Episode 71: Following What Brings You Joy with Lenny Rachitsky
Today on the Product Thinking Podcast, Melissa Perri is joined by Lenny Rachitsky, author of the popular product advice column Lenny’s Newsletter. Melissa and Lenny dig compare notes on what it’s like to move from working directly in product to creating product content and courses, and Lenny explains how his newsletter was born and its growth trajectory since, what he’s learned about how to create valuable content, what success means to him, and how to keep your energy focused on the things that light you up.
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Here are some of the key points you’ll hear Lenny and Melissa talk about:
How Lenny got into product management originally. He started his career in computer science and initially worked in coding before deciding to try and build his own company, which he did in Montreal, before joining AirBNB where he moved into product management. [02:20]
Melissa talks about how, not that long ago, there wasn’t really a career path for product management and her realization that you can be involved in management without building it yourself. [05:15]
By writing Medium post called What Seven Years at AirBNB Taught me about building that did incredibly well, Lenny realize there was an audience out there hungry for content about product management and development. Eventually, this led to his newsletter, job board, and course. [09:55]
Lenny shares how much of his work is research-based – determining the information he wants to share, and reaching out to the experts who have the best answers, then consolidating them into actionable, valuable materials for people. [14:55]
Where do we get energy from things we do? Not every type of work, or every type of content is a home run for the person creating it. Melissa and Lenny talk about how a Product mindset can be helpful with this. [18:25]
Melissa talks about how even when you’re running your own company, it’s still work, and you can still burn out. There is nothing wrong with building a lifestyle business–not everything has to be a major, venture-funded enterprise. [21:15]
Many people want to start lifestyle-type businesses. Lenny shares his advice for building something that brings you a lot of joy. One of the keys is having people to support you, and building in time for experimentation. [25:20]
Melissa shares her own philosophy on building a business that fits your lifestyle instead of changing your life to fit your business, and how to tell when it’s not working. [29:45]
There are two phases to growth–how it starts and how it grows. Lenny talks about how growth has worked in his ventures. Quality of content is paramount.[34:40]
Lenny talks about what is currently interesting and inspiring to him in Product management. [40:55]
Resources
Lenny on the web | Twitter | LinkedIn
Transcript:
Melissa:
Hello and welcome to the product thinking podcast today. We have a really special episode for you with Lenny Rachitsky. Welcome, Lenny.
Lenny:
Thank you. Thanks Melissa. It's an honor to be here.
Melissa:
Yeah, I'm excited. So, uh, Lenny is the author of Lenny's newsletter, which I'm sure a lot of you product managers are listening to or subscribing to let's say. Um, and he's been a thought leader in product management for quite a while, and we figured that this episode we're gonna dive into, you know, what do you do besides product management? So how did we get out on our own, um, working in content? Uh, we both built courses. Uh, Lenny has a job board. He does angel investing his newsletter, um, and he started a course so and forth. Um, and talk about that with you and how we got there. Um, I'll also say this is the first time I've met Lenny. So I'm really excited to, hear more about your journey and you know, how you got to where you are and we're gonna swap stories. So this will be fun.
Lenny:
I'm excited.
Melissa:
Yeah. So Lenny, how do you get into product management?
Lenny:
So I initially studied computer science in school. That's kinda, I always thought I wanted to be a software engineer when I was growing up. I'd say from middle school, I was always like, I'm gonna be a software engineer. And so got into college, computer science, graduated, got a job in San Diego to startup doing computer science, doing coding. I was actually their first engineer at the startup in San Diego. Ended up staying there for nine years as an engineer and then eventually had a product and then doing some R and D stuff. And then they got acquired. And then I kind of kept doing other things within this larger company. Then I had this kind of realization. Okay. I keep reading about startups. I keep seeing all these awesome companies starting. I'm reading hacker news all day. I should just like start a company. What am I doing at this company for this long?
And, uh, I should stop reading and just do something about this. So I ended up moving to Montreal, starting a company. I had some investor friends that agreed to invest in this idea that, that we actually had together. And my feeling was okay, I'm gonna move to Montreal. It'll be amazing. Worst thing that happens. I live in Montreal for a year. This company fails. That's not so bad. So I moved to Montreal, started this company. We launched, uh, at south by of all places. It actually got a lot of attention and that helped us raise the money, moved to San Francisco a year later, the head of product at Airbnb reached out to me because it turned out. I had met him at south by the year we launched, but I had no memory of that because I think I was at a party and very drunk at south by goes, and he remembered me, which is good.
And we started chatting. They had this idea of maybe we collaborate on a, something together, our, what we were building in Airbnb. And as it goes, that led to an acquisition eventually. And so I moved into product when I got to Airbnb, I was, I joined as an engineer. I always knew I was not an amazing engineer. And then one, I was at Airbnb. I was like, man, everyone here, amazing. I'm not gonna make it as an engineer at this company. And also I was as the CEO of our, of our startup, I was doing the PM-y things at Airbnb even before there was really a PM team. But as they were developing the PM team, they had a product was just like, okay, Lenny, you're, you're a product manager. You should move into product. The you'll do great. And, and I thought about it and decided to do that. And that was one of the better decisions I've made. And so ended up being a PM. Airbnb beast stayed there for about seven years and then left that to kind of do what I do now.
