Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer)

In my best year at Uber, I made about like 320 or $330,000 in total compensation. And when I quit my job, I was actually thinking like, am I, am I crazy because I'm leaving, especially in Europe, this is a lot of money in the table. This will be similar to something, you know, someone in a similar position would have made like 5 or 600k in total in the US but now I am making more in compensation that I made at Uber. And the difference is that now my compensation, while my earnings are keep going up as long as the newsletter is growing. So there's no theoretical cap on this. Of course there is an actual cap. There's churn. Growth is slowing over time. But it's very, very strange because I felt that I was in a really privileged position just honestly making tons of money doing a job that I loved. And this was at Uber or as a software engineer. And I'm now doing stuff that I love and, and in some strange way, I guess it even pays better.

Welcome to Lenny's podcast. I'm Lenny and my goal here is to help you get better at the craft of building and growing products. I interview world class product leaders and growth experts to learn from their hard won experiences building and scaling today's most successful companies. Today my guest is Gerge Oroz. In a sense, Gergay is the me of engineering. He's got the top engineering newsletter on Substack. It's growing really fast and like me, he does this full time. In this episode we talk about the life of newslettering full time like we both do. We get into Gerg's decision to leave his cushy tech job at Uber to go into this life full time. What the day to day life of a newsletter person is. The pros and cons of this life, what it takes to be successful, and a bunch of advice for how to get started. If you're curious about going down this route, this is a pretty unique episode and it was really fun to do. If you ever thought about writing or going down this kind of creative route, you'll love this episode. With that, I bring you Gerge Oros. This episode is brought to you by Lemon IO. You've achieved product market fit. You're able to activate, engage and retain your customers, but you don't have the engineers that you need to move as fast as you want to because it's hard to find great engineers quickly, especially if you're trying to protect your burden. Rate meet Lemon IO Lemon IO will quickly match you with skilled senior developers who are all vetted, results oriented and ready to help you grow and all that at competitive rates. Startups choose Lemon IO because they offer only handpicked developers with three or more years of experience and strong proven portfolios. Only 1% of candidates who apply get in so you can be sure that they offer you only high quality talent. And if something ever goes wrong, Lemon IO offers you a swift replacement so that you're kind of hiring with a warranty to learn more. Just go to Lemon IO Lenny and find your perfect developer or tech team in 48 hours or less. And if you start the process now, you can claim a special discount exclusively for Lenny's podcast listeners. 15% off your first four weeks of working with your new software developer. Grow faster with an extra pair of hands. Visit Lemon IO Lenny this episode is brought to you by Eppo. Eppo is a next generation a B testing platform built by Airbnb alums for modern growth teams. Companies like Netlify, Contentful and Cameo rely on Eppo to power their experiments. Wherever you work, running experiments is increasingly essential, but there are no commercial tools that integrate with a modern grow team stack. This leads to wasted time building internal tools or trying to run your experiments through a clunky marketing tool. When I was at Airbnb, one of the things that I loved about our experimentation platform was being able to easily slice results by device, by country and by user stage. Eppo does all that and more, delivering results quickly, avoiding annoying, prolonged analytics cycles and helping you easily get to the root cause of any issues you discover. EPO lets you go beyond basic click through metrics and instead use your North Star metrics like activation, retention, subscriptions and payments and EPO supports, tests on the front end, the back end, email marketing and even machine learning clients. Check out eppo@geteppo.com get e p p o.com and 10x your experiment. Velocity. Gergey welcome to the podcast.

It's awesome. Great to be here Lenny.

So I think this is going to be a pretty special and unique podcast. Your newsletter is the number one technology newsletter on Substack called the Pragmatic Engineer. By the way, my newsletter is the number one business newsletter on Substack and so we're connected in this really special weird way and I thought it would be pretty fun to just explore this weird path that we're on doing this newsletter thing and in that help listeners understand kind of the pros and cons of this life, help how to go down this route, what it takes to Be successful, all that kind of stuff. But before we get into all that, I'd love for you to spend maybe a minute just kind of giving us a little overview of your career and kind of how you got to where you are today doing this newsletter and what you spend your time on now.

My career started out as what you might consider a pretty typical software engineer career. I graduated from a university. I did a computer science degree for like a five year program, so the bachelor's and master's. I kind of worked on the side. I kind of hacked around, built small websites here and there. And during university I worked at a small web agency. And then I kind of worked my way up in the industry. So I started off at a consultant company. Like we were just building for other companies. I'm originally from Hungary, so Hungary and Europe. I then moved to uk, which was a big step up for me in terms of just getting access to, I guess, more modern software development. I was at a consulting company there as well. And I moved up to London, which, you know, like in Europe. I kind of feel it's like the New York of Europe or even the Silicon Valley. Back in the day, back before Brexit, it was the biggest tech hub. I worked at a bank, well, an investment bank there. And then on the side I was always building kind of mobile apps. And I got into Skype, I like to say Skype, but it was Microsoft, they just bought Skype at that point. And it was a lot more startupy environment, a lot more fast moving. I then moved to another startup where I was a founding engineer of a acquisition. It's a startup called Skyscanner. And then I ended up at Uber at Amsterdam, where I joined as a senior software engineer. And I kind of, I became a manager and then a manager of managers. And it was just like, I feel like looking back at that part of my career, I just felt kind of really growing all the time, just kind of taking each step one, one step at a time, which gave me a lot of appreciation for all these levels. And then just as I was on this really good kind of career path, I was on the path to being a senior engineering manager. Or who knows, one day I might have had a shot at being their director of engineering as well. I decided to leave Uber and we'll talk about it later in the podcast. But I didn't plan like this, but I started writing a newsletter and now here I am writing a newsletter where a bunch of people are reading it and it's a really unexpected turn and a really cool life as well.

Awesome. On the newsletter, just to give people a little bit of context of how big this has gotten, can you share just a couple stats about the growth of the newsletter, the size and anything else you want to share there?

Well, just today I checked and it's at 189,000 subscribers. It's the past, I think the past 90 days has been growing with 80,000 subscribers. So it's just, it's almost 1,000 people per day, which is incredible because I mean, these numbers are huge. If you're listening, you're probably thinking, wow. And that's how I feel every day as well. But I've been writing a blog for many, many years and these are numbers I never thought it would be. And the growth just seems to be accelerating. So there was a tipping point in April where the newsletter was growing. In the first like, about like nine months of the newsletter, it got to fifty thousand subscribers. And in the next five months or six or seven months, it went up by another one hundred and something thousand subscribers. This one was when Substack introduced recommendations, which has been a massive growth engine. And I guess being one of the top publications, I kind of benefited from it. But those numbers are big in. So this is a paid newsletter as well. So there's a free version and a paid version. There's thousands of people paying for the newsletter. It's a single digit percentage, but it's a very, very healthy one. And again, it just beat all my expectations. I guess we're in similar boats because our newsletter set up yours and mine is somewhat similar. We have plenty of differences as well. But I make most of my revenue from subscriptions and I don't do sponsorships or ads in the newsletter. So it's kind of like if people sign up for the free one, they get articles every now and then, and then for the paid one they get it a lot more and in more depth.

Can you give listeners a sense of just like the order of magnitude income you make from this versus your cushy tech job at Uber? You don't have to share numbers or anything like that.

