Lenny's Podcast: Product | Career | Growth - Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer)

Episode Date: November 17, 2022

Gergely Orosz writes the #1 technology newsletter at Substack, called The Pragmatic Engineer. He started his career as a software developer in the U.K., spent three years at Skype, and followed that role with four years as an engineering manager at Uber before deciding to leave big tech and work for himself. Gergely began pursuing his newsletter full-time in September 2021 and in just one year has amassed 200,000 subscribers. He now makes more money than he did at his salaried tech job, and with freedom and flexibility. In today’s podcast, Gergely shares why he left his well-paying job at Uber, how he got his first 1,000 subscribers, why this kind of work can be stressful and lonely (but ultimately rewarding), and why it takes hard work to build authority and become a great writer. Working solo can be challenging, and in this episode, both Lenny and Gergely offer tips for structuring your unstructured time and finding your focus.—Find the full transcript here: https://www.lennysnewsletter.com/p/leaving-big-tech-to-build-the-1-technology—Where to find Gergely Orosz:• Website: https://www.pragmaticengineer.com/• Newsletter: https://newsletter.pragmaticengineer.com• Twitter: https://twitter.com/GergelyOrosz• LinkedIn: https://www.linkedin.com/in/gergelyorosz/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—Thank you to our wonderful sponsors for making this episode possible:• Lemon.io: https://lemon.io/lenny• Eppo: https://www.geteppo.com/• Vanta: https://vanta.com/lenny—Referenced:• Gergely’s books: https://blog.pragmaticengineer.com/books/• Centered: https://www.centered.app/• The Pomodoro technique: https://www.forbes.com/sites/bryancollinseurope/2020/03/03/the-pomodoro-technique/• Coding Horror: https://blog.codinghorror.com/• How to Achieve Ultimate Blog Success in One Easy Step: https://blog.codinghorror.com/how-to-achieve-ultimate-blog-success-in-one-easy-step/• A Comment Is an Invitation for Refactoring: https://blog.pragmaticengineer.com/a-comment-is-an-invitation-for-refactoring/• Kent Beck’s website: https://www.kentbeck.com/• Steve Yegge’s famous rant on Google vs. Amazon: https://www.alexanderjarvis.com/steve-yegges-famous-rant-on-google-vs-amazon/• Stevey’s Tech Talk: https://www.youtube.com/playlist?list=PLZfuUWMTtMcC1DZF6HxJhqsGrBXu8Jzi7—In this episode, we cover:(04:32) Gergely’s background(07:19) The Pragmatic Engineer, growth and current subscribers (08:59) Compensation with a subscription-based newsletter vs. his salaried position at Uber(10:55) How the onset of Covid and layoffs at Uber prompted Gergely to start his newsletter(23:10) What he did immediately after leaving Uber(25:41) The day-to-day of writing a newsletter(35:08) Tips for productivity(41:19) Gergely’s favorite parts of entrepreneurship (43:15) The downsides of solo work(50:39) Why Gergely stopped making long-term plans(54:30) How to get started writing a newsletter(1:04:48) Key advice on building a successful newsletter—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [e-mail]. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

In my best year at Uber, I made about like $320,000 or $330,000 in total compensation. And when I quit my job, I was actually thinking like, am I crazy because 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 $500,000 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 are keep going up as long as the news that it was 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. I just honestly making tons of money doing an job that I loved. And this was at Uber or as a software engineer. And I'm now doing something I love. And in some strange way, I guess,

it even pays better. Welcome to Lenny's podcast. I'm Lenny, and my goal here is to help you get better at the craft of building and growing products. I interview world-class product leaders and growth experts to learn from their hard-won experiences, building and scaling today's most successful companies. Today, my guest is Gerge Oroz. In a sense, Gerge 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 Gerge'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've ever thought about writing or going down this kind of creator route, you'll love this episode. With that, I bring you Gerge Oroz.

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Gerge, welcome to the podcast. It's awesome. Great to be here, Lenny. So I think this is going to be a pretty special and unique podcast. Your newsletter is the number one technology newsletter on Substack, called the Pragmatic Engineer, by the way. My newsletter is the number one business newsletter on Substack, and so we're connected in this really special, weird way. And I thought it would be pretty fun to just explore this weird path that we're on doing this newsletter thing.

And in that, help listeners understand kind of the pros and cons of this life, 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're today doing this newsletter and what you spend your time on now. My career started out as what you might consider a pretty typical software. engineer career. I graduated from a university. I did a computer science degree for like a five-year programs that had a bachelor's and master's. I kind of worked on the side. I kind of hacked around,

built small websites here and there. And during the university, I worked at a small web agency. And then I kind of worked my way up in the industry. So I started off at a consultant company, like we were just building for other companies. I'm originally from Hungary. So Hungary and 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 like the New York of Europe or even the Silicon Valley

back in the day, back before Brexit, it was the biggest tech hub. I worked at a bank, well, an investment bank there. And then on the side, I was always building kind of mobile apps. And I got into Skype, I like to say Skype, but it was Microsoft. They just bought Skype at that point. And it was a lot of more. startup the environment, a lot more fast moving. I then moved to another startup where I was a founding engineer of an 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 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 we'll talk about 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. Awesome. On the newsletter, just to give people a little bit of context of how big this has gotten. Can you share just a couple stats about the growth of the newsletter, the size, and anything else you want to share there? Well, just today I checked, and it's at 189,000 subscribers. It's the past, I think the past 90 days has been growing with 80,000 subscribers. So it's just, it's almost 1,000 people per day, which is incredible. Because, I mean, these numbers are huge. If you're listening, you're probably thinking, wow, and that's how I feel.

every day as well. But I've been writing a blog for many, many years, and these are numbers I never thought it would be. And the growth just seems to be accelerating. So there was a tipping point in April where the newsletter was growing in the first like about like nine months of the newsletter, it got to 50,000 subscribers. And in the next five months or six or seven months, it went up by another 100 and something thousand subscribers. This one was one substack introduced recommendations, which has been on a massive growth engine. And I guess being one of the top obligations, I kind of benefited from it,

but those numbers are big in. So this is a paid news letter as well. So there's a free version and a paid version. There's thousands of people paying for the newsletter. It's a single digit percentage. But it's a very, very healthy one. And again, it just beat all my expectation. And I guess we're similar boats because our news that are set up yours and mine is

somewhat similar. We have plenty of differences as well. But I make most of my revenue from, subscriptions and I don't do sponsorships or ads in the newsletters. So it's kind of like if people sign it for the free one, they get articles every now and then. And for the paid one, they get a lot more and in more depth. Can you give listeners a sense of just like the order of magnitude income you make from this versus your cushy tech job at Uber? You don't have to share numbers or anything like that. Yeah. So I mean, I'll share a little numbers of my cushy tech job at Uber.

