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

Gergely Orosz: In my best year at Uber, I made about 320 or $330,000 in total compensation. And when I quit my job, I was actually thinking, am I crazy? Because I am leaving… Especially in Europe, this is a lot of money [inaudible 00:00:14] this will be similar to something… Someone in a similar position would’ve made five or 600K in total in the U.S. But now I am making more in compensation that I made at Uber. And the difference is that now my compensation… Well, my earnings 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 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.

Lenny: 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 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 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 creator route, you’ll love this episode. With that, I bring you Gergely Orosz.

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.

Gergely, welcome to the podcast.

Gergely Orosz: It’s awesome. Great to be here, Lenny.

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 the pros and cons of this life, how to go down this route, what it takes to be successful, all that stuff. But before we get into all that, I’d love for you to spend maybe a minute just giving us a little overview of your career, and how you got to where you are today doing this newsletter, and what you spend your time on now.

Gergely Orosz: My career started out as what you might consider a pretty typical software engineer career. I graduated from university, I did a computer science degree for a five year program, so I did bachelor’s and master’s. I worked on the side, I hacked around, built small websites here and there, and during university I worked at a small web agency. And then I worked my way up in the industry. So I started off at a consulting company, we were just building for other companies. I’m originally from Hungary, in 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 in Europe, I 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 an investment bank there, and then on the side I was always building 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 at Amsterdam, where I joined as a senior software engineer, and I became a manager, and then a manager of managers, and it was just… I feel, looking back at that part of my career, I just felt really growing all the time, just taking each step 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 career path, I was on the path to being a senior engineering manager, or who knows, one day I might have had a shot of being their director of engineering as well, I decided to leave Uber. And we’ll talk about it a little 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.

Lenny: 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?

Gergely Orosz: Just today I checked and it said 189,000 subscribers. I think the past 90 days has been growing with 80,000 subscribers, so it’s almost a thousand people per day, which is incredible. Because 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. There was a tipping point in April where the newsletter was growing… In the first about nine months of the newsletter, it got to 50,000 subscribers, and then the next five months, or six or seven months, it went up by another a hundred 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 benefited from it. But those numbers are again…

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 one. And again, it just beat all my expectations. And I guess we’re in similar boats, because our newsletter setup, 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 if people sign up for the free one, they get articles every now and then, and for the paid one, they get it a lot more and in more depth.

Lenny: Can you give listeners a sense of just 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.

Gergely Orosz: Yeah. I’ll share a little numbers of my cushy tech job at Uber. I was in Europe, and European tech salaries, or I’ll say total compensation, will be lower than for example the U.S., but it’ll be higher than let’s say regions like India or Indonesia. 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 320 or $330,000 in total compensation. This was after Uber went 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, “Am I crazy? Because I’m leaving…” Especially in Europe, this is a lot of money [inaudible 00:09:53] this will be similar to something… Someone in a similar position would’ve made five or 600 K in total in the U.S.

So I walked away from that, and I was pretty sure that I’ll just [inaudible 00:10:04] a lot less, but I’ll enjoy what I’m doing, or I’ll 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, my earnings, 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 in some strange way, I guess it even pays better. Part of it is just 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.

Lenny: Awesome. That’s a great segue to the first thing I want to talk about, but just to frame what I want to spend our time on today, there’s 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 do you 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 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 safer than at a tech job where one person can decide. And then the other piece is, assuming it keeps growing, you’re getting a raise almost every day, every week, depending on the growth rate, and that’s cool.

Gergely Orosz: That is really cool. 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 tracking what was the impact. And the crazy thing was that, when I wrote a really good article that resonated with people, sometimes it was an article that I thought was mediocre and people still loved it [inaudible 00:12:20] 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 in corporate. I mean, it’s by design, and there’s a lot of good stuff about it, but I feel that this life, and 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 for doing something awesome, you can just give yourself a raise, especially because this is just like you, mine is also a one person business right now.

Lenny: 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 going to keep accumulating. It’s pretty good. And you decide, “I’m going to 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?