Melissa:
That's great. Uh, did you have to like unlearn anything when you moved from product from software engineering, what was like the biggest hurdle for you there,
Lenny:
From engineering to product? Yeah, it was so it's interesting cuz I was already doing product things when I started this company and built it and ran it. So I, so in that I was, it was more, I didn't have time to actually code. I had to rely on other people on the team to do the building more and more. And it was actually really great. Like I really preferred other people that are better than me to build the thing, uh, versus trying to do it myself. So, so I think, I guess the thing I learned is just find smarter people than you to do the thing that, uh, that you maybe aren't the expert at. And, and so yeah, I got used to that.
Melissa:
Yeah. I, um, I was coding for a little bit before I started in product management and then nobody knew what I did so I was like, oh, I need to go into a different field or something like that. Cuz nobody knew what product management was. There was no job postings for product management, especially in New York where I was. Um, and my roommate in the, at the time when I was coming out of, uh, school had gone to be a software engineer, like straight outta school was making all this money. And I said, well, I could take, I like, I knew how to code. Um, I was not good at it. It was probably my worst class, but I could pass all the interviews and do all that. So I ended up at Barclays as a software engineer, um, after being a product manager at capital IQ because I thought, you know, this is how you make more money or something that people, you know, there was a career path.
I couldn't see a career path for product management. Uh, I learned, I hated it immediately. Like within a month I was like, I hate this viscerally. I did everything I could get out of there. Uh, just started like weasling my way back into product. And my boss was like, you have to be here for seven years before you be a product manager. And I said, no, um, just started like doing what I wanted to do and eventually left, uh, there and went to, uh, open sky, which was a startup. And when I got in there, I felt like the biggest thing I had to unlearn is I kept like specking out these products for them, for engineers to build. But I was like, oh, I can't figure out how to build that myself. So I would really pull back on the design and the scope and the specs. And they had to be like, Melissa, we're much better engineers than you ever were. So like, chill, you know, just tell us what you wanna build and we'll figure out how to build it. And that was like such a profound moment for me where I was like, oh yeah, I don't have to do this myself anymore.
Lenny:
That's interesting cuz usually an engineers kind of know that I want to be told exactly what to build. And it's interesting that you went there cuz maybe cuz you weren't an incredible engineer and it was better to be told, just build this thing.
Melissa:
Exactly. Yeah, I think so. It was just, uh, it was so different too. And I feel like coming into the startup as well, I had learned very waterfall product management. So, uh, that was my first foray into agile and experimentation and using data to drive decisions. So it was a huge learning experience for me, but I always, I always thought that like mental hurdle of getting out of engineer mode was, uh, was tricky. And now I, I feel like I couldn't code for my life. Like you let me try and I wouldn't be able to do it
Lenny:
Same.
Melissa:
So, uh, you decided to leave Airbnb, uh, and go out on your own. What made you wanna start, uh, start your own thing.
Lenny:
So I had a previous startup and I always had this feeling of I'm gonna start a company again, I'm not gonna stay at this company for many years. Maybe I'll leave in like three years and try again. And so I always had that plan, but Airbnb continued to be awesome and I kept learning a lot and uh, had really great managers that were teaching me a lot of things. And so I just kind of stick stuck around for longer than I thought. And then seven years later we have the sabbatical program at Airbnb and I was like, all right, it's time to take a break. It's been a long time. It's uh, hyper growth is, is very draining. And so I decided to take three months off and during the time off I kind of gave myself space to explore, to see if there's something else I wanted to do.
If I wanted to stick around potentially if not, what else I might wanna do. And so, uh, so at the end of three months I kind of realized, okay, I definitely wanna, I definitely want to try something else. And, but I still came back to Airbnb just to make sure that I was ready for something new. So I came back and then it was viscerally clear to me like I'm ready for something new. Uh, I there's this kind of feeling when at Airbnb that there's, you're drinking the Kool-Aid, it's like a very family like air, like Airbnb calls each other air fam. And when I got back, I felt like the Kool-Aid had worn off. I just felt like, okay, I am I'm over this job right now. So my plan was okay, let me take six months off to explore all the things, explore startup ideas, maybe explore joining another company, maybe advising or other things like that.
And so through that, I, uh, I unexpectedly landed on this, on this newsletter path, which I know we'll talk about. But, uh, but yeah, that's, I guess that's the answer to your question is I just like, it was like an emotional visceral feeling of like it's time to do something else. Luckily I had savings and you know, I was really fortunate to have a chance to explore and not have to jump straight into a new job, but that was the sign. It was just like, okay. I was just like, emotionally, it was clear. I try some new,
Melissa:
You started the newsletter. Did you start it at Airbnb? Or was this something like you totally did after you left?
Lenny:
It was very, very unexpected. I'd never really done any writing in my life prior to leaving. I Airbnb the other than, you know, product manager, specs and strategy docs and things like that. And so I left, I Airbnb plan a with start a company. I had a spreadsheet with literally 50 ideas that I've gathered over the years that my wife and I had just like come up with. And so my strategy was, let me just sort these ideas based on a bunch of attributes, things I'm most excited about highest potential unique advantages. I have things like that. And so I started working through those ideas one by one prototyping and testing and doing research in parallel. I kind of started thinking, okay, I'm starting a company. What did I learn from my time at Airbnb? Maybe I should like write this down. So I don't forget and have to relearn all these things.
