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

1. 0:00 – 7:19

   Gergely’s background

   1. GOGergely Orosz0:00

      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- I'm leaving..." Especially in Europe, this is a lot of money to say, well, this will be similar to something, you know, someone in a similar position would have made like 5 or 600K in- in total in the US. But now, I am making more in- in compensation that I made at Uber, and the difference is that now my compensation, well, my earnings are- keep going up as long as the newsletter is growing, so there's no theoretical cap on this. Of course, there's 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 love, and this was at Uber or- or as a software engineer. And I'm now doing stuff that I love and, um, in some strange way, I guess, it even pays better.

   2. LRLenny Rachitsky0:57

      (instrumental music) 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 Gergely Orosz. In a sense, Gergely is the meat 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 Gergely'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 creator route, you'll love this episode. With that, I bring you Gergely Orosz. 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 burn 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. 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 growth 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 analytic cycles, and helping you easily get to the root cause of any issue you discover. Eppo lets you go beyond basic click-through metrics and instead use your North Star metrics like activation, retention, subscriptions, and payments. And Eppo supports tests on the front end, the back end, email marketing, and even machine learning clients. Check out Eppo at GetEppo.com, GetE-P-P-O.com, and 10X your experiment velocity. Gergely, welcome to the podcast.

   3. GOGergely Orosz4:34

      It's awesome. Great to be here, Lenny.

   4. LRLenny Rachitsky4:37

      So I think this is gonna 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, 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.

   5. GOGergely Orosz5:19

      My career started out as what you might consider pretty typical software engineer career. I graduated from high school*, uh, university. I did a computer science degree for, like, a five-year program, so I had a bachelor's and- 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- a small web agency, and then I kind of worked my way up in the industry. So I started off at a consulting company, like, we were just building for other companies. I'm originally from Hungary, so Hungary in- in- in Europe. I then moved to UK, which was a big step up for me in terms of just, you know, getting access to- 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- it's like the New York of- of Europe or even a 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 startup-y 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 in 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 you 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, uh, it, it, we'll, we'll talk about it l- uh, later in the podcast, but I didn't plan, like, this, but I, 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.

2. 7:19 – 8:59

   The Pragmatic Engineer, growth and current subscribers

   1. GOGergely Orosz7:19

   2. LRLenny Rachitsky7:19

      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?

   3. GOGergely Orosz7:30

      Well, just today I checked, and it's at 189,000 subscribers. It's the, 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, which is incredible because, I mean, these numbers are huge. If you're, if you're listening, you're probably thinking, "Wow," and that's how I feel (laughs) every day as well. But I've been writing a blog for, for many, many years, and, and, 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 50,000 subscribers, and then the next five months or six or seven months, it, it went up by another 100-and-something thousand subscribers. This 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, are big. And so this is a paid newsletter as well, so there's a free version and a paid version, and there's thousands of people paying for the newsletter. It's a single-digit percentage, but it's a very, very healthy, uh, one, and again, it just beat all my expectation. And I guess we're in similar boats 'cause our, our newsletter set up, yours and mine, is somewhat similar. We, we have plenty of differences as well, but I make most of my revenue from subscriptions, and I, I don't do sponsorships or ads in the newsletter. So it's kind of like the 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, in more depth.

3. 8:59 – 10:55

   Compensation with a subscription-based newsletter vs. his salaried position at Uber

   1. GOGergely Orosz8:59

   2. LRLenny Rachitsky8:59

      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.

   3. GOGergely Orosz9:09

      Yeah. Yeah, so I mean, I'll, I'll share little numbers of, of my cushy tech job at Uber 'cause, so you know, I was in Europe, uh, and European tech salaries or tech, I'll say total compensation 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, there's regional differences, and this is true for, for big tech as well. Uber was a good example in this. But in my best year at Uber, I made about, like, 320 or $330,000 in total compensation. This was after Uber went public, so it's, it includes the, the stock, the, 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, am I crazy because I'm, I'm leaving..." especially in Europe, this means, this is a lot of money. They say, "Well, this will be similar to something," you know, someone in a similar position would have made like five or 600K in total in the US. So I walked away from that, and I was pretty sure that I'll, 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, in compensation that I made at Uber, and the difference is that now my compensation, well, 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, or as a software engineer. And I'm now doing stuff that I love, and, um, in some strange way, I guess it even pays better. I mean, part of it is just luck. Part of it is situational. I think we're gonna talk a bit more about this, but this was very, very surprising and very unexpected for me.

4. 10:55 – 23:10

   How the onset of Covid and layoffs at Uber prompted Gergely to start his newsletter

   1. GOGergely Orosz10:55

   2. LRLenny Rachitsky10:55

      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 the, 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 we 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 (laughs) and one of them can fire me, and many do every day, but it's, feels like safer than at a tech job where, like, one person can't decide.

   3. GOGergely Orosz11:50

      Oh, yeah.