Gergely Orosz: 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, before Uber I was… Now we’re talking numbers on my old job, but I was working in London as a principal engineer at Skyscanner. Skyscanner was a unicorn, one of the few unicorns in the UK, UK headquartered and all that, and I was making like 90-something thousand pounds in base salary, which is maybe a 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… And this was most of it. I got some stock as well. And I thought I was close to the top of the market in London. I knew people, and it seemed this was a really good compensation package.

And then Uber called me up saying, “Do you want to interview?” I interviewed with them, they gave me an offer, and I negotiated, and they basically doubled my compensation. I was like, wow, this is [inaudible 00:14:16] I knew about Silicon Valley compensation, but I assumed that [inaudible 00:14:20] you’re not going to get this, but Uber was getting something closer to that. So I told myself, all right, so I’m getting a really good deal, and most of it is stock, which is… Uber [inaudible 00:14:32] 2016, no-one knew if Uber will go public, although I suspected, because they contacted me to build a payments team so do a SOX compliant payment system. And you need a SOX compliant payment system if you want to go IPO.

Lenny: 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 the team working on SOX stuff and Sarbanes-Oxley, this is good.

Gergely Orosz: Yeah. So anyway, I said, all right, this is a massive lottery ticket. If it goes in, every year I make two years of salary, pretty much. That’s how I was thinking. But if not, again, don’t forget I’m in Europe where we’re used to not seeing any returns on stock. So European software engineers will not value stock as much, because they just haven’t seen success stories. So I told myself, 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 four years of savings in my bank, which… Back then I had maybe 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, 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 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, what am I doing here? I looked ahead, Uber was going to have a really bad year, I’m going to have to manage morale. Up to then, I’d helped put together this team, and 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, and 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 the family. My brother’s on his second startup, and 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 through him I know [inaudible 00:16:42] startup life is, and I felt I never did that, I always worked at big companies.

So my plan was [inaudible 00:16:47] leave Uber, raise money, and do something on platform engineering. A classic way that Uber alumni start businesses is, Uber has invested silly amounts of money to build everything custom internally. Everything that you can think of. Our [inaudible 00:17:02] system was custom, our experimentation system, our container, the way we automatically set that up, a lot of the engineering stuff. So a lot of Uber alumni just leave, and whatever they saw there, 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.

That was the plan. But before [inaudible 00:17:22] I wanted to finish a book. I’d been writing this book for, it was coming up to a year, called the Software Engineer’s Guidebook, which is just 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 take a break, and then I’ll raise the venture capital. And what happened was, I started to write this book, but I got sidetracked, I started to have fun online in terms of… I was writing on Twitter, on my blog. I accidentally published a book called Building Mobile Apps at Scale. I just 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 $100,000 in the first year. And I was like, “That’s interesting. People are buying my books.” And I self-published it through Gumroad or places where I get to keep I think 90% of the revenue, but still, this was really interesting. And I got to the point where, all right, I should now start a startup. I should do fundraising and do all that. 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 us against the world. We were like ten 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 startup. I was hoping to recreate this feeling.

And the other thing, honestly, was money. This was in 2021 before the market crashed. Just doing the maths, if you found a company, and I’ll be a CEO and the founder, maybe I’ll have a co-founder, this becomes a unicorn, by that time we will have raised five rounds of funding or six, I’ll be diluted as hell, but I’ll still have let’s say 5%. 5% of the billion is still $50 million, after you pay taxes [inaudible 00:19:30] I can buy a bunch of stuff that I don’t need. And I was asking myself, all right, and then what? And I was like, after I’ve bought everything that I don’t need, I probably want to share what I know with people, do YouTube videos and write books.