So I started writing it down that ended up as a, as a, as cliche as it is into a medium post that I called. Uh, what seven years at Airbnb taught me about building a company and shockingly, that posted incredibly well. It like got featured by medium, was on their homepage, got like hundreds of thousands of views. And so it just kind of gave me this feeling like maybe there's something there. And so I kept writing, I wrote a few more things those started to do well. And the whole time I was just like, okay, I gotta stop this writing thing cuz I really wanna start a company. And this is just a distraction. My wife every week was like, why are you you doing writing? This is like, what you want to do? Where's this gonna go? But I kept getting pulled to it and it kept going well, and I had this really important conversation with a friend at one point where I was just like, man, I, and he was a VC and was like, man, I really wanna start a company, but I haven't found anything I'm excited about yet.
But his writing thing keeps going well. So I'm not sure where I should be putting my time. And his advice was okay. You like found a thing that people value that you seem to enjoy. Maybe there's something there, even though writing is not a lucrative direction usually. So just like, see what happens if you do that for a while and put this other stuff on pause. And so that's what I did. And that's when it started to go better and better. And I moved to sub stack started, eventually started charging for it. So it was very like this organic pull where I just kind of kept trying to resist and it kept pulling me in and just kind of followed that path.
Melissa:
So you, um, so you didn't intend to do the newsletter. You kind of fell into that. What was your next step once you realized like, Hey, this is actually a job. Like I could be doing this. What, what did you think about to grow it? And, and what else did you do?
Lenny:
So when I first had the inkling that this might be a thing that lasts, I, I tried to keep doing it for a while to make sure that one, I enjoyed it two that, uh, people continued to value it and then three that I could even keep it up. So initially I just kind of kept doing it. So I did it for nine months every week, a weekly newsletter for free, just to see how far I could take this thing. And if I could keep it up, if there's like enough topics to write about every week for in theory forever. Uh, and so nine months in, uh, also right around the beginning of COVID, when, what in theory was a lot of my net worth tied in Airbnb stock, uh, collapsed. Airbnb felt like they were going outta business. No one's gonna travel for years.
It's all, it's all over. And I hadn't worked for a year and it started to get scary that maybe you should, I, maybe I need to get a job in this newsletters, like maybe move on for something to something new the same time I was like, okay, maybe I should try charging for this thing. I never had that thought before. And so what I did is I just launched the paid plan and I had launched, okay, Hey, I'm gonna start charging for some posts. If you wanna subscribe, go ahead. If not, it's all good. I'll still write some free posts. And, and so that was the move, just like launch and see what happens.
Melissa:
So then what made you start to think about like job, you do some major investing. How do you kind of think about, you know, what you are passionate about doing now and how does that translate into, you know, non-traditional product roles let's say.
Lenny:
So my whole goal initially with all this is I call it project, avoid getting a real job and the goal is keep it very simple. Just create like a really chill, happy life and not do too much. So the newsletter was like, this is awesome. I'm gonna write an awesome post every week. I'm not gonna do anything else cuz uh, I now make more doing this newsletter than I made at Airbnb. And so that was like mind boggling. I had all these kind of goals along the way of like, man, if I make, if, if I make a hundred K oh my God, this is incredible. If I make more than that, oh my God, this is insane. And now it's way beyond that. Um, and so the whole time I was just like, I don't wanna build any empires of any kind. I don't wanna ever hire anybody.
Just wanna live this chill, happy life, write an awesome newsletter. But I found that things keep pulling me things that people wanted, things that felt very valuable. Uh, and also, um, some of these things wouldn't take a lot of work. So for example, there's this job board platform pallet and they kind of pitch me on, Hey, we could launch a job board Lenny's job board and you already have this audience. Maybe you could drive people that are looking for jobs and companies that hiring. And so I experimented with that and that started doing well. Then I had this thought of a course could be really interesting cuz I don't have a place to send people when they come to me and they're like, Hey, I wanna learn to be a PM. I'm not gonna be like read all my posts and you'll be awesome. It's not, it's not like what a course could do for somebody.
So I just kinda had this feeling of like, there's a big gap. I should try to see what happens. So I took a crack at that. There's always these things that are like pulling me and I try to resist and eventually I succumb and uh, this podcast that I'm working on now is a similar thing where I'm like, I will never do a podcast. There's so many podcasts. And then, and then eventually it had enough chats with people where they're like, you should really, really do a podcast. And so I'm like, we're begrudgingly doing these things that feel like they're gonna be valuable to people and maybe aren't gonna be tons of work, but I don't know. We'll we'll see.
Melissa:
I like it. So lifestyle choice where you're like, I don't need to take a break. I wanna like not be inside a product company anymore. How do I build this up to sustain me and still like provide value to our community?
Lenny:
Yeah, absolutely. Uh, it's very much I'm trying to do as little work as I can, but, but it's hard to resist. There's just like so many interesting things out there and yeah,
Melissa:
And that's, that's a good question too. Like, you know, I feel, I feel like when you're inside a product company, right. And like you did with Airbnb for so long, you're learning and learning and learning, what are you doing now? Right. That you're not inside one company to make sure that you're keeping up with what's going on in product management and around the world. Like how do you learn? What do you, what do you go look at?