because, you know, I was in Europe and European tech salaries or tech, I'll say total compensation will be lower than, for example, the U.S., but it will be higher than, let's say, regions like India or Indonesia, you know, there's regional differences. And this is true for big tech as well. Uber was a good example on this. But in my best year at Uber, I made about like $320 or $330,000 in total compensation. This was after Uber won public. So it includes the stock, the base salary, the bonus, which was very, very good. in Europe. And when I quit my job, I was actually thinking, like, am I crazy because I'm leaving, especially in Europe, that this means that this is a lot of money to say, well, this will be similar to something, you know, someone in a similar position would have made like five or six hundred K in total in the US. So I walked away from that and I was pretty sure that I'll, I'll just be a lot less and I'll be, you know, but I'll enjoy what I'm doing or I'll kind of have, I'll just give it a go. But now I am making more in compensation than I'm, I'm just going to, I'm I made at Uber and the difference is that now my compensation, well, my burnings are keep going up

as long as the news that it was 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 an odd job that I loved. And this was at Uber or as a software engineer. And I'm now doing something that I love. And in some strange way, I guess it even pays better. I mean, part of it is this is lock. Part of this is situational. I think we're going to talk a bit more about this.

But this was very, very surprising and very unexpected for me. Awesome. Yeah, that's a great segue to the first thing I want to talk about, but just to kind of frame what I want to spend our time on today. There's kind of these four areas I want to explore. One is your decision to leave and start this life of writing, which is a very non-traditional life. Two is what the life of a paid newsletter person is like.

What do you do all day? How do you find time to do this? How do you produce so much content? Three, what it takes to be successful at this. A lot of people, I always say it's easy to start a newsletter, hard to keep it going. And I'm curious what you find is important to be successful. And then four, how to get started if you want to start your own newsletter. But before I get into that, I just wanted to add a thought that I had.

The way I think about this life in terms of comparing to the old job is, one, it feels like instead of one boss, I have thousands of micro bosses, and one of them can fire me, and many do every day, but it feels like safer than at a tech job or like one person they decide. Yeah. And then the other pieces, yeah, assuming keeps growing, you're getting a raise almost every day, every week, depending on the growth rate, and that's kind of cool. That is really cool. So I had a spreadsheet that I maintained for the first year of the publication where I listed

for every article, how much did my annual revenue go up? a week later, so kind of tracking like what was the impact. And the crazy thing was that, uh, you know, when I wrote a really good article that resonated with people, you know, sometimes it was an article that I thought was media over and people said loved it, but often it was a really good article that I put tons of working. I saw myself getting a reason. This is just something you just don't get at, I mean, it's by design and there's a lot

of good stuff about it, but this, like, I feel that this life and I'll, we'll touch more on this, but there's a lot of surprising things, both good and. bad, but this is a really good one. So you're, you know, for doing something awesome, you can just get, give yourself reasons, especially because this is just like you. Mine is also one person business right now. Yeah. Okay. So you're at Uber. You're making hundreds of thousands of dollars writing code. It's pretty sweet. Uber's growing. You probably got all these RSUs that are going to keep accumulating. It's pretty, 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? The short of it is, it was a promise to myself and COVID and Uber doing layoffs. And the longer version is that when I joined Uber, I mean, before Uber, I was, you know, now we're talking numbers on my old job, but I was working in London as a principal engineer at Sky Scanner. Sky Scatter was a unicorn, one of the, one of the few unicorns in the UK kind of UK headquarter and all that. And I was making, I think, like, 90-something thousand pounds in base salary, which is like maybe $120, 130, or $140,000, depends on how the pound is doing. Or sometimes, 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, 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 composition package. And then Uber called me up saying, hey, do I interview. I interviewed with them. They gave me an offer and I negotiated. And they basically doubled my compensation.

I was like, whole, wow, let's just stop. So I knew about silicon value compensation, but I assumed that I knew if you're not going to get this. But Uber was getting closer, something closer to that. So I told myself like, all right, so I'm getting a bunch of like a really good deal. And most of it is stock, which is Uber was, in 2016, no one knew if Uber would go public. although I kind of suspected because they contacted me to build a payment scene to to Sox compliant payment system. And you need a socks compliant payment system if you want to go IBM.

That's funny. It reminds me at Airbnb. There's all these people trying to figure out, when are we going to go public? And then there's like, oh, there's a team working on socks stuff. And Sarbanes Oxley. Oh, this is good. Yeah. So anyway, I said like, all right, well, this is a massive lottery ticket.

If it goes in like every year, I make two years of salary pretty much. like that's how I was kind of thinking. But if not, again, don't forget I'm in Europe where we're kind of used to not seeing any returns on stock. So European software engines will not value stock as much because they just haven't seen success stories. So I told myself, look, 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 have forgotten about this, but four years later, almost on the dot, COVID starts, and it really hits super hard. We're laying off people. We had to lay up 20% of the engineers.

I was already managing a group about 30 people. I had managers under me and 20% of the people or 50% had to be to let go. And I was thinking to myself like, you know, what am I doing here? Like I looked ahead. Uber was going to have a really just bad year. I'm going to have to manage morale. And up to then, I helped put together this team. We had a really good charter.

And we had to throw that charter out the window because it made no sense with the economic reality. So I thought back like, 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, a raise venture capital because I haven't done that before, but it kind of rose at a family. My brother's on a second startup. He sold his first one to SkyScan.

and I was building this startup called Kraft Docs. It's a really slick document editing system. They just raised their Series B. So he's, you know, I kind of, through him, I know what the startup life is, and I felt I never did that I was always worked at big companies. So my plan was, I leave Uber, raise money, and do something on platform engineering.

I saw Uber, a classic way that Uber alumni starts businesses, is Uber has invested silly amounts of money to build everything custom internally, like everything that you can think of our built system is what's custom, our experimentation system, our container, you know,

the way we kind of automatically said that a lot of the insured stuff. So a lot of people will all and I just leave and whatever they saw, they just build it for the world to use because no other company really does what we produce because it makes no sense, but a lot of them will pay for.