Yeah, so I mean I'll share little numbers of my cushy tech job at Uber. So you know, I was in Europe and European tech salaries or tech, I'll say total composition will be lower than for example the US but it'll be higher than, let's say regions like India or Indonesia. You know, there's regional differences and this is true for big tech as well. Uber was a good example on this but in my best year at Uber, I made about like 320 or $330,000 in total compensation. This was after Uber public, so it includes the stock, the base salary, the bonus, which was very, very good in Europe. And when I quit my job, I was actually thinking like, am I crazy because I'm leaving, especially in Europe, that this means that this is a lot of money in the table. This will be similar to something someone in a similar position would have made like 5 or 600k in total in the US so I walked away from that and I was pretty sure that I'll just be making a lot less and I'll be, you know, but I'll enjoy what I'm doing or I'll kind of have, I'll just give it a go. But now I am making more in compensation that I made at Uber. And the difference is that now my compensation, while my earnings are keep going up as long as the newsletter is growing. So there's no theoretical cap on this. Of course there is an actual cap. There's churn, growth is slowing over time. But it's very, very strange because I felt that I was in a really privileged position just honestly making tons of money, doing an odd job that I loved. And this was at Uber or as a software engineer. And I'm now doing stuff that I love. And in some strange way, I guess it even pays better. I mean, part of it is this luck, part of this is situational. I think we're going to talk a bit more about this, but this was very, very surprising and very unexpected for me.

Awesome. Yeah, that's a great segue to the first thing I want to talk about. But just to kind of frame what I want to spend our time on today, there's kind of these four areas I want to explore. One is your decision to leave and start this life of writing, which is a very non traditional life. Two is what the life of a paid newsletter person is like. What do you do all day? How do you find time to do this? How do you produce so much content? Three, what it takes to be successful at this. A lot of people, I always say it's easy to start a newsletter, hard to keep it going, and I'm curious what you find is important to be successful. And then four, how to get started if you want to start your own newsletter. But before I get into that, I just wanted to add a thought that I had. The way I think about this life in terms of comparing to the old job is one, it feels like instead of one boss. I have thousands of micro bosses and one of them can fire me and many do every day. But it feels like safer than at a tech job. Or like one person. Yeah. And then the other piece is, yeah, if assuming keeps growing, you're getting a raise almost, you know, every day, every week, depending on the growth rate. And that's kind of cool.

That is really cool. So I had a spreadsheet that I maintained for the first year of the publication where I listed for every article, how much did my annual revenue go up a week later. So kind of tracking like what was the impact. And the crazy thing was that, you know, when I wrote a really good article that resonated with people, you know, sometimes it was an article that I thought was mediocre and people still loved it, but often it was a really good article that I put tons of work in. I saw myself getting a raise and this is just something you just don't get incorporate. I mean it's by design and there's a lot of good stuff about it. But this, like I feel that this, this life and I'll, we'll touch more on this, but there's a lot of surprising things, both good and bad. But this is a really good one. So you're, you know, for doing something awesome, you can just get give yourself raises especially because this is just like you. Mine is also one person business right now.

Yeah. Okay, so you're at Uber. You're making hundreds of thousands of dollars writing code. It's pretty sweet. Uber's growing. You probably got all these RSUs that are gonna keep accumulating. It's pretty, pretty good. And you decide, I'm gonna try to make money on the Internet writing, which is an obvious way to make a lot of money. Not. And so I'm curious what got you to leave that job and explore writing and get to this writing path.

The short of it is it was a promise to myself and Covid and Uber doing layoffs. And the longer version is that when I joined Uber, I mean before Uber I was, you know, now we're talking numbers on, on my old job, but I was working in London as a principal engineer at Skyscanner. Skyscanner was a unicorn, one of the, one of the few unicorns in the uk, kind of UK headquarter and all that. And I was making I think like 90 something thousand pounds in base salary, which is like maybe 120, 130 or $140,000. Depends on how the pound is doing. Or sometimes these Days, it's almost just the same. But back then, that was a really good kind of. And this was most of it. Like, there was. I got some stock as well, and I thought I was close to the top of the market in London. Like, I kind of knew people, and it seemed this was a really good compensation package. And then Uber called me up saying, hey, do you want to interview? I interviewed with them, they gave me an offer and I negotiated, and they basically doubled my compensation. I. I was like, oh, wow, this is like, let's just stop. So I knew about Silicon Valley compensation, but I. I assumed that in Europe you're not going to get this. But Uber was getting closer, something closer to that. So I told myself, like, all right, so I'm getting a bunch of, like, a really good deal. And most of it is stock, which is. Which is Uber was. This was in 2016. No one knew if Uber would go public, although I kind of suspected because they contacted me to build the payments team to. To SOX compliant payment system. And you need a SOX compliant payment system if you want to go ipo.

So that's funny. It reminds me, at Airbnb, there's all these people trying to figure out, when are we going to go public? And then there's like, oh, there's a team working on SOX stuff and Sarbanes, Oxley. Oh, this is good.

Yeah. So anyway, I said, like, all right, well, this is a massive lottery ticket. If it goes in, like, every year, I make two years of salary. Pretty much like, that's how I was kind of thinking. But if not, again, don't forget, I'm in Europe, where we're kind of used to not seeing any returns on stock. So European software engines will not value stock as much because they just haven't seen success stories. So I told myself, look, four years later, Uber exits and I make a bunch of money. I owe it to myself to take a risk because then I'll have, like, you know, four years of savings in my bank, which, you know, back then I had like. Like, maybe like six months of savings or something. So this was the promise to myself. And then I probably would have forgotten about this, but four years later, almost on the dot, Covid starts, and it really hit super hard. We're laying off people. We had to lay off 20% of the engineers. I was already managing a group, about 30 people. I had managers under me. And 20% of the people, or 15%, had to be let go. And I was thinking to myself, what am I doing here? I looked ahead Uber is going to have a really just bad year. I'm going to have to manage morale. And up to then, I helped put together this team. We had a really good charter, and we had to throw that charter out the window because it made no sense with the economic reality. So I thought back. Like, I told myself, if I'll be here, I'll take a risk and I'll try to do something else. So I was like, all right, let me pull this trigger. And my plan was very simple. Leave Uber and start a startup. Raise venture capital. Because I haven't done that before, but it kind of runs in a family. My brother's on a second startup. He sold his first one to Skyscanner, and now he's building this startup called Craft Docs. It's a really slick document editing system. They just raised their Series B. So he's. You know, I kind of, through him, I. I know what startup life is. And I. I felt. I never did that. I was always working at big companies. So my plan was, all right, leave Uber, raise money, and do something on platform engineering. I saw Uber. A classic way that Uber alumni starts businesses is Uber has invested silly amounts of money to build everything custom internally. Like, everything that you can think of our build system as custom, our experimentation system, our container. You know, the way we kind of automatically set that up, a lot of the engineering stuff. So a lot of Uber alumni just leave, and whatever they saw, they just build it for the world to use, because no other company really does what Uber does, because it makes no sense, but a lot of them will pay for it. That was the plan. But before I wanted to do this, I wanted to finish a book. I've been writing this book for. It was coming up to a year called the Software Engineer's Guidebook, which is just kind of my advice for people to grow professionally in the field. And I figured, all right, let me leave the company in six months, I'll write the book. I'll just use my savings to kind of, you know, take a break, and then I'll raise the. The. The venture capital. And what happened was I started to write this book, but I got sidetracked. I started to have fun online, like, in terms of. I was, like, writing on. On Twitter, on my blog. I accidentally published a book called Building Mobile Apps at Scale. I just kind of did it for a few months. And the weird thing was that my plan was that I'm going to just not make any money. And this book, Building Mobile Apps at Scale, and another book that I Published about tech resumes. I just wrote these. In a few months, they started making money. They made about a hundred thousand dollars in the first year. And I was like, that's interesting. People are buying my books. And I self published it to the gumroad. So places where I get to keep, I think like 90% of the revenue. But still, this was really interesting. And I got to the point where like, all right, like, I should now start a startup. Like, I should do fundraising and do all that. And. And then I asked myself, why do I really want to do that? And the answer was two reasons. One is I love working in small teams at Uber. I'll be honest, I didn't really enjoy being a manager of managers. It felt a bit too abstract. I didn't like being in the meetings, not doing the work. What I really liked is when we had a small team and we had this really big vision and it was like us against the world. We were like 10 of us and we were just getting stuff done. We were putting out fires. It was so much fun. So that was one of the reasons I wanted to do by kind of hope was hoping to recreate this feeling. And the other thing honestly was money. You know, this is in 2021, before the market crashed. You know, just doing the math. Like if you're, if you found the company, you know, I'll be a CEO and the founder. Maybe I'll have a co founder. This becomes a unicorn. By that time, we have, we will have raised like five rounds of funding or six. I'll be deluded as hell, but I'll still have, let's say 5%. 5% of the bill is still 50 million after you pay taxes you still have left over. And I can buy a bunch of stuff that I don't need. And I was asking myself, like, all right, and then what? And I was like, well, after I bought everything that I don't, don't need, I probably want to kind of share what I know with people, do YouTube videos and kind of write books. And I was thinking to myself, like, to hold on, like, I would go off and do this for like 10 years, because that's how much you need to plan to do it. I need to stop doing what I'm doing right now because I would owe it to my investors and my team to not, you know, like spend all day on the Internet, like writing about stuff. And then I want to do this again. So it's reminded me of the story of this fisherman. I think there's one that goes Online that does the same thing of you work really hard to do what you're doing right now. So I decided, you know what? Let me just try giving this a.