And I was thinking to myself, so hold on. I would go off and do this for like ten 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 spend all day on the internet writing about stuff. And then I want to do it again. So it’s reminding me of the story of this fisherman. There’s one that goes [inaudible 00:20:08] there’s the same thing of, you work really hard to do what you’re doing right now. So I decided, let me just try giving this a go. [inaudible 00:20:14]

Lenny: Wait, what’s the story of the fisherman? I think I know what you’re talking about, but… [inaudible 00:20:18]

Gergely Orosz: The story of the fisherman is that, in Mexico, an American businessman sees a fisherman who’s just chilling, fishing. And he asks him, “What are you doing all day?” He’s like, “I fish for three hours, I hang out with my family, I [inaudible 00:20:32] chill and I sleep in every Saturday and Sunday.” He says, “All right, here’s what you should be doing. You should fish not three hours, but you should fish five days a week, eight hours a day, sell that fish, turn over a profit, hire more people to do it, then start to be head of all those people, then sell your fishing company.” He’s like, “Okay. 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 thinking, look, I have savings. I don’t have huge, but I have it for… I can still take a risk. So let me take a risk on writing. And I was thinking originally of just 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… It’s hard to predict 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. I didn’t know if today I’m going to be making like 50 bucks or 10 bucks or 300 bucks. So I was like, interesting. There’s these 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.

Gergely Orosz: And the only reason I was really hesitant to start a paid newsletter, I was thinking about doing so for at least 6 to 12 months, is I was worried about writing every single week something really, really worthwhile reading, and it’s a lot of work. But then I looked back and I saw that I wrote three books. [inaudible 00:21:58] 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 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 said, 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. I might have found myself a new job, basically. If not, I’ll just refund people. 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. It’s basically like a startup. So I told her and my family that it’s going to be a lot of work and I might not be around as much, and they supported me, and I took a plunge. I took a big breath and started off. And that’s how it went from leaving Uber to starting a venture funded startup to starting to write full time.

Lenny: 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?

Gergely Orosz: It was pretty much a year, a little bit less than a year. Might have been like ten 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. It was the first time I… I didn’t lay anyone off, but people on my team were laid off. I wasn’t told who’s going to be laid off. It was just really stressful. 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 very good about it. I think this was the breaking point. This was the point where I realized that it’s not a family, which is weird because it never was, but it kind of felt family-like, but it’s just a corporate, and I’m just a number, and this could happen to me, I guess. So I think I lost my sense of the trust in the system, that it’ll take care of me, because I saw some of my colleagues who were 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 to a holiday, and two weeks in, I just realized I need to leave. And I really had the urge to do somewhere where I’m in charge. And if you’re a manager listening to this, you might relate to this. If you’re an engineer listening to this, maybe just shut your ears or you’ll figure it out eventually. But when I was promoted into management… It wasn’t promoting into it, because it was a side step, I didn’t get [inaudible 00:24:34] or anything, but it still feels a promotion. They only promote the people who are… Only let people transition who are considered pretty good. I felt this would be a big deal. I’m now a manager. 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 budget for my team. Someone was underpaid and I couldn’t do anything except complain for HR for six months and hope that they’d do something.

So it was pretty frustrating, because I didn’t feel in charge in the sense that I didn’t have decision making [inaudible 00:25:02]. And the reason I wanted to do a startup is, I decided I liked being a manager, but I did not how I was not in charge and I couldn’t take corporate [inaudible 00:25:12] telling us to do stuff, and then we were telling them no [inaudible 00:25:16] I don’t want to do that with my people. So I decided for next job, I could be doing this, but instead I’d like to be in charge. So I’d like to 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 it is, I decided to leave in July. We have longer notice periods in Europe, so I served a longer notice period, and then left. But it was a year after the decision.

Lenny: 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?

Gergely Orosz: I started the newsletter saying I’m going to post once a week. You’ll have one pinned up 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 in 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 the second one came a lot later. But initially in the first few months I was like, 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 is not a big deal. It’s easy. As you said, let’s say you’re making 300K just writing one post a week. But it actually was pretty stressful in the beginning, because it turns out to write that post, it takes 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 [inaudible 00:27:10] a first draft. I get some feedback from people who I trust often, not always, but I often do. And then there’s an editing phase where I work with an editor who helps make sure that it’s just correct. And all these things add up. Even if I only spend a day researching the stuff, it’s a day researching, then I have a draft on day two. Day three I get feedback, on day four it’s editing, it’s almost a whole week.

