Gergely Orosz has the #1 engineering newsletter on Substack. He graduated with a computer science degree, worked at a small web agency, and slowly progressed in his career. He moved from Hungary to the U.K. to work at Skype and Microsoft. He was then the founding engineer at Skyscanner. Then he worked at Uber until he left it to start his newsletter.
You can also see the episode transcript and Gergely’s references.
The Pragmatic Engineer newsletter ▶
- Stats: As of April 30, 2023, his newsletter has more than 375K subscribers, growing at 1,000 people/day. The paid users are in the single-digit percentage. His habit of writing a blog for many years, he says, is the key factor contributing to the newsletter’s success.
- The newsletter pays better than his previous job. In Europe, in his best year, he made around $320,000 in compensation (equivalent to $600K in the U.S. pre-tax). When he left to start the newsletter, he thought he’d make less, but now he makes even more, and it has no theoretical cap (even when there is slowing growth or churn).
- Switching for higher compensation can result in a lower title, according to Gergely in “The Seniority Rollercoaster.”
In a newsletter, you have thousands of bosses (readers) instead of one boss (your manager), and many of them fire you every week (churn), and you also can get a raise every week as you continue to grow. —Lenny
"European software engineers don’t value stock compensation as much as in the USA, because returns in the European stock markets can feel underwhelming."
- The transition to writing after Uber layoffs and Covid-19: Combined with the onset of Covid and layoffs at Uber, where he would have to manage the morale when 50% of his team’s engineers were being laid off, he decided he wanted to do something else.
- He wanted a startup initially on platform engineering. His brother Balin is a two-time founder and sold his first company to Skyscanner; he also recently raised a Series B with the Craft.do document editor tool. Gergely realized that a lot of systems at Uber were custom-built and maybe that was a problem worth solving, and he wanted to work with a smaller team.
- The turning point came when he wanted to finish his book, The Pragmatic Engineer, which he accidentally published later and made quite some money. He wanted to take a six-month break to finish his book before starting up. In that time, he started writing online on Twitter and his blog (e.g. Building Mobile Apps at Scale) and realized that if he started up, he could raise capital and make a ton of money to buy things he doesn’t need, but after that he would want to write books and make YouTube videos anyway.
- Starting his newsletter full-time: He didn’t like the unpredictability of income from book sales and found paid newsletters interesting due to the prospect of recurring revenue. For two weeks he collected ideas on what to write and risked saying he would write something every week, at least for six months. If it didn’t work out, he planned to refund the paid subscribers.
Gergely recounts the parable of the Mexican fisherman and the American businessman. A Mexican fisherman leads a simple, relaxed life by the sea catching some fish. An American businessman, seeing potential for profit, suggests the fisherman expand his operations, work harder and, with 20 years of growth, sell the business and retire, living a relaxed life by the sea. The fisherman points out that he’s already living that life without going through all those steps!
The day-to-day of writing a newsletter ▶
- You can give yourself weekly raises, which you can’t get in the corporate world. Gergely made a sheet to track the rise in revenue after a new article was published; sometimes articles he felt were mediocre were loved by people, and sometimes the ones loved by him didn’t perform.
- Write on a consistent schedule, paralleling his posts. Having a specific writing schedule helps him consistently create high-quality content. He breaks down his writing process into multiple days, focusing on research, drafts, feedback from people he trusts, and editing (with an editor), and he does each article over multiple weeks, making sure he has two articles ready per week. He struggled for the first few months.
- Have someone external to be accountable to, and put in constraints so you end up finishing. Looking back, the deadlines from his time at Uber made him work better, though at the time he didn’t like them. External pressure helped ensure he was being held accountable; e.g. to publish his book, he signed a contract with a publisher for $5,000, not for the money but for the pressure from the publisher to deliver his work. He is also accountable to the thousands of readers who pay him. Every day apart from Wednesdays he has pressure to write for a deadline.
I was a very diligent employee at Uber, but when I starting working by myself (as an entrepreneur), it went out the window… I was wasting my whole day. I had to fix it.
- It’s better to break down big projects into smaller chunks. Partially the reason Gergely went down the newsletter route rather than just books was to write parts of The Software Engineer’s Guidebook as posts in the newsletter, so he could make progress and get feedback and make it less daunting. He got this idea from The Three Musketeers by Alexandre Dumas: Dumas wrote The Three Musketeers while writing for a magazine for which he had to add cliffhangers so the readers would pick up the next magazine edition to continue the story. In solving for this retention problem, Dumas broke down the work into chunks, and by the end managed to finish a whole book’s worth of content.
