Lenny Rachitsky on the Other Side of the Mic: Following the Pull, the Weekly Treadmill, and the Moments That Scared Him Most
Lenny's Podcast
Lenny Rachitsky usually asks the questions on his podcast. In this episode his wife, Michelle Rial, an author and chart-maker whose children's book Charts for Babies was about to come out, interviews him instead. Lenny said he hadn't seen her questions beforehand. The conversation covers how he ended up writing a newsletter with 1.2 million subscribers, what the work costs him, how he handles stress, and two of the hardest moments of the past few years: a fraud attack on his subscriber perks and a medical emergency during their son's birth. Along the way Lenny turns the questions back on Michelle, and the two find they share several ideas about creative work. The best material comes from real experience, it should be communicated simply, and it improves through heavy iteration.
A career nobody planned
Michelle opens with the numbers. Lenny started the newsletter in 2019, it now has 1.2 million subscribers, and the podcast is usually among the top 10 tech podcasts. When she met him he was a software engineer. He later became a product engineer and then a product manager.
She asks what he would be doing if he had never started the newsletter. Lenny says that when he left Airbnb after seven years he had a clear hierarchy of plans. Plan A was to start another company. Plan B was to join a startup as its first PM. Plan C was to join a big company as a PM. Plan D was to advise companies as a consultant. None of these was "do this crazy thing that I do now." He was prototyping startup ideas and writing about what he'd learned on the side. Michelle remembers asking him why he was writing, since in her experience there is no money in putting writing on the internet.
Without the newsletter, Lenny guesses he would have started another company. Since most startups fail, he expects he'd have been "on the struggle bus of startup life," and after that failed he would probably have joined a company as a PM.
A collection of moments, not one decision
Asked whether one moment led him to go all in, Lenny describes a series of small signals. He followed a "pull" that kept working.
The first signal was his first piece of online writing, a Medium post about what he learned at Airbnb. Medium featured it, it spread widely, and it was shared with the whole company. That gave him an early sense that he might have something to share. A few more Medium posts did well.
The second was a conversation with his friend Lee Jacobs, now a VC. Lenny told him he didn't know why he was writing when he should be focused on a startup. Jacobs said Lenny seemed to enjoy it and people seemed to like it. He called that combination rare and suggested there might be a way to make money from it later, so Lenny should double down. When Lenny retold this as "people like it and I'm good at it," Michelle added the missing element: he also enjoys it. Lenny agreed that was the real trigger and compared it loosely to ikigai.
The third moment came nine months in. Lenny had moved to Substack and tweeted that he would experiment with a weekly newsletter. After publishing every week for nine months, he realized he could probably keep going. He cites the Lindy effect, the idea that something likely lasts at least as long again as it has already lasted, and concluded he could keep writing for at least another year. He still had plenty of ideas.
That was when he added a paywall. Money was part of the reason. He had been living on the assumption that his Airbnb stock would be worth something. When COVID hit, predictions that Airbnb was finished spread across Twitter, and he felt he might need a real job. He launched the paywall to see if the newsletter could make money, and he says it did. Within about a month he was making "meaningful dollars." He counts that as another signal that the path was working.
The Joshua Tree moment he had never shared
When Michelle asks about stress-management tools, Lenny goes back to the question of what led him to this work and shares something he says he had never talked about publicly. Around the time he was starting the newsletter, he was at Joshua Tree with a friend for a bachelor party, and psychedelics were involved. He sat on a rock for about three hours, breathing deeply, while the phrase "I have wisdom to share" kept coming to him "over and over and over." He also recalls a vivid visualization of a sitting Buddha.
The experience didn't make him write any particular post. He says it gave him confidence: "okay, maybe I do have things to share," and a sense that something inside him might let him do this. Michelle jokingly asks whether he wants to say anything to their mothers or cut the segment. He keeps it in.
Does he still like it? The Indiana Jones boulder
Lenny says he likes the work "in almost every way" and can't imagine anything more fulfilling. His job is to write about interesting things, share other people's insights, and interview people to "extract wisdom," and doing it as his own business makes it more interesting.
He then describes the downside. He cites a blog post by the artist Fnnch on making a living as an artist, which opens by warning that most people should not become professional artists, because once something becomes a thing you have to do, it changes. For Lenny that means a newsletter post every week and a podcast episode every week, which he calls a treadmill. Some weeks he loves it. Other weeks he wishes he could skip one. He believes consistency is the price of this kind of business: you can't survive without shipping something good every week.
His recurring image is the boulder chasing Indiana Jones. A post had come out the day before the recording, and his attention had already moved to the next week's piece. The work never stops arriving.
He says he doesn't know the long-term answer. At some point, whether at 60, 70, or 100, he may not be able to publish weekly, and he doesn't think there is a known path for the "Substack writer, podcast life" in the long run. Michelle applies the Lindy effect: seven years in, he should be good for seven more. Lenny accepts that.
Stress, genetics, and raising a happiness baseline
Michelle says Lenny doesn't seem like a stressed person, except about their toddler's potty training and sleep. Lenny thinks he is more stressed than he appears and more than he notices himself. He sometimes gets headaches and wonders if stress is the cause. Still, he thinks he is less stressed than average and attributes that roughly 70% to genetics. His default is "it'll be all right," which he admits extends to disputes about raw chicken. The rest, he says, comes from deliberately learning to think differently and take things less seriously.
Michelle mentions his meditation practice, including a 10-day silent retreat, and a happiness course he once described to her. Lenny calls the course, an online class from the University of Pennsylvania on the psychology of happiness, "pretty transformative." His main takeaway was the idea of a baseline. Something wonderful pushes your happiness up and something terrible pushes it down, but you return to your baseline either way. The lasting lever is raising that baseline. The course's main method for doing that, as he remembers it, was optimism: keeping a positive outlook and not letting your mind spiral into "it's going to be terrible." He found the gratitude material less useful. He believes his baseline has gone up.
He also remembers a point about exercise, noting it came from research roughly 15 years ago that may since have been updated. As he recalls it, exercise doesn't make you happier. It moves you from a negative state to neutral, from minus one to zero, which helps keep you out of depression.
The "thunder round": misophonia
Michelle parodies Lenny's lightning round with a "thunder round" about sounds. Lenny has misophonia, which he describes as a real condition in the brain that makes certain sounds intensely bothersome. On a scale where 10 is worst, he rates open-mouthed chewing a 10, especially when someone next to him is "chomping away," and he finds it awkward to ask anyone to stop. Nails on a chalkboard get a five or six. A baby crying, at the level of the newborn phase when they didn't know what to do, is about an eight. A loud leaf blower in his face while he's trying to work is about a seven. Their son saying "papa" and laughing rank as the best sounds. Lenny adds that only a few very specific sounds bother him, plus general commotion when he's trying to be calm.
Why Michelle's charts spread
Lenny then turns the questions around. Michelle's first book, Am I Overthinking This?, collects charts about everyday experiences and feelings. Lenny notes that her charts are widely shared, often with her attribution cropped out, and even printed on pillows and mugs sold by sites that give her no credit. He asks why they travel so well.