That was a plan. But before I wanted to do this, I wanted to finish a book. I've been writing this book for, it was coming up to a year called the Software Engineers Guidebook, which is just kind of my advice for people to grow professionally in the field. And I figured, all right, let me leave the company.

In six months, I'll write the book. I'll just use my savings to kind of, you know, take a break, and then I'll raise the venture capital. And what happened was I started to write this book, but I got sidetracked. I started to have fun online, like in terms of I was like writing on Twitter on my blog. I accidentally published a book called Building Mobile Apps at Scale. I just kind of did it for a few months.

And the weird thing was that my plan was that I'm going to just not make any money. And this book, Building Mobile Appesat Scale, 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, hmm, that's interesting. People are buying my books. And I self-published it to the gum rules of places where I get to keep, I think, like 90% on 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 then I asked myself, why do I really want to 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 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 start by kind of

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, I'll be a CEO and the founder, maybe I'll have a co-founder. This becomes a unicorn. By that time, we have, we will have raised like five rounds of funding or six. I'll be deluded as hell, but I'll still have, let's say, 5%.

5% of the bill is still $50 million after you pay taxes still have left over and I can buy a bunch of stuff that I don't need. And I was asking myself like, right, and then what? And I was like, well, after I bought everything that I don't need, I probably want to kind of share what I know with people, do YouTube videos and kind of write books. And I was thinking to myself like to hold on. Like, I would go off and do this for like 10 years because that's how much you need to plan to do it. I need to stop doing what I'm doing right now because I would owe it to my, investors and my team to not, you know, like spend all day on the internet, like writing about stuff. And then I want to do this again. So to remind me of the story of the, of this fisherman,

I think 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 mean, wait, what's the story of the fishermen? I think I know what you're talking about. But the story of the fisherman is, is that in Mexico, an American businessman, sees a fisherman who's just chilling, fishing. And he asked him like, hey, what, what are doing like, oh, all day. It's like, well, I can't fish for three hours. I hanging out of my family. I didn't chill and I sleep in every Saturday and Sunday. It 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 behead 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 on Saturdays and sleep on Sundays. So I was kind of thinking, like, look, I have savings. I don't have like huge, but I have it for, I can still take a risk. So let me take a risk on writing. And I was thinking originally of just like spending more time to finish my book. But what I didn't like about books, even though I was making money, is they're really kind of, it's hard to predict how, like, if you're going to be making a living or there's

some people who actually like this excitement, but I didn't like it. Like, I didn't know Today I'm going to be made like 50 to 50 bucks or 10 bucks or 300 bucks. So I was like, interesting. There's this paid newsletters which I've been thinking about. You were one of the few people who shared some of your early numbers. And I figured this could be interesting because it's recurring revenue. And the only reason I was really hesitant to start a paid news letter, I was thinking about doing so for at least like six or 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, I told you I wrote two books, but there was a third one that I also published in the 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 news that are every week. I'm going to write something really in depth about software engineering. it's going to start next week, and I told myself that I'll, I told my wife as well, that I'll do this for six months, and I'll see what happens.

If there's traction, it's great. You know, I might have found myself a new, a new job, basically. If not, I'll just refund people. Like everyone who bought an annual subscription,

I didn't tell this to people, obviously, but for six months, I'm going to give it my all. You know, like it's basically like a startup. So I told her, like, in my family that it's going to 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 that's how it went from leaving Uber to start a venture funded startup to start up to starting to write full time. Awesome. And we're going to talk about what advice you have for folks that are thinking about starting something like this at the end. What was the period between leaving Uber and starting the newsletter? It was pretty much a year, a little bit less than a year. It might have been like 10 months or so, but it was a year from when

I decided to leave Uber. So Uber did layoffs in April. And it was a very much. And it was a year. It was a year. was really stressful. So it was the first time I didn't lay anyone off, but people on my team were laid off. I wasn't told who's going to be laid up. It was just really stressful. I mean, it's weird. In the sense that the people who were let go obviously worse for them, but I still felt terrible. And I just didn't feel that good about it. I think this was the breaking point. Like, I just, this was a point where I realized that it's not a family, which is weird because it never was, but it kind of felt a family-like, but it's just a corporate and I'm just a number. And, you know, This could happen to me again.

So I think I lost my sense of like the trust in the system that it'll take care of me because I saw some of my colleagues who are really good professionals. I'd argue they were better software engineers than me. They got to let go because they were in the wrong team. So this was April. And in July, I went on a holiday and like two weeks and I just realized like I need to leave. And I should. 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. You might relate to this. If you're an NGO, you're listening to this, maybe just shut your ears or you'll figure it out eventually. But when I was promoted into it's a management, and it wasn't promoting into it because it was a side step, but it didn't get salaries or anything. But it still feels like 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, right? What no one told me is, yes, I was a manager, but I was a middle manager. I didn't have too much authority. I didn't even have a budget for my team. like, you know, someone was underpaid and I couldn't do anything except complain for HR for 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 process. And the reason I wanted to do a 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 what's telling us to do stuff. And then we're telling them, no, that's BS. We can't, like, I don't want to do that with my people. So I decided as for next job, I could be doing this, but instead, I'd like,

like to be in charge, so I'd like you 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 kind of left. But it was a year after the decision. Let's talk about what your life is like these days, writing a newsletter full time. People might be listening and be like, man, $300,000 for writing an email a couple of times a week. week. That's pretty sweet. So I want to talk about the good and the bad of this life. So maybe to start, how many posts are you putting out a week? I started the news that are saying I'm going to post once a

week. Like you'll have one end-up post and I started to do that. But interesting enough, eventually I opted to two. So I now promised people to posts a week. There's a more in-depth and more timeless posts about some software enduring topic on Tuesdays. And there's something that's called the scoop, something a bit more timely where I reflect or analyze what's going on on the market. interesting stuff I'm hearing. And every now and then there's a bonus post. So I'll say two on average. But the second one came a lot later.