Tips for productivity ▶
- Gergely keeps changing tools and liked using Centered. He tried the Centered app and the Pomodoro technique, etc., which were useful for a few months but stopped working for him after a point. What Gergely mentions on changing methods is related to the idea of productivity cycles, which you can resolve by changing your tools and your routine to kickstart you into a new one. His advice is to try a bunch of these tools and see what works for you, and don’t be afraid to rotate the tools if they stop working.
- Gergely and Lenny both liked using Centered to focus better; it has a feature to turn on your video camera with others.
- Things that always work: Deadlines. Trying to squeeze in before a deadline (like going home from work) works for him. Also, pushing through the first five minutes without distractions helps him get into a flow state.
- A script to block access: He uses a self-made Python script to block access to websites like Twitter, Facebook, and LinkedIn that can pull away his attention from work by editing the browser host file. By eliminating the option to access these sites, you’re more likely to stay focused on the task at hand.
What he likes and doesn’t like about entrepreneurship full-time ▶
- What he likes:
- Open calendar and very few meetings: He enjoys the emptiness of his calendar, which is a stark contrast to his previous corporate job. Having fewer meetings and more unstructured time allows for deep focus and creative freedom. Lenny also has a rule of no meetings before 3 p.m.
- Experimenting. The freedom to write on whatever topic he wishes to.
- What he doesn’t like:
- It’s lonely: He liked working from the office and the random chats and small talk in the workplace; he compensates for it by working in a shared workspace.
- It’s surprisingly stressful: He felt guilty in the first few months, feeling that he’d been more productive while at Uber. There’s a lot of external validation and benchmarks that make it stressful. Setting and monitoring internal goals helped him overcome this, but it’s important to keep a sense of perspective and draw on past professional experiences to stay grounded.
- Exit paths are limited for writing full-time, theoretically having to do this for the rest of your life. It can be tricky to find an exit path for a full-time newsletter that doesn’t compromise the value and reputation built. You can solve this by building a publishing company around the original work with others writing for you, but that may come with its own set of challenges, such as managing employees.
- Hard to take time off: Running a solo newsletter can lead to friction with family and friends, as you may struggle to find time for them while maintaining your work. To mitigate this, he has a clear paid time off (PTO) policy and plans his content ahead before taking time off to keep the work on track.
Why Gergely stopped making long-term plans ▶
- His goal for the next year is to try to do the same work but in half the time. Plans beyond a year seem outdated or under-ambitious or overambitious to him. He sees this as a business more than part of the “creator economy” and, over time, wants to make it work for him rather than him work for it.
- Be sensitive and double down on “pulls.”: When he wrote a blog post on mobile engineering, he got 10x more messages per day asking to read the book draft than usual. Leveraging this market “pull,” he decided to make it a book.
How to get started on a newsletter ▶
Build depth in your area, write a blog post every week for two years, and good things will happen - Lenny
- Main advice: Start teaching and sharing what you know, and set good goals that you can achieve. Whether it’s a newsletter or in meet-ups or in YouTube videos. A bad goal, like “I want 200K subscribers,” you should avoid. Instead you should set good goals that you can do, like “I want to learn this language by next year.”
- Three simple steps to how to be famous on the internet, by Jeff Atwood (founder of Stack Overflow). Gergely tried following the steps for a few months but then gave up. He later realized these principles are enough to make it work on his second attempt:
- Write a blog post
- Do it 3 times a week
- Do it for 2 years
- Making a difference on Hacker News built recognition of his work, which helped the initial success of his blog. When one of his posts trended on Hacker News, some people called it wisdom and some called it idiocy, but he was excited to have people argue about his work. Over time, his posts were shared a lot on Hacker News and built him a network of readers before a proper newsletter launch.
- Build depth in your area. Getting pedigree really helped Gergely. Not having worked at Uber or his other experiences might not have led to this kind of success.
- Do some side projects. A lot of great projects come out of “pre-entrepreneurial” work, so just start doing writing or other side projects before considering it full-time.
- Look at people you look up to and see what they did.
- For Gergely, this was Kent Beck, who even after coming up with frameworks like extreme programming, decided to take a pay cut to work at Facebook just to learn.
- Another counterexample that shows you can’t guarantee success is Steve Yegge, who started to do a podcast and said up front he would try this for six months and see if it sticks, and decided to stop it and went back to working in the industry when it didn’t stick.
- Figure out if you want to do education, entertainment, or edutainment and, based on that, the media format. MrBeast could not have built the kind of following or content doing blog posts as he did via YouTube videos.
This is a human edited summary of the podcast episode with Gergely, by Gaurav Chandrashekar (@cggaurav, productscale.xyz). To listen to the full episode, go here.