Michelle says she stopped looking at the copies because it doesn't help her, and that it matters less now that Lenny's business is doing well. Her sense of whether a chart is good is internal. She often makes something, lets it sit, and later sees what it needs. When a chart still makes her laugh or cackle even though she made it, or makes her tear up, she thinks people will like it. She says she is often wrong. One chart from the book that she never shared went viral because someone posted a phone photo of the page.
She aims for charts that are simple, quick to read, and show something the viewer hasn't thought of. Short attention spans reward easy-to-digest pieces that make people feel something. Simpler charts are also less physical work to draw. She says her mind naturally runs toward "this, but then this, then this," but people respond to simplicity.
Lenny sees a parallel with how he judges his newsletter posts. He doesn't wait for outside approval; he knows a piece is good when it feels good to him. He applies this more to the newsletter than the podcast. He also describes playing editor for Michelle. Some of her charts are "too clever," with too many layers for a short attention span, and he pushes her to simplify. She says he's usually right.
Where ideas come from
Michelle says her ideas come from living life and noticing things. She is most prolific when she's meditating, because meditation trains you to observe your own thoughts. She'll notice, for example, that she was anxious about something random and find that funny. She admits this amounts to overthinking every moment, which isn't really what meditation is supposed to teach. When she focuses too much on work, she stops living and stops having ideas. Children's books work somewhat differently because they're based on concepts for kids rather than relatable adult moments.
Lenny recalls a story, which he attributes to David Sedaris, about saying yes to every invitation in order to have experiences to write about. He takes this to mean creative work requires living a real life and trying things, not sitting and waiting for ideas.
Michelle explains how Charts for Babies started. She began a notebook of charts for new parents based on early parenthood. But after reading so many kids' books with their son, she had a children's-book rhythm stuck in her head. One day in the park she turned to the back of the notebook and started writing children's rhymes, and filled it from the back. Lenny calls this another example of "following pull."
Early projects: Atheist Spot, a tutorials site, and LocalMind
Michelle asks whether anything in Lenny's past hinted at this career. He says no: it was completely unexpected to him and to everyone else. He had never written online before and considers himself an introvert who prefers to stay behind the scenes. He thinks starting during COVID helped, because he could stay home, type, and publish without going anywhere to promote himself.
He then describes some side projects he says he's never discussed. In college he was a committed atheist. He describes himself as a Jewish atheist who is now much more relaxed about what others believe. He ran Atheist Spot, which he describes as Reddit for atheist news, and attended atheist conventions. Because most articles on the site were about religion, Google AdWords filled it with ads for religious dating sites like Christian Mingle, which he found funny given the audience.
With a friend, he built a site whose tagline was "tutorials for you, by you," where people wrote how-tos on things like making eggs or taking a quick shower. Lenny calls it ahead of its time and thinks it predated Wikipedia. Michelle compares it to how she uses TikTok. He says he's proud of it.
His startup, LocalMind, was an app built on top of Foursquare and Gowalla that let you ask questions of people checked in anywhere in the world, such as whether there was a long line at a nearby restaurant. Lenny describes it as an amazing idea that "nobody needs really." You might want it once a quarter, and it's great when you do, but that isn't a business. Other tools, like Google's busyness indicator, now solve the problem. Airbnb acquired LocalMind, which is how Lenny got there.
Working alone, face blindness, and being recognized
Michelle recalls that Lenny was her first online date, on a site called How About We, and that he had "a thing for designers." He says he has no regrets. They describe themselves as a yin and yang: he is tidy and unbothered, she is chaotic and bothered. Cleaners help.
She asks whether he misses office culture, since he recently said he has no coworkers and had always been social. For years he answered no. Recently, though, he has started to feel it. Working from coffee shops with headphones on feels like "bowling alone." He has a team he collaborates with, but he misses having someone next to him working on the same thing. He is still trying hard to avoid hiring full-time employees and keep the business simple. He warns that in this kind of work "you can create a job for yourself that you hate" by doing what others want or chasing opportunities that feel big, so he's careful about what he commits to.
Lenny says he's recognized in public often, especially around the Bay Area. It started with the podcast; during the four years before that, his face was only a small Twitter avatar. He calls it "extremely weird" but says he likes it, has never had a bad experience, and wants people to say hello. He usually asks strangers what their favorite episode or post is and what they do. When Michelle asks about interruptions at bad times, he says she may be projecting. Nearly everyone, "99%," has been considerate. His favorite encounter was in San Anselmo, when a man in a red car with his son stopped traffic to shout, "Lenny, I love your podcast." Lenny later ran into him at a coffee shop and learned he runs a hamburger club in Marin.
Recognition is complicated by Lenny's face blindness, which he calls "another brain disorder." He struggles with names and faces, so when someone greets him he often can't tell whether they know him personally or from the podcast. Michelle says she sometimes acts like the assistant in The Devil Wears Prada, whispering who someone is. Lenny apologizes in advance to anyone he fails to recognize and says it has gotten worse as he meets more people.
The most stressful business moment: a fraud attack
Asked about his most stressful business moment, Lenny describes his product pass, a subscriber perk that includes free access to 23 products such as Linear, Mobbin, Lovable, Replit, and Gamma. He used to read the full list at the end of each episode but stopped once it got too long.
About a year before the recording, he launched an offer of a free year of Cursor, Lovable, Bolt, Replit, and v0. He says the offer was "way too good" and attracted fraudsters, mostly organized fraud rings in China as it turned out. The offer also went viral in a Chinese student network. The attackers found exploits in the API his team had built, and Lenny had to work with Stripe and Substack to shut them down. His engineer, Estee, barely slept for a week while patching holes as new attacks appeared. Lenny says he slept badly throughout and feared the problem could escalate until the whole business fell apart if people decided they couldn't trust him anymore.
The scariest moment of his life: the birth
For his most stressful personal moment, Lenny describes their son's birth, which Michelle notes she can't tell herself because she wasn't conscious. The induction wasn't working, so Michelle needed a C-section. The plan was for the medical team to give the anesthetic and then bring Lenny in. He waited in the hallway in a sterile "bunny suit."
About five to ten minutes in, he heard a beep. The doctor ran out, scrubbed, and ran back in, and two other staff members rushed in from down the hall. For about ten minutes nobody told him anything, though he was supposed to have been called in within a minute. He paced the hall repeating "it's going to be okay" to himself and trying to trust that the doctors knew what they were doing. He connects this to the mental habits he described earlier, and Michelle notes he could otherwise have spiraled.
Eventually staff explained that the epidural had traveled up instead of down and was stopping Michelle's heart and lungs. The team performed an emergency intubation and delivered the baby. It took about an hour for Michelle to come back, and there were plans to move her to the ICU. Lenny says the anesthesiologist told them it was a one-in-50,000 event, a very rare and dangerous worst case, and that everyone praised how well the anesthesiologist handled it. Lenny calls it probably the scariest moment of his life.
Michelle's last memory is feeling her lungs go numb, saying she couldn't breathe, and passing out. She was under general anesthesia and learned the details only months later, when she read the report with her cousin Lois, a nurse. She says it's strange to have no experience of an event that was so intense for Lenny. During that hour, Lenny held their son. Michelle half-jokes that this is why the boy prefers "papa." Their doula had planned to attend but couldn't be present for a C-section.