So I was working on parallel things at the same time, and I was often running against the deadline, I was barely finishing it, which is not what I was expecting initially. The first few months I feel was a bit more stressed, but again, the good thing is I cleared my calendar, so I said I’m not talking with anyone, I’m just doing this. So in that sense it was good. But the one thing I realized, if you look at any journalists who’s doing stuff full time, and they’re writing, not these clickbait articles, but actually in depth. You look at the Washington Post or New York Times, search for their name, and look up the articles that they write, and they’re going to be longer articles. They have like one a month. Seriously. You look at the investigative journalist, 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, even back then, “You actually write a lot of original stuff,” because a lot of my emails are about five, 6,000 words, which is considered very long.

Lenny: Yeah. When you said that people listening might be like, 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 cool that you shared the process. Do you have a specific cadence per post? It’s like Monday draft, Tuesday review, Wednesday editor. Is that how you work?

Gergely Orosz: 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, nowadays I actually write two articles. So I have the Thursday that is the scoop, which actually is a lot easier for me to write, interestingly enough. And my cadence is, on Monday I finish up the last of the post that goes out on Tuesday. It’s just small edits, but it’s already done pretty much, so it’s just a few small tweaks, and maybe I have some feedback coming in. On Tuesday, I publish this post, and I do some free writing. I write about some other ideas that I have that’s going to be future posts. On Wednesday, it’s my free day in between, where I… 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’s 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, “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. This is weird, I hated it back then, but I needed to do these things, and whenever you have a pressure, you do it. And this works with my newsletter. I put in the second 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 next newsletter for Tuesday. So almost every day except for Wednesday, I have a strong pressure to write. Which when people ask, “Gergely, how do you write so much?” Because I did the maths, and I wrote four or five books’ worth of content just last year. It’s because I have these deadlines, and as you said, I also know that thousands of people are paying me, they have expectations of me.

And so this is how it’s done. 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 [inaudible 00:30:57] $5,000 or something like that. That’s what I was offered initially. But it’s the pressure. 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 secret, or not so secret.

Lenny: Do tell.

Gergely Orosz: 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 Engineer’s Guidebook, I feel it’ll be my summary of my last ten years of what I have to share as advice, but I was worried that it’s just a big project that’s just going to take months, and I’ll lose motivation midway.

And partially, I went down the newsletter route because I liked how every week I would have to write something, and I had this sneaky idea of, what if I wrote this book where I write some posts that will be part of the book, and then the book will just 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 the idea is that I have this chapter, and I have this list, have I written about this topic in the newsletter? And you know where I got this idea from? There’s the book The Three Musketeers, from Alexander Dumas [inaudible 00:32:12]. And do you know how it was written?

Lenny: I don’t.

Gergely Orosz: 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, “All right, we need you to write something that our readers will want, so that they will buy the magazine.” 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’s really long, and I was like, hold on, if he could do this, then this is a good strategy. He was writing it because he just needed the money. That’s all. 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. 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 a newsletter, it’s going to be a bunch of other things. If you put in ways that you have to do certain things, 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 entrepreneur, I was a great… I think I was a really diligent employee. 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 just went out the window. Almost 15 years of being this star employee who really wants to do well, I found myself upset at myself for not… Just wasting my day. But I fixed it by telling people, “You’re going to get this every week,” and now I have to do it. I just have no choice.

Lenny:

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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, before I even started the newsletter. 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 and get things out the door? Two posts a week, which is a lot of work.

Gergely Orosz: So a problem that I have, and this might be unique to newsletters, 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 [inaudible 00:36:16] raising awareness. So whenever I tweet, it helps my business. So that’s a good thing. But it also justifies for me spending more time on, for example, Twitter than I would want to. So I find that I come up with a method, and it works for 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. I use this app Centered, but I know you’re also there.

Lenny: Yeah. I love that app. Also an investor [inaudible 00:36:49] disclaimer, but I love it.

Gergely Orosz: Yeah. And I found that helpful, the idea of focused time and [inaudible 00:36:56] turned on, but it might just be me, but after a while I get used to these things, and I find it not as efficient. I found the Pomodoro method for a few months useful, when you 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 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 super focused. So when I have this external thing, and I know that there’s no way [inaudible 00:37:30] I need to focus on basically the deadline. So if you have deadlines, that works.