Go with the story of the fisherman. I think I know what you're talking.

About, but the story of the fisherman is in Mexico. An American businessman sees a fisherman who's just chilling fishing, and he asked him, like, hey, what are you doing? Like, oh, all day? It's like, well, I, I kind of fish for three hours. I hang out with my family. I, I, I didn't chill, and I sleep in every Saturday and Sunday. It's just like, all right, here's what you should be doing. You should, like, fish. Not three hours, but you should fish like, you know, like five days a week, eight hours a day from, sell that fish, turn over a profit, hire more people to do it, then start to be ahead of all those people, then sell your, your fishing company. He's like, okay, so. And then what? And then you can actually buy an island and you can just fish for three hours. You can sleep in on Saturdays and sleep on Sundays. So I was kind of thinking, like, look, I have savings. I don't have, like, huge, but I have it for, I can still take a risk. So let me take a risk on, on writing. And I was thinking originally of just, like, spending more time to finish my book. But what I didn't like about books, even though I was making money, is they're really kind of. It's hard to predict how, like, if you're going to be making a living or there's some people who actually like this excitement. But I didn't like it. Like, I didn't know if today I'm going to be making like 50 to 50 bucks or 10 bucks or 300 bucks. So I was like, interesting. There's this paid newsletter, which I've been thinking about. You were one of the few people who shared some of your early numbers. And I figured this could be interesting because it's recurring revenue. And the only reason I was really hesitant to start a paid newsletter, I was thinking about doing so for at least like, six to 12 months is I was worried about writing every single week something really, really kind of, you know, worthwhile reading. And it's a lot of work. But then I looked back and I saw that I wrote three books. Well, that's why I told you I wrote two books. But there was a third one that I also published in a year. And I was like, I'm pretty sure I can write. So for for two weeks I collected ideas of what I would write about and I had this super long list. So I was like, okay, ideas also check. And then I just screw it. I'm going to take a risk. It's a bit of a more professional risk and maybe a financial one as well. I'll announce that I'm going to start a paid newsletter every week I'm going to write something really in depth about software engineering. It's going to start next week. And I told myself that I'll, I told my wife as well that I'll do this for six months and I'll see what happens. If there's traction, it's great. You know, I might have found myself a new, a new job basically. If not, I'll just refund people, like everyone who bought an annual subscription. I didn't tell this to people obviously, but for six months I'm going to give it my all, you know, like it's, it's basically like a startup. So I told her like, and my family that it's going to be a lot of work, I might not be around as much. And they supported me. And then I took a plunge. I took a big breath and started off. And that's how it went from leaving Uber to start a venture funded startup to starting to write full time.

Awesome. And we're going to talk about what advice you have for folks that are thinking about starting something like this at the end. What was the period between leaving Uber and starting the newsletter?

It was pretty much a year, a little bit less than a year. Might have been like 10 months or so, but it was a year from when I decided to leave Uber. So Uber did layoffs in April and it was really stressful. So it was the first time I didn't lay anyone off, but people on my team were laid off. I wasn't told who's going to be laid up. It was just really stressful. I mean, it's weird in the sense that the people who were let go, obviously worse for them, but I still felt terrible and I just didn't feel that good about it. I think this was the breaking point. Like I just, this was a point where I realized that it's not a family, which is weird because it never was, but it kind of felt a family like, but it's just a corporate and I'm just a number and you know, this could happen to me again. So I think I lost my sense of like the trust in the system that it'll take care of me because I saw Some of my colleagues who are really good professionals, I'd argue they were better software engineers and managers than me. They got let go because they were in the wrong team. So this was April and in July I went on a holiday and like two weeks and I just realized like I, I, I just, I need to leave and I, I should. And I really had the urge to do somewhere where I'm in charge. Yeah. And, and if, if you're a manager listening to this, you might relate to this. If you're an engineer listening to this, maybe just, you know, shut your ears or you'll figure it out eventually. But when I was promoted into management and Uber, it wasn't promoting into it because it was a size step. I didn't get salaries or anything. But it, it, you know, it still feels like a promotion. They only promote the people who transition who are considered pretty good. I felt this would be a big deal. I'm now a manager, right? What no one told me is yes, I was a manager, but I was a middle manager. I didn't have too much authority. I didn't even have a budget for my team. Like, you know, someone was underpaid and I couldn't do anything except complain for HR for six months and hope that they do something. So it was pretty frustrating because I didn't feel in charge in the sense that I didn't have decision making process. And the reason I wanted to do a startup is I decided I liked being a manager, but I did not like how I was not in charge and I couldn't take, you know, corporate for what's telling us to do stuff. And then we're telling them, no, that's bs, we can't. I don't want to do that with my people. So I decided as for next job, I could be doing this, but instead I'd like to be in charge. So I'd like to either be a founder or someone who's high up so that I can actually take full responsibility for the things that I want to do or I don't want to do. The short of is I decided to leave in July. We have longer notice periods in Europe, so I served a longer notice period and then kind of left. But it was a year after the decision.

Let's talk about what your life is like these days. Writing a newsletter full time. People might be listening and be like, Man, $300,000 for writing an email a couple times a week, that's pretty sweet. So I want to talk about the good and the bad of this life. So maybe to start. How many posts are you putting out a week?

I started the newsletter saying I'm gonna post once a week, like you'll have one in depth post. And I started to do that. But interesting enough, eventually I upped it to two. So I now promise people two posts a week. There's more in depth and more timeless posts about some software engineering topic on Tuesdays. And there's something that's called the scoop, something a bit more timely where I reflect or analyze what's going on on the market. Interesting stuff I'm hearing. And every now and then there's a bonus post. So I'll say two on average. But this, the second one came a lot later. But initially, the first few months, I was like, all right, I have this one post per week and it needs to be good. And it was interesting because you would think writing a post a week, it's not a big deal. It's easy. As you said, let's say you're making 300k just writing one post a week. But actually it was pretty stressful in the beginning because it turns out to write that post, it takes, you know, at least a few days or sometimes even longer. Sometimes it takes a week or two for me to research in terms of talking with people. I chose topics that are not covered because why would people pay for something that is out there already or well known? Then I need to write a. Write a first draft. I get some feedback from people who I trust often, not always, but. But I often do. And then there's an editing phase where I have. I work with an editor who kind of helps make sure that it's. It's just correct. And all of these things usually just kind of add up. Even if I only spend a day researching the stuff, it's like a day researching. Then I kind of have a draft on day two, Draft day three. I get feedback on day four. It's editing. It's almost a whole week. So I was working on unparalleled things at the same time. And I was often, like, running against the deadline. I was barely finishing it, which is not what I was expecting initially. So the first few months I feel was a bit more stress. But again, the good thing is I cleared my calendar. So I said, like, I'm not talking with anyone. I'm just doing this. So in that sense, that was good. But the one thing I realized, if you look at any journalist who's doing stuff full time and they're writing like, not these clickbait articles, but actually like in depth. You look at the Washington Post or New York Times, search for the name and look at the articles that they write, and they're going to be longer articles. They have like one a month. Like, seriously, like, you look at the investigative journalists, they might even have less. And they have a bit of a different level. They have to check with legal and all those things. But my editor is a journalist, so he was actually telling me like, oh, yeah, you actually, even back then, you actually write a lot of original stuff. Because a lot of my emails are about like 5,6000 words, which is considered very long.