Michelle's creative conditions: coffee, deadlines, sleep
Lenny asks about Michelle's process. He says her charts seem to appear from nowhere, followed by a little iteration. Michelle says coffee has to be the right amount, usually a single-shot latte. Too much makes her feel like a genius and then like she's having a panic attack. She has a chart about this, drawn with a coffee straw, which Lenny compares to xkcd's "Ballmer Peak," the idea that there is an optimal amount of alcohol for creativity. She describes an image she once saw, possibly not real, of a web spun by a spider on caffeine: erratic and tangential. Over-caffeinated moments produce good seeds of ideas, and then she needs to "scream into a pillow."
A deadline also helps, ideally around two hours. Thirty minutes is too short, and she admits her "time optimism" sometimes makes her late. She also needs a good night of sleep. Bad sleep plus too much caffeine gives her only frantic energy and no ideas. Finally, she needs experiences and time to think about them, almost too much. Lenny suggests "overthinking," a nod to her first book.
She draws ideas out in the simplest visual form she can, partly because she doesn't consider herself strong at drawing. She traces her mathematical way of thinking to her father, who did math, fractals, and pattern work with her as a child.
They also share an observation about their backgrounds. Michelle's family is from Venezuela, where her family still lives, and Lenny's is from Ukraine. People often react as if they had just arrived from those countries, and they sometimes have to reassure people that it's okay.
"Lenny" is his legal name
Prompted by a friend who calls him "Leonard," Michelle asks where "Lenny" comes from. Lenny, who was born in Odessa, says his official first name in the U.S. was Leonid but everyone called him Lenny. When the family became citizens, his parents legally changed it to Lenny. It isn't short for anything. He guesses that his parents asked friends for an English version of his Russian name and landed on Leonid, but he doesn't know whether it was named after anything. His family also uses a Russian diminutive nickname, which he asks strangers not to use.
Children's books and product management at home
Asked about favorite children's books, Lenny says their son decides the favorites. Lenny loves Jon Klassen's books. He first calls them sweet, then agrees with Michelle that "they all end in death." Their son now opens I Want My Hat Back by announcing that the bear ate the bunny. Both find Dr. Seuss too long, with too many invented animals when they're trying to teach real things about the world, though they enjoy the rhythm. Michelle reads to their son in Spanish.
On whether product management carries over to parenting, Lenny jokes that PM is all about influence and so is parenting. The difference, he says, is that a PM has "all the responsibility without the authority," while parents do have authority. Michelle says she sees the PM in how he structures routines: a set bedtime plan with three books and a star chart, based on what he read in books. Lenny says he isn't "an intuition guy." He looks for what the smartest people have already worked out, since plenty of parents have tried to shorten bedtime before. Michelle says it sometimes works and sometimes doesn't.
Product management in five words
Michelle says that after about ten years together she still doesn't know what product management is, and asks for five words. Lenny gives "impact, collaboration, judgment, alignment," adds "coordination," then keeps going with "organizing, planning, outcomes" until she tunes out. He admits he got "sniped" by the question and wants to keep thinking about it.
His longer definition is that a PM's job is to deliver business impact by prioritizing and solving the most impactful business problems. Michelle bans "mini CEO," but Lenny says he actually thinks the label fits, even though people keep saying otherwise. The PM should think the way the CEO thinks: the CEO's job is to make the business grow, so the PM should channel what would help their product and team make the business more successful. In his own business, he says, he is "everything," including editor-in-chief, though he has an editor and a copy editor.
Asked what from product management helped him in his current work, Lenny says honestly, nothing specific, beyond traits he already had: being organized, holding a high bar for quality, and communicating points succinctly so people grasp them. Michelle notes this matches her own emphasis on simplicity.
Why a children's book, and why experience matters
Lenny asks why Michelle moved from adult books to a children's book. She says charts naturally combine early-learning concepts. Children's books often teach opposites, colors, shapes, and feelings, and a chart can show big and small, up and down, overlapping colors making new colors, and many feelings. A second book in the series, focused on feelings, is finished and due out the following year. She had wanted to do a children's book in the abstract, but it only came once the rhyming cadence took hold while she was working on another adult book. The first draft came quickly.
She also connects the book to her father, a geophysicist who wanted her to be strong at math at a time when girls often weren't encouraged to be. She does the same with their son, showing him patterns. Raising him shaped the book: she learned how to teach him things, and as he got older that experience fed the feelings book. She also learned how to talk to children. Before having kids she tried to write a children's book, and she doesn't think it was as good.
Lenny ties this to an idea they've discussed often: the best work comes from real experience. Michelle adds the familiar advice that to write, you should read, and they read many children's books. Lenny says the same principle has been key to his newsletter. Most of his posts are now guest posts in which someone shares the best thing they've learned in their career. He focuses on practitioners "on the ground doing the thing," not people "floating in the clouds pontificating," because he considers practitioners the source of the best advice. Michelle adds communicating simply, and Lenny adds refining.
Iteration: five passes versus fifty
Michelle describes the stressful part of her process. She makes things she isn't sure are good enough, sets them aside, and returns later, sometimes with the missing idea, sometimes to find someone else has published something similar first.
Lenny asks how many iterations she does on a chart. Her median is at least five. His is much higher: he estimates he reads through a newsletter post about 50 times, adding and improving each time, before his editor, copy editor, and designer work on it. Michelle's guess was 100, and he says that may be the real answer. Michelle says she physically couldn't do that. She adds that she did many iterations on Charts for Babies, and they recall a line from a former boss, Vlad: "spend more time on it."
The conversation ends with the book's details. Charts for Babies comes out April 7, and Michelle suggests an age range of roughly zero to four. She shows its endpapers, which list the concepts it covers, including sizes, shapes, lines, numbers, directions, feelings, colors, amounts, sharing, relationships, and opposites. The main point the two return to throughout is that good work comes from real experience, is communicated simply, and is refined through many rounds of iteration. The open question Lenny leaves unanswered is where a weekly newsletter-and-podcast life goes in the long run, when he may no longer be able to keep up with the boulder.
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 and I was just watching this crazy visualization of some kind of sitting Buddha thing and that was for 3 hours. It gave me the confidence that like okay maybe I do have things to share.
What do you want to say to our mothers right now? Do you want to take this back?
My mom.
Do you want to take that back? You started your newsletter 2019 and it now has over a million subscribers.
1.2 million.
1.2.
Something that we've talked about a few times is the best stuff comes from actual experience.
People always say if you want to write, read.
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.
What do you think you'd be doing right now if you hadn't started that newsletter?
On the struggle bus of startup life, probably. And then probably after that failed, I would have joined some company as a PM.
Do you still like it?
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.
Tell me about a time you've been really stressed in your business.
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.
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That's me.
Michelle Rial, thank you so much for being here. Welcome to the podcast.
Thanks for having me.
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 and 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. Ask me whatever you want. I have no idea what you're gonna ask me and we'll see where it goes. And I'm gonna ask you some questions about your book, too. So, I'll turn that over to you, Michelle. What do you got? What do you got for me?
Hello, Lenny.
