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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. In today’s podcast, Gergely shares why he left his well-paying job at Uber, how he got his first 1,000 subscribers, why this kind of work can be stressful and lonely (but ultimately rewarding), and why it takes hard work to build authority and become a great writer. Working solo can be challenging, and in this episode, both Lenny and Gergely offer tips for structuring your unstructured time and finding your focus. — Find the full transcript here: https://www.lennysnewsletter.com/p/leaving-big-tech-to-build-the-1-technology — Where to find Gergely Orosz: • Website: https://www.pragmaticengineer.com/ • Newsletter: https://newsletter.pragmaticengineer.com • Twitter: https://twitter.com/GergelyOrosz • LinkedIn: https://www.linkedin.com/in/gergelyorosz/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Thank you to our wonderful sponsors for making this episode possible: • Lemon.io: https://lemon.io/lenny • Eppo: https://www.geteppo.com/ • Vanta: https://vanta.com/lenny — Referenced: • Gergely’s books: https://blog.pragmaticengineer.com/books/ • Centered: https://www.centered.app/ • The Pomodoro technique: https://www.forbes.com/sites/bryancollinseurope/2020/03/03/the-pomodoro-technique/ • Coding Horror: https://blog.codinghorror.com/ • How to Achieve Ultimate Blog Success in One Easy Step: https://blog.codinghorror.com/how-to-achieve-ultimate-blog-success-in-one-easy-step/ • A Comment Is an Invitation for Refactoring: https://blog.pragmaticengineer.com/a-comment-is-an-invitation-for-refactoring/ • Kent Beck’s website: https://www.kentbeck.com/ • Steve Yegge’s famous rant on Google vs. Amazon: https://www.alexanderjarvis.com/steve-yegges-famous-rant-on-google-vs-amazon/ • Stevey’s Tech Talk: https://www.youtube.com/playlist?list=PLZfuUWMTtMcC1DZF6HxJhqsGrBXu8Jzi7 — In this episode, we cover: (00:00) Gergely’s background (07:19) The Pragmatic Engineer, growth and current subscribers (08:59) Compensation with a subscription-based newsletter vs. his salaried position at Uber (10:55) How the onset of Covid and layoffs at Uber prompted Gergely to start his newsletter (23:10) What he did immediately after leaving Uber (25:41) The day-to-day of writing a newsletter (35:08) Tips for productivity (41:19) Gergely’s favorite parts of entrepreneurship (43:15) The downsides of solo work (50:39) Why Gergely stopped making long-term plans (54:30) How to get started writing a newsletter (1:04:48) Key advice on building a successful newsletter — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
Gergely Orosz reflects on his decision to leave a lucrative position at Uber, where he earned around $320,000, to pursue his passion for writing a newsletter. He discusses the initial fears of leaving a high-paying job and how he now earns more through his newsletter, emphasizing the lack of a cap on his income as it grows with his subscriber base.
"in my best year at Uber I made about like 320 or 330 000 in total compensation and when I quit my job I was actually thinking like am I am I crazy because I'm leaving especially in Europe This is a lo..."
In this segment, Lenny introduces Gergely Orosz, the creator of the top engineering newsletter on Substack, The Pragmatic Engineer. They discuss the unique lifestyle of being a full-time newsletter writer, including the pros and cons of this career path, and the challenges and rewards that come with it.
"welcome to Lenny's podcast I'm Lenny and my goal here is to help you get better at the craft of building and growing products I interview world-class product leaders and growth experts to learn from t..."
Gergely shares insights into the revenue model of his newsletter, highlighting that he primarily relies on subscriptions rather than sponsorships or ads. He discusses the balance between free and paid content and how this model has contributed to his financial success.
"with that I bring you gergay oros [Music] foreign this episode is brought to you by lemon.io you've achieved product Market fit you're able to activate engage and retain your customers but you don't h..."
Gergely reveals impressive statistics about the growth of his newsletter, noting that he has reached 189,000 subscribers and is gaining nearly 1,000 new subscribers daily. He attributes this rapid growth to a tipping point and the introduction of Substack's recommendation feature.
"in 48 hours or less you start the process now you can claim a special discount exclusively for Lenny's podcast listeners fifteen percent off your first four weeks of working with your new software dev..."