Lenny:
So most of a lot of my writing is research based. I reach out to experts or founders or VCs when it's related to a topic that they're really knowledgeable about and I rely on their insights. So for example, recent post I had were on the growth side of the newsletter is what what's like a growth rate for a startup at every stage. And so I have no idea. And so what I did is I just pinged 25 of the smartest VCs. I know, got all their insights and then synthesized the, kind of the, the trends similar to I'm working on some stuff around just like, how do, how do you develop product? Like what are the best PA uh, what are the ways companies build product and the various product development processes across all sizes of company, like when you're startup you're and, and kind of bigger and bigger. And so what I'm gonna do is just reach out to heads of product at all these companies and get their insights and then synthesize. So it's a lot of relying on other smarter people.
Melissa:
That's cool.
Lenny:
Yeah.
Melissa:
My students would just would love you. This sounds like all the, the case studies that we have to write.
Lenny:
Yeah, it's, it's a little bit like an HBS kind of like research consulting company, like of one, one person who just was research for people. Yeah.
Melissa:
Yeah. That's really cool. Uh, so one of the things we were talking about too, before, you know, we jumped on here was you mentioned, um, you tried the course. You're not sure that you, you actually love that. Uh, talk to me a little bit about how you think through, you know, stuff that you wanna keep, how are you using like product principles, I guess, to keep experimenting around different ways to work? What, what's your thought process about, you know, how you keep developing this and going forward?
Lenny:
So with the course, I, I built the course, it's like a three week live course cohort based, uh, put a lot of time into it, ran it twice. It went great. Every time people loved it, got a lot of good feedback, but every time it always felt like this huge effort and, uh, performance. And I'm not, it's not my like nature. I don't, I kind of like to be behind the scenes a little bit. And like, it really bugs me that I ended up calling my newsletter Lenny's newsletter, cuz it's like, I don't want to be this person. That's like, I have all the answers and I'm, uh, this person you should all look up to. I just like, I kind of just wanna share stuff and make it valuable to people. And so being like this like person in the middle of a 200 person course, it like, it's not my natural state .
And so I just found, I wasn't enjoying it as much as I wanted and just became this huge drain energetically and it's, it was very fulfilling and very lucrative, but I just felt like maybe I should, I'm gonna put my time into other stuff for now. And so I kind of decided, I'm just gonna take a pause on this thing for now, see where it goes, maybe refer to other awesome courses that are out there and maybe come back to it later. But it was mostly paying attention to what what's giving me joy. Where's my energy coming from. And, and so I kind of decided maybe this isn't where I wanna spend my time right now.
Melissa:
Uh, so I, so I recently started doing this, uh, kinda like catch up with, uh, Gibson Biddle and uh, and Barry O'Reilly. We do like, I don't know, like two to three times a year where we just kind of have like, we call it personal board of directors. I think that's pretty cool. Yeah. Where we just like get together. And since we're all like solo entrepreneurs, we talk about, you know, your business, how's it going? Like Gib does a lot of what you do. He does a lot of writing. Um, I do more of the courses. Um, Barry's just started a whole little incubation for startups, which is really cool.
Uh, so he founded a company that rapidly prototypes and creates startups. Um, so we kinda get together and we talk about like, you know, trajectories of how we got there, what gives us energy and stuff like that. Um, but I think that's really important to talk about too. Like I've tried a bunch of stuff. I've tried a bunch of stuff where, uh, you know, it just, it doesn't serve you after a while. Right?
So, yeah. Um, but I think it's really important to talk about, you know, where do we get energy from certain things that we do and not, not everything everybody tries is successful. I, I think, you know, sometimes people out there watch everybody on Twitter or, or, you know, LinkedIn or Facebook or whatever, floating around talking about a lot of stuff. Um, but doesn't necessarily mean that everything is a home run for them, right. Just because they're out there talking about it, you know, getting in front of it. And I find that having a product mindset really lends itself to being a solopreneur. I don't know if you feel the same way, but like, you know, feel fast, try something new, just keep going with it, you know, iterating on it. All of those things have served me pretty well in the past, but I'm curious how, like maybe you, you take some of those things, um, you know, startup lessons, product lessons learned with you into this new world.
Lenny:
Yeah, absolutely. And you mentioned Gibson and he's, he's what I think of as, when I think of, I'm not naturally made for performing and presentations and courses, like he's the opposite extreme of that. He's like born for that and he's so good at it. And uh, and so that again gave me evidence of maybe this isn't where I should be spending my energy cuz there's people like Gibson out there that are just so, so good at it. Um, and in terms of trying, so, so the thing I've learned with this kind of content world that I'm in, um, I basically have to, I have people paying me every day for an annual plan. And so that means at least for a year, I have to keep going or give people a refund, which is not easy. And then if you extend that out, basically I have to write every week for the rest of my life, this newsletter world, like there isn't like an exit plan, really, maybe selling it, but then I don't know how you, how I sell any newsletter.
It's challenging. And so, so I think the, even more importantly, what I find the reason you have to pay attention to your energy and what gives you energy is that you have to keep at this. It's not like, oh, you do this for a few months and you're done. Like, this is an ongoing thing. You have to keep going and going and going, going. And so it's even more important for that reason that you're actually enjoying this thing you're doing. And it's not just, if you haven't created this bad job for yourself, you're like, oh my God, you have to like do this email forever. And it sucks. And I have to like figure something out all the time. Um, otherwise the content's not gonna be great. You're gonna hate it and just carry this like bad situation for yourself. So even more important to pay attention to things that give you energy.