The other thing is, if I start to spend three or four minutes doing something focused, and I get the flow of it. So a trick I sometimes do when I’m just, I just don’t feel 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 [inaudible 00:37:57] host file, I just kill all LinkedIn, Twitter, Facebook, whatever sites. So I just cannot reach it. It’s just a very simple Python script that I wrote for myself. And then in the first few minutes I’m 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, and I’m now actually heads down and doing it. And this has been the thing that has 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.

Lenny: Awesome. That’s a really cool trick, the host file trick. So that’s [inaudible 00:38:43] something that you have to be 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.

Gergely Orosz: Yeah. So there is definitely going to be extensions that you can use, and on this podcast we’ll have a variety of people. If you’re a software engineer, it’s pretty simple, and even if you’re not, you can look it up [inaudible 00:39:10] when you override your host file, you can actually block [inaudible 00:39:13] what you do. And I did this because I wrote a script where I need to run the script, and I need to run 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 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 [inaudible 00:39:50] let’s 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 competing with people on uninterrupted time and closing stuff. So that to me is a… I’ll do one last [inaudible 00:40:23] 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 forced to do work, because I knew that people on the other side of the world might be watching me, even if it was not true.

Lenny: 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 I guess that’s the three that work best for you.

Gergely Orosz: 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.

Lenny: It’s cool Centered does that for you, and it has music and all the things. So I 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.

Gergely Orosz: 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 I get a little bit cagey [inaudible 00:41:51] I have this one meeting in the whole day. So I like how it’s [inaudible 00:41:55] manage your time [inaudible 00:41:58] so that’s the best part.

And I also like how much in charge I am. Initially it freaked me out, in the sense of how much creative freedom I have. I can write about whatever. I can change a format, I can do this, I can do that. It can be a little bit overwhelming, because I also 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, and obviously more in a corporate setting. But I guess that’s just gotten extended. So these are the two favorite things, is the open calendar or very few meetings, and experimenting, trying out stuff and being able to decide what I want to try out.

Lenny: 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 11:00, I just can’t do anything really deep until that point, and then afterwards I have to get back on track. And having that deep focus time is so important for this work, even though 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 sucky parts of this path that you’ve taken?

Gergely Orosz: One is obviously it’s lonely. I do miss… I had a really good team at Uber, and it wasn’t just a team, it was the people. I liked… Everyone has different views on remote work. I actually didn’t enjoy remote work as much, because I just liked hanging out with people. I guess I’m that more outgoing type, and I really like walking up to the coffee station and having a chat with people, or at lunch sitting next to someone and talking about it. And obviously in some sense 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 compensate for that by working in a shared workspace, a shared office, which is a techy workspace. So everyone needs to work in tech. So I actually get to say hi to people and have a little 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. I was doing so many things. In a day, I would start my day let’s say at 9:00 or at 8:30, and I’d finish it up at, I don’t know, 6:00 or 5:30, it depends. I would probably have, on an average day, I would have a good eight meetings, I would finish two or three documents, I would send over this, send over that. I actually have… Looking at my output, 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 the downside is, I felt very guilty and a little bit frustrated for myself, for 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. 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. People are not going to subscribe or pay for ten newsletters on the same topic, so that makes it a little bit more… It’s not the same as when you work in tech, and you just 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 whenever looking at your subscriber numbers, which brings a bunch of stress that I didn’t expect. And I’m a successful newsletter [inaudible 00:45:47] I think my success is quite rare. There will be one or two or a handful of people who have similar success, but I’m an outlier. So that’s another thing that I think is just good [inaudible 00:45:58] putting out there. And the downside is, you don’t really know how well you’re doing. 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 several months actually, after I started. Or did I make a good one? And I think for a lot of these questions and doubts, having past professional experience working at a company is really useful to set yourself grounded.

Lenny: 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, 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 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 that we could do.

Gergely Orosz: Yeah. And it’s a really good example, because for a lot of companies, and I assume 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 exit and 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. This is what a lot of book publishing companies… So basically 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 it’s not a one-person newsletter any more. Or you keep doing this, until you either stop and then the revenue stops, or you might be able to sell it, but at really under value.

