Nov 17, 2022 · 1h 14m · lennys-podcast
Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this in-depth interview, Lenny Rachitsky speaks with Gergely Orosz, creator of The Pragmatic Engineer, exploring how he transitioned from engineering management at Uber to building Substack's top technology publication while sharing actionable frameworks for creator monetization, productivity, and editorial depth.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 21.3% of the talking time here. How this is scored →
Lenny as informed peer 4.0 Guest teaching 2.9 Guest disagreement 0.3 Lenny pushing back 0.2
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 57:50 Contrarian take on code comments requiring refactoring
Gergely describes intentionally taking a controversial stance on software engineering practices, sparking polarized arguments across Hacker News.
Hardest push from Lenny ▶ 1:04:31 Lenny reframing pedigree into authentic operational experienceLenny refuses to let company prestige stand alone as the critical factor, arguing instead that genuine hands-on experience scaling systems is the true foundation.
Biggest teaching moment ▶ 32:10 Alexandre Dumas serial publishing masterclassGergely educates Lenny and the audience on how classical literature like The Three Musketeers utilized forced episodic deadlines to ensure prolific output.
Lenny holds their own ▶ 1:04:35 Lenny demonstrating deep understanding of content credibilityLenny articulates why superficial creators fail by contrasting them with operators who possess authentic battle-tested experience.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Gergely Orosz's Career Path from Engineering to Writing | 3 | 2 | 0 | 0 | Lenny sets up the peer-to-peer framing between the top business and tech Substacks. Gergely summarizes his software engineering trajectory from Hungary to London, Skyscanner, and Uber. | |
| Rapid Subscriber Growth and Monetization of The Pragmatic Engineer | 4 | 3 | 0 | 0 | Lenny inquires into the magnitude of earnings compared to big tech compensation. Gergely compares European engineering total compensation to the uncapped upside of paid newsletter subscriptions. | |
| Navigating Uncapped Earnings and Autonomous Career Models | 5 | 2 | 0 | 0 | Lenny contributes his own framework on having thousands of micro-bosses and shares an Airbnb analogy regarding SOX compliance. Gergely recounts how COVID layoffs pushed him to abandon VC fundraising in favor of self-publishing. | |
| Corporate Realities: Navigating Layoffs and Middle Management Frustrations | 2 | 3 | 1 | 0 | Gergely describes the disillusionment of middle management where titles confer responsibility without budgetary authority. Lenny listens and prompts the timeline breakdown. | |
| Crafting In-Depth Articles and Publishing Cadence Strategies | 4 | 4 | 0 | 0 | Lenny contrasts public perception of writing ease against actual workload demands. Gergely educates on long-form investigative cadence and references Alexandre Dumas's serial monetization technique. | |
| Sponsor: Automating Security Compliance with Vanta | 5 | 3 | 0 | 0 | Lenny relates closely to attention fragmentation and discusses productivity tooling. Gergely explains his programmatic approach to blocking distractions using custom Python scripts and the hosts file. | |
| The Joys of Autonomy: Open Calendars and Creative Liberty | 6 | 2 | 0 | 0 | Both hosts exchange operational insights into open calendar strategies, isolation, and lack of traditional equity exits in solo media businesses. Lenny elaborates on his strict afternoon meeting rule and personal PTO system. | |
| Adopting a Business Mindset and Doubling Down on Audience Pull | 4 | 3 | 0 | 0 | Gergely discusses treating creator work as a business and recognizing market pull from organic Twitter reactions. Lenny corroborates that free time inevitably gets absorbed by new creator initiatives. | |
| The 6-Year Overnight Success: Blogging Foundations and Hacker News Traction | 4 | 4 | 1 | 0 | Gergely demystifies his overnight traction by revealing six prior years of blogging and viral Hacker News debates. Lenny validates the reference to Jeff Atwood's Coding Horror principles. | |
| Developing Domain Expertise, Controllable Goals, and Industry Pedigree | 5 | 4 | 1 | 2 | Lenny pushes back gently on pedigree, stressing that raw operating track record and real-world scale matter far more than corporate brand names. Gergely agrees and illustrates the point with Kent Beck's tenure at Facebook. | |
| Core Success Factors: Depth, Experimentation, and Written vs. Video Media | 4 | 4 | 0 | 0 | Gergely summarizes key advice including domain depth and analyzes the competitive dynamics between long-form text and video platforms. Lenny synthesizes the core takeaways into actionable rules. | |
| Connecting with Gergely Orosz and Sourcing Insider Tech Scoops | 2 | 1 | 0 | 0 | Lenny and Gergely wrap up the episode, with Gergely soliciting anonymous insider tech scoops for upcoming culture investigations. |
Statements from this episode (27)
Rachitsky: Pragmatic Engineer is Substack's top tech newsletter
“Your newsletter is the number one technology newsletter on Substack, called the Pragmatic Engineer, by the way.”
Rachitsky: Lenny's Newsletter is Substack's top business publication
“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.”