But initially, you know, the first few months I was like, I have this like one post per week and it needs to be good. And it was interesting because you would think writing a post a week is, it's not a big deal. Like it's easy. Like it's as you said, let's say you're making 300K just writing one post a week. But it actually because it was pretty stressful in the,

the beginning, because it turns out to write that post, it takes, you know, at least a few days or sometimes even longer, sometimes it takes a week or two for me to research in terms of talking with people. I chose topics that are not covered because why would people pay for something that is out there already or well known? Then I need to write off. I write 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 kind of helps make sure that it's just correct. And all of these things, you just kind of add up. Even if I only spend a day researching, the stuff is like a day researching, then I kind of have a draft on day two, draft day three, I get feedback and day four

it's editing. It's almost a whole week. So I was working on peril of things at the same time. I was often like running against the deadline. I was barely finishing it, which is not what I was expecting initially. So the first few months I feel was a bit more stressed. But again, the good thing is I cleared my calendar. So I said, like, I'm not talking with anyone. I'm just doing this. 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, like, not these clickbait articles, but actually like in depth, you look at the Washington Post and New York Times, search for their name and look at the articles that they write and they're going to be longer articles. They have like one a month. Like seriously, like you look at the investigative journalist, they might even have less. Because, 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 actually write a lot of original stuff because a lot of my emails are about like 5,000, 6,000 words, which is considered very long. Yeah. When you said that people listening might be like, oh, when 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 kind of the process. Do you have like a specific cadence per post? It's like Monday, draft, Tuesday, review, Wednesday, editor. Is that how you work? I write every post over multiple weeks, most of them. Some of them I might be able to write faster.

But what I now have is 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, interesting enough. And my cadence is that on Monday, I finish up the, the last of the post that goes out on Tuesday. It's a small edits, but it's already done pretty much. So it's just a few small tweaks.

Maybe I have some feedback coming in. On Tuesday, I publish this post and I do some free writing. I kind of write about some other ideas that I have. There's going to be future posts. On Wednesday, it's kind of 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 saying you just need to chill. Maybe that's it, but one thing I miss from the corporate world, and you know, if you're listening and you're in a job and you're thinking, oh, Gary's job is so amazing, one thing that I liked and I really miss about working at Uber is I actually had a schedule. This is weird. I hated the back then, but I was, I needed to do these things. And whenever you have a pressure, you do it. And this works with my news. I put in a second post, user, I think, to have a bit more pressure because the second part of Wednesday, I'm already starting to write my Thursday newsletter. On Thursday, I write that Thursday, I write that Thursday.

news letter and a Friday, I'm now writing the next news letter for Tuesday. So almost every day except for Wednesday, I have a strong pressure to write, which when people ask like, Gregory, how do you write so much? Because I did the maths and I wrote like four or five books worth of content just last year. It's because I have these deadlines. And as you said, Like I also know that thousands of people are paying me. You know, I have like, they have expectations of me. And so this is what's done. Like if you, if you want to write a book, the easiest way is go to a publisher and sign a contract,

not because of the money in software engineering. You're not going to get much to look like $5,000 or something like that. That's what I was offered initially. But it's the pressure. Like, you absolutely should go to a publisher or, or, you know, like have some external someone to hold you accountable and then you'll get it done. And I'll let you know another kind of, you know, secret or not so secret. Do you tell? In my mind, when I started a newsletter a year ago, it's cross strolls, like, I want to write

this book, which I think will be a great book, the Software Endure's Guidebook. I feel, you know, it'll be my kind of, you know, summary of, like, my last 10 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 I, partially, I went down the newsletter route because I was, I liked how every week I would have to write something. And I had the sneaky idea of, hey, what if I wrote this book where I kind of write some

posts that will be part of the book. And then the book will just kind of come together partially. And I've kind of been doing that. I haven't been telling people, but some of the posts are going to be, not exactly, but they're the ideas. I have this chapter and I have this list like, have I written about this topic in the newsletter? And I got, you know where I got this idea from?

There's the book, Three Musketeers. No from Alexander Dumacchorce. Yeah. Yeah. And you know how it was written? I don't. So he wrote the book for a magazine. He was apparently just low on money, and he started to write for this magazine, who told them,

like, all right, we need you to write something that our readers are want, but we want so that they will buy the magazine. And I think he was getting a cut of some sales or something. So he needs to write in a way that was interesting and then cut it off in a way that people would come back and buy the next one. And he wrote a whole book and that book, when I read it, it was really long. I was like, hold on. If he could do this, then this is kind of a good strategy.

Like he was writing it because he just needed the money. And then he wrote a really good book on the way. So one big learning for me from newsletters. And I would argue that you can use this not just for newsletters, any business that you do. You know, if you're going to go out and start a new business, you'll probably have some ideas and it's not just going to be newsletters. It's going to be a bunch of other things. if you put in ways that you have to do certain things,

you know, put in constraints for the things that you need to do, and then you're going to do that. Without that, when you're on your own, when you're entrepreneur, I was a great, like I think I was a really diligent employee. Like I always tried to get my work done, show up on time. I try to meet all expectations. But what I noticed is when I started to work for myself, it just went out the window.

Like almost 15 years of, you know, being this like star employee who really wants to, to do well, I find myself upset up myself for not, you know, just kind of 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. This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate growth. If your business stores any data in the cloud, then you've likely been asked or are you going

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Vanta. Over 3,000 fast-growing companies use Vanta to automate up to 90% of the work involved with SOC2. Vanta can get you ready for security audits in weeks instead of months, less than a third of the time that it usually takes. For a limited time, Lenny's podcast listeners get $1,000 off Vanta. just go to vanta.com slash Lenny. That's V-A-N-T-A-com slash Lenny to learn more and to claim your discount. Get started today. I definitely wanted to dig into that a little bit deeper. This issue that folks in our line at work run into, which is unstructured time and having to create your own structure, I had the same exact problem when I started this thing. Like, before I even started the newsletter, like, how do I use my time?

Well, how do I create some kind of deadline for myself? So I'm curious what other tricks you found to help you stay productive and focus because there's Twitter, there's Instagram, TikTok, there's all these things that. pull my attention and I've learned a couple things I'll share that have been helpful, but I'm curious what have you found to help you focus and get things out the door to posts a week, which is a lot of work. 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, well, that means that 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 because also Twitter for me is also something that is very useful in generating people raising awareness. So whenever I tweet, it kind of helps my business. So that's a good thing, right? But it also, it justifies for me spending more time on, for example, Twitter than I want to. So I find that I come up with a method and it works for like a few months and then I need to change it because my brain just learned to work around. So I'll tell you a few things that I did, and I'll tell you where I'm at right now.