   4. LRLenny Rachitsky11:51

      Yeah. And then the other piece is, yeah, assuming it 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.

   5. GOGergely Orosz11:57

      That is really cool. So I, 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, uh, you know, when I wrote a really good article that resonated with people, you know, so- 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 y- you just don't get at- at, uh, in corporate. 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- 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, f- for doing something awesome, you can just get, give yourself raises, especially 'cause this is just like you, mine is also a one-person business right now.

   6. LRLenny Rachitsky12:49

      Yeah. Okay. So you're at Uber. You're making hundreds of thousands of dollars writing code.

   7. GOGergely Orosz12:55

      (laughs)

   8. LRLenny Rachitsky12:55

      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, uh, not. And so I'm curious, what got you to leave that job and explore writing and get to this writing path?

   9. GOGergely Orosz13:20

      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- 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 headquartered 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 (laughs) or sometimes, you know, 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- 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- I negotiated and they basically doubled my compensation. I- I- I was like, "Oh- oh, wow, this is... Like let- let's just stop." So I knew about Silicon Valley compensation, but I- I assumed that in Europe you're not gonna get this. But Uber was getting closer, something closer to that. So I- 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 will go public. Although I kind of suspected because they contacted me to build a payment team to do SOX-compliant payment system and you need a SOX-compliant payment system if you wanna go IPO. (laughs) So-

   10. LRLenny Rachitsky14:44

       That's funny. It reminds me at Airbnb there's all these people trying to figure out, "When are we gonna go public?" And then there's like, "Oh, there's a team working on SOX stuff and Sarbanes-Oxley. Oh, this is good." (laughs)

   11. GOGergely Orosz14:55

       Yeah. So- so anyway, I- I- I said like, "All right, well this is a massive lottery ticket if- 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- I'm in Europe where we're kind of used to not seeing any returns on, on stock. So European pe- uh, software engineers will not value stock as much 'cause they just haven't seen success stories. So I told myself, "Look, if 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've forgotten about this, but four years later, almost on the dot, uh, COVID starts and it really hit super hard. We're laying off people. We- we- we had to lay off 20% of the engineers. I was a- I was- I- I was already managing a group of 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 like, you know, "What am I doing here?" Like, I looked ahead, Uber was gonna have a really just bad year. I'm gonna have to manage morale and up- up- up- up- 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 'cause it made no sense with the economic reality. So I re- I- I thought back like, "Hmm." 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, 'cause I- I haven't done that before, but it kind of runs in the family. My brother's owned 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, uh, so he's, he... Like, you know, I kind of, I- I'm... Through him, I- I know what startup life is and I- I felt I never did that I was always with the big companies. So my plan was all right, leave Uber, raise money and do something up on platform engineering. I saw Uber... (laughs) A- 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 is almost custom, our experimentation system, our container, you know, the- the- the way we kind of automatically set that up. A l- a lot of the engineering stuff. So a lot of U- Uber alumni just leave and whatever they saw there, they would just build it for the world to use, because no other company really does what Uber does 'cause it makes no sense but a lot of them will- will pay for it. That was the plan. But before I- I- I, well let's do this, I wanted to finish a book. I'd been writing this book for, it was, uh, 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- 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- in terms of I was like writing on- on Twitter, on my blog. I accidentally published a- a book called Building Mobile Apps That Scale. I just kind of did it for a few months. And the weird thing was that my plan was, uh, that I'm gonna just not make any money. And this book, Building Mobile Apps That Scale, and another book that I published about tech resumes, I just wrote these in a- in a few months, they started making money. They- they made about $100,000 in the first year and I was like, "Hmm, that's interesting. People are buying my books." And I self-published it through 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, I asked myself, why do I really wanna do it? 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 was, felt a bit too abstract. I didn't like the being in the meetings not doing, not doing, you know, like, the, the, the work. What I really liked is when we had a small team and we had this really big kind of 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 a startup. I kind of hope, was hoping to recreate this feeling. And the other thing, honestly, was money. You know, this was in 2021 before the market crashed. You know, just doing the math, like if you're, if you found the company, you know, and I'll be the 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 billion is still 50 million. After you pay taxes, you still have leftover and, you know, 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 wanna kind of share what I know with people, do YouTube videos and kind of write books. (laughs) And I was thinking to myself, like so hold on. Like I would go off and do this for like 10 years, 'cause that's how much you need to plan to do it. I need to stop doing what I'm doing right now because, uh, I, I, 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 wanna do it again. So it's reminding me of the story of the, of this fisherman. I, I think that there, there's, there's one that goes online that does the same thing of like, you work really hard to do what you're doing right now. So I decided like, you know what? Let me just try giving this a go. Like, I really like writing.