Gergely discusses the promise he made to himself to take risks after his time at Uber, especially in light of the company's growth and his own financial stability. He reflects on how this promise motivated him to leave a secure job and pursue his passion for writing.
"great to be here Lenny so I think this is going to be a pretty special and unique podcast your newsletter is the number one technology newsletter on sub stack called the pragmatic engineer by the way ..."
In this segment, Gergely outlines his career journey from a typical software engineer to a successful newsletter creator. He shares his experiences at various companies, including Skyscanner and Uber, and how these roles shaped his decision to venture into entrepreneurship.
"which was a big step up for me in terms of just you know getting access to to I guess more modern software development I was at a consulting company there as well and I moved up to London which you kn..."
Gergely explains the transition from his corporate career to writing a newsletter full-time. He discusses the challenges he faced during this shift and how he navigated the uncertainties of starting a new venture in a non-traditional field.
"leave Uber and uh it we'll talk about a little later in the podcast but I didn't plan like this but I started writing a newsletter right now here I am writing a newsletter where a bunch of people are ..."
Gergely compares his previous salary at Uber with his current earnings from the newsletter, revealing that he now makes more money while enjoying greater freedom. He discusses the potential for unlimited income growth as his subscriber base expands.
"sub Sac introduced recommendations which has been a massive growth engine and I guess being one of the top obligations that kind of benefited from it but those numbers are are again so this is the pai..."
In this segment, Gergely shares the realities of working solo as a newsletter creator, including the challenges of loneliness and the need for self-discipline. He emphasizes the importance of structuring unstructured time to maintain productivity.
"about like 320 or 330 000 in total compensation this was after Uber went public so it includes the the stock the the base salary the bonus which was very very good in Europe and when I quit my job I w..."
Gergely Orosz shares his experience of transitioning from a well-paying job in the UK to Uber, where he was offered a significantly higher salary. He reflects on the excitement of negotiating his compensation package, which included stock options, and the uncertainty surrounding Uber's future at that time. This segment highlights the financial motivations that often drive tech professionals to pursue opportunities in high-growth companies.
"headquarter and all that and I was making I think like 90 something thousand pounds in base salary which is like maybe 120 130 or 140 000 depends on how the pound is doing or sometimes you know these ..."
In this segment, Gergely discusses the challenges he faced at Uber during a period of layoffs. He reflects on the stress of managing a team while witnessing colleagues being let go, which led him to question his place within the corporate structure. This moment served as a catalyst for his decision to leave and pursue a different path, emphasizing the emotional toll of corporate instability.
"goes in like every year I make two years of salary pretty much like that's how I was kind of thinking but if not again don't forget I'm I'm in Europe where we're kind of used to not seeing any Returns..."
Gergely outlines his initial plan to leave Uber and start a venture-backed startup, inspired by his brother's entrepreneurial journey. He shares his vision of creating a platform engineering company, reflecting on the allure of startup life and the desire for autonomy. This segment captures the ambition and risks associated with leaving a stable job for the uncertain world of startups.
"now he's building this startup called craft docs it's a really slick put document editing system they just raised their series B so he's like you know I kind of through him I know what startup life is..."
Gergely recounts how he began writing books during his transition from Uber, unexpectedly generating significant income from self-published works. He discusses the realization that he could monetize his writing, which shifted his focus from starting a startup to exploring the potential of a paid newsletter. This segment highlights the evolving nature of his career and the opportunities that arose from his writing endeavors.
"that I'm gonna just not make any money and this book building mobile apps at scale another book that I published about tech resumes I just wrote These in a few months they started making money they ma..."
In a reflective moment, Gergely shares a parable about a fisherman and a businessman, illustrating the tension between hard work and enjoying life. He connects this story to his own journey, contemplating the balance between pursuing financial success and finding personal fulfillment. This segment emphasizes the philosophical considerations that accompany career decisions in the tech industry.
"can buy a bunch of stuff that I don't need and I was myself like right and then what and I was like well after I bought everything that I don't need I probably want to kind of share what I know with p..."
Gergely discusses his decision to start a paid newsletter, weighing the risks and rewards of committing to a regular writing schedule. He reflects on the challenges of producing quality content consistently and the initial hesitations he faced. This segment provides insights into the mindset required for transitioning to independent writing and the entrepreneurial spirit behind newsletter creation.
