Wow, has it already been five years?! The newsletter hits a big milestone this week, and it wouldn’t have been possible without subscribers. Thanks to everyone who’s read an article or listened to a podcast episode during that time!
Before we get into the latest issue, I’d like to point you to two upcoming events in New York City which I’ll be at. It would be great to meet some of you! They’re free to attend:
**Wednesday, 16 September, 6pm:**What happens when you mix a whiteboard, two senior turbopuffer engineers, and myself, with the spotlight on database internals? We’ll draw out turbopuffer’s database architecture and geek out over it, then hang out afterwards. Join us
.Sign up here.**Thursday, 17 September, 5:30pm:**A fireside chat between WorkOS founder, Michael Grinich, and me, with him asking the questions. We’ll get into stories about the tech industry – including a few which probably won’t get published
Sign up here.
If you’re at LDX3 New York on 15-16 September (Tue & Wed), I’ll be doing a keynote on Tuesday morning and hanging out around the Antithesis booth during the day. See the full agenda and get tickets.
I checked the calendar and it is indeed half a decade – almost to the day in 2021 – since I published the first-ever issue of The Pragmatic Engineer:
On launch, the paid version of The Pragmatic Engineer cost $100/year, or $10/month (this has since increased to $150/year or $15/month). *As a special offer, I’m “resetting” the price of the publication to annual subscribers for $100/year: claim this offer here. The offer ends in a week, on 8 September. *
My personal expectations weren’t high back then; the subscription model for newsletters on platforms like Substack was starting to take off, but the focus was strongly on politics, business, and finance. It wasn’t clear if there was any demand for a publication about software engineering, written by a software engineer.
I soon found out there was demand that surpassed all my expectations – and then some! Fast forward to today; the newsletter has more than 1.1M readers, tens of thousands of paid subscribers, a podcast, and more than 500,000 YouTube subscribers.
**But the numbers aren’t the most validating thing for me; that would be the feedback sent in by readers. **Via email, in DMs, or in-person at events, it’s great to hear how an article or a podcast we published helped someone try a new approach, or to gain confidence that theirs was the right one, or that an article helped convince a team to change things. It also means a lot to learn that The Pragmatic Engineer helps people feel more confident about keeping up in this fast-changing industry.
*Thanks again for your support! *It’s the reason why The Pragmatic Engineer is a viable business and a growing publication, and means we can “scale up” our coverage to deliver ever-more detail about how software gets built, today.
Today’s issue covers:
**Diving deeper, year after year.**The evolution of the Pragmatic Engineer’s coverage over five years, getting in through the “front door” instead of the “back door” for deepdives, launching the podcast, The Pragmatic Summit, and growing our team.**What’s next?**What we’re excited about, the second Pragmatic Summit, and how you can expect us to stay focused on how building software is changing, and the ways that successful engineers, teams, and companies adapt.**Cash-prize writing contest:**Software is changing faster than ever. Send us your essay about how things are changing for you, for the chance to win cash prizes worth up to $10,000.Read more on how to take part.
The Pragmatic Engineer was 15 years in the making and not an overnight success; I started to write a blog in 2007 about software development, which was “rebooted” as “The Pragmatic Engineer Blog” in 2015. At the time, it was read by almost nobody!
In 2019, I launched an email digest (“v0” of the newsletter), and a year later, I decided to focus on the newsletter fulltime. This was, after I resigned at Uber, as a manager, following job cuts in 2020. The pandemic hit Uber hard: during those cuts, a quarter of my team was laid off and the rest were disbanded due to the pandemic. I took an employment break, planning to finish ‘ The Software Engineer’s Guidebook’ in six months and then start a VC-funded startup.
In the end, finishing the book took another two years, and I didn’t kick off that VC-funded startup I was originally planning to do. Instead, I decided to go all-in on writing a newsletter targeted exclusively at software engineers and engineering leaders.
The Pragmatic Engineer started off with one in-depth article on an interesting topic per week, including these ones:
The Platform and Program Split at Uber: platform teams were starting to go “mainstream” across the industryHow Big Tech runs tech projects and the curious absence of Scrum: this article made a splashThe perfect storm causing an insane tech hiring market: the job market in late 2021 was one of the hottest ever seenGrowing a junior-heavy team: this was published when it was hard to hire seniors and many teams were junior-heavy
This time, the newsletter took off and crossed 1,000 paid subscribers six weeks after launch. By the end of 2021, it was the #1 paid technology newsletter on Substack (!!), with 2,700 paid subscribers and 30,000 free subscribers. Most surprising was that the growth happened via word-of-mouth, and from me posting about issues on social media, without spending on ads and marketing. Growth has continued since then; for example, as per the Brex Benchmark, The Pragmatic Engineer is the third most expensed newsletter at startups, globally, in 2026, and remains one of the fastest growing ones.
If you have a learning & development budget or something similar in your workplace, you can probably expense the newsletter. Here’s an email template to send to your manager. And you can also get the newsletter on “launch” price, at a 33% discount.
In the second year, I added a Thursday article called ‘The Scoop’ – now ‘The Pulse’ – alongside the research-heavy Tuesday articles. Unlike those articles, The Scoop covered tech news and developments on a weekly basis and wasn’t ‘evergreen’ material. But as I talked with more techies, I got to spot new trends and patterns, often months before mainstream publications covered them.