Aka babe. Yeah. So, you started your newsletter 2019 and it now has over a million subscribers.
1.2 million.
1.2. And your podcast is very frequently one of the top 10. Is that right?
Yep. It's like right around... Yeah, it's top 10 tech podcast.
Yeah.
Yes. Hell yeah.
I love it. When I met you, I think you were something called a product engineer.
I was a software engineer. Let's see. When you met me. No, I think I was still a software engineer. Yeah.
I think you went from software engineer to product engineer to product manager.
Yeah. Yeah, that's right.
I'm wondering what do you think you'd be doing right now if you hadn't started that newsletter?
If I like stayed in my job.
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, but you can answer either one.
So is the question after I left Airbnb what would I be doing or is it like if I didn't
Just if you hadn't or if you had gotten a different job, do you think you would have gotten a different job, stayed there?
So when I left my job, I was at Airbnb for seven years. I had like plan A, start a company again. Plan B, join a startup as like 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 like do this crazy thing that I do now. I had a lot of startup ideas. As I was exploring the startup ideas, as you remember, I was just like tinkering and prototyping and building stuff. And then on the side, I was writing things that I learned and things I wanted to share. And 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. And 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.
I don't know if I said things that you're good at. I just said like as a person there's no money putting writing on the internet. I don't make any money unless people buy my book. Yeah. Plug.
Yeah.
Yeah. So I guess to answer your question I'd probably find another company to start and I probably would have failed considering most startups fail. So I'd probably be in this like oh no, is this thing a thing I should be doing? I'd be on the struggle bus of startup life probably. And then probably after that failed I would have joined some company I guess as a PM.
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?
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... this is like the first thing I wrote on the internet, did very well, is this post on what I learned at Airbnb. Like Medium featured it. It went all over the place. Branches 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 this is working. People seem to like it. 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 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 is 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. 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 going to move to Substack. I'm gonna 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. And I just remember this moment nine months in where I was like, huh, I've been doing this every week for 9 months, which means I could probably do this for nine more months. 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. So, 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. 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, 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 might have... it was like 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. So 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. You know, I made meaningful dollars like a month in.
So, speaking of Venn diagram, you said I'm good at it and people like it
and people like it.
Oh, and I like doing it. You like doing it.
That's a really good... cuz I didn't mention that.
Okay.
That's so true that it's right. Yeah.
Yeah. I think ikigai is like five things, right? It's like a whole bunch of stuff. Yeah. But that's a trigger point cuz it was just like people like it and I'm good at it,
but without that I actually enjoy it.
I think you said I like doing it.
Okay, cool. Do you still like it?
I do in almost every way. Like I can't imagine doing something more fulfilling and interesting, which is 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 like so interesting. It's my own thing which makes it extra interesting. But I think a lot about this artist fnnch who wrote this blog post, how to become an artist. And at the top of his post, he's just like you should not become a professional artist most likely because, yeah, because once it's a thing you have to do, it changes it. You have to do it. So now I'm on this like... this is the downside, but I just want to preface with saying this is incredible and 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, 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 it kind of 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 though to not do it this week. But that's part of this life, you know, 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. So it's a part of it. So 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 that work you put into it, over. What's coming out next week, and it's like every week. So the big question I don't have an answer to is where this all goes long term because someday, whether it's 70 years old or 100 years old or 60 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 an answer to like Substack writer podcast life long term, like what do you do?
Like according to the Lindy, right?
There you go.
So 2019, now it's seven more years.
Seven years since the news...
Seven years.
So I can... yeah, good luck.
Seven more years, you don't run out of ideas.
Okay, so we got seven years. I can do that.
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, sleep, the toddler or baby sleep stuff.
Yeah.
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?
I think there's an element of I am 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 work on it. Like I've 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, it'll be all right. It'll be all right. As you know, something we argue about, it'll be all right. That's some like raw chicken. That'll be fine.
That's fine.
So, okay. Do you have any tools or any kind of... like I know you've done different types of meditation. We've done breathing together. Do you have a favorite? Do you
Oh, to like calm down and de-stress.
And you did a 10-day silent meditation right before you ended up writing the post.
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 bachelor party trip with some friends. This isn't where you think it's going.
I hope not.
So, it was a trip to Joshua Tree with a friend and there were psychedelics involved on this trip. And 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 and I just remember sitting there for probably 3 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. And it's just like I have wisdom to share. And that was for three hours.
That made you write the post.
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 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.
What do you want to say to our mothers right now? Do you want to take this back?
My mom want to take that back?
No. No. Do you want to crop it out?
This is... Okay, Mom. I did some stuff.
It's okay. We... Okay, so it's time to share.
And then yeah. You did 10-day meditation. You did a specific type of meditation that seemed to me to affect you in physical ways.
Yeah.
And then you told me once about a happiness course you took.
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 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... everyone's got this baseline.
That was actually a big learning from that course, is everyone's just kind of this baseline level of happiness and you could be like at 100, you could be at zero, probably most people in between somewhere, and like something amazing happens, you go way 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 going to be terrible. So it was a lot of just like, think more positively. And I feel like my baseline level of happiness has gone up and I think that, yeah.
I think you told me exercise too, like used to run.
Yes, that was a really good insight. So exercise, the science, this was like, I don't know, 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. So you're negative one without exercise and exercise brings you to zero so that you're not depressed, basically.
Speaking of stress.
Okay, then I have a question for you.
Oh, okay. Let's do this. Let's do this. Because I know on your podcast you have a lightning round.
Okay.
We're going to do a thunder round.
Is that extra fast or what does that mean?
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?
Yeah, it's like... 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...
Okay. Thunder round is going to be top five worst sounds, or you can rank these sounds.
Okay. Okay. You're going to give me the five...
Like best sound to worst sound.
Okay.
Right. So like 10 is worst.
Okay. What are...
10 is best? I don't know.
What are the best sounds?
Okay. What's... Okay. Okay. Let's say chewing. Chewing, one to 10.
Chewing like with mouth open. Just like with the worst. Yeah, I hate it. 10 is the worst.
10 is the worst.
It's, you know, it's probably... yeah, it's 10. Nine or 10.
Or like nails on a chalkboard. What's that?
That's like less bad for me.
Right? What's the number?
Like if it's someone sitting right next to me just like chomping away.
Yeah.
And it's so awkward to ask anyone to stop. I hate doing that. It's like, so they're like, "Shut up."
Sweet. You're sweet.
But it's just like, what? I'm just sitting here eating. Leave me alone.
Yeah. That's how I feel whenever I do it by accident near you.
Yeah.
Okay. So, nails on a chalkboard. What's...
That's like six. I don't know. Five.
What about...
I don't mind this.
What about like a baby crying, or... what's a baby crying versus your baby crying?
Baby crying like... so, 10 is the worst.
Yeah.
So, like how loud? Like very loud.
Like in newborn phase, like didn't know what to do, like...
Oh, yeah. That was really like when Jude was born.
Yeah.
Oh, yeah. That's pretty hard. Okay. Like eight.
Okay. Okay. What about like when Jude says papa?
Yeah. One. One is the best. Yeah. And...
Is there any other sound you...
Jude laughing.