But I use, for example, apps. Like I use this app center, but I know you're also there. Yeah. Love that app. Also, investor, disclaimer, but I love it. 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 it not as efficient.

I found the pulmonary 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. So 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't,

I need to focus on, you know, it's basically the deadline. So if you have deadlines that works, the other thing is if I start to get I spend three or four minutes doing something focused and I kind of get the flow of it. So a trick I sometimes do when I'm just like, I just don't feel like doing anything is I set a timer of 20 minutes and then I say, all right, no distractions. I have a script where I just kill. I use a max on the host file.

I just kill all LinkedIn, Twitter, Facebook, whatever size. So I just cannot reach it. Like, it's just a very simple python strip that I wrote for myself. And then I, in the first few minutes, I'm kind of grumbling. I'm like, I wish I could do this. I wish I could just look at Twitter to research. But about five minutes in, there's a switch when I'm like, I'm now actually like, heads down and doing it.

And this has been the thing has consistently worked. The interesting thing is that I feel guilty a lot of times that I'm not working as far as I could. And I do wonder if it's guilt or if it's my mind or body telling me, that it just wants a break or it wants to do something else. I still haven't figured it out, but I'm on the way there. Awesome. That's a really cool trick, the host file trick.

So that's something that you have to be kind of technical to do. I imagine there's some Chrome extensions that could do that to some extent for folks. But the whole idea there is force your brain not to have any way to look at something that'll be distracting by blocking your computer from even being able to go to the site. That's awesome. Yeah. So there is definitely going to be extensions that you can use. I mean, but if, well, on this podcast, we'll have a variety of people.

If you're a software engineer, it's pretty simple because even if you're not, you can look it up in the whole spout. When you override your whole file, you can actually block things, what you do. And I did this because I wrote a script where I need to run the script and I need to run 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 the software engineers. I don't like them because I feel they're either two opinion.

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 minutes, 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 easier or something that I just need to rotate. But for example, when I back back. went back to Centard. I have no affiliation, by the way, so I'm just telling us. But I really liked how they keep evolving as well to do like cooler things. I have a community element where you're competing with people on uninterrupted time and closing stuff. So that to me is like I'll do one last thing. One last thing on Centard again, I have no affiliation. What I really liked about Centered is it allows you to turn on your video camera. And I felt to really kind of force 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. Yeah, I love that feature. It's centered.com. By the way, folks want to check it out. So to summarize some of your tips, which I love, centered deadlines, totally work for me too, blocking sites so that you can't get distracted by Twitter and LinkedIn and TikTok and all the things. And then, yeah, I guess that's the three, right? The three that work best for you. Yeah, and the simple thing started 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. One side decides I should do it. What's cool center does that for you, and it has music and all the things. Yeah, so I like that a lot. Awesome. What do you love most about this life that you lead now versus what you used to do? And then I'm going to ask you the opposite, but let's start there.

I really like that. It forces me to have my calendar empty, because for so many years, years, my calendar was this giant mess of meetings on top of meetings, and I would barely have any time to actually have focused time. Now I actually have the opposite. I usually have a lot of focus time, and I had very, very few meetings or things. And even now, like, I kind of get like a little bit like cagey, like, oh, I have this one meeting in the whole day. So I like how it's flip. Yeah, it's kind of like, it's kind of that manager time to major 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 a 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 as Uber, we also experimented a lot. obviously more in a corporate setting, but I guess that's just kind of gotten extended. So these are the two favorite things, is the open calendar or like very few meetings and experimenting, trying out stuff and being able to decide what I want to try out. Plus one on both those. I have a rule of no meetings before 3 p.m.

And it generally works 99% of the time. And the reason I do that is to your point, if there's a meeting at like 11, I just like, can't do anything really deep until that point. And then afterwards, I have to, like, get back on track. And having that deep focus time is so important for this work, even though, like, half the time I'm on Twitter and distracted, as long as I get enough time to focus, good things happen. Okay, opposite.

What are some of the most surprising downsides and kind of sucky parts of this path that you've taken? Well, one is obviously it's lonely. So I do miss. I had a really good team. Meadow Cooper and it wasn't just a team, it was the people. It liked like, you know, everyone has different views on remote work. I actually didn't, and I didn't enjoy remote work as much because I just liked

hanging out with people. I guess I'm that kind of more outgoing type. And I really like, you know, 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 sometimes it was annoying because I wanted to get work done. But for the most part, I miss it more than I haven't. So I miss not having that. I kind of compensate for that by working for me to share workspace.

like a shared office, which is a techie workspace. So everyone needs to work in tech. So I actually get to say hi to people and have a little small, small talk. The structure is weird because I felt really guilty for the first few months because I felt that at Uber I was more productive because I had to be like I was doing so many things. Like in a day, you know, I would start my day, let's say at 9 or at 830 and I finish it up at I know like 6 or 530.

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 have like looking at my output, like, you know, now I write a lot, but I wrote a lot. I think I roll almost as much in terms of emails, chat messages, etc.

So like the downside is I felt very guilty and a little bit frustrated for myself for, you know, feeling that I'm slacking off. That's one. And the other thing, it is surprisingly stressful. So when you start off, It's kind of lonely. Not many people do this, what we do. You know, that's also one of the reasons that we connected

because it's a very small community. And even within the community, I feel in the, 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 to economy as well. You know, like people are not going to subscribe or pay for 10 different, or 10 newsletters on the same topic.

So that makes it a little bit more. you know, it's not the same as when you work in tech and it, you just kind of share exactly everything that you should do because you can only win. So there's that part, but there's a lot of external validation. So like whenever, you know, looking at your subscriber numbers, which brings a bunch of stress that I didn't expect. And I'm a successful user. Like I think my success is quite rare.

You know, there will be one or two or like a handful of people who have similar success, but I'm kind of an outflier. So that's another thing that I think is just good. putting out there. And a downside is you don't really know how well you're doing. There's external goals are kind of meaningless internal goals, either you smash them or you don't reach them. So there's this constant sense of where am I, how am I, and how do I judge myself? Did I make a mistake for leaving my job? I actually asked myself for like several months actually after I started or did I make a good one. And I think for a lot of these kind of questions and doubts, having past professional experience working at a company is really useful to set yourself grounded.