"I was kind of thinking like look I have savings I don't have like huge but I have it for I can still take a risk so let me take a risk on on writing and I was thinking original of just like spending m..."
In this concluding segment, Gergely summarizes his transition from Uber to writing full-time, highlighting the support from his family and the commitment he made to his new venture. He reflects on the challenges and rewards of this journey, setting the stage for advice he will share later in the podcast. This segment encapsulates the essence of his career shift and the motivations behind it.
"if there's traction it's great you know I might have found myself a new a new job basically if not I'll just refund people like everyone who bought an annual subscription I didn't tell this to people ..."
Gergely Orosz discusses the initial challenges he faced when committing to writing a weekly newsletter. He explains how he started with one post per week, which evolved into two, and the extensive process behind creating quality content. Gergely highlights the stress of meeting deadlines and the importance of thorough research and editing in producing valuable articles.
"saying I'm gonna post once a week like you'll have one end up post and I started to do that but interesting enough eventually I I upped it to two so I now promise people two posts a week There's a mor..."
In this segment, Gergely shares his current writing schedule and how he manages to produce two articles a week. He outlines his workflow, including drafting, editing, and feedback processes, and reflects on the pressure that comes with having a dedicated audience. Gergely emphasizes the importance of deadlines in maintaining productivity and accountability.
"working on unparalleled things at the same time I was often like running against the deadline I I was barely finishing it which is not what I was expecting initially so the first few months I feel was..."
Gergely reflects on the differences between his structured corporate job at Uber and the unstructured nature of freelance writing. He discusses the challenges of self-discipline and the need for external accountability when working independently. Gergely shares insights on how he has adapted to this new environment and the importance of setting expectations for his audience.
"I might be able to write faster but what I now have is nowadays I actually write two articles so I have I have the Thursday that is the the scoop which actually is a lot a lot easier for me to write i..."
In this segment, Gergely talks about how he leverages constraints to enhance his writing process. He shares his strategy of using deadlines and external pressures to stay focused and productive. Gergely also discusses his approach to writing a book alongside his newsletter, illustrating how he integrates newsletter content into his larger writing projects.
"as you said like I I also know that thousands of people are paying me you know I have like like they have expectations of me and so this is how it's done like if you if you want to write a book the ea..."
Gergely draws inspiration from historical writers like Alexandre Dumas, explaining how they managed to produce compelling content under financial constraints. He reflects on how this approach can be applied to modern writing endeavors, emphasizing the value of creating content that engages readers while also fulfilling personal and professional goals.
"this chapter and I have this list like have I written about this topic in the newsletter and I got you know where I got this idea from there's the book The Three Musketeers from Alexander to my course..."
Gergely discusses the significance of creating structure in a freelance environment. He shares his experiences with various productivity tools and methods, including the Pomodoro technique, to maintain focus. Gergely emphasizes the need for self-imposed deadlines and the role of technology in managing distractions while working on his newsletter.
"I always try to get my work done show up on time I try to meet all expectations but what I notice is when I start to work for myself it just went out the window like for almost 15 years of you know be..."
In this segment, Gergely addresses the challenges of staying focused amidst digital distractions. He shares his strategies for minimizing interruptions from social media and other online platforms while writing. Gergely highlights the importance of creating a distraction-free environment to enhance productivity and maintain a consistent writing output.
"for a limited time Lenny's podcast listeners get one thousand dollars off vanta just go to vanta.com Lenny that's v-a-n-t-a.com Lenny to learn more and to claim your discount get started today I defin..."
Gergely elaborates on his methods for establishing a focused work environment, including using apps to block distracting websites. He discusses the psychological aspects of maintaining concentration and the importance of setting clear boundaries to enhance productivity. Gergely shares insights on how to cultivate a mindset conducive to deep work.
"I I find that I come up with a method and it works for like a few months and then I need to change it because I my brain just learns to work around it so I'll tell you a few things that I did and I'll..."
In this final segment, Gergely reviews various tools and techniques he has experimented with to boost his productivity. He emphasizes the importance of finding the right tools that suit individual working styles and the need for continuous adaptation. Gergely encourages listeners to explore different methods to discover what works best for them in their writing and freelance endeavors.
"Facebook what whatever size so I I just cannot reach it like like it's just a very simple python that I wrote for myself and then I in the first few minutes I'm kind of grumbling I'm like I wish I cou..."