Okay. Okay. What about like another bad sound?
I don't know.
Okay. You can ask me now if you want.
Okay.
If you're getting...
No, no, no. There's not that many bad sounds. It's just like very specific bad sounds that I'm just like...
Basketball.
You know? If I'm trying to be calm and there's like a bunch of commotion, like... Okay. Like a gas, you know, blower.
Oh, when I'm trying to work.
That's I think a notorious one for people.
What is that? A 10?
It's like if it's super loud and right in my face, I would say let's say a seven.
Okay.
Not so bad.
You can ask your question now if you want, or I have more for you.
I'm going to ask you a question. So you make these incredible genius funny charts. There's one example on 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. So 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 over the years. What makes your charts so sharable so widely? Why do they go so viral so often?
By the way, I stopped looking at that because it doesn't help me. Anyway...
That's good. I think that's for the best.
Well, I think what's the good...
I think as your thing has gotten more successful, it's like not as important to me. I do think it's interesting that they are often like detached from me, which is, I don't know why, but...
Yeah, people want to get credit.
When they do... and 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 like moment happens, or I'm like, oh no, this is what it needs, and then I'm like, now I can feel that it'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, 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 going to like this. I am often wrong.
And 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 it went viral, is like just a photo of a page of a book that people loved.
Like it wasn't even like a digital high-quality picture. It's just like some random photo. Yeah.
Yeah. Which is interesting as well. And 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. And if it makes them feel something is another thing.
And it's also nice to make something that isn't a lot of like physical labor, 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, then this. People like it when it's really simple.
Yeah. I love your point about the way you know a chart is done is intrinsically you feeling like this is hilarious. This makes you laugh. Makes you feel something. And that's similar to the way I think about my newsletter posts. And yeah, more the newsletter than the podcast, is it just to me feels like this is 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, 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, and that's a little much. You have to like simplify it a little bit.
Yeah.
Yeah. You're my editor sometimes.
I try, but you're like, no, you're like, I don't care. I don't care about your feedback.
You're usually probably right.
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. Now you have a children's book. You're working on like charts for parents. You have all this other stuff going on. Where do your ideas come from, Michelle?
The ideas come from just living life and noticing a lot of things. And then also kind of observing a lot. 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, that's funny that I was anxious about that random thing. I've never thought about it that way before." And which is interesting because it is kind of like overthinking every moment, which meditation shouldn't be teaching you to do, but that's what happens.
But 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 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 and...
Noticing. Yeah.
Yeah. Noticing.
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. So he's just like, "Sure, let's go to Vegas right now. Let's do it." So I feel like that's a lot of the work here, is just to live real life. You can't just kind of sit there and come up with ideas. You have to try stuff and do crazy things.
Yeah. So my first children's book, which is out soon, 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 rhythm in my head of children's books. And so I just turned to the back of the notebook and started writing more like children's book rhymes involving...
The back of a notebook because you're working on a different book and you're not in this notebook? Oh, this is...
Notebook to put my questions in for you. Yeah. And so I started off in the front. I'm not going to show you.
So you start in the front on a different idea.
I just started off in the front, charts for new parents, and then I got, you know, a few in, you know, like a good amount in, and then I was just in the park, right, and then I kind of was just like, "Yeah, but 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.
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. Okay, back to you, Michelle.
Back to you.
Back to you. Back to you. Through me. Through you.
Yeah, exactly. Okay. Okay. So, I do want to ask you this question, inspired by a friend who like reverse nicknames you and says like Leonard. Is your full name Leonard? Where's Lenny come from?
And by the way, reverse nickname meaning they give you a nickname without you like asking them to?
Well, there's people who give you a nickname without you asking. That's... Yes. He gives you the full name.
Oh, he makes it long.
Yeah, it's not a thing. I'm just making it up.
Okay, I like that. Okay. So the question is my real name. So when I moved to the US from Ukraine, which we recently chatted about on a podcast with Boris, which turned out to be big news...
Odessa.
People... Odessa. Yeah. My parents named me Leonid. That 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.
It's just Lenny. No Leonard. Oh, Leo. Yeah.
Oh, yeah. Leonardo.
Just Lenny.
Just Lenny. Yeah.
I love it.
And Leonid, as in it's a Russian name, or there's also the like star constellation.
Oh, the Leonid. I don't know. I think they just asked their friends, just like, my Russian name is Luna? And so I think they just like, what's the English version of that? And I'm guessing some of their friends are just like, Leonid. I don't know if they named it after anything specific.
Can I share any of your nicknames?
I'm going to assume no. What are my nicknames? Okay, go for it.
I don't know who they are. Like, lick.
Okay, sure. I could share that. Sure.
Do you like it?
Yeah.
Do people call you that?
Well, it's like my family calls me that.
Okay.
Yeah, it's like a Russian little nickname. Grunchic.
Yeah. And you... Okay. But like strangers, can they call you that?
No. Don't call me that.
Okay. And speaking of strangers, how do you feel when people approach you, and is it weird at all? 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?
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 podcast, interestingly. I had the newsletter for four years.
Yeah. You got to be stealth.
Yeah. Like my face was tiny in some Twitter profile, but once I started the podcast, people just... yeah, it was like very weird the first time it started happening, and now it happens 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. 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 with someone just trying to say hi to me. So, please say hi.
What? Okay, that's great.
And I often ask people what's their favorite podcast episode or favorite newsletter, because I'm just curious. I always ask, just like, you're a founder, you're a product person, like, what's your story? Yeah, it's really...
What about if you're at a coffee shop and you have headphones on and somebody says like, "Hey." Or if you're like playing with your kid, what do you think?
I think you're projecting, right, about what you wouldn't want.
Girl, yeah.
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 want to be rude
Or you're like in a focus. Yeah. But then
Yeah, it hasn't been a problem yet. Almost like 99% of people have been very considerate.
Yeah. And I don't want people to feel like they can't just talk to me and say, "Yeah, that's cool." Yeah. They're always so cool. I like that. Yeah.
Is there any like instance of delightful? Like maybe the first time this happened.
We live in Marin and I was walking 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," and this wasn't even in San Francisco. It was in San Anselmo and it was shocked. And then he just kept, he like held up traffic just to say hello. I'm like, "Oh my god."
Yeah, I wouldn't do that.
Yeah, probably wouldn't do that. And then I met him later. He runs a hamburger club in Marin. He's very cool. Cuz I saw him again at another coffee shop. So that was quite delightful.
I love that. Okay, you just said something. Okay, people coming up to you. Okay, you're going to have to cut this.
See, no, we're not going to cut it because this is what I go through, too, as a podcast interviewer.
I thought of something I lost there.
This is what I'm constantly dealing with. That is a challenge of the interviewer.
And I think it's fun for people to see cuz you're like, "Okay, I have to think about what I'm going to say next." And then you're like, they stop, and then you're like, "Oh, what was it going to be?" So that's why when I do the podcast, I'm secretly writing notes to myself constantly.
So, okay, check your notes.
Yeah. Well, okay. I closed my... Okay, I should have written it down. Let's talk about like thinking back to what kind of hints that you would start this newsletter or like things that you worked on when you were younger that are like a little or like a mildly adjacent, or like, you know, cuz you had some like some websites, you had Atheist Spot, you had like, you had some tutorials
Tutorials, that's one.