I actually want to ask you about that. But I'll add a couple of things that I also find are major downsides of this life because it's not all rainbows and butterflies. One is with a paid newsletter especially, but even with a sponsored newsletter, you basically have to get something awesome at every week. In theory for the rest of your life, people are buying an annual plan every day. So that means at least a year. You have to write something awesome if you want to stop. But it's hard to stop because, as you pointed out, the income is very meaningful. And that's a hard thing to give up.

And so I'm not sure exactly the exit path that there is that exists for us where we 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. Yeah. And it's a really good example because for a lot of companies and, you know, I'm assuming a lot of listeners are working in tech. Typical thing is you work hard, you build equity at a company or you build the value of the company and then you can sell that company and then you can have an exit and you can do whatever for what we're doing. It's really tied to us.

So however much or little my news that I 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 makes it unique. It makes it harder to compete with, which is. is cool, but it does not create that much of an exit path unless you start to build a company around it, build an organization that can run without you. For example, you know, this is what a lot of book publishing companies. So basically either you build a publishing company where you start to hire people who start to write some of the articles initially and then later more of them, but that's, you know,

it's not one person use that anymore. Or you keep doing this and then, you know, until you either stop and then the revenue stops or you might be able to sell it, but it really undervalue. Yeah, I really don't want to manage people. I don't want to have employees. So building like a media company with writers, that doesn't sound too fun. But maybe that's where this goes. That is one route for sure. The other downside I'll just add is the fact that you have to write something awesome every week,

it's hard to take meaningful time off because if you stop producing great stuff, people leave. And I invented this PTO policy for myself where I take four weeks a year off where I don't do a newsletter. But that means I can't take more than a week off usually, like two of 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. All we're on the topic.

Yeah, but a lot that were very early. So I think the whole concept of pain news is new. So I think we're going to do a lot of experimentation. And also, a lot of it, I think you need to figure out what your needs are. So in the first year, I did not take a holiday, like in terms of a, Or even when I did, I was writing. And, and, you know, it caused a bit of friction with, let's say, my family. And now I'm solving it in a different way.

So I am trying to take more time off now. And I'm doing it by working ahead with some of the less time sensitive things. But it is tough. So the downside that we haven't mentioned, but I'm just going to call it out is holiday. Like the great thing. I never felt, well, I felt a little guilty sometimes. I'm taking holiday, but when I went to holiday, I took it off. 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 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, you know, like we should conscious about burnout as a whole. So you need to solve for that. And I'm, I'm starting to solve for that as well. Yeah. Okay. Enough about the downsides. Overall, it's pretty amazing making hundreds of thousands of dollars writing an email once a week slash twice a week. So just to wrap up on that, I'm curious, where do you think this goes long term for you? And then I want to talk about just like

what it takes to be successful. But before there, where do you think this goes long term? I stopped making long term plans because, you know, three years ago, you would have asked me what I wanted to do. And I was like, I want to be, I don't know, like a manager of managers. And then I became one. And then then I would have asked what, what is my dream? I would have been like, well, it's a stretch, but maybe I want to be a site lead. And I didn't become one per se.

But I never thought of, you know, writing a news that are now writing a successful newsletters. So I'm kind of going with the flow. I'm seeing this less, by the way, as a news letter 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 half. 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 kind of detach as well. I can actually enjoy my weekends as opposed to like, you know, I think I need to write this. I need to write that. So I also want to make it work for me. And I'm not going to marry to the idea of like, hey, it needs to be like it always needs to be an user or et cetera.

Right now it is. But, you know, where I see it's 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 when you're stuck on. I love software engineering. So this is a great format. But over time, it might shift.

So I'm kind of keeping my options open. And what I've learned from this journey is you need to create time to be able for that spark to come. So one of my goals for the next few years is to not spend 50 hours a week on the newsletters 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. news that are only came because I gave myself six months of unpaid. I'm not going for work. I've been

an Israeli LinkedIn emails. And it kind of just the idea came and the inspiration came and the motivation came. There's a lot of similarities with my approach. I don't think too far long term. I have no idea what's going to happen. I just kind of take it to I see where a poll 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. And one last thing to Sushan, you said something really important to the poll.

And I want to double down on that. One of the biggest best things about doing what we do when you're in charge of your time is you can double down on polls. So when I could Uber, like I said, my plan was I'll write this book for six months. Two months in, I just put a draft about a really long blog post about mobile engineering. And I got like a lot of messages, like a lot.

Like my, I usually get like, used to get like three or four messages on Twitter per day. I got 20 in an hour, people saying, can I read the draft? And I was like, huh, that's interesting. I just felt this poll of like this huge interest of people caring about this.

It was this really long blockposts about how mobile engineering, during at scale. And someone suggested on a private business, you could probably turn this in the e-book. And I was like, oh, that's a good idea because it's a really long blog post. So I said, it's going to be an e-book and it'll be pay what you want. And then people start to buy it. And I was like, that's interesting. So I didn't have much else to do. So I was able to double down and said, like, you know what, for the next two months, I'm going to write this book because it seems there's an interest in it. And I can have iterated. I turn 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 poll. And same thing with the newsletter. So we're going to talk about, you know, 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. I never expected the people who would care about building a large mobile app, you know, more than a few hundred people. Turns out they do, thousands do. Let's actually jump to that. Let's talk about just how to get started for folks that are like, hmm, 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 1,000 subscribers? Well, I mean, I'll tell the story that it's kind of true and people will think it's amazing. And I'll tell the real deal behind it. Okay, great. I mean, 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, like, if maybe a thousand on LinkedIn or something like 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 six news,

that I had a thousand pay subscribers. And this sounds like a fairy tale. 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 kind of accidental work behind this.

I started a blog six years before. Actually, I was, 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 like, like it was 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 fit up with this. The blog wasn't going anywhere. And I was just writing for myself, by the way, but

I didn't like how it was just all over the place. And I said, you know what, I'm going to start a blog. It'll be about software engineering. And I'll call the Promatic Engineer. I bought the domain. And I read this blog post from Jeff Atwood, who's the founder of Stack Overflow. And back in 2010 or 2000, I think in 2007 when I was still in college, he had the most popular blog on the internet for software engineers. It was called coding horror and all the software engineers. I knew read it like and we're drinking it. Like it was it was like next level wisdom every single week, like twice a week. Yeah, you read it as well? Yeah, I used to be an engineer and I was all up in that. And I think coding horror came from a forget the book, but there's a book with that graphic.

