Lenny Rachitsky Answers Questions From His Wife: How a Newsletter Nobody Planned Became a Business

Lenny explains that when he left Airbnb after seven years he had four plans: start a company again, become a startup's first PM, join a big company as a PM, or advise companies. None of them involved writing. He was prototyping startup ideas and writing on the side, and Michelle remembers urging him to focus on what he was good at because she saw no money in writing on the internet.

He names several moments that pulled him along. His first widely read post, on what he learned at Airbnb, was featured by Medium and shared around the company. A friend who is now a VC pointed out that he enjoyed it and people valued it, a rare overlap, and suggested he double down.

Nine months into a weekly Substack newsletter, Lenny realised that he could probably do it for nine more, a thought he links to the Lindy effect. At the same time his Airbnb stock looked less reliable, so he added a paywall to see whether he could earn money. It worked, and within about a month he was making meaningful dollars.

Asked whether he still likes the work, Lenny says he cannot imagine anything more fulfilling or interesting. His job is to write about interesting things, share other people's insights and interview people, and it is his own business. He mentions an essay arguing that you should not become a professional artist, because once you have to do it, it changes it.

The downside, he says, is the treadmill of publishing a post and a podcast episode every week. His image is of the Indiana Jones boulder chasing him: as soon as one post goes out, the next week's work begins. Some weeks he loves it, others he would rather skip, but he says this consistency is the price of being able to do it at all.

He admits he does not know where this goes in the long run, since he may not be able to keep up the pace at 60 or 70. Michelle jokes that, by the Lindy effect, the newsletter that started in 2019 has about seven more years in it, and Lenny says that is something he can do.

Lenny thinks he is more stressed than he looks, citing occasional headaches, but probably less stressed than the average person. He credits about 70% to genetics, with the rest coming from learning to adjust the way he thinks and not take things too seriously. Michelle notes that this is a running disagreement between them, with Lenny insisting that things will be fine.

He says one of the moments that gave him the confidence to write came on a bachelor-party trip to Joshua Tree, where he sat on a rock for about three hours under the influence of a psychedelic. The phrase "I have wisdom to share" kept repeating in his mind, and it left him feeling there might be something inside him worth sharing. He had also done a ten-day silent meditation before writing his post.

Another formative influence was an online University of Pennsylvania course on the psychology of happiness. Its main lesson was that everyone has a baseline level of happiness, that good and bad events pull you away from it only temporarily, and that the thing to work on is raising the baseline, partly through optimism. Exercise, as he remembers it, does not make you happier but lifts you out of the negative.

Lenny asks Michelle why her charts go so viral, noting that they are often shared without credit or put on mugs and pillows by others. She says it matters less to her now, and that she has stopped looking. She knows a chart is working when it still makes her laugh or tear up after she has let it sit, though she admits she is often wrong, and one viral image was just a casual photo of a page from her book.

She believes people like things that are simple, quick and easy to digest, show them something they have not thought of, and make them feel something. Lenny says his approach to newsletter posts is similar: he decides internally that something is good rather than waiting for approval. He adds that Michelle's charts can be too clever, with too many layers, and that he sometimes plays editor.

Her ideas come from living and noticing, and she has been most prolific when meditating, because it teaches you to observe your own thinking. Focusing too much on work means she stops living and stops having ideas. Lenny compares this with a writer who says yes to every invitation to collect experiences, and notes that her first children's book began as observations of new parenthood in the back of a notebook.

Asked what in his earlier life hinted at the newsletter, Lenny says nothing did. He had never written online, saw himself as an introvert who liked staying behind the scenes, and says that the newsletter beginning during Covid helped because he could type from home without telling anyone in person.

Michelle prompts him to recall past side projects. In college he ran atheistpot.com, a Reddit-like site for atheist news, whose AdWords ads were mostly religious dating sites. He also worked on Tutorials, a site where people contributed how-tos, which he says was ahead of its time and not unlike TikTok.