   12. LRLenny Rachitsky20:14

       Wait, wait, what's the story of the fisherman? I think I know which you're talking about, but the-

   13. GOGergely Orosz20:17

       The story of, of the fisherman is, is that in Mexico, an American businessman sees a fisherman who's just chilling, fishing, and he asks him, like, "Hey, what, what are you doing, like, uh, all day?" He's like, "Well, I, I kind of fish for three hours. I hang out with my family. I, I, I then chill and I sleep in every Saturday and Sunday." He says 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 behind of all those people, then sell your, your fishing company." He's like, "Okay, so and, and then what?" "And then you can actually buy an island and you can just fish for three hours. You can sleeping on Saturdays (laughs) and, and sleep on Sundays." So I was kind of thinking like, look, I have savings. I don't have like huge, but I, I have it for... I can still take a risk. So let, 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 gonna be making a living or there's some people who actually like this excitement, but I, I didn't like it. Like, I didn't know if today I'm gonna be, be making like 50 d- 50 bucks or 10 bucks or 300 bucks. So I was like, hmm, interesting. There's this paid newsletters which I've been thinking about, and 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, 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... 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 says, "Screw it. I'm gonna take a risk." It's a bit of a more professional risk and, and maybe a financial one as well. I'll announce that I'm gonna start a paid newsletter. Every week I'm gonna write something really in depth about software engineering. It's gonna start next week. And I told myself that I'll... and 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, but for six months I'm gonna give it my all. You know, like it's, it's basically like a startup. So I told her like, um, and my family that it's gonna be a lot of work. I know 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, and that's how it went from leaving Uber to start a venture funded startup to starting to write full-time.

   14. LRLenny Rachitsky23:05

       Awesome. And we're gonna talk about what advice you have for folks that are thinking about starting something like this at

5. 23:10 – 25:41

   What he did immediately after leaving Uber

   1. LRLenny Rachitsky23:10

      the end. What was the period between leaving Uber and starting the newsletter?

   2. GOGergely Orosz23:14

      It was pretty much a year, a little bit less than a year. Might have been like, 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, it was really stressful. So it was the first time I, I, I didn't lay anyone off, but people on my team were laid off. I wasn't told who's gonna be laid off, but it's, it was just really stressful. I mean, it's-

   3. LRLenny Rachitsky23:32

      Yeah.

   4. GOGergely Orosz23:32

      It's weird, you know, in, in a sense that the people who were let go obviously worse for them, but I, I still felt terrible and I, I just didn't feel that good about it. I, I think this was the breaking point. Like I, I just, this was the point where I realized that it's not a family, which is weird 'cause it never was, but it kind of felt family-like, but it's just a corporate and I'm just a number and, uh, you know, this could happen to me again. So I think I, I, 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 or managers than me, they got let go 'cause they were in, in the wrong team. So this was April, and in July I went on holiday and like two weeks and I just realized like, I, I, I just, I need to leave and, and I should... And I really had the urge to do somewhere where I'm in charge. You know, 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.

   5. LRLenny Rachitsky24:27

      (laughs)

   6. GOGergely Orosz24:27

      But when I was promoted into, into management and it were... it wasn't promoting into it 'cause it was a side step, but I didn't get salaries or anything, but it, it, you know, it still feels like a promotion. They only promote the people who are only let people transition who are, are considered pretty good. I felt this would be a big deal. I'm now 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, if someone was underpaid, then I couldn't do anything except complain for HR for, for six months and hope that they do something. So it was pretty frustrating 'cause I, I didn't feel in charge in the sense that I didn't have decision-making powers. And the reason I wanted to do startup is I decided, like, I liked being a manager, but I did not like how I was not in charge and I couldn't take, like, you know, corporate for, for what's telling us to do stuff. And then (laughs) we were telling them, "No, that's BS. We can't... I, I don't wanna 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 wanna do or I, I don't wanna do. The, the short of it is I decided to leave in July. Uh, I, I, uh, we have longer notice periods in Europe so I, I s- I served a longer notice period and then kind of left. But it was a year after the decision.

6. 25:41 – 35:08

   The day-to-day of writing a newsletter

   1. GOGergely Orosz25:41

   2. LRLenny Rachitsky25:41

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

   3. GOGergely Orosz25:59

      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, I upped it to two. So I now promise people two posts a week. There's, uh, the 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, I'll say two on, on, on average. But the s- the second one came a, a lot later. But initially, you know, in the first few months, I was like, all right, I have this, like, one post per week and it, and it needs to be good. And it was interesting because you, you would think writing a post a week is, is not a big deal. Like, it's, it's, it's easy. You know, like, it's, it's, it's, uh... As, as you said, let's say you're making 300K just writing one post a week. But it actually bec- i- 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 'cause w- why would people pay for something that is out there already or, or well known? Then I need to write up, uh, 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 a editing phase where I have a, I work with an editor who kind of helps make sure that it, 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 S- 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, on parallel things at the same time, and I was often, like, ru- running against the deadline. I, I was barely finishing it, which is not what I was expecting initially. So the first few months I, I feel was a bit more stressed. But again, I, I c- the good thing is I cleared my calendar. So I said like, "I'm, I'm not talking with anyone. I'm, I'm just doing this." So in that sense, it 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 actual, uh, like, in-depth. You look at The Washington Post or New York Times, search for their name and look at the articles that they write, and they're gonna be longer articles, they have like one a month. Like, like, seriously. Like, you look at the investigative journalists, they, they might even have less 'cause it... And, you know, 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, you actually write a lot of original stuff," 'cause a lot of my emails are, are about like 5,000, 6,000 words, which, which is considered pretty long.

