Leaving big tech to build the #1 technology newsletter

Gergely Orosz, a former Uber engineering manager and author of The Pragmatic Engineer, explains how he left a high-paying big-tech career to build one of the largest technology newsletters on Substack. The conversation covers his path into full-time writing, the day-to-day rhythm and downsides of a one-person paid newsletter business, and advice on building the depth and consistency needed to succeed.

01Key learnings

• Build real depth in a specific field before writing about it, since credibility from hands-on experience is hard to fake and readers notice.
• Set controllable goals, such as publishing on a fixed cadence, rather than outcome goals like subscriber counts you cannot directly command.
• Create external deadlines and accountability, such as promises to paying readers or a publisher, to overcome the procrastination that comes with self-employment.
• Follow pull signals: when a post unexpectedly draws strong demand, double down on it, as Gergely did by turning a long blog post into a book.
• Use practical focus tools like timed sessions, site blockers, or calendar blocking to protect deep work time from social media and messaging distractions.
• Recognize that a paid newsletter is hard to exit because its value is tied to you; plan for burnout, holidays, and whether you want to eventually build an organization around it.
• Share knowledge consistently through a blog, talks, or videos for years, since a steady cadence compounds into an audience over time.
• Choose your medium deliberately: writing suits readers who want to scan technical content, while video competes with heavy production and entertainment platforms.

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.