Fireside Chat with fmr Airbnb Product Lead, Lenny Rachitsky

Hey, everyone, my name is Carlos and I'm the founder and CEO of Product School, and I'm here with Lenny Raczicki, who is a former product lead at Airbnb and also product celebrity. He's going to tell us all about it. Hey, Lenny.

Hi, Carlos. That video just makes me want to go build shit right now. Energy.

Yeah, when product management became cool not.

So long ago, really, that music. Oh, my God.

So, Lenny, thank you for being in the show with us. I want to take this opportunity to learn a bit more about your journey as a product person. But also, I think you have a very interesting approach to it and now the stuff that you are doing currently. So why don't we start from the beginning and tell us a little bit more about how you got started.

Yeah. I was born in Ukraine. My family moved to la, grew up in la, went to school in San Diego, UC San Diego, Computer science. I kind of always wanted to be a software engineer in my mind. So graduated there, joined a startup in San Diego as their first engineer. Ended up leading the engineering team over the years and stayed there for a while. And while I was there, I kind of realized, hey, I want to start a company someday. And so I kind of set this goal of, okay, in two years, I'm going to start a company. And as it turned out two years later, I met some friends in Montreal who were starting an accelerator program to help startups. And so I just decided I'm going to quit my job, move to Montreal, start this company and see what happens. And so I moved to Montreal, like in the beginning of winter in December. And I've never been in a winter like that before as a. As an adult. And so it was a whole adventure. So, yeah, started the company there, raised money, moved to San Francisco about eight months later and ended up selling the company to Airbnb. At Airbnb, I moved into product from engineering CEO to pm. And so that was kind of the first taste I had of product other than running the company, and stayed there for seven years. Led the supply growth team for a couple years, led the conversion team for a couple years, launched the superhost program, revamped the review system, worked on a community platform for a few years, and left that about a year and a half ago and was going to start a company. Decided not to. And now I spend my time writing a newsletter mostly.

Well, I want to double click on a few things that you mentioned, because that's really interesting. So you mentioned that you moved from Ukraine to California and then from California to Montreal to start your own startup. Why did you decide to do that? Especially in the winter?

I just thought it was going to be too easy otherwise. I need to add winter and French speaking and international travel to make it a little more interesting. Just kidding. I had some friends that were starting, basically they were starting this accelerator and they're just, they're just like, hey, move to Montreal. We'll fund you. We're going to help you with this company. It's a good excuse to just leave the job you're at and do something different. So it's kind of an opportunistic thing. And I met them while I was at a conference in Montreal and the kind of, the conversation started while I was there. So it was kind of just the serendipitous thing where I. Where I just took advantage of this cool opportunity.

And I'm glad you did that because in a way, I've met a lot of product leaders and founders that really have that mindset of saying yes by default, taking a risk, and you never know, right? So maybe without taking that risk, you wouldn't be doing the same stuff that you are doing today. So I uploaded. And then again, you took another risk. You said that you were working as a purchasing engineer, but then you started your own startup and that got acquired by Airbnb. So guide me through that process. How did Airbnb know about you? And then why did they give you a product management job if you didn't have official product management experience?

So the way we got in touch with Airbnb, and I will say I never in my mind, in my, I don't know, thinking, ever thought that we'd end up at Airbnb. Because the company we started was a location based mobile app that helped you figure out where to go and, and find out what's going on around the world. And so Airbnb was never like, here's a company, we'll sell to you someday. It was just completely unexpected. And the way that happened is we launched at south by in 2012, 2011, we launched at south by Southwest in Austin. And turns out I met the head of product at Airbnb at a party that I don't remember because I think I was very drunk, but he remembered me. And so a year later he came back and just was. He like pinged me and was wondering what we're up to. And it turned out they were trying to solve a problem at Airbnb around helping travelers find things to do and places to go. And they just didn't have the people to build it at that time. So they were looking for companies to acquire. And so we started the conversation initially as a partnership and then quickly turned into, hey, do you want to just join us and sell your company to us? So yeah, another one of those serendipitous moments where you just go do stuff. The way I think about this stuff is you kind of want to plant seeds as many, as many places as you can and kind of hope that flowers bloom eventually. So, for example, going to south by or going to this conference in Montreal where I met this, this friend again, just leads to really interesting, interesting things happening. And then the second question of how I got into pm. Simple answer is I was the CEO of our company and we joined as a team. And so I continue to lead the team as a kind of the head of the team. Which translates to you're in all the PM meetings and you're doing all the PM stuff. And even though there was no real PM team at that point, the head of product was just like, yeah, you're doing a great job at this or good enough job and you're in the meetings already. So what if you just move from engineering to product? And I did it and I'm very happy I did.