   4. LRLenny Rachitsky28:32

      Yeah. When you said that people listening might be like, "Oh, when e- 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-"

   5. GOGergely Orosz28:44

      (laughs)

   6. LRLenny Rachitsky28:44

      "... write one good thing a week?" So I think there's both sides to it. And it's-

   7. GOGergely Orosz28:48

      Yeah.

   8. LRLenny Rachitsky28:48

      ... 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?

   9. GOGergely Orosz28:58

      I write every post over multiple weeks, most of them. S- some of them I, 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, the Thursday that is the, The Scoop, which actually is a lot, lot easier for me to write, interestingly enough. And, and my cadence is that on Monday I, I, I finish up the, the last of, of the post that goes out on Tuesday. It's a small edit, but it's already done pretty much. So it's, 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 gonna be future posts. On, on Wednesday, it's kind of my, my free day in between where I... Uh, it's interesting 'cause what, what, what I feel is when I don't have pressure, I tend to not do much stuff, which might just be my mind saying, "You just need to chill." May- maybe that's it. But e- one thing I miss from the corporate world, and, you know, if, if you're listening and you're in a job and you're thinking, "Oh, Gergely's job is so amazing," one thing that I liked and I really miss about working at Uber is I actually had a schedule. (laughs) This is weird. I hated it back then. But I was t- I, I, I needed to do these things, and whenever you have a pressure, you do it. And this works with my newsletter. Uh, I, I put in a second post newsletter, 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, the next newsletter for, for Tuesday. So almost every day except for Wednesday, I have a strong pressure to write, which when people ask like, "Gergely, how do you write so much?" 'Cause I- I did the maths and I wrote like four or five books worth of content just last year.

   10. LRLenny Rachitsky30:36

       (laughs)

   11. GOGergely Orosz30:36

       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 the- th- they have expectations of me. And so-This is (laughs) how it's done. Like if you, if you wanna write a book, the easiest way is go to publisher and sign a contract. Not because of the money. In software engineering, you're not gonna get much. A little, like, $5,000 or something like that. D- That's what I was offered i- initially. But it's the pressure. Like, you absolutely should go to a publisher or, or, you know, like have some external, someone to hold you accountable, and then you'll get it done. And I'll, I'll, I'll, I'll let you in on another kind of, you know, secret, or not so secret.

   12. LRLenny Rachitsky31:16

       Do tell.

   13. GOGergely Orosz31:16

       In my mind, when I started n- using it a year ago and this crossroads, like, "I wanna write this book," which I think will be a great book, The Software Engineer's Guidebook. I, I feel, you know, it'll be my kind of, you know, summary of, like, m- l- my last 10 years of what I have to share as, as advice. But I was worried that it's, 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 kinda write some posts that will be part of the book? And then the book will just kind of come together partially." And I ki- I've kinda been doing that. I haven't been to- telling people, but some of the posts are gonna be th- no- not, not exactly, but they're the ideas. They're, I have this chapter and I have this list, like, "Have I written about this topic in a newsletter?" And I got... You know where I got this idea from? There's a, the book, Three Musketeers. You know, the...

   14. LRLenny Rachitsky32:10

       Mm-hmm.

   15. GOGergely Orosz32:10

       From Alexandre Dumas, of course.

   16. LRLenny Rachitsky32:12

       Yeah.

   17. GOGergely Orosz32:12

       Yeah. And d'you know how it was written?

   18. LRLenny Rachitsky32:15

       I don't.

   19. GOGergely Orosz32:16

       So he, 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, we, we need you to write something that our readers will want, but we want so that they will buy the, 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, is really long. And I was like, "Hold on, if he could do this, then this is kind of a good strategy." Like, he was writing it 'cause he just needed the money. Like, that's all. And then he wrote a really good book on, on the way. So one big learning for me from newsletters in, I would, I would argue that you can use this not just for newsletters, but any business that you do. You know, if you're gonna go out and start a, a new business, you'll probably have some ideas and, uh, it, it's not just gonna be a newsletter. There's gonna be a fun- bunch of other things. If you put in ways that you have to do certain things, you know, p- put in constraints for the things that you need to do, and then you're, you're gonna 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, I, 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 started to work for myself, it, it just went out the window. Like, the almost 15 years of, you know, being this, like, star employee who really wants to do well, I, I would find myself upset at myself for not, you know, just kinda wasting my day. But I fixed it by, (laughs) by telling people, "You're gonna get this every week." And now I have to do that. I just have no choice.