There's a book and there's a graphic. Yeah, yeah, yeah. And, and there's a graphic. Yeah. And, and He wrote a post, which really stuck me for years. He said how to be famous on the internet. He said, like, there's three simple steps. 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 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 Primatic Engineer, I said, I'm kind of tired of my old blog being all over the place and there's no focus and no one really cares about it. I'm going to do what Jeff Affwood said. I'm going to publish, okay, it's not going to be twice a week,

but I'll like for every two weeks, I'm going to publish an article and I'll do it for a year. So I started to do this. I published six block posts about software engineering, kind of, you know, going into topics that I carried over research and all that. And then I gave up. I'm saying this because I kind of gave up and I looked it for,

for a few months, but then something interesting happened. I had a huge traffic spike, and it crashed my shared hosting at the, the time. And it came from the site called Hacker News that I ever heard about. And people were discussing my post and they were adding, like a lot of things. And I was like, huh, that's interesting. People care about what I wrote like six months ago. What was that post, by the way? It was called A Comment is an invitation for refactoring. I wrote my view that if there's a

comment and a code, that means that comment should be deleted. I should just refactor the whole thing. And it exploded at 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, you know, software engineers in Silicon Valley argue about my stuff. Like I saw some of the karma people, some really high karma people were really, you know, going pro or con. So that's what I thought. Like, it's just like by writings that some people might read it. It's not guaranteed.

And I started to write on that blog like once every few months, depending on kind of my mood. But I never stopped doing it. And I partially did it. I always hoped that it would get. on this site called Hacker News, but by the way, for a while, I didn't even know you could submit it, so I never submitted my own things. But the other thing was, I just kind of liked it. And I kind of had this habit. And over years, like, I had this blog from 2015. For six years, I was writing that blog. And in the last year, when I worked at Uber, 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, for example, distributed systems. And more and more of these posts just started to just pop up on half for years. 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 its values and people care about what I, what I write. And to your, 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, like how to do performance reviews. I wrote one about the primal nature of software and new salaries where I observed that there's kind of three different tiers that are, like, there's big tech and there's, like, local companies. And I think what happened is when I announced that I'm going to write this newsletter, I also put it on the blog. A lot of people realize that they, oh, I've been reading this pragmatic insure.

I don't know, I don't know who is behind it, but I like it. Let me sign up. Like, I do want to get like an email every week instead of the things that were every now and then. So there was years of work, and I wish I could tell you, you know, how to build a successful newsletter. But the best advice I have is still what Jeff Appwood does, except how to, 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 going to write for yourself and you keep improving, you'll be a better writer, that's for sure. If you're lucky or if you're right about stuff, you might start to attract people who think similarly. So, you know, step one is get started. Step two is keep it up. And my suggestion is simply just for yourself.

Like, the weird thing is until I started my newsletter, I never thought I would turn this ever into business. but it always felt rewarding. So I never, like, if you're starting out writing and using to do what I'm doing one day, you know, like it might work out. But interesting enough, I never even thought that this was an opportunity. So people listening to this that are thinking about Shedek's for this life, I think, if you think about your story, you wrote a book, you blogged for a while before this,

you worked at Uber for a number of years. In a sense, it comes across a little bit like, man, there's no way I can be successful. if that's the background I need to have. I have to have written things and worked at an awesome tech company. What advice do you give folks that are coming to you being like, Gerge, should I start a newsletter? This makes sense for me. Do you need the kind of background that you have? Do you think?

Well, don't forget that when I started like my blog, I didn't have any of this. And this is while you were at Uber. This is before you started the newsletter. It was before before I was at Uber. I was maybe at SkyScanter or maybe at Sky. But I was even blogging before. So I was talking at conferences before. So my advice really would be is like if you're thinking of a newsletter or something similar,

start teaching and sharing what you know and what you're observing. This could be a newsletter. This could be a YouTube video. This could be going to meetup. I actually 10 years ago, I went to a lot of meetups where I presented all sorts of as I met a lot of cool people. I would say, you know, share your knowledge one way or the other. And as you're doing it, you're going to learn a lot more.

So what I find, this is true when I was a manager, people, you know, we have to set goals. And I told people there's like two types of goals you can set. One is the goal, you know, people said this goal. I want to be promoted the next thing where I want to lead this big project. And those are bad goals because it's not in your control. So sending a goal that I want to have a successful newsletter with like, I don't know, 20,000 subscribers. That's a goal where you're not in charge. A good goal is what you can do.

So a good goal, for example, is I want to learn this. new language in the next year, which I'm going to spend time on work. Or I want to leave a work at 5 p.m. on Friday to be home to found. So set those goals that you can't control. And this is how actually my, my, you know, 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, proud about that.

Or whenever I learned something, I actually want to share it every now and then. So I would say set those goals. And the rest will come probably. Again, like don't get me wrong. Like I'm not trying to talk people out of doing it, but for me, a lot of this was luck. And the other thing that I would suggest is be curious and look at your professional career as well. One thing that definitely helped me is getting pedigree. This was so much conscious.

I come from, you know, a small country from, you know, a really good university, which no one knows about. But, you know, I 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, JPMorgan in London, I was pretty picky of where I would go next. So that's why when Skype came along, I was like, this is great. Like, everyone knows Skype.

I love Skype. It was the same thing with Uber. So there's, especially these days, like, people would not pay nearly as much as energy as me if I worked at, you know, small parts limited. So there's that part as well. So you need to kind of manage 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 stuff on the side. It's interesting how it's now flipped. I'm now doing these things. This is my main thing, which used to be my side project. And I guess one last advice is do some side projects. Like, all of this starts to the side project. Like at work, no one's really going to appreciate that you're doing a news that or this or that.

You know, try stuff on the side, assuming that you have time. Or if you don't have time, try to make time. Because I feel a lot of what we're doing is this pre-entrepreneurial. And the only way you're going to get the, muscles if you start some small things. You talk about the pedigree being important. I think there's also an even deeper point that you actually need like real experience doing real things that scaled and worked and mattered and worked with amazing people to actually build the foundation to write about, share wisdom from. And that's really important. There's a lot of people starting

newsletters and tweeting who like haven't done much and don't have a lot of real life experience to share. And I think that's the core of a lot of what we do is it needs to be based on real things that worked and that you've learned or that you have access to other people who have learned these things. I would say that. But, you know, one thing that I'll double down on it, that's a really good observation is if you actually, if you're serious, like one day I will want to, you know, write a book or a newsletter. It's kind of the same thing. Or teach people about stuff. You know, look at the people that you look up to that you actually trust. You know, this maybe it's me or maybe it's huge, but it's more likely people like Kent Beck, for example.

