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Gergely Orosz (The Pragmatic Engineer)17 November 2022

Leaving big tech to build the #1 technology newsletter

7Frameworks
15Insights

Episode overview

Gergely Orosz explains how Uber’s layoffs and a promise to take a risk led him away from a lucrative engineering-management career and eventually toward The Pragmatic Engineer. He describes the research, drafting, feedback, and editing required to publish two substantial newsletters each week, along with the freedom, income, loneliness, stress, and weak exit options of a personality-led subscription business. Orosz and Lenny Rachitsky also discuss building expertise, sharing work consistently, creating external deadlines, and following audience pull when testing a creative business.

Key ideas

  • Orosz left Uber after layoffs broke his trust in the corporate system and reminded him of an earlier promise to take a meaningful risk.
  • The Pragmatic Engineer grew to 189,000 subscribers, with Substack recommendations becoming a major growth engine.
  • A rigorous newsletter post can require days of research, drafting, feedback, and editing; Orosz uses fixed publication deadlines to create structure.
  • Running a solo newsletter offers creative control, an open calendar, and uncapped earnings, but also loneliness, performance anxiety, limited holidays, and no simple exit.
  • Orosz uses short focus timers and blocks distracting sites through his computer's hosts file to overcome resistance and enter focused work.
  • His early newsletter traction rested on years of blogging, industry experience, books, conference talks, and articles that circulated on Hacker News.
  • His core advice is to develop genuine depth, share useful knowledge consistently, set goals within your control, and test a format for long enough to judge audience pull.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Self-Mastery3 steps

Controllable Goals

Set goals inside your control (inputs), not outcomes you can't guarantee

Read →
Entrepreneurship3 steps

Double Down on the Pull

When something you made gets unexpected traction, drop the plan and lean all-in

Read →
Influence3 steps

Earn the Right to Teach

Build real depth and pedigree first — then your writing has something worth reading

Read →
Productivity3 steps

Manufactured Deadlines

Impose external constraints so solo creative work actually ships

Read →
Productivity3 steps

The 20-Minute Focus Ignition

Beat the hardest part of deep work — starting — by force-blocking distractions for 20 minutes

Read →
Strategy4 steps

The Time-Boxed Leap Bet

De-risk a scary career leap by treating it as a fixed-length experiment with a fallback

Read →
Marketing3 steps

The Two-Year Publishing Cadence

Write a post several times a week for two years and an audience will find you

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 8

  • Lenny RachitskyCoinedtoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    “welcome to Lenny's podcast I'm Lenny”

    ▶ Watch at ~0:30approx.
  • Gergely OroszMentionsmy career started out as what you might consider a pretty typical software engineer career

    “today my guest is gergay oros”

    ▶ Watch at ~1:00approx.
  • Gergely OroszCoinedmy career started out as what you might consider a pretty typical software engineer career

    “right now here I am writing a newsletter where a bunch of people are reading it”

    ▶ Watch at ~6:30approx.
  • Alexandre DumasCoinedthere's the book The Three Musketeers from Alexander to my course

    “there's the book The Three Musketeers from Alexander to my course”

    ▶ Watch at ~32:00approx.
  • Kent BeckCoinedKent back for example he's the creator of tdd and he's risen a lot of books

    “Kent back for example he's the creator of tdd and he's risen a lot of books”

    ▶ Watch at ~1:05:00approx.
  • Kent BeckMentionsKent back for example he's the creator of tdd and he's risen a lot of books

    “what I love about Ken Beck is he's been the middle of it”

    ▶ Watch at ~1:05:30approx.
  • Steve YeggeMentionshe used to work at Amazon and then at Google he wrote this internal email about platforms

    “he used to work at Amazon and then at Google he wrote this internal email about platforms”

    ▶ Watch at ~1:08:00approx.
  • MrBeastMentionsif you watch YouTube you know Mr B says someone who you probably came across

    “if you watch YouTube you know Mr B says someone who you probably came across”

    ▶ Watch at ~1:09:30approx.

