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

Gergely Orosz left a high-compensating engineering management role at Uber to launch The Pragmatic Engineer, now Substack's top tech newsletter with 189,000 subscribers and revenue exceeding his prior $320,000–$330,000 total compensation. He discusses the pivot driven by layoffs, a self-promise after Uber's IPO windfall, and audience pull from prior writing, along with the mechanics, tradeoffs, and principles behind sustaining a solo writing business.

Pivot from Uber to Full-Time Writing

Orosz planned to leave Uber for a VC-backed platform engineering startup after fulfilling a promise to himself: take a risk post-IPO stock gains, enabled by four years of savings. COVID layoffs in 2020—managing 30 engineers and losing 15–20%—eroded trust in corporate stability, prompting exit in July after a stressful notice period. Initial focus shifted from startup to finishing his book The Software Engineer's Guidebook, but self-published ebooks like Building Mobile Apps at Scale earned $100,000 in year one via Gumroad. Recognizing recurring revenue potential over unpredictable book sales or diluted startup equity (e.g., 5% of a unicorn yielding $50 million post-tax but delaying writing), he launched the paid newsletter after six years of sporadic blogging, committing to weekly in-depth software engineering posts for six months.