Gergely Orosz

Author and Newsletter Writer at The Pragmatic Engineer

Author of The Pragmatic Engineer, the number one technology newsletter on Substack with nearly 200,000 subscribers, former engineering manager at Uber who left his cushy tech job to build a one-person media business that now outearns his previous compensation.

The Growth Architect The Growth Scientist

Dimension Profile

Strategic Vision 50%

Execution & Craft 55%

Data & Experimentation 30%

Growth & Distribution 55%

Team & Leadership 35%

User Empathy & Research 35%

Key Themes

creator economy for technical professionals leaving big tech for independent work paid newsletter business model writing as a full-time career recurring revenue versus one-time content accountability through deadlines

Episode Summary

Gergely Orosz shares his journey from engineering manager at Uber to running The Pragmatic Engineer, the top technology newsletter on Substack with nearly 200,000 subscribers. The conversation covers his decision to leave a $330K tech job, the surprising economics of paid newsletters as a one-person business, the daily cadence and pressure of producing two in-depth posts per week, and practical advice for anyone considering the creator path in tech.

Leadership Principles

→ The fisherman parable applies to tech careers — sometimes you're working really hard to end up doing what you could be doing right now
→ External accountability and deadlines are the secret to prolific writing output — pressure from paying subscribers creates consistent production
→ Taking a risk requires having savings and a time-boxed commitment — give it six months with full intensity, like a startup

Notable Quotes

"In my best year at Uber, I made about 320 or $330,000 in total compensation. But now I am making more in compensation that I made at Uber. And the difference is that now my earnings keep going up as long as the newsletter is growing."
— On the financial upside of the newsletter creator path versus big tech

"I would go off and do this for like ten years, because that's how much you need to plan to do it. I need to stop doing what I'm doing right now. And then I want to do it again. So it's reminding me of the story of this fisherman."
— On the realization that starting a VC-funded startup would just delay what he really wanted to do

"If you want to write a book, the easiest way is go to a publisher and sign a contract, not because of the money. But it's the pressure. You absolutely should have someone to hold you accountable."
— On why external deadlines and accountability are essential for creative output

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