Recent examples have included us reporting the odd tokenmaxxing trend a month before the Financial Times did so, or covering the extreme work patterns at AI startups months before The Wall Street Journal picked up the story, or The Economist republishing my Trimodal Nature of Software Engineering Compensation diagram four months later across their digital and print editions.
Until mid-2023, I mostly wrote deepdives on engineering topics without the involvement of companies that weren’t interested in showing me how they did things from the inside.
At the end of 2022, I heard from former colleagues at Uber that the ridesharing giant was moving off its own data centers, and moving onto the cloud, and onboarding to GCP and Oracle. I gathered plenty of details from current and ex-Uber workers, but the infra leadership didn’t engage with me via official channels.
So, I went ahead and published ‘Inside Uber’s move to the Cloud’, which got the majority of details right, except for a few. Inside Uber, the article was criticized for not getting everything correct, but that would’ve involved me talking on the record to Uber’s infra leadership, which they didn’t do!
In 2023, the newsletter had 350,000 readers and was starting to make a name for itself, which began to open some previously closed doors. I increasingly got details from engineers at companies via the “front door” rather than the “back door” route of informal contacts and scraps of information. Uber’s cloud migration was the final deepdive of its type; after that, going through the “front door” became easier, with companies sharing details with me about what they were doing. This change led to more accurate and detailed articles, including:
Since then, deepdives about interesting, cutting-edge tech companies have become a regular part of our publishing schedule. And as a bonus, we’ve figured out a “recipe” for getting access to folks at tech companies who are usually off-limits to the media, which leads to more exclusive content for readers.
In the fall of 2024, I launched The Pragmatic Engineer Podcast with two intentions:
**Share previously “private” conversations.**When doing a deepdive about an interesting company or technology, I usually did a call with engineers. These fascinating, one-hour-long conversations got summarized in a paragraph or two in articles, but I always felt there was more that readers would be interested in.**Meet interesting people.**I was spending most of my days behind a keyboard writing deepdives, with the occasional video call when researching engineering teams. I hoped that doing a podcast would just allow me to meet more people!
Simon Willison, one of the most grounded voices in AI engineering, was the first podcast guest, and feedback was warm and positive. I always look forward to talking with guests due to their experience and significant industry contributions; the likes of Grady Booch, Nicole Forsgren, and Mitchell Hashimoto – or for their unusually deep expertise – like context engineering with Dex Horthy, developer productivity with Laura Tacho, and building software without looking at the code with Peter Steinberger. These days, when I go to a conference, more people talk to me about the podcast than the written articles, which is interesting.
**Over time, I’ve developed a preference for in-person podcast conversations instead of video calls. **When the podcast launched, I had a home studio set up for the remote recording of on-screen meetings:
But you might have noticed that these days, podcast episodes are in-person conversations more often than they are video calls. I find that conversation flows better in person, and that the format is more engaging for everyone involved than a conversation on a screen is. It also offers an opportunity to hang out before and after the recording! Of course, the logistics of in-person recording are more complicated due to travel, and when there’s someone I’d really like to get on the show but it’s tricky to arrange, we stick with the remote option.
**I’d like to hear your suggestions about future guests for the podcast. **Let us know who you’d like to hear from and why. Send suggestions here.
In summer 2025, I attended the LeadDev Conference in London and enjoyed it so much that I asked if we could organize a conference for The Pragmatic Engineer, with deepdives and podcast guests for readers and listeners.
We spent the second half of last year organizing the first-ever Pragmatic Summit, which took place in February this year in San Francisco, with great help from the excellent Statsig team (many of whom now work at OpenAI). With 500 attendees, 15 standout speakers – and with it being the first-ever conference I’d organized – it was a smashing success. A one-minute video recap of the event:
Based on the feedback from attendees, there will be another Pragmatic Summit in San Francisco next year. I’ll share details in the coming weeks; we’re in the middle of putting this event together now!
Predictably, the most time-consuming task in The Pragmatic Engineer is working on deepdives. We often spend up to two months on a single deepdive, educating ourselves on the topic being covered, talking with expert engineers, and generally getting deep into a topic in order to deliver a deepdive worth reading.
I say “us” because this year, Jessica Salmon and Ivan Klaric joined the team. Both are software engineers with startup and Big Tech experience, who enjoy spending time getting to understand topics and contributing to longform articles.
With a larger team than before, we’ve continued to produce deepdives for readers. A few recent ones:
**I’ve found there are no shortcuts for producing an in-depth article on a relevant topic for readers. You simply have to put the time and effort into it. **This involves spending a lot of time on thinking and understanding things, going directly to engineers who build what we want to learn about, and then spending even more time on organizing research material into a lengthy article that’s informative and hopefully not dull to read.
Needless to say, we’ve experimented with the analytical powers of AI tools in parts of the research process. The technology is good at gathering publicly-available sources and does a decent job of summarizing them, but that’s been more or less the limits of AI’s usefulness for our purposes to date – except as a spelling and grammar checking tool after a full draft is written by a person.
If anything, AI can easily lead you down the wrong track by theorizing about non-existent connections and confidently espousing theories which some basic critical thinking could easily debunk!
Aside from research and correcting (most) typos, we don’t use AI in this publication. That’s because we are writing for a rea…