Resources · 42

  • UberUsescompany · Uber

    “in my best year at Uber I made about like 320 or 330 000 in total compensation”

    ▶ Watch at ~0:00approx.
  • Lenny's PodcastCoinedpodcast · Lenny Rachitsky

    “welcome to Lenny's podcast I'm Lenny”

    ▶ Watch at ~0:30approx.
  • Lemon.ioRecommendscompany

    “learn more just go to lemon.io Lenny and find your perfect developer or Tech Team”

    ▶ Watch at ~2:30approx.
  • AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk

    “EPO is a Next Generation a b testing platform built by Airbnb alums”

    ▶ Watch at ~3:00approx.
  • NetlifyUsescompany

    “companies like netlify contentful and Cameo rely on about to power their experiments”

    ▶ Watch at ~3:00approx.
  • ContentfulUsescompany

    “companies like netlify contentful and Cameo rely on about to power their experiments”

    ▶ Watch at ~3:00approx.
  • CameoUsescompany

    “companies like netlify contentful and Cameo rely on about to power their experiments”

    ▶ Watch at ~3:00approx.
  • EppoRecommendssoftware · Eppo

    “check out EPO at getepo.com get eppo.com and 10x your experiment velocity”

    ▶ Watch at ~4:00approx.
  • SubstackUseswebsite · Substack Inc.

    “your newsletter is the number one technology newsletter on sub stack”

    ▶ Watch at ~4:30approx.
  • The Pragmatic EngineerCoinednewsletter · Gergely Orosz

    “your newsletter is the number one technology newsletter on sub stack called the pragmatic engineer”

    ▶ Watch at ~4:30approx.
  • MicrosoftMentionscompany · Bill Gates and Paul Allen

    “it was Microsoft they just bought Skype at that point”

    ▶ Watch at ~6:00approx.
  • SkypeUsessoftware

    “I got into Skype but like I say Skype but it was Microsoft they just bought Skype”

    ▶ Watch at ~6:00approx.
  • AmsterdamMentionsplace

    “I ended up at Uber at Amsterdam where I joined as a senior software engineer”

    ▶ Watch at ~6:30approx.
  • SubstackMentionswebsite · Substack Inc.

    “sub Sac introduced recommendations which has been a massive growth engine”

    ▶ Watch at ~8:00approx.
  • SkyscannerUsescompany

    “I was working in London as a principal engineer at Skyscanner”

    ▶ Watch at ~13:30approx.
  • Craft DocsMentionssoftware

    “now he's building this startup called craft docs it's a really slick put document editing system”

    ▶ Watch at ~16:00approx.
  • The Software Engineer's GuidebookCoinedbook · Gergely Orosz

    “I've been writing this book for it was coming up to a year called the software engineer's guidebook”

    ▶ Watch at ~17:00approx.
  • Building Mobile Apps at ScaleCoinedbook · Gergely Orosz

    “I accidentally published a book called building mobile apps at scale”

    ▶ Watch at ~17:30approx.
  • UberMentionscompany · Uber

    “Uber did layoffs in April and it was it was really stressful”

    ▶ Watch at ~23:00approx.
  • The Three MusketeersMentionsbook · Alexandre Dumas

    “there's the book The Three Musketeers from Alexander to my course”

    ▶ Watch at ~32:00approx.
  • SOC 2Mentionsother

    “sock 2 is a way to prove your company is taking proper security measures to protect customer data”

    ▶ Watch at ~34:00approx.
  • VantaRecommendssoftware · Christina Cacioppo

    “just go to vanta.com Lenny that's v-a-n-t-a.com Lenny to learn more and to claim your discount”

    ▶ Watch at ~34:30approx.
  • TwitterUseswebsite · Twitter

    “I use Twitter for a lot of research”

    ▶ Watch at ~35:30approx.
  • CenterUsessoftware

    “I use this app sender that I know you're also there”

    ▶ Watch at ~36:30approx.
  • LinkedInUseswebsite · LinkedIn

    “I just kill all LinkedIn Twitter Facebook what whatever size”

