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.

Listen now on Apple, Spotify, Google, Overcast, and YouTube.

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Find the full transcript here: https://www.lennyspodcast.com/episodes/

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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/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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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

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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

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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

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.