Yeah. When you said that people listening might be like, oh, one post a week is easy. I think most people are the opposite. They're just like, I can't write anything. I don't have time for any writing. How can you ever write one good thing a week? So I think there's both sides to it. And it's. It's cool that you shared kind of the process. Do you have like a specific cadence per post? It's like Monday draft, Tuesday review, Wednesday editor. Is that how you work?

I write every post over multiple weeks. Most of them, Some of them I might be able to write faster. But what I now have is now nowadays I actually write two articles. So I have. I have the Thursday that is the scoop, which actually is a lot easier for me to write. Interesting enough. And my cadence is that on Monday I finish up the last of the posts that goes out on Tuesday. It's a small edit, but it's already done pretty much. So it's just a few small tweaks. Maybe I have some feedback coming in. On Tuesday, I publish this post and I do some free writing. I kind of write about some other ideas that I have that's going to be future posts. On Wednesday. It's kind of my free day in between where it's interesting. Because what I feel is when I don't have pressure, I tend to not do much stuff which might just my mind saying, you just need to chill. Maybe that's it. But one thing I miss from the corporate world and if you're listening and you're in a job and you're thinking, oh, Gerge's job is so amazing. One thing that I liked and I really miss about working at Uber is I actually had a schedule. This is weird. I hated the back then, but I was. I needed to do these things. And whenever you have a pressure, you do it. And this works with a newsletter I put in the second post user. I think to Have a bit more pressure because the second part of Wednesday, I'm already starting to write my Thursday newsletter. On Thursday, I write that Thursday newsletter. And on Friday, I'm now writing the next newsletter for Tuesday. So almost every day except for Wednesday, I have a strong pressure to write, which when people ask, like, Gergey, how do you write so much? Because I did the maths and I wrote like four or five books worth of content just last year. It's because I have these deadlines. And as you said, like, I. I also know that thousands of people are paying me. You know, I have like. Like they have expectations of me. And so this is how it's done. Like, if you. If you want to write a book, the easiest way is go to a publisher and sign a contract. Not because of the money. In software engineering, you're not going to get much like $5,000 or something like that. That's what I was offered initially. But it's the pressure. Like, you absolutely should go to a publisher or have some external someone to hold you accountable and then you'll get it done. And I'll let you in on another kind of secret or not so secret, do tell. In my mind, when I started newsletter a year ago in this crossroads, I want to write this book, which I think will be a great book, the Software Engineers Guidebook. I feel it'll be my kind of summary of my last 10 years of what I have to share as. As advice. But I was worried that it's just a big project that just gonna take months and I'll lose motivation midway. And I partially. I went down the newsletter route because I liked how every week I would have to write something. And I had the sneaky idea of, hey, what if I wrote this book where I kind of write some posts that will be part of the book and then the book will just kind of come together partially. And I've kind of been doing that. I haven't been telling people, but some of the posts are going to be. Not exactly, but they're the ideas. I have this chapter and I have this list. Like, have I written about this topic in the newsletter? And I got. You know where I got this idea from? There's the book the Three Musketeers from Alexander Dumakors. Yeah, yeah. And you know how it was written?

I don't.

So he wrote the book for a magazine. He was apparently just low on money and he started to write for this magazine who told them, like, all right, we need you to write something that our readers don't want, but we want so that they will buy the magazine. And I think he was getting a cut of some sales or something. So he needs to write in a way that was interesting and then cut it off in a way that people would come back and buy the next one. And he wrote a whole book. And that book, when I read it, it was really long. I was like, hold on, if he could do this, then this is kind of a good strategy. Like he was writing it because he just needed the money. And then he wrote a really good book on the way. So one big learning for me from newsletters then I would argue that you can use this not just for newsletters, but any business that you do. You know, if you're going to go out and start a new business, you'll probably have some ideas. And it's not just going to be newsletters, it's going to be a bunch of other things. If you put in ways that you have to do certain things, you know, put in constraints for the things that you need to do and then you're going to do that without that when you're on your own, when you're an entrepreneur. I was a great, like, I think I was a really diligent employee. Like, I always tried to get my work done, show up on time. I tried to meet all expectations. But what I noticed is when I start to work for myself, it just went out the window. Like almost 15 years of, you know, being this like star employee who really wants to do well. I find myself upset at myself for not, you know, just kind of wasting my day. But I fixed it by, by telling people, you're going to get this every week. And now I have to do it. I just have no choice.

This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate growth. If your business stores any data in the cloud, then you've likely been asked or you're going to be asked about your SOC2 compliance. SOC2 is a way to prove your company's taking proper security measures to protect customer data and builds trust with customers and partners, especially those with serious security requirements. Also, if you want to sell to the enterprise, proving security is essential. SOC 2 can either open the door door for bigger and better deals or it can put your business on hold. If you don't have a SoC2, there's a good chance you won't even get a seat at the table. But getting a SoC2 port can be a huge burden, especially for startups. It's time consuming. Tedious and expensive. Enter Vanta. Over 3,000 fast growing companies use Vanta to automate up to 90% of the work involved with SoC2. Vanta can get you ready for sale security audits in weeks instead of months, less than a third of the time that it usually takes for a limited time. Lenny's podcast listeners get $1,000 off Vanta. Just go to Vanta.comLenny that's V A N T A.comLenny to learn more and to claim your discount. Get started today. I definitely wanted to dig into that a little bit deeper. This issue that folks in our line of work run into, which is unstructured time and having to create your own structure. I had the same exact problem when I started this thing like, and before I even started the newsletter. Like, how do I use my time well? How do I create some kind of deadline for myself? So I'm curious what other tricks you found to help you stay productive and focus? Because there's Twitter, there's Instagram, TikTok, there's all these things that pull my attention. And I've learned a couple things I'll share that have been helpful. But I'm curious, what have you found to help you focus on and get things out the door? Two posts a week, which is a lot of work.

So a problem that I have, and this might be unique to newsletters or I'm not sure. I use Twitter for a lot of research and unfortunately what that means is when I start to write something, it can really pull my attention because I have Twitter open and then I get a message from someone. It's a little bit like Slack, but I'd argue it can be worse because also Twitter for me is also something that is very useful in generating people, raising awareness. So kind of whenever I tweet, it kind of helps my business. So that's a good thing. Right? But it also, it justifies for me spending more time on, for example, Twitter than I want to. So I find that I come up with a method and it works for like a few months and then I need to change it because my brain just learns to work around it. So I'll tell you a few things that I did and I'll tell you where I'm at right now. But I use, for example, apps like I use this app center, but I know you're also there.

Yeah, love that app. Also investor and disclaimer. But I love it.