    ▶ Watch at ~37:30approx.
  • CenterRecommendssoftware

    “check it out so to summarize some of your tips which I love”

    ▶ Watch at ~40:30approx.
  • Coding HorrorCoinedwebsite · Jeff Atwood

    “it was called coding horror and all the software Engineers I knew Reddit”

    ▶ Watch at ~56:00approx.
  • Stack OverflowCoinedwebsite · Joel Spolsky and Jeff Atwood

    “Jeff Atwood who's the founder of stack Overflow”

    ▶ Watch at ~56:00approx.
  • Hacker NewsUseswebsite · Y Combinator

    “it came from the site called Hacker News that I ever heard about and people were discussing my posts”

    ▶ Watch at ~57:30approx.
  • A Comment Is an Invitation for RefactoringCoinedother · Gergely Orosz

    “it was called a comment is an invitation for refactory”

    ▶ Watch at ~57:30approx.
  • The Trimodal Nature of Software Engineering SalariesCoinedother · Gergely Orosz

    “I wrote one about the trimodal nature of software new salaries”

    ▶ Watch at ~59:30approx.
  • JPMorganUsescompany

    “after I got to let's say JP Morgan in London I was pretty picky of where I would go next”

    ▶ Watch at ~1:03:00approx.
  • FacebookUsescompany · Meta

    “then he went to work at Facebook”

    ▶ Watch at ~1:05:30approx.
  • GoogleMentionscompany · Google

    “people were turning down Facebook and Google offers to go at Uber”

    ▶ Watch at ~1:06:30approx.
  • YouTubeMentionswebsite · Google

    “there's actually YouTube A lot of people are are becoming pretty successful on YouTube”

    ▶ Watch at ~1:07:30approx.
  • AmazonMentionscompany · Jeff Bezos

    “he used to work at Amazon and then at Google”

    ▶ Watch at ~1:08:00approx.
  • SourcegraphMentionscompany

    “he's actually started the head of engineering at source graph”

    ▶ Watch at ~1:09:00approx.
  • NetflixMentionscompany · Netflix

    “you're competing with the likes of Spotify Netflix education”

    ▶ Watch at ~1:11:30approx.
  • SpotifyMentionssoftware · Spotify

    “you're competing with the likes of Spotify Netflix education”

    ▶ Watch at ~1:11:30approx.
  • pragmaticengineer.comRecommendswebsite · Gergely Orosz

    “you can find me at pragmatic engineer.com there is a bunch of stuff listed there”

    ▶ Watch at ~1:12:30approx.
  • The Pragmatic EngineerRecommendsnewsletter · Gergely Orosz

    “if you work in Tech consider signing up to my my newsletter”

    ▶ Watch at ~1:13:00approx.
  • lennyspodcast.comRecommendswebsite · Lenny Rachitsky

    “you can find all past episodes or learn more about the show at lennyspodcast.com”

    ▶ Watch at ~1:14:30approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 3

Hot Take47:00

A one-person newsletter has no real exit path

Unlike a startup where you build equity and sell, a solo newsletter is tied to the person and can't really be sold or walked away from. Gergely notes it might be worth four or five times annual revenue on paper, but you can't sell it like that, and the only true exit is to build an organization that runs without you, which he doesn't want.

  • The business is worth maybe 4-5x annual revenue but can't be sold like a normal company.
  • Because the value is tied to the writer, you can't really walk away.
  • The only exit is building a publishing company with hired writers, or stopping and losing the revenue.
  • You have to produce something great every week, in theory for the rest of your life.

“you basically have to get something awesome at every week in theory for the rest of your life”

Lenny · 46:30

“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…”

Gergely Orosz · 47:30
#newsletter#business-model#exit#creator-economy
Hot Take1:04:30

You need real experience and pedigree, not just writing skill

Both agree the foundation of a credible newsletter is real, scaled work with great people, not writing ability alone. Lenny criticizes people starting newsletters with little real experience to share, and Gergely advises becoming an expert first, plus deliberately working your way into high-pedigree companies so people pay attention.

