
Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer)
Gergely Orosz (guest), Lenny Rachitsky (host), Narrator
In this episode of Lenny's Podcast, featuring Gergely Orosz and Lenny Rachitsky, Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer) explores from Uber engineering leader to Substack’s top tech newsletter mogul Former Uber engineering manager Gergely Orosz shares how he left a highly paid big-tech career to build The Pragmatic Engineer, now Substack’s #1 technology newsletter. He walks through the multi-year path that led to this decision: years of blogging, book-writing, and accumulating hard-won experience at companies like Skyscanner and Uber.
From Uber engineering leader to Substack’s top tech newsletter mogul
Former Uber engineering manager Gergely Orosz shares how he left a highly paid big-tech career to build The Pragmatic Engineer, now Substack’s #1 technology newsletter. He walks through the multi-year path that led to this decision: years of blogging, book-writing, and accumulating hard-won experience at companies like Skyscanner and Uber.
Gergely and host Lenny Rachitsky compare the realities of running paid newsletters full-time, including income potential, workload, loneliness, lack of structure, and the difficulty of taking real vacations. They dig into the systems, habits, and tools required to consistently produce high-quality content, and the psychological pressures of having “thousands of micro-bosses.”
They also discuss the importance of deep domain expertise, career “pedigree,” and long-term public writing as foundations for creator success, while emphasizing experimentation, constraints, and following pull from the market. The episode closes with practical guidance for aspiring newsletter or creator-business builders on how to get started and what to expect.
Key Takeaways
Years of consistent public work laid the foundation for rapid newsletter success.
Gergely’s ‘overnight’ success (1,000 paid subscribers in six weeks) was built on six-plus years of focused blogging, speaking, and book-writing that quietly built trust and an audience long before the newsletter launched.
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Deep domain expertise and credible experience are critical for a high-value newsletter.
His time as a senior engineer and manager at firms like Skyscanner and Uber gave him both unique insights and credibility; he argues you should first become genuinely good at something, then teach and write about it.
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Treat a newsletter as a business with constraints, cadence, and experimentation.
He imposes strict publishing commitments (two posts a week) and views them as forcing functions that drive output, learning, and iteration—similar to running a startup with recurring deliverables.
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Deadlines and self-imposed constraints are the most reliable productivity tools.
Gergely uses hard publish dates, focus blocks, a custom hosts-file script to block distracting sites, and tools like Centered to create pressure and remove excuses, because unstructured time naturally leads to drift.
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Creator life trades one boss for thousands of ‘micro-bosses’—with more upside.
While newsletters bring more autonomy and potentially higher uncapped income than a corporate job, they also create stress via churn, subscription metrics, and the need to continuously deliver value to many paying customers.
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The medium matters: writing is less crowded and more scannable than video.
He notes that long-form technical blogs are rarer today as many creators migrated to YouTube, creating an opportunity in written, in-depth content that engineers prefer for learning and quick scanning.
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Set process goals you control, not outcome goals you don’t.
Instead of targeting ‘X subscribers,’ he recommends goals like publishing on a fixed cadence or learning a specific skill; these are under your control and, over time, tend to compound into audience and revenue.
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Notable Quotes
“In my best year at Uber, I made about $320 or $330,000 in total compensation… and now I’m making more than that from the newsletter.”
— Gergely Orosz
“It feels like instead of one boss, I have thousands of micro-bosses, and any one of them can fire me.”
— Lenny Rachitsky
“I stopped making long-term plans… three years ago I wanted to be a manager of managers, and now I’m writing a newsletter full-time.”
— Gergely Orosz
“If you want to write a book, the easiest way is to go to a publisher and sign a contract—not for the money, but for the pressure.”
— Gergely Orosz
“If you’re serious about one day teaching people about something, first become an expert somewhere, somehow.”
— Gergely Orosz
Questions Answered in This Episode
Given the dependence on constant content, how can newsletter creators design a sustainable ‘exit’ or partial step-back without killing their business?
Former Uber engineering manager Gergely Orosz shares how he left a highly paid big-tech career to build The Pragmatic Engineer, now Substack’s #1 technology newsletter. ...
Get the full analysis with uListen AI
For someone earlier in their career without big-tech pedigree, what concrete steps can they take over the next 3–5 years to build the depth and credibility needed for a valuable newsletter?