Lenny: Yeah. I really don’t want to manage people. I don’t want to have employees. And so building 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 a week off usually [inaudible 00:48:58] 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 another downside, just [inaudible 00:49:08] topic.

Gergely Orosz: Yeah. But a lot [inaudible 00:49:11] very early. So I think the whole concept of paying users 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 in terms of… Or even when I [inaudible 00:49:25] I was writing, and it caused a bit of friction with my family. And now I’m solving it in a different way, so I am planning 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.

Gergely Orosz: So a downside we haven’t mentioned, but I’m just going to call it out, is holiday. The great thing at… I never felt… Well, I felt a little guilty sometimes taking holiday, but when I want a holiday, 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. 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 that as well.

Lenny: Yeah. Okay. Enough about the downsides. Overall, it’s pretty amazing making hundreds of thousands of dollars writing an email once a week/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 what it takes to be successful, but before there, do you think this goes long term?

Gergely Orosz: I stopped making long term plans, because 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, a manager of managers.” And then I became one. And then [inaudible 00:51:01] what is my dream? I would’ve been like, “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 writing a newsletter, or now writing a successful newsletter. So I’m going with the flow. 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 a business, and I’m trying to put on that business hat. 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 me detach as well. I can actually enjoy my weekends as opposed to thinking, “I need to write this, or I need to write that.” So I also want to make it work for me.

And I’m not married to the idea of, it always needs to be a newsletter, et cetera. Right now it is, but where I see us going is, I’ll keep building the business, I’ll keep playing to my strength, which is I love talking with people, I love writing [inaudible 00:51:56] I love software engineering. So this is a great format, but over time it might shift. So I’m keeping my options open. And what I’ve learned from this journey is, you need to create time for that spark to come. So one of my goals for 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 going for work, I didn’t ask for any LinkedIn emails. And the idea came and the inspiration came and the motivation came.

Lenny: 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 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.

Gergely Orosz: Yeah. And one last thing to touch on, you said something really important [inaudible 00:53:06] pull, 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 pulls. So [inaudible 00:53:18] Uber, like I said, my plan was, I’ll write this book for six months. Two months in, I just put a draft [inaudible 00:53:24] a really long blog post about mobile engineering, and I got a ton of messages, a lot. I usually 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, that’s interesting. I just felt this pull, of this huge interest of people caring about this. It was this really long blog post about mobile engineering at scale, and someone suggested on a private message, “You could probably turn this into a ebook.” And I was like, 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 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. I said, for the next two months, I’m going to write this book, because it seems there’s an interest in it. And [inaudible 00:54:07] 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 how I got 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 that people would care about building a large mobile app, more than a few hundred people. Turns out they do. Thousands do.

Lenny: 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?

Gergely Orosz: I’ll tell the story that is kind of true, and people will think it’s amazing, and also the real deal behind it.

Lenny: Okay, great.

Gergely Orosz: I announced my newsletter, I told people, “I’m going to go full time on this.” I had maybe 10,000 Twitter followers and, I don’t know, maybe 1,000 on LinkedIn or something that. 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 [inaudible 00:55:15] I had 1,000 paid subscribers. And this sounds like a fairytale. And if you do this, I guarantee you’re not going to get the same results. In fact, you’ll probably see way smaller numbers.

What I didn’t tell is that there was at least six years of accidental work behind this. I started a blog six years before… Actually, I’ve always been blogging since I graduated. I had this personal blog where I just published all sorts of random things about software engineering, but it was really… Sometimes it was about an app that I published, sometimes it was a problem that I came across. It was is all over the place. And I 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 how it was just all over the place.

And I said, “I’m going to start 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 Jeff Atwood, who’s the founder of Stack Overflow, and back in 2010, or 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 it. It was next level wisdom every single week, twice [inaudible 00:56:26] a week. You read it as well?

Lenny: [inaudible 00:56:29] Yeah. I used to be an engineer, and I was all up in that. And I think Coding Horror came from a… I forget the book, but there’s a book with that graphic.

Gergely Orosz: There’s a book, and there’s a graphic. 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. 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 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 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, going into topics that I [inaudible 00:57:25] research and all that, and then I gave up.