  • The content must be based on real things that worked and that you learned firsthand.
  • Many new newsletter writers haven't done much and lack real experience to draw on.
  • Gergely's advice: become an expert somewhere before you start, to be credible.
  • He deliberately built pedigree (JP Morgan, Skype, Uber) so his work got attention.

“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”

Lenny · 1:04:30

“become an expert somewhere somehow before you start because you'll be a lot more credible”

Gergely Orosz · 1:07:00
#credibility#career#pedigree#advice
Hot Take1:10:30

In-depth writing is an underserved medium as everyone moves to video

A YouTuber friend told Gergely that his early-2010s blog benefited from timing: while YouTube is now saturated with high-production content, few people write in-depth regularly anymore. Gergely adds that written content is more efficient for software engineers, who can scan it, making writing an underrated advantage even as competition shifts to video.

  • A friend with 200k YouTube subscribers noted YouTube is now crowded with high-grade production.
  • Far fewer people write in-depth, regular blog content, so the medium is underserved.
  • Fewer writers means less competition for those who stick with in-depth writing.
  • Writing is more efficient for engineers who prefer to scan rather than watch long videos.

“I don't see many blogs that are are writing in-depth stuff regularly I feel everyone went over to YouTube or Tick Tock”

Gergely Orosz · 1:11:00
#writing#youtube#medium#competition

Explainer· 1

Explainer1:02:00

Good goals vs bad goals: set the ones you control

From his time managing people, Gergely distinguishes bad goals (a promotion, hitting 20,000 subscribers) that depend on outcomes outside your control from good goals (learn a language this year, leave work at 5pm Fridays) that you can actually execute. He applied this to his own blog, where the goal was simply to publish, not to be read.

  • Bad goals like 'get promoted' or 'hit 20,000 subscribers' aren't within your control.
  • Good goals are actions you can take: learn a new language, share what you learned.
  • His early blog goal was to write once a month, which he could control and be proud of.
  • Setting controllable goals is how the rest tends to follow.

“those are bad goals because it's not in your control”

Gergely Orosz · 1:02:00

“a good goal is what you can do”

Gergely Orosz · 1:02:30
#goals#career#advice#management

Story· 6

Story09:00

The newsletter now pays more than his peak Uber compensation

Gergely walked away from a European big-tech package he thought he'd never match, expecting to earn far less as a writer. Instead the newsletter's income surpassed his Uber comp, and unlike a salary it keeps rising as subscribers grow, with no theoretical cap. He frames it as a surprising, partly situational outcome he never predicted.

  • His best year at Uber (post-IPO) was about 320-330k total compensation.
  • A comparable US role might have paid five or six hundred K, so Europe felt like leaving money behind.
  • He now earns more than at Uber, and earnings climb as the newsletter grows.
  • There's no theoretical cap, though churn and slowing growth are the real-world limits.

“in my best year at Uber I made about like 320 or 330 000 in total compensation”

Gergely Orosz · 09:30

“I'm now doing something I love and um in some strange way I guess it even pays better”

Gergely Orosz · 10:30
#newsletter#compensation#creator-economy#uber
Story13:00

A promise to himself and COVID layoffs pushed him out of Uber

Gergely joined Uber betting the mostly-stock offer was a lottery ticket, promising himself that if it paid off in four years he'd take a risk on something of his own. When COVID forced Uber to lay off half his 30-person org, he lost trust that the company was a family and decided to leave.

  • Uber roughly doubled his Skyscanner comp, mostly in stock, in 2016 before anyone knew it would IPO.
  • He promised himself: if Uber exits and pays off in four years, he owes it to himself to take a risk.
  • COVID layoffs cut ~20% of engineers, and he had to let go 50% of his own group.
  • Watching strong colleagues get cut for being on the wrong team broke his trust in the system.