   20. LRLenny Rachitsky33:51

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7. 35:08 – 41:19

   Tips for productivity

   1. LRLenny Rachitsky35:08

      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 c- having to create your own structure. I had the same exact problem when I started this thing, like, in, 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've found to help you stay productive and focused, because there's Twitter, there's Instagram, TikTok. There's all these things (laughs) 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 and get things out the door two posts a week, which is a lot of work.

   2. GOGergely Orosz35:49

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

   3. LRLenny Rachitsky36:46

      Yeah, love that app.

   4. GOGergely Orosz36:48

      ... uh, and...

   5. LRLenny Rachitsky36:48

      Also-

   6. GOGergely Orosz36:48

      Yeah, investor-

   7. LRLenny Rachitsky36:49

      ... investor, disclaimer, but I love it.

   8. GOGergely Orosz36:51

      Yeah. And I found it helpful the idea of, like, focus time and then it turned on. But it might just be me, but after a while I kind of, like, get used to these things and I find them 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 have 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 like super focused. So like when I have this external thing and I know that there's no way I can... I need to focus on, you know, 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 Mac, so on the hosts file I just kill all LinkedIn, Twitter, Facebook, whatever sites. So I just cannot reach it. Like, 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 and 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 that's consistently worked. The interesting thing is that 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.

   9. LRLenny Rachitsky38:39

      Awesome. That's a really cool trick. The hosts file trick. So that's not like 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 being able to go to the site. That's awesome.

   10. GOGergely Orosz38:59

       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... And even if you're not, you can look it up in the hosts file. When you override your hosts file, you can actually block things, what you're doing. I did this because I wrote a script where I need to run the script and I need to run through the script again to unblock it. And it's kind of cool because I put it together for myself. So I usually find that the tools that other people use, maybe this is just me or maybe it's the 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 work the best for me. But as you said, there's a bunch of really good tools. So my advice to people would be, you know, 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

   11. NANarrator40:07

       Yeah.

   12. GOGergely Orosz40:07

       Telling you this, but I really liked how they keep evolving as well to do like 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 like... I'll do one last thing on Centered. Again, I have no affiliation. 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.

   13. LRLenny Rachitsky40:37

       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 worked best for you?

   14. GOGergely Orosz40:55

       Yeah. And the simple thing start a 20-minute timer and you say, "For 20 minutes I need to focus 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 a charm. Once I decide to actually do it.

   15. LRLenny Rachitsky41:13

       Well, it's cool Centered does that for you and it has music and all the things.

   16. GOGergely Orosz41:17

       Yeah.

   17. LRLenny Rachitsky41:17

       Yeah, so I like that a lot. Awesome.

8. 41:19 – 43:15

   Gergely’s favorite parts of entrepreneurship

   1. LRLenny Rachitsky41:19

      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.

   2. GOGergely Orosz41:27

      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 focus time. Now I actually have the opposite. I usually have a lot of focus time and I have very, very few meetings or things. And even now like I kind of get like a little bit cagey, like, "Oh, I have this one meeting in the whole day." So I like how it's flipped.

   3. LRLenny Rachitsky41:54

      Yeah. (laughs)

   4. GOGergely Orosz41:56

      It's kind of like manage your time to make your time. So 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. You know, 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, you know, 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.

   5. LRLenny Rachitsky42:47

      Plus one on both those. I have a rule of no meetings before 3:00 PM 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-... 11:00. I just, like, can't do anything (laughs) 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.

9. 43:15 – 50:39

   The downsides of solo work

   1. LRLenny Rachitsky43:15

      Okay, opposite, what are some of the most surprising downsides and kind of sucky parts of this path that you've taken?

   2. GOGergely Orosz43:24

      Well, one is obviously it's lonely. So I- I- I do miss... I had a really good team at Uber. And it wasn't just the team, it was the people. I liked, like, you know, everyone has different views on remote work. I actually didn't en- I didn't enjoy remote work as much because I just liked hanging out with people. I- 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 with them. And obviously sometimes it was annoying 'cause I wanted to get work done, but for the most part I- I miss it more than I have. And so I- I miss not having that. I kind of compensate for that by working in a shared workspace, like a sh- shared office, which is a techy workspace. So everyone needs to work in tech. So I actually get to say hi to people and- and have a little small, small, small talk. The structure is weird 'cause I felt really guilty for the first few months 'cause I felt that at Uber I was more productive 'cause I had to be. Like, I- I- I was doing so many things. Like, in a day, you know, I would ha- I would start my day let's say at 9:00 or at 8:30 and I finished it up at, I don't know, like 6:00 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- 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- 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, 'cause it- it's a very small community. And even within the community, I feel in the, the newsletter community, it's- it's different. You're all running your own business and there is some level of competition. So you might not... Because it's- it's a little bit of a tension economy as well, you know? Like, people are not gonna subscribe or pay for ten different, or ten newsletters on the same topic. So that, that- that makes it a little bit more... You know, it's, 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- 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 up a bunch of stress that I- I didn't expect. And I'm- I'm- I'm a successful newsletter. Like, I- I think my success is, is quite rare. You know, there will be one or two, or- 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. A- 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- 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- 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.