And I’m saying this because I kind of gave up, and I left it 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 a site called Hacker News that I [inaudible 00:57:41] heard about, and people were discussing my posts, and they were adding a lot of things. And I was like, that’s interesting. People care about what I wrote six months ago.

Lenny: What was that post, by the way?

Gergely Orosz: It was called, “A comment is an invitation for refactoring.” I wrote my view that if there’s a comment in a 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, and it was these two crowds battling it out. And I was like, wow, I actually made software engineers in Silicon Valley argue about my stuff. I saw some of the [inaudible 00:58:17] people, some really high [inaudible 00:58:18] people were really going for [inaudible 00:58:21]. So that’s when I thought [inaudible 00:58:23] my writings, some people might read it, it’s not guaranteed.

And I started to write on that blog once every few months, depending on my mood, but I never stopped doing it. And I partially did it [inaudible 00:58:35] always hoped that it would get onto 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 had this habit, and over years… 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 wrote about my work, in terms of the things that I could write about, not about the details that we did, but some of the learnings [inaudible 00:59:02] 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, so people… I started to get this validation, people care about what I write.

And to 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, and there was a very famous post about performance management, how to do performance reviews. I wrote one about the tri-modal nature of software engineering salaries, where I observed that there’s three different tiers that are… There’s big tech and there’s 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 realize that they… “I’ve been reading this Pragmatic Engineer, I don’t know who is behind it, but I like it. Let me sign up. I do want to get 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 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, two things will happen. First of all, you’re going to [inaudible 01:00:11] 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 step one is get started. Step two is keep it up. And my suggestion is [inaudible 01:00:26] for yourself. The weird thing is, until I started my newsletter, I never thought I would turn this ever into a business, but it always felt rewarding. So I never… 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.

Lenny: So people listening to this that are thinking about, should I explore this life? 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, 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 it make sense for me?” Do you need the background that you have, do you think?

Gergely Orosz: Don’t forget that when I started my blog, I didn’t have any of this.

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

Gergely Orosz: It was before I was at Uber. So I was maybe at Skyscanner, or maybe at Skype, but I was even blogging before. I was talking to conferences before. So my advice really would be, 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. Actually, ten years ago I went to a lot of meetups where I presented all sorts [inaudible 01:01:54] I met a lot of cool people. I would say, 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, we had to set goals, and I told people there’s two types of goals you can set. One is [inaudible 01:02:12] 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 a goal that I want to have a successful newsletter with, 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 I want to leave work at 5:00 PM on Fridays to be home with family. So set those goals that you can control.

Gergely Orosz: And this is how actually my blog started initially. My goal was, I want to write once a month. And I did that for a while, and I was proud about that. Or 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, don’t get me wrong, 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 come from a small country, from a really good university which no-one knows about, but I didn’t grow up in let’s say Silicon Valley, so I actually made a subconscious point to try to work my way up. And after I got to let’s say JPMorgan in London, I was pretty picky of where I would go next. So that’s why, when Skype came along [inaudible 01:03:36] this is great. Everyone knows Skype, I love Skype. And it was same thing with Uber.

So especially these days, 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 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 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. All of this starts as a side project. 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 pretty entrepreneurial, and the only way you’re going to get these muscles, if you start some small things.

Lenny: 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 a foundation to write about, share wisdom from. And that’s really important. There’s a lot of people starting newsletters and tweeting who 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 worked and that you’ve learned, or that you have access to other people who have learned these things.

Gergely Orosz: I would say that, but one thing that I’ll double down [inaudible 01:05:09] that’s a really good observation is, if you’re serious, like one day I will want to write a book or a newsletter, it’s kind of the same thing, or teach people about stuff, look at the people that you look up to that you actually trust. Maybe it’s me a bit or maybe it’s you, but 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 people, I think he’s coming up 50 or 60 [inaudible 01:05:36] if he listens to this, sorry if… I don’t want [inaudible 01:05:38] seem old, but what I love about Kent Beck, is he’s been in the middle of it. He has always worked in the industry, and that he wrote about it. But for example, I think he invented or he was a co-inventor of… Was it TDD or extreme program… Anyway, one of these methodologies.