His startup, Local Mine, was an app on top of Foursquare and Gowalla that let people ask questions of those checked in somewhere, such as whether a venue had a long line. It was sold to Airbnb, which is how he got there. He says it was an amazing idea that nobody needed often enough to make a business.

Michelle asks whether Lenny misses office culture. For years he said no, but he now admits that he does miss having someone beside him working on the same thing. He has a team, Michelle and Twitter, and likes to work from coffee shops, but it is not the same as jamming with a colleague.

Even so, he is trying hard never to have full-time employees and to keep things simple. His concern is that you can build a complicated business, or create a job you hate, by following opportunities that merely feel big or that other people want from you, so he is careful about what he commits to.

He also describes how hard recognition has become because of what he calls face blindness: he is bad with names and often cannot place people who greet him, and it has worsened as he has met more people through the show. Walking around the Bay Area, people often recognise him, which he says started with the podcast and which he enjoys.

On the business side, Lenny describes the launch of an offer in which subscribers received a free year of Cursor, Lovable, Bolt, Replit and v0. In his words it was too good, and fraud rings, many apparently in China, set up attacks to steal the free products. He worked with Stripe and Substack, and an engineer on the team barely slept for a week patching holes in their API.

He says the risk was that trust in him would collapse, and the offer even went viral through student networks in China. For about a week it was hard for him to sleep because new rings kept appearing.

The personal story is about the birth of their son. After a C-section was needed, Lenny waited in the hall in a sterile suit when he heard a beep and saw staff rush in. He was told nothing for around ten minutes. He later learned that the epidural had travelled upward, affecting Michelle's heart and lungs, and she had to be intubated while the baby was delivered. The anesthesiologist described it as a one-in-50,000 event, and Lenny calls it the scariest moment of his life. He says he paced the hall telling himself it would be okay.

Lenny asks Michelle how she creates a chart, and she explains that coffee matters, but only a little: a single-shot latte, because too much leaves her with erratic, tangential ideas. They refer to a comic about a "Ballmer peak" for alcohol and a coffee version of the same idea.

She also likes a time limit, with a commitment about two hours away, since it makes her feel like a machine trying to reach a result, though she admits that she is a time optimist and often runs late. A good night's sleep helps, and she says the raw material is experiences and thinking about them, maybe overthinking.

She says she often jots things down in the world and then puts them on paper in a way that visualises them, because she is not strong at drawing. Her father, a geophysicist, did a lot of math with her as a child, including fractals and patterns, and she thinks in a similar mathematical way.

Michelle asks if product management has helped Lenny at home. He says that PM is about influence, which is much like parenting, though a parent also has authority. Michelle says she sees his PM style in bedtime routines, where he sets out a plan and a reward, and she observes that he reads books about every parenting problem. Lenny says he is not an intuition guy and prefers to ask what the smartest people have learned.

Asked to describe product management in five words, he offers impact, collaboration, judgment and alignment, then adds coordination, organizing, planning and outcomes. His fuller definition is to deliver business impact by prioritizing and solving the most impactful business problems, and he insists a PM should think the way the CEO would.

What carried over from PM into his current work, he says, is being very organized, keeping a high bar for quality and communicating points simply.

Lenny asks why Michelle moved to children's books. She says charts are full of early-learning concepts such as opposites, colours, shapes and feelings, and she had a rhythm of children's rhymes in her head from reading so many books with their son. The book Charts for Babies is aimed at ages 2 to 4 and came quickly in a first draft. A children's book she tried before having kids was not as good, because she had not yet learned how to speak to children.

Lenny ties this to something he sees in his newsletter: the best material comes from experience. Most posts are now guest posts by people sharing the best thing they learned on the job, and he says practitioners doing the work, not those pontificating, are the best source of advice. Michelle adds that, as people say, if you want to write you should read.

On iteration, Michelle says she often sets a piece aside and returns to it with new ideas, though she finds that stressful. Lenny says a post goes through about 50 drafts of improvements before his editor, copy editor and designer step in, and that Michelle probably does about 100 on a chart. Charts for Babies is due on April 7, and they close by joking that the secret to success is iteration and spending more time on it.