Yeah. And I found it helpful, the idea of like focused time and turned on. But it might just be me. But after A while. I kind of like get used to these things and I find it not as efficient. I found the Pomodoro method for a few months useful when you kind of have the 25 minute intervals. And the one thing that has never failed me, but I just find it hard to do is I find it hard to start. I, I, I have this, this kind of benefit that I have all this time. Sorry. There's two things that always work. One is it's almost time for me to go home and then I'm, I'm like super focused. So like, when I have this external thing and I know that there's no way, I can't, I need to focus on, you know, it's basically the deadline. So if you have deadlines, that works. The other thing is if I start to get, I spend three or four minutes doing something focused and I kind of get the flow of it. So a trick I sometimes do when I'm just like, I just don't feel like doing anything is I set a timer of 20 minutes and then I say, all right, no distractions. I have a script where I just kill, I use a max on the host file. I just kill all LinkedIn, Twitter, Facebook, what, whatever sites. So I just cannot reach it. Like, like it's, it's just a very simple Python script that I wrote for myself. And then I, in the first few minutes, I'm kind of grumbling. I'm like, I wish I could do this. I wish I could just look at Twitter to research. But about five minutes in, there's a switch when I'm like, I'm now actually like heads down and doing it. And this has been, the thing has consistently worked. The interesting thing is that I, I feel guilty a lot of times that I'm not working as hard as I could. And I do wonder if it's guilt or if it's my mind or body telling me that it just wants a break or it wants to do something else. I still haven't figured it out, but I'm on the way there.

Awesome. That's a really cool trick, the host file trick. So that's something that you have to be kind of technical to do. I imagine there's some Chrome extensions that could do that to some extent for folks. But the whole idea there is force your brain not to have any way to look at something that'll be distracting by blocking your computer from even and being able to go to the site. That's awesome.

Yeah. So there is definitely going to be extensions that you can use. I mean, but if, well, and you know, on this podcast we'll have a variety of people. If you're a software engineer, it's pretty simple because even if you're not, you can look it up in the host file. If, when you override your host file, you can actually block things, what you do. And I did this because I wrote a script where I need to run the script and I need to run to the script again to unblock it. And it's kind of cool because I put it together for myself. So I. I usually find that the tools that other people use, maybe this is just me or maybe this is software engineers. I don't like them because I feel they're either too opinionated or they're not opinionated enough. So I don't know if this is just the fact that I used to like to build my own tools and my own scripts, because I can. So I found that my scripts worked the best for me. But as you said, there's a bunch of really good tools. So my advice to people would be look up all of these methods, try them out. You won't know until you try them. And again, I had stuff that worked really well for a certain amount of time. I don't know why. Maybe I just get bored easily or something that I just need to rotate. But for example, when I went back to Centered, I have no affiliation, by the way, so I'm just telling this. But I really liked how they keep evolving as well to do cooler things. They have a community element where you're kind of competing with people on uninterrupted time and closing stuff. So that to me is a, like, I'll do one last thing, one last thing on Centered. Again, I have no physician. What I really liked about Centered is it allows you to turn on your video camera. And I felt really kind of forced to do work because I knew that, you know, people on the other side of the world might be watching me, even if it was not true.

Yeah, I love that feature. It's Centered app, by the way, if folks want to check it out. So to summarize some of your tips, which I love, Centered deadlines totally work for me too. Blocking sites so that you can't get distracted by Twitter and LinkedIn and TikTok and all the things. And then, yeah, I guess that's the three, right? The three that work best for you.

Yeah. And. And the simple thing started a 20 minute timer and you say for 20 minutes, I need to focus on, on this thing. On your iPhone or somewhere else, it's just 20 minutes. But during that time, you cannot do anything else. And just try it. It works for me like, like a charm one side once I decide to actually do it.

What school center does that for you? And it has music and all the things. Yeah, so I like that a lot. Awesome. What do you love most about this life that you lead now versus what you used to do? And then I'm going to ask you the opposite, but let's start there.

I really like that it forces me to have my calendar empty because for so many years my calendar was this giant mess of meetings on top of meetings, and I would barely have any time to actually have focused time. Now I actually have the opposite. I. I usually have a lot of focus time and I had very, very few meetings or, or things. And even now, like, I kind of get like a little bit like, cagey, like, oh, I have this one meeting in, in. In the whole day. So I like how it's kind of. It's kind of like manager time to make your time. So that. That's the best part. And I also like how much in charge I am. So initially it kind of freaked me out in the sense that how much creative freedom I have, I can write about whatever, I can change the format, I can do this, I can do that. It can be a little bit overwhelming because I also kind of know that people are going to be reading this and what are they going to think about it. But I do like that it's very entrepreneurial, so I get to experiment a lot as well. Which reminds me a little bit of my old job, because at Uber we also experimented a lot, obviously more in a corporate setting. But that, I guess that's just kind of gotten extended. So, you know, these are the two favorite things is the open calendar or like very few meetings and experimenting, trying out stuff and being able to decide what I want to try out plus.

One on both those. I have a rule of no meetings before 3pm and it generally works 99% of the time. And the reason I do that is, to your point, if there's a meeting at like 11, I just like can't do anything really deep until that point. And then afterwards I have to like, get back on track. And having that deep focus time is so important for this work. Even though like half the time I'm on Twitter and distracted. As long as I get enough time to focus, good things happen. Okay, opposite. What are some of the most surprising downsides and kind of sucky Parts of this path that you've taken.

Well, one is obviously it's lonely. So I do miss. I had a really good team at Uber and it wasn't just a team, it was the people I liked. Like, you know, everyone has different views on remote work. I actually didn't, I didn't enjoy remote work as much because I just liked hanging out with people. I guess I'm that kind of more outgoing type and I, I really like, you know, walking up to the coffee station and having a chat with people or at lunch sitting next to someone and, and talking about it. Obviously sometimes it was annoying because I wanted to get work done. But for the most part I miss it more than I have and so I miss not having that. I kind of compensate for that by working in a shared workspace, like a shared office, which is a techie workspace. So everyone needs to work in tech. So I actually get to say hi to people and have a little small, small, small talk. The structure is weird because I felt really guilty for the first few months because I felt that at Uber I was more productive because I had to be like I was doing so many things like in a day, you know, I would, I would start my day, let's say at 9 or at 8:30 and I finish it up at, I don't know, like 6 or 5:30. It depends. I would probably have, on an average day I would have like, you know, like good eight meetings. I would like finish like two or three documents. I would send over this, send over that. Like I actually had like looking at my output, like, you know, I now I write a lot, but I wrote a lot. I think I wrote almost as much in terms of emails, chat messages, et cetera. So like the downside is I felt very guilty and a little bit frustrated for myself for, you know, feeling that I'm slacking off. That's one. And the other thing, it is surprisingly stressful. So when you start off, it's kind of lonely. Not many people do this, what we do, you know. That's also one of the reasons that we connected because it's a very small community and even within the community, I feel in the newsletter community it's different. You're all running your own business and there is some level of competition. So you might not. Because it's a little bit of attention economy as well, you know, like people are not going to subscribe or pay for 10 different or 10 newsletters on the same topic. So that, that makes it a little bit more, you know, it's not, not the same as when you work in tech and you just kind of share exactly everything that you do because you can only win. So there's that part, but there's a lot of external validation. So, like, whenever, you know, looking at your subscriber numbers, which brings a bunch of stress that I didn't expect. And I'm. I'm a successful newsletter. Like, I. I think my success is quite rare. You know, there will be one or two or like a handful of people who have similar success, but I'm kind of an outlier. So that's another thing that I think is just good putting out there. And the downside is you don't really know how well you're doing. There's external goals are kind of meaningless internal goals. Either you smash them or you don't reach them. So there's this constant sense of where am I, how am I, and how do I judge myself? Did I make a mistake for leaving my job? I actually asked myself for like, several months actually after I started, or. Or did I make a good one? And I think for a lot of these kind of questions and doubts, having past professional experience working at a company is really, really useful to kind of set yourself grounded.

I actually want to ask you about that, but I'll add a couple of things that I also find are major downsides of this life, because it's not all rainbows and butterflies. One is with a paid newsletter especially. But even with a sponsored newsletter, you basically have to get something awesome out every week in theory, for the rest of your life. People are buying an annual plan every day, so that means at least a year you have to write something awesome if you want to stop. But it's hard to stop because as you pointed out, the income is very meaningful. And that's a hard thing to give up. And so I'm not sure exactly the exit path that there is that exists for us where we may have to keep writing something awesome for the rest of our life. But I imagine something will emerge and we'll think of something else that we could do.