And then [inaudible 01:05:58] went to work at Facebook. He took a title cut to be a software engineer, and then he hosts the TDD workshop, the test driven development workshop, and no-one showed up at Facebook. And Facebook did no testing, which went against all commercial wisdom. And he took that risk joining this company where he could have been… People would’ve knelt down to him anywhere else, but he went to this company where he just wanted to learn. He’s this lifelong learner. He’s right now writing a book. But what I think [inaudible 01:06:26] if you want to be someone who people listen to, yes, do cool and interesting stuff, push yourself to get into 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 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 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.

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

Gergely Orosz: One is habit of 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 one, but it’s kind of true. So become an expert 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 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 with experience in the industry or you have insights, wisdom, observations to share, start doing so, in whatever format. 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 Yegge. Steve Yegge is… Have you heard of Steve Yegge?

Lenny: Yeah. He wrote some epic long…

Gergely Orosz: He used to work at Amazon, and then at Google he 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 then he quit Google and he started to do a podcast that’s on YouTube. You could check it out, it’s called Stevey’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 up front when he started the first one, he said, “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 [inaudible 01:08:59] I think it’s really fun to listen to. And in the end, it was I think successful. It got a couple thousand or maybe even 10,000 subscribers, but it wasn’t this rocket ship. And I think what he did, he just stopped after six months, and he actually started head of engineering at Sourcegraph, he actually went back [inaudible 01:09:15] industry. But what I love about this, it shows that you cannot guarantee having success, but you can do what he did, which is start something, do a cadence, see if it sticks. If not, either pivot or do something else. I feel the world is kind of about that as well.

Gergely Orosz: If you think about… Take a step back of, what is a successful newsletter? What is a successful podcast? What is a successful YouTube channel? And it’s stuff that’s interesting. It’s either entertaining or educational. But all of these things, you can’t really put a finger on. If you watch YouTube, Mr. Beast is someone who you probably came across, I actually like watching his videos and [inaudible 01:09:56] how good he does it, but it’s not something you can [inaudible 01:09:59] 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.

Lenny: This is great. I feel like I can 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.

Gergely Orosz: I’m pretty sure. And here’s an interesting thought as well, just for closure. 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 2015, 2016, and I started my YouTube channel in 2019 or something like that. And on YouTube, there’s so much quality, there’s super high great productions, 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 medium.” And I’m saying this, not [inaudible 01:11:16] but 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, which might be good or bad.

So if you’re going to be a really well known person on YouTube, you might get more people watching you, but you’ll 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 even scan through the whole thing. It’s just really time consuming.

So I think, decide if you want to do entertainment, which for these podcast listeners, I don’t think that’s in the question, you’re competing with the likes of Spotify and Netflix. Education, which is a little bit more dry, but it’s really useful. Or edutainment, which is entertaining education. And once you figure that out, either if it’s education or edutainment, you can figure out what format might work both for the medium and for you. And at 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.

Lenny: Gergely, 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 the different creator 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?

Gergely Orosz: You can find me at pragmaticengineer.com. There is a bunch of stuff listed there 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 always tell people we’re a complimentary newsletter. If you work in product or have an interest in product [inaudible 01:13:11] newsletter is an awesome choice. With software engineering management, it goes the other way. And it’s not just… People are telling me when they’re data scientists or even product folks, sometimes they get some value out of it.

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 change in the workplace, like your company is just rolling out agile [inaudible 01:13:36] team at Twitter did, feel free to ping me, just a short search for sending scoop to the Pragmatic Engineer. I treat everything as anonymous, so you can tell me interesting stuff. I’m typically interested in the stuff that you might not read about in the traditional media, but us techies really care about.

And finally, if you work at Google and you want anonymity to talk to me, just ping me, because one of my next articles will be Google’s engineering culture. I wrote one about Facebook, one about Amazon, and I tried to talk with mostly software engineers to get a sense of how these companies work from a software engineer and engineer manager perspective.

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

Gergely Orosz: Awesome. It was great being here, Lenny.

Lenny: Thank you so much for listening. If you found this valuable, you can subscribe to the show on 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.

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