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

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: (00:00) 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 podcast@lennyrachitsky.com.

Gergely OroszguestLenny Rachitskyhost
Nov 16, 20221h 14mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

From Uber engineering leader to Substack’s top tech newsletter mogul

  1. 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.
  2. 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.”
  3. 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.

IDEAS WORTH REMEMBERING

5 ideas

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.

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.

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.

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.

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.

WORDS WORTH SAVING

5 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

Leaving a lucrative big-tech engineering career to pursue writing full-timeEconomics, growth, and business model of a paid Substack newsletterDaily workflow, time management, and focus systems for solo creatorsPsychological and lifestyle tradeoffs of creator life (freedom vs. stress, loneliness)The role of deep expertise and career pedigree in building audience trustHow to start and grow a newsletter: from long-term blogging to paid subsFrameworks for experimentation, goal-setting, and following market pull as a creator

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