   3. LRLenny Rachitsky46:33

      I actually want to ask you about that. But I'll add a couple things that I also find are major downsides of this life, 'cause 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. E- 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, 'cause 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 might 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 (laughs) that we could do.

   4. GOGergely Orosz47:19

      Yeah. And it- it's, it's a really good example, 'cause for a lot of companies, and, you know, I- I'm assuming a lot of listeners are working in tech. Typical thing is you work hard, you build equity in a company or you build the value of the company, and then you can sell that company and then you could have an exit and you can do whatever. For what we're doing, it's really tied to us. So however much or little my- 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's, that- that makes it unique, it- it makes it harder to compete with, which is cool. But it does not create that much of an exit path unless you- you start to build a- 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 you either 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 a one person newsletter 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- to sell it, but it'd really undervalue.

   5. LRLenny Rachitsky48:24

      Yeah. I- I really don't want to manage people. I don't want to, like, have employees. (laughs) 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- 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- 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.

   6. GOGergely Orosz49:09

      Yeah. But a lot of them were very early. So I think the whole concept of paid newsletter is, is new, so I think we're gonna do a lot of experimentation. And, 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, uh, or o- even when I did-

   7. LRLenny Rachitsky49:25

      Yeah, same.

   8. GOGergely Orosz49:25

      ... I was writing. And, and, you know, it, it caused a bit of friction with, uh, let's say, my, my family and, and now-

   9. LRLenny Rachitsky49:32

      Mm-hmm.

   10. GOGergely Orosz49:32

       ... uh, I, I, I'm solving it for, uh, in a different way. So I am planning to take more time off now, and I am pl- uh, I'm doing it by, by working ahead with some of the less time-sensitive things. But it is tough. So, uh, uh, downside, uh, we haven't mentioned, but I'm just gonna call it out, is holiday. Like, the, the great thing, uh, I, I never felt... Well, I felt a little guilty sometimes taking holiday, but when I went to holiday, I took it off. Wh- when I, 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, that was really, really good. So this might be true, by the way, if you start any business, especially while it's, it's just yourself, it's, it's, uh, it's hard to, to turn off. And I think most people don't mind, I don't mind, but it gets to you, you know? Like, we should be conscious about burnout as a whole, so y- you need to solve for that. And I'm, I'm, I'm starting to solve for that as well.

   11. LRLenny Rachitsky50:30

       Yeah. Okay, enough about all the downsides. Overall, it's pretty amazing making-

   12. GOGergely Orosz50:35

       It is.

   13. LRLenny Rachitsky50:35

       ... hundreds of thousands of dollars writing an email once a week slash twice a week.

   14. GOGergely Orosz50:38

       (laughs)

10. 50:39 – 54:30

    Why Gergely stopped making long-term plans

    1. GOGergely Orosz50:39

    2. LRLenny Rachitsky50:39

       So just to (laughs) wrap up on that, um, I'm curious, where do you think this goes long term for you? And then I, and I wanna talk about just, like, what it takes to be successful. But before there, where do you think this goes long term?

    3. GOGergely Orosz50:49

       (laughs) I stopped making long-term plans because, you know, three years ago, you would've asked me what I wanted to do and I was like, "I want to be, I don't know, like, an, uh, like a, a manager of managers," and then I became one. And then, then I, if you would've asked me, "What, what is my dream?" I would've been like, "Well, it's a stretch, but maybe I wanna be a site lead." And I didn't become one per se, but I, I never thought of, you know, writing, uh, 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, 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 wanna make it sustainable. I wanna make it successful. And I find that this thinking really helps me 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, I need to write that." So I also wanna make it work for me. And I'm not gonna marry to the idea of like, hey, it needs to be... Like, it always needs to be a newsletter, et cetera. R- right now it is, but, you know, wh- where I see this going is, is l- I'll keep building the business. I'll, I'll keep playing to my strength, which is, I, I love talking with people. I love, uh, writing ... I love software engineering, so this is a great format. But over time, it, it, it might shift. So I'm kind of keeping my, my options open. And what I've learned from this journey is, you need to create time to, 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 'cause the reality is this newsletter only came 'cause I gave myself six months of unpaid, n- 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.

    4. LRLenny Rachitsky52:36

       There's a lot of similarities with my approach. I don't think too far long term. I have no idea what's gonna happen. I just kinda take it to... S- I see where a pull is coming from, and if it feels like an interesting opportunity and something that I'd be excited to work on, I, 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 (laughs) fill that gap because that's what I've been doing. But, uh-

    5. GOGergely Orosz53:02

       Yeah. And one-

    6. LRLenny Rachitsky53:03

       ... but that's... Yeah.

