By playing, you agree to uListen's Terms and Privacy Policy and YouTube's Terms of Service.

Lenny's Podcast

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.

Gergely OroszguestLenny Rachitskyhost

Nov 17, 20221h 14mWatch on YouTube ↗

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

CHAPTERS

Jump to publisher timestamps

Chapter summaries

Hook: Outearning Uber with a one-person newsletter
Gergely opens with the surprising economics of leaving a high-paying Uber role to run The Pragmatic Engineer. He explains how subscription revenue can scale without a traditional compensation ceiling, even if growth eventually slows.
- •Uber total comp peaked around $320–$330k in Europe
- •Newsletter earnings now exceed his Uber compensation
- •Subscription business has upside tied to growth (with real-world caps like churn)
- •Doing work he enjoys more—while earning more—was unexpected
Show framing: Two top Substack newsletters compare notes
Lenny introduces the episode’s focus: what it’s like to run a paid newsletter full time. He lays out the discussion areas—leaving a tech job, day-to-day workflow, what drives success, and how to start.
- •Lenny frames newslettering as a non-traditional career path
- •Episode structure: decision to leave, daily life, success factors, how to start
- •Shared context: both run top Substack newsletters full time
- •Promise of practical advice and honest pros/cons
Gergely’s path to big tech: Hungary → London → Skype/Microsoft → Skyscanner → Uber
Gergely walks through his engineering career progression across countries and company types. He describes the steady step-by-step growth that eventually put him on a senior management track at Uber.
- •Computer science education plus early side projects
- •Career moves across Hungary, the UK, and London’s tech scene
- •Roles at consulting, banking, Skype/Microsoft, and Skyscanner
- •Joined Uber in Amsterdam; grew into engineering management
The Pragmatic Engineer’s scale: subscriber growth, paid mix, and recommendations
Gergely shares concrete metrics showing how large the newsletter has become and what drove the acceleration. He highlights Substack recommendations as a major growth lever and explains the paid/free model.
- •~189,000 total subscribers at the time of recording
- •~80,000 new subscribers in ~90 days (~1,000/day)
- •Substack recommendations created a major inflection point
- •Revenue primarily from subscriptions (no ads/sponsorships in the newsletter)
Compensation comparison: trading a capped salary for compounding subscriber revenue
They dig deeper into how newsletter income compares to a senior role at Uber. Gergely describes the psychological leap of walking away from a top-of-market package and the later realization that the newsletter could surpass it.
- •European big-tech comp context vs. US equivalents
- •He expected to earn less after leaving
- •Now earns more than Uber and sees continuing upside with growth
- •Luck + timing acknowledged as part of the outcome
Why he left Uber: a promise to himself, COVID shock, and the reality of layoffs
Gergely recounts the moment the corporate “safety” illusion broke—COVID-driven layoffs and reshuffling priorities. He connects this to an earlier commitment: if Uber stock paid off, he would take a real risk afterward.
- •Uber offer in 2016 dramatically increased comp (stock-heavy)
- •Personal “promise” to take a risk after a liquidity event
- •COVID triggered layoffs and major charter changes
- •Layoffs revealed how little control middle managers have
What happened after quitting: startup plans, then books and an unexpected writing business
After leaving, Gergely initially planned to raise venture capital for a platform engineering startup. Instead, writing gained momentum—self-published books started selling, shifting his conviction toward recurring subscription revenue.
- •Initial plan: venture-funded startup inspired by Uber’s internal tooling
- •Wanted to finish The Software Engineer’s Guidebook first
- •Self-published books (e.g., mobile scaling) generated meaningful revenue
- •Chose paid newsletter model for predictability vs. spiky book sales
Newsletter operations: two posts/week, deep research, and an editor-driven workflow
Gergely explains what it takes to publish high-quality, paid technical writing on a schedule. He details the research, drafting, feedback, and editing pipeline—and why “one post a week” is still intense when it’s original.
- •Shifted from 1 post/week to a 2-post cadence (Tuesday deep dive + Thursday Scoop)
- •Topics chosen to be non-obvious and not widely covered
- •Process: research + interviews, drafting, trusted feedback, professional editing
- •Long-form output (often ~5,000–6,000 words)
Productivity systems for solo creators: deadlines, focus tools, and blocking distractions
They discuss the core challenge of self-directed work: creating structure with no manager and endless distractions. Gergely shares the practical tactics he cycles through as his brain adapts over time.
- •Twitter is both a research tool and a major distraction
- •Uses focus tools (e.g., Centered) and timeboxing approaches
- •Pomodoro-style intervals and “just start for 20 minutes” trigger flow
- •Custom hosts-file script blocks distracting sites to force deep work
Best parts of entrepreneurship: empty calendar, autonomy, and rapid experimentation
Gergely contrasts corporate life with the autonomy of running a one-person business. He emphasizes how fewer meetings and full creative control enable faster iteration and more satisfying work.
- •Calendar flips from meeting-heavy to focus-heavy
- •High autonomy: full control over topics, formats, and experiments
- •Enjoys the entrepreneurial loop of trying, learning, and adjusting
- •Reclaims deep-work time that was scarce in management roles
Hard truths: loneliness, stress, no clean exit, and difficulty taking real time off
They explore the darker side of a solo newsletter business: isolation, constant performance pressure, and uncertainty about long-term sustainability. Lenny and Gergely also discuss how the model complicates vacations and “exiting.”
- •Loneliness and missing team energy; coworking as a partial fix
- •Stress from constant metrics/validation and subscriber churn concerns
- •Newsletter value is tightly tied to the creator—hard to sell or step away
- •Time off is difficult; burnout risk requires proactive planning
No long-term plan: following “pull,” creating slack, and designing sustainability
Gergely explains why he stopped making rigid long-term plans after his career took unexpected turns. He describes treating the newsletter as a business, doubling down on audience pull, and aiming to reduce hours to create space for new ideas.
- •Career surprises made long-horizon plans feel unreliable
- •Reframes creator work as building a sustainable business
- •Doubling down on “pull” signals (audience demand) guided pivots
- •Goal: reduce workload (e.g., from ~50 hours/week to ~20) to enable new opportunities
How to start (and what actually drove his early traction): years of writing, depth, and cadence
Gergely demystifies his fast early growth by revealing the long lead-up: years of blogging, credibility, and distribution via places like Hacker News. He closes with advice on building expertise, committing to a cadence, and choosing the right medium.
- •Early “fairytale” launch numbers were built on ~6 years of prior blogging
- •Hacker News spikes validated ideas and built awareness over time
- •Advice: build depth/credibility, share what you learn, and stick to a cadence
- •Experiment with formats (newsletter, YouTube, meetups) and adapt based on feedback

Publisher timestamps

Get more out of YouTube videos.

Read along on your phone, search it beside the video, or ask your favorite AI app what was said.