That's amazing. And it's actually one of the most common paths that we've seen. A lot of founders become product managers and also I've seen a lot of product managers at some point decide to start their own companies. And the mindset is fairly similar. So it's good to know a real example here. But also, did you know what product management was at that time?

That's a good question. It's hard to even remember, but I definitely didn't know what I was doing. I knew the term product manager and I had to figure it all out. And fun story, they were called producers at Airbnb early on. They weren't called product managers because the founders wanted PMs to be more like a producer of movie where you create the most amazing experience for your audience. And so for like a couple years they were called producers. And a lot of applicants were very confused when we put job postings out. They thought we were looking for like Emmy Award winning Hollywood producers when we were not. And so yeah, I had to figure it all out and I was not doing a good job for a long time. Looking back, I think I was a terrible PM early on. And the biggest ramp up for me career wise was I had this one manager early on that like maybe a couple Years in that taught me a lot about the job and that's when I actually figured out how to do it well. So that's something I've learned is find a good manager.

Yeah. And also what are some of the. Cause I guess the skills that brought you to Airbnb serve you well, like being curious, being crappy, like knowing some of the technical things. But at some point, especially in a hyper growth company like Airbnb, as you start rising through the ranks, how do you really what are some of the skills that you had to acquire?

1 is just being adaptable. I took a personality test once and like a strengths finder test and my biggest strength that turned out was adaptability. And I find that that is super important both as a PM and as a founder because you don't really know what's coming. You don't have a lot of control over where things are going to go. And especially as a PM where you're kind of like working on copy tweaks in the morning and then thinking about five year strategy in the evening. You have to be good at bouncing between all those things and then just, I don't know, reorgs and resources being pulled and products not working out. So being adaptable I find is really important for both those functions. Another I found is anticipate being able to anticipate what's coming around the corner. Because as a pm, a lot of your job is unblocking your team and I find a lot of the work to unblock is to think ahead of what is going to come at you. Like is your manager going to ask you for a roadmap for the next quarter or is a reorg about to happen or is this product about to fail? And so I find thinking ahead and looking around corners super valuable and important. So I built that over time.

How big was Airbnb when, when you joined and when you left?

There is a couple unofficial product managers when I joined and so I was maybe like the third or fourth PM and now there's I don't know, maybe 200 and I think it's about a 5,000 person org.

That's a big deal, Lenny. And you quite casually mentioned that you launched a superhost feature which is still there and it's really powerful.

Yeah, that was an interesting experience. We can talk about. To me, one of the biggest learnings from that project actually is when we looked at it after the fact, it didn't really move any metric initially. Our hope was this is going to help host improve or it's going to increase retention of hosts or something like that. But it turned out nothing changed because we launched it as an experiment. But in spite of that, if you look back, it's clear it was a really important thing to add to Airbnb because the hosts that are good, really, really care about it and really are proud of being super hosts, and it becomes a part of their identity, and hosts strive to get there. And so it's a good example of a project where, like, you can't really measure the impact, but it just clearly is a good thing for the. For the marketplace and the product.

So then after your experience growing the product team at Pro, at Airbnb, then. Then what's next?

You mean after Airbnb? Yeah. So I was gonna. I had 50 startup ideas I was gonna explore, and I thought I wanted to start a company again or like, join a startup or something like that. But as I left, I. I started thinking, what did I actually learn about my experience at Airbnb? I started, like, writing down these things, and it ended up turning into a medium post, and that ended up turning into a newsletter. And that started going well. And so I basically put the startup stuff on. On pause. And now I spend most of my time on this newsletter, which is essentially an advice column around product and growth and anything that stresses you out at the office. And so my life is that plus angel investing.

I'm going to give you a shout out because I'm very skeptical of a lot of publications and content out there on product management. I always complain because I think it's very hard to validate if this is true or not. But I am an avid reader of your newsletter and I think the content is really good, mostly because it's not just one person's opinion. Like, I think you do a really good job researching and really getting the best minds out there to. To kind of share their experiences. And then you do a good job consolidating and presenting results.

Thank you. I really appreciate that, man. And a lot of that honestly comes from kind of an imposter syndrome of I don't know if I have the answer. And I don't want people to make large decisions on just my perspective on things I don't actually have experience doing. And so that's why I often reach out to other experts or do this like, you know, very in depth research, talking to founders of these really epic companies. Because. Because I don't know. I don't know what the right answer is. And I'd rather crowdsource it to People that know what they're doing as much as I can.