“the short of it is it was a promise to myself and covet and Uber doing layoffs”

Gergely Orosz · 13:00

“if four years later Uber exits and I make a bunch of money I owe it to myself to take a risk”

Gergely Orosz · 15:00
#career#uber#layoffs#risk
Story17:30

Self-published books he expected to make nothing made $100k

Planning to spend six months writing one book before raising venture capital, Gergely got sidetracked and self-published two others in a few months. He assumed they'd earn nothing, but they made about $100k in the first year while he kept roughly 90% of the revenue, which made him rethink the startup plan entirely.

  • His original plan was to leave Uber, write a book, then raise VC for a platform-engineering startup.
  • He instead published 'building mobile apps at scale' and a book on tech resumes in a few months.
  • The books made about $100k in their first year despite low expectations.
  • Self-publishing let him keep roughly 90% of the revenue.

“they started making money they made about a hundred thousand dollars in the first year”

Gergely Orosz · 18:00

“I self-published it to the drum rolls of places where I get to keep I think like 90 of the revenue”

Gergely Orosz · 18:00
#writing#self-publishing#income
Story19:30

The fisherman parable that killed his startup plan

Doing the math on founding a VC-backed startup, Gergely realized that even a unicorn outcome would end with him wanting to teach, write, and share what he knows, exactly what he could do right now. He invokes the fisherman parable, where a decade of hard work only earns you the relaxed life you already had, to justify skipping the startup and writing instead.

  • A successful startup might net ~5% of a billion-dollar company after five or six rounds of dilution.
  • After buying things he didn't need, he'd want to share knowledge and make videos anyway.
  • The fisherman parable: work for years to eventually afford the simple life you already have.
  • He had enough savings to take the risk on writing directly, so he did.

“I would go off and do this for like 10 years because that's how much you need to plan to do it”

Gergely Orosz · 19:30
#career#entrepreneurship#philosophy
Story43:00

The surprising downside: it's lonely

Gergely, an outgoing person who liked office life, found working solo unexpectedly lonely. He misses the casual chats at the coffee station and lunch with colleagues, and now compensates by working from a shared techie office so he can say hi and make small talk.

  • He genuinely enjoyed his Uber team and the people, not just the work.
  • He misses spontaneous conversation at the coffee station and over lunch.
  • Solo work was lonelier than he expected, more than he anticipated.
  • His fix is a shared workspace full of other tech people for small talk.

“one is obviously it's lonely”

Gergely Orosz · 43:00

“I really like you know walking up to the coffee station and having a chat with people”

Gergely Orosz · 43:30
#remote-work#loneliness#creator-economy
Story57:30

The Hacker News post that split engineers into two camps

Months after giving up on his refocused blog, Gergely got a traffic spike that crashed his shared hosting, traced to a Hacker News discussion of a post he'd written six months earlier titled 'a comment is an invitation for refactoring'. High-karma engineers argued fiercely, some calling him an idiot and others calling it wisdom, and it showed him that people cared what he wrote.

  • He published six blog posts, gave up, then months later saw a huge traffic spike.
  • The spike came from Hacker News, a site he'd barely heard of, and crashed his hosting.
  • The post argued that a comment in code means the code should be refactored instead.
  • Silicon Valley engineers split into two loud camps arguing over it, proving people cared.

“it was called a comment is an invitation for refactory”

Gergely Orosz · 57:30

“some people called me an idiot some people called me the absolute wisdom”

Gergely Orosz · 57:30
#blogging#hacker-news#audience#writing

Tool· 1

Tool37:30

His focus stack: a 20-minute timer, a site-killing Python script, and a camera

To beat the distraction of Twitter (which he also uses for research), Gergely sets a 20-minute no-distractions timer and runs a simple Python script that edits his Mac's hosts file to block LinkedIn, Twitter, and Facebook until he re-runs it. He also likes focus apps like Sunsama for their video-camera feature, which makes him feel watched and accountable.