So the question is like what are the things I did earlier that helped me with the work you... Or yeah, just cuz just looking back, like anything that is kind of like makes it obvious that you would have started this newsletter or like a little more
I don't think there's anything that would have 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 kind of stay behind the scenes. So, it's a very unexpected path for me. And 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 like tell everyone. I could stay like in my little hole. But just to follow through on these things you pointed out that I did earlier, cuz 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. I was like a very big atheist and I'm still an atheist, Jewish atheist, 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 want to believe."
So I used to run a website called theatheistspot.com, which was Reddit for atheist news, which is not a, you know, Reddit is that. It's fine, you don't need it. But I went to like, there's like conventions. We went to atheist conventions. So I did that, and 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. So it's 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 I worked with a friend on this other project called Tutorials, which was so ahead of its time. The idea was tutorials, tutorials for you by you.
Nice.
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 it was all these
That's like TikTok, right?
It's like TikTok. It was before Wikipedia, I think.
I know. Yeah.
Yeah. It's like YouTube. It's like
That's like what I watch TikTok for, is like watching people make
Yeah. And parenting advice and
Things to be afraid of.
Yeah. And dance videos. Yeah. So it was
That's what your thing was, or that's what TikTok is?
That's what TikTok is, right? Yeah. So, yeah, I was really proud of that.
Yeah. Yeah.
It sounds like it was ahead of its time. Localmind was ahead of its time.
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.
I still need it.
Like, you need it once in a while. So just to briefly explain what that is, it was an app that sat on top of Foursquare and Gowalla when that was very cool and allowed you to ask questions of people checked in anywhere in the world. So if you're like, is there a long line at The Mill, which is near here? Should I go? Is there a long line? What's like the special?
You just use that basically the
Yeah, we use the Google, does it like, is it busy? Yeah. Like, you know, all these other ways that you could solve this problem. It was very cool. It was amazing. Nobody needs it really.
If there's still things you want to ask
You need it like once in a while. You like once a quarter and it's holy, that's so good.
But you know, you can't make a business out of that, so
I'm glad that we exited.
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Okay. So, you were mentioning the Atheist Spot with a bunch of religious dating sites. Yeah.
Reminded me that you were my first online date ever on a
Snatched.
platform called HowAboutWe, and I remember that, I mean, you had had other dates.
Where's this going?
Anyway? No, but I remember you were like, had, see, I think you had a thing for designers.
Yeah.
And I wonder if you regret that preference, like designer, artist, sort of like
No, not at all.
stereotype. No. Like I'm not like, like you're pretty neat.
Yeah. Yeah. It's true. You're kind of chaotic. Yeah. Which is... We could talk about your process, but it's like it's a messy process. It's true. You know, we have a good yin-yang.
Yeah. Yeah. I'm just
Yeah. You're unstressed, unbothered. I'm bothered.
Yeah. I'm just things everywhere.
Yeah. We got cleaners. They help things out.
Yeah. It's true. You know.
Oh, yeah. Privilege.
It's worth it.
Okay. So, you're okay with designers still? Good. And then
As a wife.
Yeah. Right. Right. Highly recommend. Okay. Yeah.
Great. So, yeah, I was going to ask like, do you have any tips for, because it's like, you know, there's something you said recently which is like, you don't have any coworkers. I was like, I'm your coworker. We work at home.
But yeah. Do you ever feel like lonely? Not, because you were always really social. And then this goes into, too, like even before you were niche famous or whatever we want to call it. Sorry. People are always coming up to you on the street, like, you know, from Airbnb, from Airbnb, because you're organizing things and
Do you feel like you miss office culture?
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'm just doing my own thing and I don't need people around. But I've kind of started to feel that a little bit of just like, huh, there's no one. Like I just sit at home all day and just like
Our dog likes to be right next to you.
Yeah. Yeah. He's sweet.
Yeah. So I do feel like I do miss it now. It's not like a huge problem, but it's just like, you know, it'd be cool to just jam with someone on stuff, and I have a team and I have you and Twitter.
Well, you like to go to coffee shops.
I like to go to... Yeah.
What do you get?
But it's like bowling alone kind of. I don't know. It's like, is that a good metaphor? Like
And you put your headphones on. Yeah. And you're focused. It's like
Yeah. So it would 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. It's like a new thing I've realized that I miss is being around other people, like working on the same thing.
Yeah. So speaking of other people like 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.
Absolutely.
So people who do know you come up to you and you're like waiting to know if they just listen to your podcast or if you
Like, I know, if I know that, like
Yeah.
Yeah. This is a big problem for me. It's like another brain disorder, 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?
Yeah. Sometimes I feel like The Devil Wears Prada assistant where I'm like, "That's Emily. You worked with her at Airbnb," or that's
You don't do that. You need to do that.
I do it sometimes.
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, sorry. I'm really bad at it. And yeah, it's gotten worse because now I know more people through the podcast and newsletter and like
Right. And you just know a lot of people.
Yeah. It's like faces.
You're very kind with people.
I try. I try.
Try.
Okay. So, going back to the like 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.
Okay. So, on the business side, 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. I stopped doing this because there's too many now. At the 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 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 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's like such a nightmare because we're just like waking up to, like every night it was like hard to sleep, and I have this engineer, Estee, who's so incredible, and he like didn't sleep for a week, stopping, filling all these holes, because there's a 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 the student network. They just, holy, you get a year free of Cursor and Lovable and Replit and Bolt and v0. So it was very stressful.
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, yeah, it was
Complicated.
Complicated.
Normally, I feel like I would tell the story, but
You weren't awake.
But this is also like a When Harry Met Sally, but it's like how the pregnant person almost died, you know. But okay, but it's from your perspective, because I didn't get to experience it.
Right.
So,
Yeah. So what happened is we had to, you had to do a C-section. They gave you an... 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, the partner, in. And so I was waiting in the hall, waiting for them to do the anesthetic,
Your scrubs.
They gave me a whole bunny suit. Yeah. Super sterile. Just standing there 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 5, 10 minutes in, I just hear beep, and the doctor runs out, scrubs her hands, runs back in, and then all the two other people run from another room down the hall into the room. They're like, uh-oh. And
You were scared. You were
I was scared.
I was very scared because I had no idea what was going on. That didn't sound good.
Nobody told you anything.
Nobody was telling me anything. 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.
Yeah. And you were supposed to be in there after like a minute.
Yeah. It's going to be quick. Yeah. Yeah. I was supposed to be like, "Come on in. We're going to do this," you know, and like you're awake during it, you know, in real life. So, I just remember pacing down the hall, using, coming back to the lessons I've learned, just like, it's gonna be okay. It's going to 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 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, and they had to intubate you and do an emergency intubation and get the baby out, and then it took like an hour for you to come back. They were going to put you in ICU to help you come back. So that was very scary, cuz you weren't there. I didn't know what's going on.
And you got to hold the baby for like an hour.
Yeah.
Without... So that's why he's like a, he's like only papa. He's another person that prefers you.
Who's the other person?
Our dog.