Yeah, and it's a really good example because for a lot of companies, and I'm assuming a lot of listeners are working in tech, typical thing is you work hard, you build equity at a company or you build the value of the company, and then you can sell that company and then you can have an accident. You can do whatever for what we're doing. It's really tied to us. So however much or little my newsletter will make, it'll have a value, let's say four or five times the annual revenue as a business. But you cannot really sell it like that and you cannot really walk away. So that makes it unique, it makes it harder to compete with, which is cool. But it does not create that much of an exit path unless you start to build a company around it. Build an organization that can run without you. For example, you know, this is what a lot of book publishing companies. So basically either you build a publishing company where you start to hire people who start to write some of the articles initially and then later more of them, but that's, you know, it's not one person use that anymore. Or you keep doing this and then, you know, until you either stop and then the revenue stops or you might be able to sell it. But it really undervalue.

Yeah, I really don't want to manage people. I don't want to like have employees. And so building like a media company with writers, that doesn't sound too fun. But maybe that's where this goes. That is one route for sure. The other downside, I'll just add, is the fact that you have to write something awesome every week. It's hard to take meaningful time off because if you stop producing great stuff, people leave. And I invented this PTO policy for myself where I take four weeks a year off where I don't do a newsletter, but that means I can't take more than like a week off, usually like two weeks in a row. I don't know, people probably won't care, but it feels like things start to not go great if I just don't keep producing great stuff. So that's, that's another downside. Just while we're on the topic.

Yeah, but a lot of that we're very early. So I think the whole concept of paid news is new. So I think we're going to do a lot of experimentation and also a lot of it. I think you need to figure out what your needs are. So in the first year I did not take a holiday like in terms of. Even when I did, I was writing and you know, it caused a bit of friction with let's say my family and. And now I'm solving it for in a different way. So I am trying to take more time off now and I'm doing it by working ahead with some of the less time sensitive things. But it is tough. So downside we haven't mentioned, but I'm just going to call it out. Is holiday like the great thing? I never felt. Well, I felt A little guilty sometimes, taking holiday, but when I went to Holly, I took it off. When I had my son born at Uber, they gave me a four month paid holiday. I took the whole four months. I just logged off. It was great. It wasn't my company. I was still getting stock. You know, the stock price was independent of mostly what I was doing, just being honest. And that was really, really good. So this might be true, by the way, if you start any business, especially while it's just yourself, it's hard to turn off. And I think most people don't mind. I don't mind, but it gets to you. We should be conscious about burnout as a whole. So you need to solve for that. And I'm starting to solve for as well.

Yep. Okay, enough about the downsides. Overall, it's pretty amazing. Making hundreds of thousands of dollars writing an email once a week slash twice a week. So just to wrap up on that, I'm curious, where do you think this goes long term for you? And then I want to talk about just like what it takes to be successful. But before there, where do you think this goes long term?

I stopped making long term plans because, you know, three years ago you would have asked me what I wanted to do and I was like, I want to be, I don't know, like a manager of managers. And, and then I became one and then, then I would have asked, what, what is my dream? I would have been like, well, it's a stretch, but maybe I want to be a site lead. And I didn't become one per se, but I never thought of, you know, writing a newsletter or now writing a successful newsletter. So I'm kind of going with the flow. I'm, I'm seeing this less, by the way, as a newsletter or creator or creator economy as people like to see it. I see this as, as a business. And I'm trying to put on that business hat like I'm, I'm building a one person business. I want to make it sustainable, I want to make it successful. And I find that this thinking really helps kind of detach as well. I can actually enjoy my weekends as opposed to like, you know, thinking, oh, I need to write this, I need to write that. So I also want to make it work for me. And I'm not going to marry to the idea of like, hey, it needs to be, like, it always needs to be a newsletter, etc right now it is. But you know, where I see as going is, is I'll keep building the business, I'll keep playing to My strength, which is I love talking with people, I love writing on stuff, I love software engineering. So this is a great format, but over time it might shift. So I'm kind of keeping my options open. And what I've learned from this journey is you need to create time to be able for that spark to come. So one of my goals for the next few years is to not spend 50 hours a week on a newsletter, which I'm doing right now, but spend 20 and then maybe take a few weeks off and have that spark come. Because the reality is this newsletter only came because I gave myself six months of unpaid. I'm not looking for work. I didn't answer any LinkedIn emails. And it kind of just. The idea came and the inspiration came and the motivation came.

There's a lot of similarities with my approach. I don't think too far long term. I have no idea what's going to happen. I just kind of take it to I see where pull is coming from and if it feels like an interesting opportunity and something that I'd be excited to work on, I explore it, like the podcast, for example. And on that point I will say, once you find that you can spend maybe 20 hours on a newsletter, I guarantee you'll find more work to fill that gap, because that's what I've been doing.

One last thing to touch on. You said something really important to the poll and I want to double down on that. One of the biggest, best things about doing what we do when you're in charge of your time is you can double down on polls. So when I quit Uber, like I said, my plan was I'll write this book for six months. Two months in, I just put a draft about a really long blog post about mobile engineering. And I got like a lot of messages. Like a lot. Like my. I usually get like used to get like three or four messages on Twitter per day. I got 20 in an hour, people saying, can I read the draft? And I was like, huh, that's interesting. I just felt this pull of like this huge interest of people caring about this. It was this really long blog post about how mobile engineering at scale and someone suggested on a private, you could probably turn this in the ebook. And I was like, oh, that's a good idea because it's a really long blog post. So I said it's going to be an ebook and it'll be pay what you want. And then people start to buy it. And I was like, that's interesting. So I didn't have much else to Do. So I was able to double down and said, like, you know what, for the next two months, I'm going to write this book because it seems there's an interest in it. And I kind of iterated. I turned it into a book that was free for two months, but I got sponsorship. The point was I was able to double down on this pull and same thing with the newsletter. So we're going to talk about, you know, how I got to the first few thousand subscribers. But the point was I was able to double down on something that I felt like, this is super interesting. I never expected. I never expected that people would care about building a large mobile app. You know, more than a few hundred people. Turns out they do. Thousands do.

Let's actually jump to that. Let's talk about just how to get started for folks that are like, this is cool, I want to do a newsletter. Let's talk about just how you got started briefly, and then what you think it takes to be successful in the life of a newsletter person. So how'd you actually get your first thousand subscribers?

Well, I mean, I'll tell the story that is kind of true and people will think it's amazing and I'll tell you the real deal behind it.

Okay, great.

I mean, I announced my newsletter. I told people I'm gonna go full time on this. I had maybe 10,000 Twitter followers and I don't know, like maybe a thousand on LinkedIn or something like that. And people started signing up the next day. I had a hundred subscribers in the first day before I published anything. And within six weeks, when I published my six newsletter, I had a thousand paid subscribers. And this, this sounds like a fairy tale. And if you do this, I guarantee you're. You're not going to get the same results. In fact, you'll. You'll probably see way smaller numbers. What I didn't tell is that there was at least six years of kind of accidental work behind this. I started a blog six years before I actually, I was. I've always been blogging since I graduated. I had this, like, personal blog where I just published all sorts of random things about software engineering. But like, like, it was really, really, like sometimes an app that I published, sometimes there's a problem that I came across. It was just all over the place. And I kind of got fed up with this. The blog wasn't going anywhere, and I was just writing for myself, by the way, but I didn't like how it was just all over the place. And I said, you know what? I'm going to start a blog. It'll be about software engineering and I'll call the Pragmatic Engineer. I bought the domain and I read this blog post from Jeff Atwood, who's the founder of Stack Overflow. And back in 2010 or 2000, I think in 2007, when I was still in college, he had the most popular blog on the Internet for software engineers. It was called Coding Horror. And all the software engineers I knew read it and were drinking was next level wisdom. Every single week, like twice, a few videos a week. Yeah. You read it as well?