Okay. And then going back to your question of, of product principles, I think if more it's like founder principles than even product principles, things like waiting for the market to kind of pull you in a direction and not assuming people want a thing. Uh, like you said, iterating quickly, trying things, not being afraid to try something and fail. Um, and then I think also similarly lot founders start a company that they don't actually enjoy. Like they're building a product for a customer that they don't care about at all. And that sucks cuz then you're stuck for, I don't know, five years working on this thing that doesn't really mean a lot to you. So I think, I think that's another reason just yeah. Still stick to things that are giving you joy that you're excited about. Not just doing cuz it's an opportunity.
Melissa:
I think people take that for granted when they wanna do startups. Like I know a lot of, a lot of my students sometimes, um, other people I've met, you know, they wanna do a startup for the sake of a startup where they wanna go out on their own because they wanna make their own schedule. But either way, at the end of the day, it's like, it's still work. It's still something that you have to build and you spend all of your time around it. So I do think like if you, if you don't enjoy, if you're not getting joy from it, it starts to burn you out. Like it takes such a mental toll on you.
Um, and even just, you know, doing what we do, where you get to make your own schedules, you get all the joys of building your own company. It's still hard at the end of the day. Uh, and that like happened to me when I was consulting. Like I first started all of this stuff that I do, um, consulting with companies. I go in, I teach in product management and I sometimes play like the interim CPO role and be a VP of product or help them set up product organizations. And uh, I ended up like, you know, hiring a whole team around it and scaling it and really trying to like build a thriving, like consultancy out of it. And it, it burnt me out so hard because, um, I started doing all of the admin work and the sales work that went with it. And I don't like that.
I'm like a product person. I like the product work. Right. Like I wanna, I wanna learn new things about product. I wanna see how product strategies manifest. I wanna know like why certain companies win. And uh, I didn't get to do that once I built it all up, but there was this, um, pressure that I got from more from like the VC world. And I wonder since you are pretty connected with them too, if you, if you ever see that or hear about it. Right. Um, I kind of got dismissed as like only building a lifestyle business for what I do. Right. And there was this kind of attitude, um, in the VC world or anybody I talked to that dealt with that type of stuff like, oh, you're only building a lifestyle business. Like you're never gonna be able to cash in on it for like tons of equity and make a hundred million dollars.
And that bothered me at first cuz I was like, I'm building, I'm making way more money than I ever did full time. Like I'm building a pretty thriving business where I get to like do things I really enjoy. Um, but there was always this dismissive tone about like what I did, which was like, oh, you cute little cute little business over here, you know? Um, from people who work in that world. Uh, but I kind of came to realize like, yeah, I'm not trying to build like a company that's gonna exit or something or like that's not the point of what I do. And that wasn't really my goal. And once I started to like separate myself from that, I, I found a lot of happiness of what I do and what I go after. Um, but I'm curious if you've ever gotten that kind of feedback or heard that from, you know, your VC world too.
Lenny:
I was, I was lucky in that I wanted a lifestyle business. That was my, my goal is don't build anything massive. Don't build an empire, don't raise money, don't ever hire anyone. So that was actually my intention and I, I happily called it a lifestyle business. When V when VCs call it a lifestyle business, I think generally just what that means is it's not gonna be like a billion dollar company that grows really fast. Um, so I think, I think it's important to recognize when, when it's a lifestyle business, it can still be an incredibly powerful, huge, successful business, especially for the founder. But the thing is that you should never raise money for that kind of thing. That's the main mistake. A lot of founders make, they raise money, they wanna build lifestyle business, and then they're on this treadmill where they have to keep raising and raising and then sell it for a lot.
Melissa:
Yeah. And I think the nature of like what we do, doesn't really warrant that, which is why you have to find like something that's profitable for your lifestyle business, something that works out to kind of help you with those economics, you know, of yourself. But, uh, I, yeah. I like look at the stuff that I do and I'm like, yeah, I don't really amount looking to sell it. I'm not looking to raise money. Um, but sometimes I feel like in our tech cultures, it's, you're not successful unless you raise money or something like that. But
Lenny:
Yeah, that is, that is definitely true. And it creates a lot of FOMO for founders of like, man, we gotta raise a bunch of money. We gotta announce it. Some of the founders I respect most are ones where they raise from awesome VCs and just keep it very quiet for a long time. Mm-hmm because they know it's not really gonna help them. They'd rather stay under the radar. So I think it's just a, a thing you have to learn and recognize that that isn't success. It's success is actually success. building a thriving business.
Melissa:
Yeah. So one of the questions that I get, um, asked a lot, and I'm curious about your, how you would advise people for this, right. Is how do I start? I wanna go off on my own. I wanna do content production or consulting. Like I get a lot of people who ask about how to start with consulting or start with teaching. What's your advice for people who want to build some kind of, you know, lifestyle business outside of a traditional product role in, in, you know, internally in a company,
Lenny:
I'd love to hear your answer to that, but I'll, I'll ex I'll share what I, what I did. The first thing is you wanna actually build a lot of experience so that you can rely on, especially if you're gonna be trying to do content stuff, advising consulting, um, the people that do well have actual real experience that they can rely on. Cuz once you leave, it starts to fade and you kind of, it gets worse and worse and you start to lose, lose your connection to the real work. And so the more of that you have the, the better you're gonna do and the more people are gonna just trust your advice and insights. The other thing that I found really powerful, what I did is I, I gave myself six months to explore and tinker without a full-time job. It's a, it's hard to do if you don't have savings or some other, or like a spouse that can support you.