    7. GOGergely Orosz53:03

       ... one last thing to touch on. You said something really important with pull, and I wanna double down on that.

    8. LRLenny Rachitsky53:08

       Mm-hmm.

    9. GOGergely Orosz53:08

       One of the, 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 pulls. 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, am I... I, I usually get, like... Used to get, like, three or four messages on Twitter per day.

    10. LRLenny Rachitsky53:33

        Mm-hmm.

    11. GOGergely Orosz53:33

        I got 20 in an hour. People saying, "Can I read the, the draft?" And I was like, "Huh, (laughs) that's interesting." I, 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, on a private message, "You could probably turn this into an e-book." And I was like, "Oh, that's a good idea 'cause it's a really long blog post." So I said, "It's gonna be an e-book, and it'll be pay what you want." And then people started 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 gonna write this book 'cause it seems there's an interest, uh, in it." And, uh, I kind of iterated. I, I, 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- we're gonna talk about, you know, how I got to the first few thousand subscribers. But the point was, I was able to double down on, 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.

11. 54:30 – 1:04:48

    How to get started writing a newsletter

    1. GOGergely Orosz54:30

    2. LRLenny Rachitsky54:30

       Let's actually jump to that. Let's talk about just how to get started for folks that are like, "Hmm, this is cool. I wanna 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?

    3. GOGergely Orosz54:48

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

    4. LRLenny Rachitsky54:56

       Okay, great.

    5. GOGergely Orosz54:57

       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 1,000 on LinkedIn or something like that.

    6. LRLenny Rachitsky55:06

       Mm-hmm.

    7. GOGergely Orosz55:06

       And people started signing up the next day. I had 100 subscribers in the first day before I published anything.And within six weeks, when I published my sixth newsletter, I had 1,000 paid subscribers. And this, this sounds like (laughs) a fairytale. And if you do this, I guarantee you're n- you're not gonna 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 re- really, like, sometimes it was about an app that I published, sometimes it was a problem that I came across. It was just all over the place. And I kind of got fed up with this. It, it, it... 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, "Do you know what? I'm gonna start a, a blog. It'll be about software engineering and I'll call it The Pragmatic Engineer." I bought the domain and I read this blog post from, um, Jeff Atwood, who's the founder of Stack Overflow. And back in 2010 or twen- 2000... I think in 2007 when I was still in college, um, he had the most popular blog on the internet for software engineers. It was called Coding Horror and all the software engineers that I knew read it, like, and were drinking it. Like, it was, it was like next level wisdom every single week, like twice or three times a week.

    8. LRLenny Rachitsky56:27

       I was reading it.

    9. GOGergely Orosz56:27

       Yeah. You read it as well?

    10. LRLenny Rachitsky56:29

        Yeah. I used to be an engineer and I was all up in that and I think Coding Horror came from, uh... I forget the book, but there's a book with that graphic showed-

    11. GOGergely Orosz56:36

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

    12. LRLenny Rachitsky56:38

        Yeah, yeah, yeah.

    13. GOGergely Orosz56:39

        And, and he wrote a post which really stuck with me for years. He said, "How to be famous on the internet." He said like, "There's three simple steps." He says, "One, write a blog post. Two, do this, like, three times a week. Three, do it for two years. And I guarantee if you do this, you're gonna 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 gonna do what Jeff Atwood di- said. I'm gonna publish... Okay, it's not gonna be twice a week, but I'll like... For, for every two weeks, I'm gonna publish a, a, 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 cared or researching and all that. And, and then I gave up. (laughs) And I'm, I'm saying this because I kind of gave up and I left it for, for a few months, but then something interesting happened. I had a huge traffic spike, and it crashed my, 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 post and they were adding, well, like a lot of things and I was like, "Huh. That's interesting. People care about what I wrote, like, six months ago."

    14. LRLenny Rachitsky57:49

        What was that post, by the way?

    15. GOGergely Orosz57:50

        It was called A Comment is an Invitation for Refactoring.

    16. LRLenny Rachitsky57:54

        Hmm. Cool.

    17. GOGergely Orosz57:54

        I wrote my, my view that if there's a comment to the code, that means that comment should be deleted and you should just refactor the whole thing.

    18. LRLenny Rachitsky58:01

        Mm-hmm.