So then you said you started with a medium post, which I think it's great. I actually give this advice to people who are thinking about getting into product and, like, okay, you don't have to ask for permission. You don't even need that job. Like, you can literally set up a medium page or WordPress or whatever it is and just start writing or doing whatever makes you happy. And then how do you go from a post that's getting some traction to then deciding, well, I'm going to try to make a living out of it and use substack, Right?

Yeah, it was so one thing I took away from a friend. His advice was, when you're looking for something new to work on, just kind of follow the things that give you energy, do more of that, and do less of the things that suck up your energy and SAP you have energy. And so as I was working on startup ideas and a little bit of advising and even thinking about getting, like, another PM job, I just found the writing kept pulling me in and giving me energy, and it just felt good. Plus, people seem to value it. So. So essentially, I just kept putting more time into it. And so that first medium post just did really well. That also helped. It was like, I don't know, one of the top 300 most clapped medium posts. So that felt good. And then I just kept writing. And then I also kept tweeting, like, little nuggets from the post. And people seem to value it. One thing I learned, actually, coming out of a company like Airbnb is you don't even realize how much you learned over that time, because TEA is just, like, all obvious or you think everyone knows it or no one cares about it. And so just putting things out helps you realize how much you've learned and how not everybody actually knows all those things. So to your point, there's so much value in just, like, putting stuff out just to see what happens and seeing if it's valuable. And if it is, then just continuing to provide value. And yeah, the medium post, I just, like, tried the substack thing and it kept going. It started going well, and that's it. I just kept continuing it and people kept telling me it was good, so just kept going, that's it. What was the name of what? The substack?

Yeah.

Oh, it's just Lenny'snewsletter.com I had no idea what I was going to do with it, so I just signed up for Substack. I'M like, all right, Lenny's newsletter, I'll go with that for now. And now I'm stuck with it.

So now, Lenny, you are going to need to find another Lenny in order to continue your lesson.

Yeah, that is true, man. I don't know how you stop a paid newsletter. Like, people are paying me for a year ahead. And I don't know if there's an exit strategy eventually other than finding a different Lenny. That's. That is probably the only route.

I like what you said about making people commit and pay upfront because I think it also establishes commitment for you to be able to deliver value. And it also proves that people care about what you have. Right. We always talk about the concept of an MVP and testing, testing, and. Well, I think the best validation is if someone pays for it. Not only says that he's willing to pay, and even they pay upfront, that means that you are onto something.

Yeah. A lot of people ask me how I stay motivated to keep writing, but there's no better motivation than people paying you and expecting a post every week that is amazing. That's worth the money that they're paying. So that's the solution to motivation also.

So obviously you are a product person. So then you start using a platform, you start tweaking it. But like, what is your stack like? Do you see this as relying on one single channel, or do you use or rely on other types of channels or strategies? It's a combination of free versus paid.

In terms of the content.

Yeah.

So I guess in terms of the writing, I use Coda for organizing my content, calendar and collecting ideas and topic ideas. And then. And then just like Google Docs, I keep it really simple. Coda, Google Docs for collaborating on a post. And then just substack for the email itself. I just copy it from coda to substack. And then in terms of where I share stuff, mostly substack, Twitter and LinkedIn. So I kind of just like write a newsletter post, summarize it on Twitter, and then copy and paste that to LinkedIn. And then in terms of the type of things I write, there's kind of three categories, questions that I answer myself, questions where I get a guest post, someone that knows a lot about the topic to answer the question. And I use Google Docs to work with them on that. And then these research posts. Right. Interview a bunch of founders. And so I use Google Docs again for that. Keep it simple.

And that's great. And I think I want to emphasize this point because sometimes you don't need to over engineer the process. Right. Like you can rely on what's out there and focus on what you are best at. In this case, adding good content to your audience.

So, and actually to that, to that point, there's something I always think about is there's so many things that I could also be doing, like a podcast and a book and a course and all these things. And I'm just trying very hard to stay close to just like doing one thing really well and not falling for all these other gravitational pulls of things I could be doing and maybe should be doing. Because it's easy just to add more work to your life and it's easy to just do all the things people think you should be doing. But I'm actively trying to just stay very focused on what do I actually enjoy and how do I just make one thing really good.

I completely agree. And I think a trend that is supporting that is that now technology is easier to adopt in many ways. We see a lot of no code, low code tools that allow anyone to literally sign up and start just tweaking something, right. Like you can use webflow or substack. I think it's perfect. You don't need to even set up an account, an email provider. You just go and I don't know, do you think this could be a trend for other people? How is this going to affect the role of a product manager who, you know, in the past the mindset was like, well, you need to be an engineer, right?