But I found that that that was the key for me, particularly because I ended up doing a thing I never expected to do. And so I gave myself six months, ended up being a year. I had this chat with my wife six months in like, okay, I haven't figured it out yet. I have six more months. The thing that really helped me do that is I created a personal runway where I kind of figured out here's how much budget I'm gonna burn through to take off a year or six months initially. And that, that just made us both feel better. Okay. Here's money. We're setting aside. It's a, a bet that this will lead to something bigger and better. And in then that time is how I doing a bunch of tinkering following where my energy was pulling me doing things that were giving me energy, doing more of those things, doing less things that sat my energy.
For example, I thought I was gonna be like advisor person. And I started a bunch of advising. I just did not love it. And that quickly pointed me to, okay, stop doing that. See what else is giving you energy. And, and so the key there was just having this block of time where I can explore. And one little trick that I learned that I used in that time, actually, that folks can, can use is I created these, uh, sprints for myself where every two weeks I came up with, here's my goals for my like personal goals and work goals. And I emailed three friends. Here's what I'm gonna do over the next two weeks. Here's three things I'm gonna get done personally, and then work wise. And then at the end of the two weeks I checked in on here's how I did. And I found just sending that email, created this accountability for myself in this kind of unstructured time to make progress in a lot of stuff. And I had like a mid spring check-in a weekend where just like, here's how things are trending. And I never expected anyone to reply to these emails. It was just let me just done this and put it out there. And I did that for a year and that helped me keep going and helped me stay productive.
Melissa:
Yeah. I started, I think what I do now while I had a full time job and it wasn't a lot of work. Like I kind of did it a little bit of nights and weekends type thing. But the way I started too was, um, I had started incorporating a bunch of like data driven experiment, work into my work at open sky. And my boss was actually like, Hey, you should teach this. Like not a lot of people really work this way and this is pretty awesome. Um, and I later found out that a lot of the experiments I ran there actually helped us pivot the company. But sometimes you don't learn about that. when you're, when you're just a product manager. Um, so which was pretty cool though. I was happy. Like everybody came back and told me about the impact that I had later on, which was really nice.
Uh, so I started, uh, I started with a thing called Skillshare. I had gone to a bunch of different in person classes when Skillshare was live in New York city. I did like baking classes and, and coding classes. I tried to Ruby for a while. It's awful at it. Um, so I said, why don't I just try teaching, you know, product management courses at night and see how that goes. Um, and it worked and I was trying to get people to sign up for the online version because Skillshare had this thing that was like, if you got a hundred people on your wait list, um, you could publish it online when they moved to an online platform. So I was on Twitter. I barely used Twitter before, but I was like hashtag tagging everything outta product management, trying to get people to sign up, um, made it to the hundred.
But from there somebody saw me and asked me if I wanted to come speak on that topic at one of their, uh, conferences. So that was like the first conference I was able to speak at. And from there, I kept speaking at more conferences, even when I had a full-time job, I started writing more about it, documenting my learnings like you did from Airbnb. Um, and then teaching this class and then eventually teaching workshops at conferences. And then once I had enough of an audience, I kind of pulled that out and said, I'm gonna run a weekend workshop or something like that instead. And just sell tickets to it, partner with meetups or partner with, um, companies to sell tickets for it. Uh, and I started that way and I loved that part of it. Like I love, I see I'm, I'm the opposite. I'm like give, I love being on stage.
I love teaching. I love, I love talking all that stuff. Um, but that's how I really got started. And then I went to, uh, a startup accelerator in Italy after I, my second, not my second, but like my full time role after open sky, I was there for a while. And then I went to a startup accelerator in Italy and I kept, um, doing that where I'd work with companies. I partnered with some startup accelerators to teach product management to them. Uh, and I went, oh, I guess I can like maybe keep doing this. And the talks for me at first became a way to like travel the world. Um, cuz I'd lived in Italy for almost a year. I was like, I don't wanna leave. I love like bouncing around, going to see cool places. And I got invited to conferences all over the world.
So I was like, this is fun. I wanna go see people. I wanna see new places. Um, but then it also catches up where I was like, well I have to do some work now too. and see how I make money for it. So at first I was charging for the workshops and I'd host like a workshop in every different location. Um, and just utilize a network there, meet up ping meetups, ping, anybody who like lived in the area to help sell tickets. Um, and then from there I started freelancing as well and advising, um, and I'd come in and do a little bit of teaching, but then a little bit of advising and then moved more into a lot of consulting. Um, still doing workshops, still doing teaching. Uh, and then I started the online school from there because I found that I was like just teaching the same thing over and over and over again.
So I'm like in person four days teaching repeatedly. And I was like, there's gotta be a better way to scale this. I can't. Yeah. Technology. Right. Haha. Um, so I, I was like, there's gotta be a different way to do this. I can't just like I was living. I think I lived in London for like two months teaching workshops there for a company. Um, and that's when I started to think about how to put it online. Cuz I said it, it catches up with you for a while. So like you're hustling, you're hustling and you're hustling. And I went, I wanna go from places I wanna keep traveling, but I don't want to have to like live somewhere else for two months or like be somewhere else for a year while I'm consulting and traveling. And that's kind of been like one of my principles of how I think about my work now. Like I, I love going to conferences and speaking at conferences, but I don't want to have to have to do that every single time. So I'm like, how do I put things online? How do I, how do I get some of the me time back so that I'm not just, you know, on a plane, I took 147 flights one year for consulting. Yeah. And it like, I, I re I was like crying on the way to the airport. I was like, I don't wanna do this anymore.