You know, cuz you're now for now. Cuz you're, you know, you're a sweet, sweet guy. But yeah, it's...
Yeah, that was really scary.
Stressful. Thought it was going to be okay.
Yeah, that was the thing that helped. But it was very scary cuz it's just like life could be completely different now. Like something like, you know, you could have like the guy, the anesthesiologist, said it was a one in 50,000 chance and it's like the worst scenario that is very rare and very dangerous. And so it was extremely scary, and luckily he did a great job and everyone's like, he killed it. He knew exactly what to do. He handled it really well. Yeah.
Yeah.
Yeah. And I don't have any memory. You remember this?
It numbed my
just came back.
Numbed my lungs and I was like, I can't breathe. And then I numbed my spinal brain stem and then I passed out.
How about that?
How about that? I didn't had to get to have any
Yeah. How does it... Looking back? Are you... Are you
We don't have to talk about it.
Okay.
Looking... No. Yeah. It's, that's what you said, but it's interesting to not have an experience around it. And the experience was like, the live experience is more.
Yeah. It's probably the scariest moment of my life.
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, like months later I read it. I actually had someone else read it who was in the field and she's like... it was your cousin Lois, and she like moved her thick glasses, like, wow.
Yeah, she was like a nurse back then. Yeah.
Anyway, stressful moment. Yeah, so you used your tools.
Yeah, I used my tools. Otherwise, you know, that's a good point, cuz it could have been like spiral, like, oh my god.
And we had a doula, but she had left.
The doula was going to be there, but for Cesarean she's like, I can't be here.
Yeah.
Okay. Okay, I want to ask you a question, but unless you have something we want to follow up,
okay, so you come up with these incredible charts. They're just like, you know, 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 cuz you just, it pops out of nowhere and then there's a little bit of iteration and 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? Feel like coffee is a big part of it.
Coffee is like, it's like not too much. There's one I have that it's like, I mean, it has to be the perfect amount of coffee. So I actually usually get a single shot.
Do you know about the Ballmer Peak, by the way? Quick tangent.
Okay.
Okay. So there's a concept called the Ballmer Peak.
Yeah.
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 so the Ballmer Peak.
I have one like that about coffee, but it's not. It's made out of a little coffee straw and it's like
we're going to show this on YouTube if you're watching this so you can see the chart. 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, I mean, coffee is a drug, right? So if I have too much, it is like a drug and I feel like a genius and I'm having all these ideas, but then I think it's too like... I don't know if this was a real image, but there was an image of spider webs and it's like, this is a spiderweb that ingested some this, I don't
LSD and stuff.
Oh yeah. And this is a spider that had coffee. And it's like instead of a regular web, it's like a web that goes like this. Like it's just erratic and tangential. And I have some really good seeds of ideas in those moments. Then I have to go scream into a pillow or something.
Well, is that when you have too much coffee, or
when I have too much coffee? But if there's a point like right before that.
So single shot latte.
Single shot is what I get. Single shot latte, at least an hour. Sometimes it's good to have somewhere I have to be, a time limit, and then I'm kind of like, I feel like a machine, and it's like trying really hard to get somewhere. And then the other thing is just, a lot of it is writing something down as I'm out in the world, like writing, and then 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, you know, fractals and visualization and patterns, and so I sort of think that way, like mathematically kind of, and yeah, so it helps me to visualize an idea in the simplest way possible.
Let me just say this is very cool that we're doing this. This is really fun.
So sweet.
Oh
yeah, this is really nice. Yeah, this is our Odessa moment.
Yeah,
you were born in Odessa, too.
No, no, but one of my questions was like, I don't know. This would be like if I were in the audience, it would be more like a comment on
versus a question.
Yeah, we're pretending to be a question. Yeah, our families are both from countries, like mine from Venezuela, yours from Ukraine, where people are always like, oh, does that... like we didn't just arrive
right
from Venezuela or Ukraine, so it's not
the same.
Yeah.
So, we have to almost make them feel okay, like it's okay. I mean, so my family still lives in Venezuela, but
Okay. So, I asked you a question. Okay. Oh,
that's back to you.
Okay, great.
Yeah. Well, yeah. No. Okay. Let me reflect back what you said because this is really interesting. So, a single shot, like... So, it's like some kind of neurostimulation. I don't know. Single shot, just enough. I like this deadline piece. That was really interesting.
It's like not too much time, not like 30 minutes. Although that can be why I'm late often, is I'm like, I've almost got it. I just, you know, I'm a time optimist, as you know, that I'm like, I think I have it. But a good time is like two hours, I have to be somewhere in two hours.
Interesting. Okay. So those are two elements, and then was there another for optimal creativity?
Oh, a good night of sleep. Yeah.
Yeah.
The bad night of sleep plus too much caffeine, then you don't have any, you know, you have no ideas. You just have the frantic piece of the caffeine, the mental energy.
Anything else? This is really interesting. I think just the idea of what creates creativity.
Just like experiences, experiences and thinking, and almost like thinking too much about them.
Thinking, I like that. Maybe overthinking.
Yeah. Right. Yeah.
Back to you, Michelle Rial.
Oh, back to me, to you. Yeah. Okay. So, we did the thunder round. We did the worst things to hear. Okay. And the best sounds, which, your son's... yeah, laugh.
Yeah.
Yeah.
Agreed. Do you... Okay, we probably know your favorite product management books. Do you have a favorite children's book, other than mine
to read, to read to, and also in April?
And also maybe you could do more than one because, you know, they like, maybe there's one when you was a baby
like I feel like a chart is
and you never take my ideas because I feel like you don't want to
I don't want to
you want it to be your ideas.
Yeah.
But I feel like there's books you love that are children's books, and books your kid loves.
Yeah.
Right. And it's like, I hate reading this one, but he loves it, so we're going to do it.
Yeah.
So, it's like he decides what his favorites are. I love Jon Klassen books. They're so beautiful and just sweet. So, those have been read.
Are they sweet?
They're actually not sweet. You're right. There's like death in all of them.
Yeah.
Yeah. They all end in death.
Yeah. Like dude's new thing is like, he ate the bunny.
Is it the bear? The bear book.
Yeah.
Like, he stole my hat. Yeah.
Yeah.
Yeah. Yeah, like we start the book and he's like, he ate the bunny. Where's the bunny? Like, in his belly.
But is... yeah. Is there any overlap? You think there's a favorite that, that one is his favorite, that you now love, that you didn't love initially?
Yeah. Like Dr. Seuss, I think we similarly feel it's way too long as one, cuz it's like 50 pages, 60 pages. Like words to say. It's a lot of words, and there's just all these made-up animals and
and like he's like, what's a Zong?
Yeah.
Like, there, that's a Zong.
Yeah. You're trying to teach them real things in the world and then he's like, what was that tale of a song? Like, what?
Vipper from VIP. Yeah.
No. Yeah.
Yeah. I don't know. I don't like that.
But we like reading them.
We've kind of... Yeah. There's like a rhythm.
Well, anything in Spanish I read to him, obviously. And yeah. I mean, anything you want to say about, like, I don't know. Is there any sort of product... anything you've learned in product management or growth that has translated to parenting?