  • A 20-minute timer with a hard 'no distractions' rule gets him past the friction of starting.
  • A self-written Python script blocks social sites via the hosts file and must be re-run to unblock.
  • About five minutes in, a switch flips and he's heads-down in flow.
  • The focus app's video-camera feature makes him feel watched, forcing him to work.

“it's just a very simple python that I wrote for myself”

Gergely Orosz · 38:00

“about five minutes in there's a switch and I'm like I'm now actually like heads down and doing it”

Gergely Orosz · 38:00
#productivity#focus#tools#distraction

Takeaway· 4

Takeaway11:30

Thousands of micro-bosses and a raise for every great post

Lenny reframes the newsletter life as having thousands of micro-bosses instead of one manager, each of whom can quietly cancel. Gergely tracked in a spreadsheet how much his annual revenue rose a week after each article, and found a great post effectively handed him an instant raise, something a corporate job never does.

  • Instead of one boss, you have thousands of subscribers, any of whom can 'fire' you by unsubscribing.
  • Gergely kept a first-year spreadsheet tracking revenue change one week after each article.
  • A well-received article translated directly into a visible, self-awarded raise.
  • This tight feedback loop between good work and pay doesn't exist in a big corporate.

“instead of one boss I have thousands of micro bosses and one of them can fire me and many do every day”

Lenny · 11:30

“for doing something awesome you can just get give yourself a raise”

Gergely Orosz · 12:30
#newsletter#incentives#creator-economy
Takeaway30:00

Self-imposed deadlines are why he can write four books a year

Working alone, Gergely found his 15-year track record as a diligent employee evaporated, so he engineered external pressure by promising thousands of paying readers a post every week. He credits deadlines, not talent, for producing four-to-five books' worth of content a year, and cites how Dumas wrote The Three Musketeers as a serialized magazine job for money.

  • Left to himself, even a lifelong star employee wasted days without structure.
  • Committing publicly to paying subscribers created inescapable weekly deadlines.
  • He wrote roughly four to five books' worth of content in a year because of these deadlines.
  • Dumas wrote The Three Musketeers serialized for a magazine because he needed the money.

“I wrote like four or five books worth of content just last year it's because I have these deadlines”

Gergely Orosz · 30:00

“put in constraints for the things that you need to do and then you're gonna do that”

Gergely Orosz · 33:00
#productivity#deadlines#writing#discipline
Takeaway48:30

Why it's so hard to take time off from a paid newsletter

Because subscribers leave if you stop producing, time off is genuinely hard. Lenny invented a personal PTO policy of four weeks a year, capped at about one to two weeks at a stretch. Gergely contrasts this with Uber, where a four-month paid parental leave didn't affect his stock, and warns about burnout in a one-person business.

  • Stop producing great work and subscribers leave, so breaks are risky.
  • Lenny's self-made PTO is four weeks a year, rarely more than one to two weeks in a row.
  • At Uber, Gergely took a full four-month paid leave when his son was born and still got paid.
  • He now works ahead on less time-sensitive posts and treats burnout as a real risk to solve for.

“I invented this PTO policy for myself where I take four weeks a year off”

Lenny · 48:30

“they gave me a four month paid holiday”

Gergely Orosz · 49:30
#burnout#time-off#newsletter#sustainability
Takeaway56:30

Jeff Atwood's three steps to be famous on the internet

Gergely credits Coding Horror founder Jeff Atwood's old post 'how to be famous on the internet' as the advice he keeps returning to: write a blog post, do it a few times a week, keep going for two years, and you'll be famous. He found it ironic at first but increasingly believed it, and it's still the best advice he can offer.

  • Jeff Atwood ran Coding Horror, the most popular blog for software engineers around 2007.
  • His formula: write, publish a few times a week, sustain it for two years.
  • Gergely initially found it ironic but came to believe it genuinely works.
  • It remains his core advice, just with slightly less conviction that success is guaranteed.

“there's one write a blog post two do this like three times a week three you can do it for two years and I guarantee…”

Gergely Orosz · 56:30
#blogging#advice#consistency#audience