Lenny:
You're not enjoying, that's a signal. Your energy is not there.
Melissa:
Exactly. So like, I think that's just such important principles to like, whenever you go into doing something for yourself, whether it's a startup or, you know, creating your own thing, um, it's just like, where's my energy coming from. Like, what's killing it, what's going towards it. So I think those principles are, are super important.
Lenny:
If I were to pull out, uh, pattern in our two stories, it feels like, uh, tinker and try stuff. That's interesting. Find something that's working and just kind of double down on that and then expand from that once that thing starts to work, but also watch out for things that you do that feel like good ideas and then just like hate doing or just aren't worth your time and then, and then stop and then just kinda keep exploring.
Melissa:
Yeah. And there's also this underlying thing. I don't think a lot of people talk about, I'm curious to hear your thoughts onto it, right? It's like, it's the money aspect of it, especially when you're working for yourself. Cuz I, I always looked at that as like, um, and it's very different when I, I had a team as well. Like when I had a team, I was so stressed all the time cuz I was like, I need to make sure I make money. So I pay my people and it made me incredibly stressed out. Um, but with me it's a little bit, you know, different cuz it's just me and I can choose whether I take a break or not, but I'm not really that type of person. So sometimes there's things that make you money and you also have to say no, cuz it zaps your energy and killing that. I feel like is such a hard decision cuz we're like, oh, but the money.
Lenny:
Mm-hmm yeah, we get used to it. Yeah. The course is the course is a good example. That there's a story that actually I did like a PR thing where they, I dug into the numbers. So it's all out there. But with the course I made uh, 300K and that's like incredibly high ROI even for the amount of time that went into it. But I just felt like I could do more than that by doing things that I really enjoy. Um, and so it is hard to turn that kind of money down and not do it again and again and again, but, but it's just because I feel like there's bigger opportunities and it'll be better if you really enjoy it. But that is real.
Melissa:
Yeah. And that's some discipline. Do you think you would have made that choice had that been where you started instead of the newsletter?
Lenny:
That's uh, such a good question. Uh, and I wouldn’t be all over the course if that was the first thing I did, cuz that is incredible and not something I ever thought I could make from doing anything like this. So I think it would be very different, which is a good lesson. Like maybe the thing you start works out really well, but if you find something else that is even more interesting, maybe, maybe try to do that. But that is, that is a really good point.
Melissa:
Yeah. How did you grow your audience for your newsletter too? Like what types of things did you do to make sure that your writing and your work was out there being shared, you know, getting on people's radar?
Lenny:
So I'd say there's kind of two phases to growth that I found. There's like the general flywheel of how it grows now. And once it got past a certain point and then there's how it started. So in terms of how it grows now, it's basically all word of mouth and some Twitter. I find that anything I do, that's not just write awesome stuff. Doesn't have any impact. I've tried all kinds of stuff. I've tried paid ads, I've tried cross promotion. I've tried guest posts down the road. None of it matters. This creates like a tiny little spike versus when I write stuff that's not great growth plateaus when I write something awesome. Growth grows so broadly once you get going, it's all about the quality of your content. When I started the things that helped me get going, one is I did a couple guest posts on P blogs that were basically the same kind of audience.
Lenny:
I did a guest post for Andrew Chen's blog. And then I did a guest post, uh, on the first round review. And that kind of got me to the first 500 to thousand newsletter subscribers. And the, the other things that helped a lot is I, as I was starting to write on medium, I started tweeting kind of summaries of the same things I was writing. So I was kinda like tweeting little nuggets of thoughts and that started to grow and I started to get more Twitter followers. So kinda sharing things on Twitter as you're starting, uh, ended up being really helpful. Cuz then I tweeted, Hey, I'm starting a newsletter should follow me. It'll be great. So that was really helpful. I think that might be the, the, the two main things that helped actually I have a deck out there. I dunno if you do show notes, but we can link to it in the, in the description. I walk through the whole journey of how I got my first 10,000 subscribers watching this, you can check it out on the website.
Melissa:
Um, great. That's cool. So a lot of good content. Here's another thing I hear from people. I'm curious your perspective on it. Um, and I know I got this feedback as well when I just started writing, escaping the build trap, um, Riley originally O'Reilly originally or somebody, I don't think it was O'Reilly it was Wiley. They wanted me to write a book on UX and agile UX. And I said, I don't, I'm not really passionate about that right now. I'm wanna write about product management cuz I don't see a lot of companies doing this well, plus it's like what I get called for every day. And um, yeah, my book is Lenny's holding it up right now, right there. Yeah. So, um, I, I told them, I was like, I really wanna write a book on product management. And O’Reilly was like, no, everybody's written one on product management before already it's been done. Um, and then O'Reilly was like, sure, that's fine. So that's why I went with them. Um, but I got like a lot of feedback at the beginning when I was writing this book, like it's all been said before, like Mary Cagan has already written inspired. Um, there's a book about agile product management out there too. Like there's tons of product books. How could I possibly find something interesting to write about? And I feel like a lot of people who are thinking about, you know, doing blog posts, like I always encourage, especially like chief people wanna be chief product officers. I always encouraged them to like put out there what they're learning and their philosophies and stuff, because that's what people are gonna read when they go to hire them. Like, it's great because you get a little insight into how they think and how they'll be as a product leader. Um, but I get a lot of people are like, oh, everything's been said already, I don't have anything interesting. How do you come up with, you know, new, not even new content, but like how do you think about your content? And do you get thoughts like that?