You know, product management is all about influence, and that's basically parenting.
That's why he likes you better.
Why? Cuz I can influence. But you also have to make him do stuff, you know.
Yeah. Yeah.
They're like, you do have authority, you know? All the responsibility without the authority, but you do have authority. So it's easy. They have the, they feel like all the
authority. It's true. Just like, nope, here's, you sit there.
Yeah. I feel like I see your product management in that, like, I should be the one making him a chart, but you make him the, like, if bedtime gets too long, you're like, here's how bedtime's going to go. We're going to read you three books. You get a star. And then also I'm answering for you. Sorry. Go on.
Other things where I'm kind of like, yeah, it just happens the way it's happened, and 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." And it's going to work. Sometimes it works, sometimes it doesn't.
Right. Yeah. I'm not an intuition guy. I'm just like, "What if the smartest people figured out about this?" This isn't the first time somebody has tried to shorten bedtime,
right? Shorten bedtime, sleep through the night,
right?
Yeah.
Yeah. There's like smart people that have tried this stuff before.
Yeah. And can tell me what they've done.
Small eye roll. 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 as your wife of however many years, like 10, I still don't think I know what product management is. Can you tell me in five words?
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 order is how you think about product management. Like, you know, the order you put them in. And what else? I'll just say some stuff because it's really interesting. Coordination.
I think that's five.
Organizing, planning.
Okay. Outcomes.
I have just tuned out.
There's so many, like, shut up. So boring. And I'm just like, what should I have said? That's what I'm going to think about now. But yeah, it's a crazy weird job. All these different things. Yeah. Now I'm just sniped. I want to keep thinking.
Yeah. I keep
I'll give you my definition of product management.
Yeah. You can't say mini CEO.
No, no mini CEO. That's not cool. Although I actually do think a PM is a mini CEO. I think people keep saying you're not, but I think you are.
Yeah. You can't say, like, not a project manager.
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.
Yeah.
You're like, this is why I never know what it is. It's so boring. What are you even talking about?
Cool.
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. You know, their job is to think, what would the CEO do on this specific product or feature? Because the CEO's job is make this business 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.
Do you feel like you're doing that as the... I guess you are
I'm everything, you know, in my current world, right?
You're editor-in-chief too.
Editor-in-chief. Yeah.
Yeah.
Yeah. But I have a copy editor. I have an editor. So, I've helped.
Oh, right. Yeah.
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.
That's like,
whoa, look at this. We're the same. Introducing
the key is just communicating something simply.
Wow.
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 did you decide to do a children's book? I wanted to do a children's book based on the first adult book because I thought that charts are, they're like a ton of early learning concepts put together. So if you look at children's books, you know, 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. So 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 the series that I'm
It's coming out next year.
Yeah. But yeah, I finished it, but you know, it still takes about a year to come out after that. But yeah, it was this... I wanted to work on it in the 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... it was more like a cadence. I had just this, you know, in my head, and yeah, I just tried it and it came really quickly, the first draft. And yeah, I always wanted to make one because as a little girl, my dad, he was a geophysicist, he wanted me to be strong at math. You know, cuz at the time it was kind of like girls weren't encouraged necessarily to be good at math, so from just a young age he was always showing me. I did the same with our son too, always showing him patterns and turns, and like, oh, if you flip it, it's like that. And it's just really fun for me. And 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. 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, and now it feels more natural. And so I had 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 child.
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 because you had a children's book like you 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.
Yeah. And then also like another thing I thought about was just reading so many children's books. People always say if you want to write, read, and yeah we read a lot, we read still a lot of books and it just got me in that zone too.
Yeah. It just makes me think about something I think has been key to my newsletter success is it is based on like real life doing the thing. Like 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 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. 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 communicating it simply.
Simply and just like refining. I don't even get into just all the work that goes into refining.
And then yeah, you always talk about like... Yeah. Another thing I do is like I often make, it's stressful because I make things and I'm not sure if they're good enough yet and I put them to the side and then I come back 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 going to 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." So that's cool to like have something sitting like with maybe with your podcast and
Yeah. Well, let me ask you this and I'll answer for myself. How many iterations do you do on a chart on average? Like how many times do you like edit it and refine it?
It depends. Yeah.
Yeah. What's like the median?
At least five.
Okay. Like for me I think it's like 60.
I was going to say 100.
Okay. That's probably the real answer.
I can't even physically do that. It's like I need... Yeah.
Yeah. It's just like
Well, what do you mean by
So, like when I write a newsletter post, I go through it probably, let's say, 50 times making it better. Like 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 a designer help me.
You don't do that with your emails though.
No, I should.
I do do that with my emails, which I shouldn't be doing that. Like I read them over and over.
You do? Okay. I used to. I used to.
But no, I do. Yeah.
Anyway.
Yeah.
Anything else?
Oh, I mean, yeah. Let me... Do you want to plug?
Absolutely. When is it coming out?
April 7th.
April 7th. So, it's like a few weeks, I think, from when this comes out. Assuming this comes out.
Yeah.
We'll see how it turns out.
We're going to check it out.
We'll check it out. If you're seeing this, we checked it out. It was a success.
It was okay.
So Charts for Babies coming out April 7th.
April 7th. April 7th.
All your favorite retailers.
Yep. Local bookstores.
Local bookstores.
Wherever you buy your book.
What's the age range of kids?
It's 2 to four. It's called for babies. I did do a chart recently about like how long is your baby a baby, and yeah, it's like baby is this, infant is like one to two, and then it's like it's your baby infinity. Yeah. So I've noticed like we still call him, not really anymore, like the baby.
Oh, for sure.
Yeah. But he's like almost three and so yeah, it could be like I would say zero to four and yeah, you know what? Should I grab it?
Yeah, let's grab it. Let's just break the frame.
I, people on the recording hit, but the first, like the end paper is what this is called. It shows all the like things you can learn. Sizes, shapes, lines, numbers, directions, feelings, colors, amounts, sharing concepts, relationships, opposites. Anyway, I'm not good at self promotion clearly. So I'll stop it. Yeah, it's a lot of learning.
It's beautiful. It's hilarious. It's clever. It's
Early learning concept,
funny, simply illustrated, rhyming.
We'll link to it.
Yeah.
Congrats on releasing this book. I know it was a lot of work.
Thanks. It was a lot of work. I did have a lot of iterations.
The secret to success.
Yeah.
Iteration. Editing.
Editing. Okay. Spending more time is what your old boss used to say.
Spend more time on it.
Spend more time,
Vlad. Yeah.
Anyway.
Okay. All good. We done. Michelle, thank you so much for being here.
Thank you for having me.
I'll ask you my typical questions that I ask at the end. Where do people find you online? How can listeners be useful to you?
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,
Right?
Yeah. I don't know when this will be out. You can either pre-order it or order it.
Great.
One of the... Yeah.
Parenthesis pre, but order.
Yeah. Yeah. Michelle, thanks for being here.
And I hope you like it and thank you. Thanks for having me.
My pleasure.
I know you have a high bar.
Absolutely. You hit it.
Okay, great. And yeah, I hope you were okay with the interview.
A+. It's going to do numbers. All right, let's get out of here. Okay, bye everyone.
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