Gergely Orosz shares his approach to productivity by creating custom scripts and tools that suit his workflow. He emphasizes the importance of experimenting with different tools to find what works best for individual needs, highlighting his experience with the Center app that encourages focus through community engagement.
"you can look it up in the whole spot if when you override your host file you can actually block things what you're doing I did this because I wrote a script where I need to run the script and I need t..."
Gergely discusses the benefits of having an empty calendar after leaving his corporate job. He contrasts his previous life filled with back-to-back meetings with his current focus on deep work and creative freedom, allowing him to experiment and explore new ideas without the constraints of a traditional work environment.
"yeah and and the simple thing started 20 minute timer and you say for 20 minutes I need to focus on on this thing on your iPhone or somewhere else it's just 20 minutes but during that time you cannot ..."
In this segment, Gergely reflects on the loneliness that comes with working solo after leaving a collaborative environment at Uber. He shares how he misses the camaraderie of his team and the casual interactions that fueled his creativity, while also discussing the challenges of maintaining motivation in isolation.
"want to try out plus one on both those I I have a rule of no meetings before 3 pm and it generally Works 99 of the time and the reason I do that is to your point if there's a meeting at like 11 I just..."
Gergely opens up about the unexpected stress of running a successful newsletter. He discusses the pressure of subscriber numbers, the guilt of productivity, and the challenges of self-validation in a competitive landscape, emphasizing the need for a supportive community in the entrepreneurial journey.
"workspace so everyone needs to work in Tech so I should get to say hi to people and and have a little small small talk the structure is weird because I felt really guilty for the first few months beca..."
Gergely explains the pressure of consistently delivering high-quality content as a newsletter creator. He discusses the difficulty of taking time off and the importance of maintaining a steady output to keep subscribers engaged, while also contemplating the long-term sustainability of his writing career.
"yourself grounded I actually want to ask you about that but I'll add a couple things that I also find are major downsides of this life because it's not all rainbows and butterflies one is with a paid ..."
In this segment, Gergely shares his thoughts on the future of his newsletter and the potential paths it could take. He emphasizes the importance of flexibility and openness to new opportunities, while also reflecting on the balance between work and personal life as he continues to grow his business.
"company around it build an organization that can run without you for example you know this is what a lot of book publishing companies so basically either you build a Publishing Company where you start..."
Gergely discusses the necessity of taking breaks and the challenges of doing so as a solo entrepreneur. He reflects on his past experiences with paid time off at Uber and the difficulty of disconnecting from work, stressing the importance of avoiding burnout while managing a successful newsletter.
"and now I I I'm solving it for in a different way so I am trying to take more time off now and I am I'm doing it by by working ahead with some of the less time sensitive things but it is tough so the ..."
Gergely Orosz discusses the importance of creating time for inspiration in his writing process. He shares his goal of reducing his work hours on the newsletter to allow for creativity to flourish, emphasizing that taking breaks can lead to new ideas and motivation.
"but over time it might shift so I'm kind of keeping my my options open and what I've learned from this journey is you need to create time to to be able for that spark to come so one of my goals for th..."
In this segment, Gergely explains how he capitalized on the interest generated from his blog posts. He recounts how a surge of engagement led him to focus on writing a book, illustrating the importance of responding to audience feedback and interest.
"that's what I've been doing but uh one one last thing to touch on you said something really important to poll and I want to double down on that one of the one of the biggest best things about doing wh..."
Gergely shares the story of how he quickly gained his first 1,000 subscribers after launching his newsletter. He highlights the foundational work he had done over six years, including blogging and building an audience, which set the stage for his newsletter's success.
"and said like you know what for the next two months I'm gonna write this book because it seems there's an interest in it and I can iterate it I I turn it into a book that was free for two months but I..."
Gergely reflects on the advice from Jeff Atwood about becoming known on the internet through consistent blogging. He emphasizes the importance of regular writing and how it can lead to unexpected opportunities and audience engagement.
"that I had a thousand paid subscribers and this this sounds like a fairy tale and if you do this I guarantee you're you're not going to get the same results in fact you'll you'll probably see way smal..."
In this segment, Gergely discusses the significance of having a background and experience in the field before starting a newsletter. He shares how his years of blogging and working in tech provided him with the credibility needed to attract subscribers.