He's the creator of TD and he's risen a lot of books. He's one of my favorite kind of people. I think he's coming up like 50 or 60. He listens to the story. I don't want him to make him to see me old. But what I love about Kent Beck is he's been the middle of it. Like he has always worked kind of in the industry and that he kind of wrote about it. But for example, he was he invented, I think he invented or he was a co-inventure of

was a TDD or Extreme Program, anyway, one of these methodologies. And then he went to work at Facebook. He kind of took a title cut to be a software engineer. And then he hosts a TDD workshop, a test-driven development workshop, and no one showed up at Facebook. And Facebook did no testing, which went against all conventional wisdom. And he took that risk joining this company where, you know, he could have been like, you know, like people would have knelt down to him anywhere else.

But he went to this company where he just wanted to learn. He is his lifelong learner. He's right now writing a book. But what I think away from it is, if you want to be somewhat of people, listen to like, yes, do cool and interesting stuff. Push yourself 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 was the other way around. But back in 2016, people were turning out Facebook and Google offers to go at Uber,

which we all thought would change the world. So yeah, you know, like you do need to, get into those teams that are doing interesting stuff, prove that you can do that. And you'll have a lot more interesting stories to share. That's for sure. If you had to boil down advice for how to be successful in this life of a newsletter, you have to boil it down to just like one or two key pieces of advice. What would you say? One is have enough depth in the field, whatever field you do. So, you know, this might mean that. I think I don't want to say that. If you don't have experience,

don't start from, but it's kind of true. So like 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, you know, I would say choose a field that you're going to be good at. And you can start on the side, you know, doing this,

assuming you have something, you're someone who's experienced in the industry, or you have kind of insights, wisdom, observations to share, start doing so in whatever format. You know, I do newsletters. There's actually YouTube, a lot of people are becoming pretty successful on YouTube sharing their thing. Three, have a cadence and stick to it to some extent because you do need to keep repeating it. And then four, don't be afraid to try out new things. A good example of a person who did this is Steve Yega. Steve Yega is, have you heard of CVA's? Yeah, he wrote some epic.

long. 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's terrible. And he was really well known at Google, because he wrote stuff inside Google. So he's experienced, knows a lot of stuff.

And they put Google and he started to do a podcast. It's on YouTube. You can check it out. It's called Stevie's podcast. And what he did is every week, he recorded an episode and he talked about a bunch of his learnings, a lot of stuff. And he was pretty clear. front when he started the first one, he said, like, what I'm doing is, I'm going to do just for six

months, and I'll see if it sticks, see if people care about it or people watch it. Now, this guy had a lot of experience, really fun. I think it's really fun to listen to in India. And, you know, it was, I think, successful. It was like it got to a couple thousand or maybe even 10,000 subscribers, but it wasn't this like this rocket ship. And I think what he did, he just stopped that for six months. And he's now, he actually started the head of engineering at S-Source graph. He actually went back in an industry. But what I love about this, you know, it shows that, you know, you cannot guarantee having success, but you can do what he did,

which is like, you know, start something to 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. If you think about, you know, take a step back of,

what is a successful news letter? What is a successful podcast? What is a successful YouTube channel? And it's stuff that's kind of interesting. It's either entertaining or educational. But all of these things, you can't really kind of put a finger on. Like if you watch YouTube, you know, Mr. Beast is someone who you probably came across.

I actually like watching his videos and amuse how good he does it. But it's not something you can, you know, anyone would have written in the book. So there is a sense of trying to understand what people care about. And a good way to understand is either experiment or observe or just try out stuff. This is great. I feel like I could boil this down even further from everything you just. said, which is build depth in an area, then write a blog post twice a week for two years. And good things will happen.

I'm pretty sure. And here's an interesting thought as well, just as for closure. I was talking with someone on why my news that are so successful. It's just really successful, and I also 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, some more than my news letter. And he said this.

He's like, what I noticed is you started your blog in like 2015, 2016. And I started my YouTube channel like in 2019 or something like that. And he said on YouTube, there's so much quality. There's like super high grade productions. There's like everyone is doing YouTube and he said, you know what I don't see? I don't see many blogs that are writing in-depth stuff regularly. I feel everyone went over to YouTube or TikTok. So there is the other angle of the medium.

And I'm kind of saying this, not say, 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, you know, like which might be good or bad. So if you're going to be really well-known person on YouTube, you might get more people watching you, but we'll have a lot of 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, for, learning about stuff because I can't even scan through the whole thing. It just really time gives you. So I think you decide if you want to do entertainment, which for these podcast listeners, I don't think that's kind of in the question you're competing with the likes of Spotify, Netflix, education, which is a little bit more dry, but it's really useful. Or edutainment, which is entertaining education. And once you figure that out, either if it's education or entertainment, you can figure out

what format might work both for the medium and for you. And at the end of the day, you need to enjoy it. Like, I personally have learned over time to love writing. Like, 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. Gurgh, 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 kind of path. Just two final questions. Where can folks find you online if they want to reach out learn more, and how can listeners be useful to you? 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, etc.

Everything is there. And you can also sign up to my newsletter. Listener is being useful to me. If you work in tech, consider signing up to my newsletter. I mean, I always tell people like, we're a compliment your newsletter. If you work in product or have interest in product, your newsletter is an awesome choice. With software engineering, engineering management, it kind of goes 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. If you know, I write this column called the scoop every Thursday, if you hear any interesting scoop happening, especially real for techies, this might be some changes in the workplace. Like, you know, your company is just rolling out agile like team at Twitter. I did. Feel free to ping me. Just search for sending scoop to the pragmatic engineer. I treat everything as an ennemus, so you can tell me interesting stuff.

I'm typically interested in the stuff that you might not read about than the traditional media, but we, as techies, really care about. And finally, if you work at Google and you want to anonymously talk to me, just ping me because 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, you know, how these companies work from a software engineer and engineer manager perspective. awesome. I hope this comes out before that a post comes out. But if not, then enjoy that post.

Gerge, thank you so much for being here. This was awesome. And maybe we'll do a V2 as things continue to grow. Awesome. It was great being here, Lenny. Thank you so much for listening. If you found this valuable, you can subscribe to the show on 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 lenniespodcast.com. See you in the next episode.