Lenny:
Absolutely. When I was starting the newsletter, I felt like man, it's too late. Everything's out there. Everything's done. Uh, what am I gonna contribute? And a few things I've learned along the way. One is there's, there's absolutely tons and tons of content out there, but there's not tons of really good stuff. That's actually actionable and practical, concrete based on actual research and, and insights and experience. There's a lot of like superficial stuff. So that's one thing I've learned is don't be, don't don't feel like the content out there is actually useful to people. The other is people really value your perspective and your unique take on stuff. Uh, assuming you have an interesting take. And so don't take that for granted, especially if you have really good experience at really successful companies. And then the other thought I have is just like, okay, people keep asking questions like on Twitter, on LinkedIn to their VCs, like how do I build this thing? How do I grow this thing? How do I develop a product development process, all these questions that somebody's probably answered well, but the fact that people keep asking them means they haven't found that other piece of content it's not actually good or useful to them or there's looking for something different. And so my feelings until founders and product managers, stop asking all these questions. There's still opportunity to answer those questions with your experience and your take. And I don't know if that'll ever run out.
Melissa:
Important to remember. Uh, I wrote a, my medium post up blew up was product owner versus product manager. What's the difference. Um, to me I'm like, there's no difference. Uh I still get asked that every single day. Right. And I'm like, I wrote this post six years ago on it, maybe longer, I think six or seven years ago on it. Um, it's seen hundreds of thousands of, you know, people have viewed it already. It's the first thing that shows up when you Google it. And I still get asked that question all the time.
Lenny:
So I'm like funny that they ask you, like who wrote about it cuz I'm sure they ask like other people also who had no who ha who didn't write about it. So yeah, that's, that's a really good microcosm of like, yeah. Nope. Assume nobody has read most, anything that is awesome that you think has already been covered. even if you did it.
Melissa:
Yeah. And I find that too. I love personally hearing people's case studies of how they did it inside their company with like examples of it. To me that never gets old. I don't think we have enough of those out there because I think people are really, I don't know. I don't think companies are, are super secretive about how they do things, but, um, it does take somebody like wanting to share it, to get it out there. Otherwise it's just never gonna get out there.
Lenny:
Yeah. That's actually, what I've discovered about this life is I have this unfair advantage where I have a lot of time to do research and interview people and synthesize people working at a company have not none of that time. Mm-hmm . And so once you give yourself this freedom to do this thing and you get enough, you get a working where you can do this sort of full time. You have such an advantage over anybody else trying to do anything like this because yeah, they just don't have time. And there's such a correlation between time. You put into writing content, whatever, and how much value it is it creates and how much people want it. So once you create this, like flywheel for herself, you're gonna have an automatic advantage of anybody else that's using it kind of on the side or part-time. And a lot of that is exactly what you said is spending time researching, interviewing, talking to people synthesizing versus just like here's, I'm pontificating on some idea I have. That's not as useful. Yeah.
Melissa:
I like that. Is there anything in product management right now that's um, or, you know, tech in general, that's making you really interested that you wanna go in and research more about?
Lenny:
So many things. I, I wanna do a survey of just like, how are companies actually developing product these days? Like how long are their planning cycles generally? How do they shift that over time? What kind of artifacts do they put out generally? So I wanna do, I did the, I did this, uh, really cool survey of what, of what skills companies value most when they're hiring, when they're promoting, um, things like that. It's like, I call it the comprehensive view of product management or something like that. So I wanna do something like that around the product development processes, like what in practice, what are people really doing? Cool. So I'm really excited to do that. Um, another question I've been I've I've been seeing this trend of founders are really resistant to product managers. Initially, there's like this, I don't wanna hire product manager for a long time and I, I wanna dig it a little bit into that of like what's happened to these people where they're so afraid of product managers and, and then how do you help people see that somebody's gonna do this job. It's gonna be you or might be engineers, but you gotta make sure somebody's doing it cuz it is a job.
Melissa:
Yeah, I see that a lot. And I'm excited to see what you research about that and where to come the other side. I feel like I spend a lot of time with founders trying to convince them to hire their first VP of product, you know, once they start scaling or hire their first product manager or even when they just don't have a lot of time. And it'd be really interesting to dive into that. So excited to read. I'm excited. cool. Well, thank you so much, Lenny, for being with us. Uh, if people wanna learn more about you, uh, I know you have a podcast coming out, where can they go on the website to find you,
Lenny:
Uh, Lenny's newsletters dot Com's probably the best place. I also have like a general website of all my things that I do, uh, at LennyRachitsky.com. If you can spell it, it'll probably be in the title of this podcast. And then I'm just on Twitter at Lenny San, S A N. You could DM me, DMs are open, uh, PM me anytime.
Melissa:
Great. Well thank you so much. And definitely go check out those links. We will have them linked on of our website once we publish this and uh, stay tuned next Wednesday for another episode of the product thinking podcast. We'll see you next time.
Lenny:
I'll be listening.