    19. GOGergely Orosz58:01

        And it exploded on Hacker News. Some people called me an idiot, some people called me th- absolute wisdom. Like, and it was like 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, you know, karma of people, some really high karma people were really, you know, going pro or con. So that's when I thought like, "Interesting, like, my writings, some people might read it. It's not guaranteed." And I started to write on that blog like once every few months, d- depended on kind of my mood, but I, I never stopped doing it and I partially did it, I always hoped that it would get on this site called Hacker News. But I... By the way, for a while, I didn't even know you could submit it, so I never submitted (laughs) my own things. But the other thing was I just kind of liked it and I kind of had this, 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, I, I... 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, 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 that people care about what I, what I write. And to your... To, to the question of the success of, of the newsletter, by the time I launched the newsletter, I had a lot of posts that a lot of software engineers read. I... And there was a very famous post about performance management, like, h- 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 gonna 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's behind it, but I like it. Let me sign up. Like, I, I do want to get, like, an email every week in- instead of the things that were every now and then." So, there was years of, 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, 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... And you write for yourself and you keep improving, you'll, 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, is keep it up, and my suggestion is step three, do it for yourself. Like, the weird thing is until I started my newsletter, I never thought I would turn this ever into business. But it w- it always felt rewarding so I never... (laughs) Like, if, if, if you're starting out writing a newsletter to, to do what I'm doing one day, you know, like, it might work out. But interesting enough, I, I never even thought that this was an opportunity, so...

    20. LRLenny Rachitsky1:00:48

        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, "Gergely, should I start a newsletter? Does this make sense for me?"Do you need the kind of background that you have, do you think?

    21. GOGergely Orosz1:01:20

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

    22. LRLenny Rachitsky1:01:25

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

    23. GOGergely Orosz1:01:28

        It, it was before, before I was at Uber.

    24. LRLenny Rachitsky1:01:30

        Mm-hmm.

    25. GOGergely Orosz1:01:30

        So it was, I, I was maybe at Skyscanner or maybe at Sky, but I was even blogging before, so I was talking at conferences before. So my, my advice really would, 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 meetup. I actually, 10 years ago, I went to a lot of meetups where I presented all sorts of... 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 gonna learn a lot more. So what I find, uh, this is true when I was a manager, (laughs) people, you know, we have to set goals, and I told people, "There's, like, two types of goals you can set." One is goal... P- p- you know, people will set this goal, "I want to be promoted the next, uh, thing," or, "I want to lead this big project." And those are bad goals because it's not in your control. So setting... Similar to 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 gonna spend time on work," or, "I, I want to, you know, leave, uh, work at 5:00 PM on Fridays to, to be home with family." So set those goals that you can control. And this is how actually my, my, you know, my, my block started initially. My goal was like, "I want to write, like, once a month." And I did that for a while, and I was, I was proud, uh, proud about that. Or I, when- whenever I learn something, I actually want to share it every now and then. So I would say set those goals and, and the rest will come probably. Uh, again, like, don't, don't get me wrong, like, I, 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. I- if this was so- somewhat conscious. I, I come from, you know, a, a small country, from, you know, a really good university, which no one knows about, but, you know, I, 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, in London, uh, I was pretty picky of where I would go next. So that's why when Skype came along, I was like, "This, this is great." Like, everyone knows Skype. I, I, I love Skype. And s- it was the same thing with Uber. So there's, especially these days, like, a, a lo- people would not pay nearly as much attention to me if I, if I worked at, you know, Small Parts Limited. So there's that part as well. So you need to kind of manage some, some of these things, you know, 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 those, this all, stuff on the side. It's interesting how it's now flipped. I'm now doing these thing, this is my main thing, which used to be my side project. And, I guess one, one last advice is do some side projects. Like, all of this starts as a side project. Like, uh, uh, at work, no one's really gonna appreciate that you're gonna- doing a newsletter or this or that. You know, try stuff on the side, assuming that you have time or, or if, if you don't have time, try to, to make time, 'cause I, I feel a lot of what we're doing is, is pretty entrepreneurial, and the only way you're gonna get these muscles if you, if you start some small things.

    26. LRLenny Rachitsky1:04:31

        You talk about the pedigree being important. I think there's also an even deeper point that you actually need, like, real experience doing real things that scaled and worked and mattered and worked with amazing people to actually build a foundation to write about, share wisdom from, and that's really

12. 1:04:48 – 1:06:59

    Key advice on building a successful newsletter

    1. LRLenny Rachitsky1:04:48

       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.

    2. GOGergely Orosz1:05:05

       I would say that, but, you know, o- one thing that, that I'll, I'll double down on it, that's a really good ob- 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, lo- look at, look at the people that you look up to that, that you actually trust. You know, there's... May- maybe it's me a bit 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, 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. Uh, if he listens to this, sorry, if... I, I don't want him to make me seem old, but what I love about Kent 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, uh, uh, uh, e- either... Was it TDD or Extreme Programming?

    3. LRLenny Rachitsky1:05:56

       Mm-hmm.

    4. GOGergely Orosz1:05:56

       Anyway, one of these methodologies. And, and then he went to work at Facebook. He kind of took a, a, a, a title cut to be a software engineer, and then he hosted the TDD workshop, the 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, 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 take away from it is if, if you want to be someone who people listen to, like, yes, do cool and interesting stuff. Push yourself to, to get into the places that 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, uh, 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.

Episode duration: 1:14:50