

      ... I can't even physically do that. It's like I n- I need... Yeah.

    24. LR

      Yeah. It's just like-

    25. MR

      Well, what do you mean by-

    26. LR

      So, like, when I write a newsletter post, I go through it probably, let's say 50 times, making it better. Like, I, I start, there's, like, 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, like 50 times. And then I have my editor go through it, and I have a copy editor go through it, and the designer help me.

    27. MR

      You don't do that with your emails, though.

    28. LR

      I... No.

    29. MR

      [laughs]

    30. LR

      I should.

Episode duration: 1:06:53

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