Yeah. So yeah, like what are product managers going to do when it's all low code, no code tools other than work on those tools? I think, I don't know. I think we're screwed. It's time to shut it down. Time to help become engineers. Just kidding. I think, I think there's always going to be enough new products being built by teams that I'm not worried about that, but it probably even accelerate the profession because I think people now will be able to build the skills to be a product manager using some of those tools without even having an engineer or designer involved. So that's kind of interesting. I haven't thought about that much, but it'll give you just more opportunities to build the skills.

And some of the tools that you mentioned, like Medium, for example, they try to keep your audience within Medium, which it can be risky, right, for a content creator to then potentially migrate that audience to a different platform. So guide me through the process. Why did you decide to use Substack and in case you decide to Tap into a different channel. How do you think about really moving your community from one tool to another if you don't own the tool?

Yeah, this is a really deep and interesting topic. So Medium, their whole pitch is we're going to make it really easy to write a blog post and then we're going to send you readers, but you don't actually own any of the people reading. You have no way to reach out to them or contact them or, or move them anywhere else. You have like followers on Medium which are not worth anything really. And in my experience, you don't really get much traffic from Medium. It's almost all your own traffic, unless you get lucky and they pick you to be in some collection and then you get a lot of traffic. So the issue is you're writing all this content that's basically driving growth for Medium with a little bit of brand building for yourself and maybe some call to actions that you're sending people to go do. But it's really not where you build something long lasting that you can own. And that's basically the pitch of Substack and some of these other platforms is you're collecting email addresses that you can use and you can own long term and build this direct relationship with your audience. You can charge eventually if you want. Like, I never planned to charge for my newsletter. It was not even. I just wanted to use Substack because it was free and easy and had a blog and a newsletter combined and it was very easy. And so but yeah, the pitch with Substack is you can export these email addresses and go anywhere else anytime you want. You can export the content and go anywhere you want. They make it really easy to pay to charge people if you ever want to charge them, which is just like a nice thing to have in the future if you ever consider it. And, and it's basically, it doesn't look as beautiful as Medium, but it's essentially the same product as Medium, so. So I'm happy there.

Yeah. And I've seen two trends there. One is a lot of these products that you mentioned offer a free plan. So you can just go. You don't even need to think about if you eventually want to monetize or anything, or if you even have to pay for anything. You just focus on doing something and then see if it sticks, which I think it helps. And then another trend that I've noticed is the integration. Back in the day, I think there was too much focus on building a platform that can meet every single use case. And now we are Seeing how all of these tools integrate with each other. So you can really have a tool that is great at newsletters, which is different from, say, Slack, that is great at building community, which is different from Twitter. And then you can kind of decide your own ecosystem without any real technical expertise.

Yeah, I think of Patreon in that kind of topic. Like, what is the right wedge into taking kind of owning the creator market and marketplace and platform. Like, Patreon went at it with, we're going to let you do anything and charge anything you want, like, for everybody, every type of creator. Substack is like, okay, we're going to be very focused on writers and you can charge for your writing and that's it. And then there's like. But then maybe there's like the community direction. Maybe it's like, start with a community and then that builds into a creator platform in a way to monetize. And I don't know what the right answer is, but. But for me at least Substack just makes sense. And there's other platforms. But yeah, I'd say the. I don't know if we want to keep talking about Substack, but the business model innovation they had that was really clever is they make email free, which no one else does. There's no other place, as far as I know, where you can send tens of thousands of emails for free. So their trick is you start that and build it up for free and then eventually maybe start charging and then they make money.

That's fascinating. I think for us product people, this is a beautiful time because we can literally play around with every single thing. And I think once you have a product mindset, you can look at products in a very different way. As you said, you can understand what's their business model. You can know what are some of the pros and cons in terms of integrations or moving your community around and then you can move fast. And that's some of the things that I always encourage people to acquire, which is, it's not about the title sometimes, it's more about that mindset that is going to help you understand what's going on behind the scenes.

Yeah, that's such a good point. And just like, you could try all these things for free, like Slack is free and which is what I use for my community. And then like, Substack is free and there's no reason not to just try it other than just pride, where if it doesn't go well, people are going to. You think people are going to feel like you're an idiot. But that's not true. Like when I launched the newsletter, I just tweeted, hey, I'm just going to experiment with this thing. I don't know what it's going to be, but let's just see what happens. And no one's going to be like, oh, you idiot, you stopped that newsletter. You don't know what you're doing. But that doesn't happen. No one cares. People aren't even paying attention.