"stuck with me for years he said how to be famous on the internet I said like there's three simple steps there's one write a blog post two do this like three times a week three you can do it for two ye..."
Gergely advises on the importance of setting achievable goals when starting a newsletter. He contrasts good goals, which are within one's control, with those that are not, emphasizing the need for focus and consistency in writing.
"and it exploded Hacker News some people called me an idiot some people called me the absolute wisdom like and it was these two crowds battling it out and I was like wow I actually made you know softwa..."
Gergely encourages aspiring writers to engage in side projects as a way to build skills and explore their interests. He shares how his side projects contributed to his growth and eventual success in launching his newsletter.
"build a successful newsletter but the best advice I have is still what Jeff Atwood does except I have less conviction but if you start writing and you do it regularly you know two things will happen f..."
In this segment, Gergely emphasizes the value of real-life experience in building a successful newsletter. He discusses how having a solid foundation in the industry allows writers to share meaningful insights and attract an audience.
"well don't forget the what I started like my blog I didn't have any of this so and this is while you're at Uber this is before you started the newsletter it was before before I was a dreamer so I was ..."
Gergely shares insights on learning from established figures in the tech industry. He highlights the importance of following and understanding the work of respected professionals to inform one's own writing and career path.
"control and this is how actually my my you know my blog started initially my goal was like I want to write like once a month and I did that for a while and I was I was proud and proud about that or I ..."
Gergely Orosz emphasizes the importance of gaining real experience and starting small projects to develop entrepreneurial skills. He discusses how many aspiring newsletter writers lack the necessary life experience to share valuable insights, highlighting the need for a solid foundation built on real-world accomplishments.
"this or that you know try stuff on the side assuming that you have time or or if you don't have time try to to make time because I feel a lot of what we're doing is this pre-entrepreneurial and the on..."
In this segment, Gergely shares insights about learning from respected figures in the tech industry, like Kent Beck. He illustrates how real-world experience and a willingness to learn can enhance credibility and authority in writing, especially for those looking to establish themselves in the tech newsletter space.
"you've learned or that you have access to other people who have learned these things I would say that but you know one thing that that I'll I'll double down that's a really good observation this if yo..."
Gergely distills his advice for aspiring newsletter writers into actionable steps: develop depth in your field, maintain a consistent writing schedule, and be open to experimentation. He stresses the importance of building expertise before starting to write, ensuring credibility and relevance in the content shared.
"a title cut to be a software engineer and then he hosts the tdd workshop that has driven development workshop and no one showed up at Facebook and Facebook did no testing which went against all commer..."
Discussing the significance of consistency, Gergely highlights how regular content creation can lead to success in the newsletter space. He shares examples of others who have successfully navigated their creative journeys, emphasizing the need for persistence and adaptability in the face of challenges.
"for how to be successful in this life of a newsletter you have to boil it down to just like one or two key pieces of advice what would you say one is have enough depth in the field whatever field you ..."
Gergely reflects on the competitive landscape of content creation, particularly in blogging versus video platforms like YouTube. He discusses the advantages of writing, especially for tech professionals, and how fewer people are currently focusing on in-depth written content, presenting an opportunity for aspiring writers.
"their thing three have a Cadence and and stick to it to some extent because you you do need to keep repeating it and then four don't be afraid to try out new things a good example of a person who did ..."
In this segment, Gergely discusses the importance of identifying whether your content should be educational or entertaining. He emphasizes the need to enjoy the process of content creation, as passion can significantly enhance the quality and engagement of the material produced.
"started the head of engineering at source graph he actually went back in industry but what I love about this you know it shows that you know you cannot guarantee having success but you can do what wha..."
Gergely concludes with reflections on the joy of writing and how it can transform into a fulfilling career. He encourages aspiring writers to find what they love about their craft, suggesting that passion can lead to success and satisfaction in the world of newsletters and content creation.
"I'm pretty sure and here here's an interesting thought as well just as for closure I was talking with someone on why my newsletter is so successful it's just really successful and I honestly don't kno..."
Gergely shares how listeners can connect with him and benefit from his newsletter. He invites tech professionals to engage with his content and contribute insights, emphasizing the value of community and shared knowledge in the tech industry.
"once you find that thing whatever that might be it just makes it easier gergy it's always so fun talking about newsletter stuff I don't have many people to talk about this life with I hope this was us..."