Gergely
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.
Career Skills
Financial safety nets from equity exits can provide the necessary runway to transition from a stable corporate career to high-risk entrepreneurial or creative paths.
"I told myself, if four years later Uber exits and I make a bunch of money, I owe it to myself to take a risk, because then I'll have four years of savings in my bank... I decided to leave Uber. And we..."
Communication Skills
High-quality technical writing requires a multi-stage process involving deep research, peer review, and professional editing.
"To write that post, it takes at least a few days or sometimes even longer. Sometimes it takes a week or two for me to research... I write a first draft. I get some feedback from people who I trust oft..."
External accountability and strict deadlines are essential for maintaining high-volume writing output.
"I wrote four or five books' worth of content just last year. It's because I have these deadlines... I also know that thousands of people are paying me, they have expectations of me."
Engineering Skills
True engineering culture is best understood by analyzing the lived experiences and internal processes of individual contributors rather than official company narratives.
"I'm typically interested in the stuff that you might not read about in the traditional media, but us techies really care about... I wrote one about Facebook, one about Amazon, and I tried to talk with..."
Growth Skills
Platform-native recommendation systems can create powerful, automated growth flywheels for high-performing content.
"There was a tipping point in April where the newsletter was growing... This was when Substack introduced recommendations, which has been a massive growth engine, and I guess being one of the top publi..."
A pure subscription model aligns the creator's incentives entirely with the audience's value rather than advertisers' needs.
"So this is a paid newsletter as well. So there's a free version and a paid version, and there's thousands of people paying for the newsletter... I make most of my revenue from subscriptions, and I don..."
Marketing Skills
Long-term consistency in publishing high-quality content is the foundation for building a massive audience and distribution channel.
"I started a blog six years before... I said, 'I'm going to start a blog, it'll be about software engineering and I'll call it The Pragmatic Engineer.'... I said, 'I'm going to do what Jeff Atwood said..."
A 'fairytale' launch is usually the result of years of prior audience building and reputation management on social platforms.
"I announced my newsletter, I told people, 'I'm going to go full time on this.' I had maybe 10,000 Twitter followers and, I don't know, maybe 1,000 on LinkedIn... What I didn't tell is that there was a..."