Yeah, I used to be an engineer and I was all up in that. And I think Coding Horror came from. Forget the book. But there's a book where that graphic.

There's a book and there's a graphic.

Yeah, yeah, yeah, yeah.

And he wrote a post which really stuck with me for years. He said, how to be famous on the Internet. He said there's three simple steps is one, write a blog post. Two, do this three times a week. Three, do it for two years. And I guarantee if you do this, you're going to be famous. And I always thought it's kind of ironic, but the more I read it, the more I thought he actually means something with it. And when I started this blog, the Pragmatic Engineer, I said, I'm kind of tired of my old blog being all over the place and there's no focus and no one really cares about it. I'm going to do what Jeff Atwood said. I'm going to publish. Okay, it's not going to be twice a week, but like for every two weeks I'm going to publish an article and I'll do it for a year. So I started to do this. I published six blog posts about software engineering. Kind of, you know, going into topics that I care researching and all that. And then I gave up. And I'm saying this because I kind of gave up and I looked at for a few months, but then something interesting happened. I had a huge traffic spike and it crashed my shared hosting at the time. And it came from this site called Hacker News that I never heard about. And people were discussing my posts and they were adding a lot of things and I was like, huh, that's interesting. People care about what I wrote like six months ago.

What was that post, by the way?

It was called a comment is an invitation for refactoring. I wrote my view that if there's a comment in the code, that means that comment should be deleted and you should just refactor the whole thing. And it exploded on Hacker News. Some people called me an idiot. Some people called me absolute wisdom. Like, and it was these two crowds battling it out. And I was like, wow, I actually made, you know, software engineers in Silicon Valley argue about my stuff. Like, I saw some of the karma of people, some really high karma. People were really, you know, going pro or con. So that's when I thought, like, it's just like by writings, some people might read it. It's not a guarantee. And I started to write on that blog, like once every few months, depending on kind of my mood. But I never stopped doing it. And I partially did it. I always hoped that it would get on this site called Hacker News. But by the way, for a while I didn't even know you could submit it. So I never submitted my own things. But the other thing was I just kind of liked it and I kind of had this habit. And over years, like, I had this blog from 2015 for six years I was writing that blog. And in the last year when I worked at Uber on the side, I kind of wrote about my work, like, in terms of the things that I could write about. Like, not about the details that we did, but some of the learnings that I did, for example, distributed systems. And more and more of these posts just started to just pop up on Hacker News. People would either submit it or sometimes when I submitted it, it would just do well. And I was thinking just so people, I started to get this validation. People care about what I write. And to your question of the success of the newsletter. By the time I launched a newsletter, I had a lot of posts that a lot of software engineers read. There was a very famous post about performance management, like how to do performance reviews. I wrote one about the tri modal nature of software engineering salaries where I observed that there's kind of three different tiers that are like, there's big tech and there's like local companies. And I think what happened is when I announced that I'm going to write this newsletter, I also put it on the blog. A lot of people realized that they, oh, I've been reading this Pragmatic engineer. I didn't know. I don't know who is behind it, but I like it. Let me sign up. Like, I do want to get like an email every week instead of the things that were every now and then. So there was years of work. And I wish I could tell you, you know, how to build a successful newsletter. But the best advice I have is still, what Jeff atwood does, except I have less conviction. But if you start writing and you do it regularly, you know, two things will happen. First of all, you're gonna. You write for yourself and you keep improving. You'll be a better writer, that's for sure. If you're lucky or if you're right about stuff, you might start to attract people who think similarly. So, you know, step one is get started. Step two is keep it up. And my suggestion is step two, drift for yourself. Like, the weird thing is, until I started my newsletter, I never thought I would turn this ever into business, but it always felt rewarding. So I never, like, if you're starting out writing a newsletter to do what I'm doing, one day it might work out. But interesting enough, I never even thought that this was an opportunity.

So people listening to this that are thinking about, should I explore this life? I think if you think about your story, you wrote a book, you blogged for a while before this. You worked at Uber for a number of years. In a sense, it comes across a little bit like, man, there's no way I can be successful if that's the background I need to have. I have to have written things and worked at an awesome tech company. What advice do you give folks that are coming to you being like, gerge, should I start a newsletter? Does this make sense for me? Do you need the kind of background that you have? Do you think?

Well, don't forget that when I started, like, my blog, I didn't have any of this. So.

And this is while you were at Uber. This is before you started the newsletter?

It was before, Before I was at Uber. So I was maybe at skyscanner or maybe at sky, but I was even blogging before, so I was talking at conferences before. So my advice really would be, is like, if you're thinking of a newsletter or something similar, start teaching and sharing what you know and what you're observing. This could be a newsletter. This could be a YouTube video. This could be going to a meetup. I actually, 10 years ago, I went to a lot of meetups where I presented ulcers. I met a lot of cool people. I would say, you know, share your knowledge one way or the other, and as you're doing it, you're going to learn a lot more. So what I find this is true when I was a manager, people, you know, we had to set goals. And I told people, there's like two types of goals you can set. One is goal. You know, people set this goal. I want to be promoted the Next thing. Or I want to lead this big project and those are bad goals because it's not in your control. So setting similar. Setting a goal that I want to have a successful newsletter with like, I don't know, 20,000 subscribers. That's a goal where you're not in charge. A good goal is what you can do. So a good goal, for example, is I want to learn this new language in the next year, which I'm going to spend time on.

Or.

Or I want to, you know, leave work at 5pm on Fridays to be home with family. So set those goals that you can control. And this is how actually my blog started. Initially my goal was like, I want to write like once a month. And I did that for a while and I was proud about that. Or I. Whenever I learn something, I actually want to share it every now and then. So I would say set those goals and the rest will come probably again. Like, don't get me wrong, like, I'm not trying to talk people out of doing it, but for me, a lot of this was luck. And the other thing that I would suggest is be curious and look at your professional career as well. One thing that definitely helped me is getting pedigree. If this was somewhat conscious. I come from, you know, a small country, from, you know, a really good university, which no one knows about. But you know, I, I didn't grow up in, let's say, Silicon Valley, so I actually kind of made a subconscious point to try to work my way up. And after I got to, let's say, JP Morgan in London, I was pretty picky of where I would go next. So that's why when Skype came along, I was, this is great. Like, everyone knows Skype. I, I love Skype. And it was the same thing with Uber. So there's especially these days, like a. People would not pay nearly as much attention to me if I worked at Small Parts limited so there's that part as well. So you need to kind of manage some of these things, figure out what you want to do. For a long time I pretty much thought that I just want to climb the corporate ladder and prove that I'm good enough at all these companies. I was just doing all of this stuff on the side. It's interesting how it's now flipped and now doing these things. This is my main thing, which used to be my side project. And I guess one last advice is do some side projects. Like all of this starts as a side project, like at work. No one's really going to appreciate that. You're doing a newsletter or this or that. Try stuff on the side, assuming that you have time or if you don't have time, try to make time. Because I feel a lot of what we're doing is this pre entrepreneurial. And the only way you're going to get these muscles, if you start some.

Small things, you talk about the pedigree being important. I think there's also an even deeper point that you actually need real experience doing real things that scaled and worked and mattered and worked with amazing people to actually build the foundation to write about, share wisdom from. And that's really important. There's a lot of people starting newsletters and tweeting who like, haven't done much and don't have a lot of real life experience to share. And I think that's the core of a lot of what we do, is it needs to be based on real things that have, that worked and that you've learned or that you have access to other people who have learned these things.