Yeah, that's what now in the enterprise context, sometimes it's called product led growth. Obviously it's different, but the notion of users can adapt a product. They don't need to swipe a credit card, they don't need to ask for permission, they can collaborate with others. And if it sticks, at some point it's going to get to the top and you're going to feel pretty much forced to get a paid version.

Yeah, bottom up growth.

I'm all for it. So Lenian, are you feeling the itch to go back at building a company, building a product as a PM at a larger organization? What's next for you?

This is it, man. I have no future plans beyond this. This newsletter was kind of my, I call it my project, avoid getting a real job. And so far it's working. And so at this point, I'm just going to continue making this newsletter better and more valuable. I'm finding the community that's built around the newsletter is also becoming super valuable. So I'm trying to find ways to bring more value to the paid subscribers. And so I'm just trying to make it better and better. And that's it. Simple.

That's good. I think simple sometimes is best. Right? We kind of get, I call it the feature trap. I see too much focus sometimes on shipping, shipping, shipping, instead of just making what you have better and easier for others.

Yeah, exactly. That's like the point I was making earlier. There's all these gravitational pulls that make you think you want to do all these other things, but it's hard enough to do one thing really well and I don't want to lose sight of that. But maybe I'll do some of those other things later. But for now I'm just kind of like organically watching to see what people are gravitating towards and finding value and trying to just make those better.

Yeah. Well, in the, in the meantime, in addition to reading your newsletter, I think your Twitter is really interesting and I find it for me personally, I have problems paying attention to the same thing. For a Long period of time. So being able to just kind of dissect some of the main highlights and then decide if I want to go deeper or not, it's really useful.

So, yeah, that's. That's what I've learned about Twitter and sharing. Writing that you've done is people think you want to, like, tease something on Twitter and just like, here's a little nugget, go read the full post. But I find no one actually wants to read the whole thing. They just want the kind of the nugget, the golden nuggets from the post. And so what I find is I just share all of that right on Twitter. So here's like the most important and valuable thing from the post right here. And you don't have to go read it if you don't want. And that's what ends up being valuable to people. And then they end up following and reading the post anyway if they think that that tweet is interesting. So that's what I do. I just share, give away all the goods on Twitter as much as possible to make it easy for people to consume.

I do the same stuff at product school. Over 90% of our content is absolutely free. Books, reports, jobsport, the whole thing. And we give it up front. It's not that there is a teaser and then if you want more, come and pay. Obviously, there are super users that really want more, and that's perfectly fine. That's also a way for you to reinvest in growth. But I'm a big believer in building a community first approach.

Yeah, I did the opposite. I did community second, but it's turning into an interesting thing. So I'm curious where it all goes.

So in terms of, I would say, advice to yourself, you were to look back at the days where you were calling in California and then meeting someone in a party, going to Montreal, and the whole thing. For people who are thinking about breaking into product, what do you think would be a good first or second step?

Yeah, it's breaking the product is so hard. And imagine you guys talk about this a lot at product school. It's such a unclear path. Yeah, I think one is just like, find opportunities to build the skills that a PM needs to build and then demonstrate that you've built the skills. Because if you're joining as a new PM, rarely do people want to hire new PMs. They always want someone that's already been a PM. And so the way to avoid that trap is, I don't know, just like build and demonstrate that you have the skills to be a product manager. And then similar to the experience I had at Airbnb, and I guess just, like, look for opportunities to, like, get that first PM gig. And I find the best ways to do that, which are not often accessible, is at a company transitioning into the PM role. I find that's, in my experience, the easiest and safest path. But you just have to kind of get lucky to be at a company that has that. That's big enough, that has a role, and someone's willing to kind of sponsor you there.

But, yeah, not easy, but worth it. That's what I always say at the same time.

Agreed.

From the outside, it looks so cool. And the whole thing, the reality is that it's not always that. That fancy. And from the inside, you know, a lot of people want to get out too.

Yeah. No, the PM job sucks. Like, I don't know, 70% of the time, it's very hard. And there's a lot of shit that you have to deal with. But for the right person and personality, I don't know what better role there is to do. If you're entrepreneurial, if you like to kind of be at the center of things, if you're not actually an amazing engineer, designer, or data scientist or researcher, it's an awesome gig. And there's no other role I would want, maybe, other than a founder at a company, so. Yeah. But it's hard.

Ditto. So it's been great to chat with you. Is there anything else you would like to add?

No, man, that's great. I love what you guys are doing. And go product managers.

Go product managers. Thank you, Danny. Have a good one.