Orosz: London was Europe's top tech hub before Brexit
“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.”
Orosz: Pragmatic Engineer reached 189K subscribers, adding 80K in 90 days
“Well, just today I checked and it said 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 a thousand people per day”
Orosz: Peak total compensation at Uber in Europe was $330,000
“In my best year at Uber, I made about like 320 or 330,000 dollars in total compensation. This was after Uber went public. So it's, it includes the stock, the base salary, the bonus, which was very, very good in Europe.”
Orosz earns more from his newsletter than his $330,000 Uber peak
“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 newsletter is growing.”
Rachitsky: Solo newsletters feel safer than tech jobs due to distributed risk
“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…”
Orosz: High-effort newsletter articles create immediate annual revenue raises
“I had a spreadsheet that I maintained for the first year of the publication where I listed for every article, how much did my annual revenue go up a week later? So kind of tracking, like, what was the impact? And the crazy thing was that you know, when I wrote…”
Orosz: European engineers undervalue equity because Europe lacks startup success stories
“European software engineers will not value stock as much because they just haven't seen success stories.”
Orosz: Uber's overinvestment in custom internal tools birthed alumni startups
“Uber has invested silly amounts of money to build everything custom internally, like everything that you can think of. Our build system is custom, our experimentation system, our container, you know, the way we kind of automatically set that up a lot of the en…”
Orosz made $100,000 in one year self-publishing tech books
“This book, Building Mobile Apps at Scale, another book that I published about tech resumes. I just wrote these in a few months. They started making money. They made about a 100,000 dollars in the first year.”
Orosz: Uber laid off my team members without informing me beforehand
“Uber did layoffs in April and it was really stressful. So it was the first time I didn't lay anyone off, but people on my team were laid off. I wasn't told who's going to be laid up.”
Orosz: Uber engineering middle managers lacked authority and team budgets
“What no one told me is, yes, I was a manager, but I was a middle manager. I didn't have too much authority. I didn't even have a budget for my team. Like, you know, someone was underpaid and I couldn't do anything except complain for HR for six months and hope…”
Orosz: External publisher deadlines are the easiest way to finish books
“If you want to write a book, the easiest way is go to a publisher and sign a contract, not because of the money. In software engineering, you're not going to get much, like, 5000 dollars or something like that. That's what I was offered initially, but it's the…”
Orosz: Pragmatic Engineer newsletter posts double as serialized book chapters
“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, I've kind of been doing that. I haven't been telling people, but some …”
Orosz: Entrepreneurs must create artificial constraints to maintain productivity
“If you put in ways that you have to do certain things, you know, put in constraints for the things that you need to do, and then you're going to do that. Without that, when you're on your own, when you're an entrepreneur, I was a great, like, I think I was a r…”
Rachitsky: Avoid meetings before 3 PM to protect deep focus time
“I have a rule of no meetings before three PM. And it generally works, 99% of the time, and the reason I do that is, to your point, if there's a meeting at, like, 11, I just, like, can't do anything really deep until that point, and then afterwards I have to, l…”
Orosz: Solo newsletters cannot achieve traditional exits without building an organization
“From what we're doing, It's really tied to us. So however much or little my newsletter will make, you know, 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 aw…”
Rachitsky limits himself to four separate vacation weeks to prevent subscriber churn
“And I've invented this PTO policy for myself where I take four weeks a year off where I don't do a newsletter. But that means I can't take more than like a week off usually, like two weeks in a row.”
Orosz plans to reduce newsletter work hours from 50 to 20 weekly
“One of my goals for the next few years is to not spend 50 hours a week on a newsletter, which I'm doing right now, but spend 20.”
Rachitsky: Reducing newsletter hours inevitably leads creators to add more work
“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.”
Orosz: Pragmatic Engineer gained 1,000 paid subscribers in its first six weeks
“I announced my newsletter. I told people I'm gonna go full-time on this. I had maybe 10,000 Twitter followers and I don't know, like maybe a thousand on LinkedIn or something like that. And people started signing up the next day. I had a hundred subscribers in…”
Orosz: Code comments mean the code should be refactored and deleted
“If there's a comment to the code, that means that comments should be deleted and you should just refactor the whole thing.”
Orosz: Professionals should set controllable input goals, not outcome targets
“One is the goal, you know, people will set this goal. I want to be promoted the next thing, or I want to lead this big project. And those are bad goals because it's not in your control. So setting similar, setting a goal that I want to have a successful newsle…”
Orosz: Having big tech employer pedigree drives audience attention for writers
“So there's, especially these days, like a lot, people would not pay nearly as much attention to me if I worked at, you know, small parts limited.”
Orosz: In 2016, candidates routinely rejected Google and Facebook for Uber
“When I went to Uber in 2016, it was one of the highest regarded places back in 2016 and 20 17. 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.”
Orosz: Writing faces less competition than YouTube as creators shift to video
“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 gonna be a really well-known person on YouTu…”