I would say that. But you know, one thing that, that I'll, I'll double down on that. That's a really good observation. Is if you actually, if you're serious, like one day I will want to, you know, write a book or a newsletter. It's kind of the same thing. Or teach people about stuff. You know, look at, look at the people that you look up to that, that you actually trust. You know, this, maybe it's me or maybe it's you, but it's more, it's more likely people like Kent Beck, for example. He's the creator of TDD and he's written a lot of books. He's one of my favorite kind of people. I think he's coming up like 50 or 60 if he listens to this. Sorry if I don't want him to make old. But what I love about Ken Beck is he's been in the middle of it. Like he, he has always worked kind of in the industry and then he kind of wrote about it. But for example, he, he was. He invented. I think he invented or he was a co inventor of, of. Was it TDD or Extreme Program? Anyway, one of these methodologies. And then he went to work at Facebook. He kind of took a P. A title cut to be a software engineer. And then he hosted the TDD workshop, a test driven development workshop. And no one showed up at Facebook and Facebook did no testing, which went against all conventional wisdom. And he took that risk joining this company where, you know, he, he could have been like you know, like people would have knelt down to him anywhere else but, but he went to this company where he just wanted to learn and he, he's this lifelong learner, he's, he's right now writing a book. But what I think away from is if, if you want to be someone who people listen to, like, yes, do cool and interesting stuff, push yourself to, to do these interesting things. That's how when I went to Uber in 2016, it was one of the highest regarded places back in 2016. And in 2017 it, it was the other way around. But back in 2016 people were turning down Facebook and Google offers to go at Uber, which we all thought would change the world. So yeah, you know, like you do need to get into those teams that are doing interesting stuff. Prove that you can do that and you'll have a lot more interesting stories to share, that's for sure.

If you had to boil down advice for how to be successful in this life of a newsletter, you have to boil it down to just like one or two key pieces of advice. What would you say?

One is have enough depth in the field, whatever field you do. So this might mean that. I think, I don't want to say that if you don't have experience, don't start from. But it's kind of true. So become an expert, start somewhere somehow before you start because you'll be a lot more credible. I think there's no shortage of reporters and journalists who don't know about stuff, but they can interview people, but that doesn't give anything extra. And I think people feel that. So, you know, I would say choose a field that you're going to be good at and you can start on the side doing this. Assuming you have something you're someone who's experienced in the industry or you have kind of insights, wisdom, observations to share, start doing so in whatever format. You know, I do newsletters, there's actually YouTube. A lot of people are becoming pretty successful on YouTube, sharing their thing. Three, have a cadence and stick to it to some extent because you do need to keep repeating it. And then four, don't be afraid to try out new things. A good example of a person who did these is Steve Yeager. Steve Yeage is. Have you heard of Steve Yeager?

Yeah, he wrote some epic long.

He used to work at Amazon and then at Google and at Google wrote this internal email about platforms, about how Amazon is great at platforms and Google is terrible. And he was really well known at Google because he wrote stuff inside Google. So he's experienced, knows a lot of stuff. And they put Google and he started to do a podcast. It's on. It's on YouTube. You can check it out. It's called Stevie's Podcast. And what he did is every week he recorded an episode and he talked about a bunch of his learnings, a lot of stuff. And he was pretty clear upfront. When he started the first one, he said, like, what I'm doing is I'm going to do this for six months and I'll see if it sticks, see if people care about it or people watch it. Now, this guy had a lot of experience. Really fun. I think it's really fun to listen to. And in the end, you know, it was, I think, successful. It was like, it got to a couple thousand or maybe even 10,000 subscribers, but it wasn't this, like this rocket ship. And I think what he did, he just stopped that for six months. And he's now. He's actually started the head of engineering at sourcegraph. He actually went back in the industry. But what I love about this, you know, it shows that, you know, you cannot guarantee having success, but you can do what. What he did, which is like, you know, start something, do a cadence, see if it sticks. If not, either pivot or. Or do something else. I. I feel the world is kind of about that as well. If you think about, you know, take a step back of, you know, what is a successful newsletter, what is a successful podcast, what is a successful YouTube channel? And it's stuff that's kind of interesting. It's. It's either entertaining or educational, but all of these things you can't really kind of put a finger on. Like if you watch YouTube, you know, Mr. Beast is someone who you probably came across. I actually like watching his videos. I am used how good he does it, but it's not something you can, you know, anyone would have written in a book. So there is a sense of trying to understand what people care about. And a good way to understand is either experiment or observe or just try out stuff.

This is great. I feel like I could boil this down even further from everything you just said, which is build depth in an area, then write a blog post twice a week for two years, and good things will happen, I'm pretty sure.

And here's an interesting thought as well. Just as foreclosure, I was talking with someone on why my newsletter is so successful. It's really successful and I honestly don't know why. And this person told me something interesting. This is a person who Had a really successful YouTube channel with about 200,000 subscribers. So more than my newsletter. And he said this, he's like, what I noticed is you started your blog in like 2015, 2016, and I started my YouTube channel like in 2019 or something like that. And he said on YouTube there's so much quality, there's like super high grade productions, there's like everyone is doing YouTube. And he said, you know what I don't see, I don't see many blogs that are writing in depth stuff regularly. I feel everyone went over to YouTube or TikTok. So there is the other angle of the media medium. And I'm kind of saying this, not say, but you know, it might be an advantage these days, fewer people write because I think a lot of people find it hard and more people will do videos. And you can take advantage of some of these shifts, you know, like which, which might be good or bad. So if you're, if you're going to be a really well known person on YouTube, you might get more people watching you, but you will have a lot more competition. And the last thing is that for me, writing especially with software engineers, it's really efficient because I can scan through it. I don't like YouTube videos especially for learning about stuff because I can't really scan through the whole thing. It just really time consuming. So I think you decide if you want to do, you know, entertainment, which for these podcast listeners, I don't think that's kind of in the question. You're competing with the likes of Spotify, Netflix Education, which is a little bit more dry but it's really useful. Or Edutainment, which is, you know, entertaining, entertaining education. And once you figure that out, either if it's education or edutainment, you can figure out what do to format might work both for the medium and for you. And at the end of the day you need to enjoy it. I personally have learned over time to love writing. I love being in the zone. So for me it's not really work, but it's fun. And once you find that thing, whatever that might be, it just makes it easier.

Gerge it's always so fun talking about newsletter stuff. I don't have many people to talk about this life with. I hope this was useful to people who are exploring this path, thinking about it, or even a different creator kind of path. Just two final questions. Where can folks find you online if they want to reach out or learn more? And how can listeners be useful to you?

You can find me@pragmaticengineer.com There's a bunch of stuff listed there from from the Twitter LinkedIn, my talent collective, some of the companies that I invest in, et cetera. Everything's there and you can also sign up to my newsletter listeners being useful to me. If you work in tech, consider signing up to my newsletter. I mean I always tell people like we're a complimentary newsletter. If you work in product or have interest in product, your newsletter is an awesome choice. With software engineering, engineering management, it kind of goes goes the other way. And it's not just people are telling me like when they're data scientists or even product folks sometimes they get some value out of it. If you know I write this column called the Scoop every Thursday. If you hear of any interesting scoop happening, especially relevant for techies, this might be some changes in the workplace. Like you know your company is just rolling out agile like team at Twitter did. Feel free to ping me. Just search for sending Scoop to the Pragmatic Engineer. I treat everything as anonymous so you can you can tell me interesting stuff. I'm typically interested in the stuff that you might not read about in the traditional media, but we as techies really care about. And finally, if you work at Google and you want to anonymously talk to me, just ping me because I'm one of my next articles will be Google's Engineering Culture. I wrote one about Facebook, one about Amazon and and I tried to talk with mostly software engineers to get a sense of how these companies work from a software engineer and engine manager perspective.

Awesome. I hope this comes out before that post comes out, but if not then enjoy that post. Gerge, thank you so much for being here. This was awesome and maybe we'll do a V2 as things continue to grow.

Awesome. It was great being here. Lenny.

Thank you so much for listening. If you found this valuable, you can subscribe to the show on our Apple Podcasts, Spotify or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.

Com.

See you in the next episode.