Gergely and host Lenny Rachitsky compare the realities of running paid newsletters full-time, including income potential, workload, loneliness, lack of structure, and the difficulty of taking real vacations. ...
Get the full analysis with uListen AI
How much of newsletter success is attributable to quality of content versus timing, platform features (like Substack recommendations), and network effects?
They also discuss the importance of deep domain expertise, career “pedigree,” and long-term public writing as foundations for creator success, while emphasizing experimentation, constraints, and following pull from the market. ...
Get the full analysis with uListen AI
What are the warning signs of burnout or unhealthy relationship to metrics (subs, churn, revenue) in creator businesses, and how can they be mitigated?
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If you were starting from scratch today, with no existing blog or audience, what exact 12-month plan would you follow to test whether a paid newsletter is viable?
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Transcript Preview
In my best year at Uber, I made about, like, 320 or $330,000 in total compensation. And when I quit my job, I was actually thinking like, "Am I, Am I crazy because I'm- I'm leaving..." Especially in Europe, this is a lot of money to say, well, this will be similar to something, you know, someone in a similar position would have made like 5 or 600K in- in total in the US. But now, I am making more in- in compensation that I made at Uber, and the difference is that now my compensation, well, my earnings are- keep going up as long as the newsletter is growing, so there's no theoretical cap on this. Of course, there's an actual cap. There's churn, growth is slowing over time, but it's very, very strange because I felt that I was in a really privileged position just honestly making tons of money doing a job that I love, and this was at Uber or- or as a software engineer. And I'm now doing stuff that I love and, um, in some strange way, I guess, it even pays better.
(instrumental music) Welcome to Lenny's Podcast. I'm Lenny and my goal here is to help you get better at the craft of building and growing products. I interview world-class product leaders and growth experts to learn from their hard-won experiences building and scaling today's most successful companies. Today, my guest is Gergely Orosz. In a sense, Gergely is the meat of engineering. He's got the top engineering newsletter on Substack, it's growing really fast, and like me, he does this full-time. In this episode, we talk about the life of newslettering full-time, like we both do. We get into Gergely's decision to leave his cushy tech job at Uber to go into this life full-time, what the day-to-day life of a newsletter person is, the pros and cons of this life, what it takes to be successful, and a bunch of advice for how to get started if you're curious about going down this route. This is a pretty unique episode, and it was really fun to do. If you ever thought about writing or going down this kind of creator route, you'll love this episode. With that, I bring you Gergely Orosz. This episode is brought to you by Lemon.io. You've achieved product-market fit, you're able to activate, engage, and retain your customers, but you don't have the engineers that you need to move as fast as you want to because it's hard to find great engineers quickly, especially if you're trying to protect your burn rate. Meet Lemon.io. Lemon.io will quickly match you with skilled senior developers who are all vetted, results-oriented, and ready to help you grow, and all that at competitive rates. Startups choose Lemon.io because they offer only handpicked developers with three or more years of experience and strong, proven portfolios. Only 1% of candidates who apply get in, so you can be sure that they offer you only high-quality talent. And if something ever goes wrong, Lemon.io offers you a swift replacement so that you're kind of hiring with a warranty. Learn more, just go to lemon.io/lenny and find your perfect developer or tech team in 48 hours or less. And if you start the process now, you can claim a special discount exclusively for Lenny's Podcast listeners, 15% off your first four weeks of working with your new software developer. Grow faster with an extra pair of hands. Visit lemon.io/lenny. This episode is brought to you by Eppo. Eppo is a next-generation A/B testing platform built by Airbnb alums for modern growth teams. Companies like Netlify, Contentful, and Cameo rely on Eppo to power their experiments. Wherever you work, running experiments is increasingly essential, but there are no commercial tools that integrate with a modern growth team stack. This leads to wasted time building internal tools or trying to run your experiments through a clunky marketing tool. When I was at Airbnb, one of the things that I loved about our experimentation platform was being able to easily slice results by device, by country, and by user stage. Eppo does all that and more, delivering results quickly, avoiding annoying prolonged analytic cycles, and helping you easily get to the root cause of any issue you discover. Eppo lets you go beyond basic click-through metrics and instead use your North Star metrics like activation, retention, subscriptions, and payments. And Eppo supports tests on the front end, the back end, email marketing, and even machine learning clients. Check out Eppo at GetEppo.com, GetE-P-P-O.com, and 10X your experiment velocity. Gergely, welcome to the podcast.
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