From an Unanswered Email to a Summit: How The Pragmatic Engineer Came to Be
The Pragmatic Engineer
The Pragmatic Summit opened in San Francisco on 11 February 2026 with a welcome address from its host, Gergely Orosz, author of The Pragmatic Engineer. He didn't preview the day's talks. He told the story of how a newsletter, a book, a podcast, and now an in-person event grew out of one frustration: nobody was writing about engineering management and software careers as they are actually practised inside tech companies. He then explained what he believed made the event different and what he hoped attendees would take from it.
Looking for Advice That Didn't Exist
The story starts eight years earlier, when Orosz became an engineering manager at Uber. Uber had an apprentice management program. He described it as "really cool": it gave him training and put him in touch with other new managers who, in his words, had no clue what engineering management was either.
Then he got a new manager, Shaolin. In their first one-on-one she asked how she could support him. He told her that Uber was new to him. Working inside a Silicon Valley company growing faster than any company in history, as he characterised the Uber of that time, was new territory, and he wanted to learn from the best. Shaolin offered to connect him with people. She also suggested he research the best magazine money could buy and subscribe to it.
He picked Harvard Business Review. It wrote well about management, but it didn't feel like it addressed his actual job: leading a team inside a tech company and working with technology. The articles felt generic. So he emailed HBR and offered to write for them about engineering management as it looked inside Uber. He never got a reply. The audience laughed when he added that someone there is probably kicking themselves now.
He kept going anyway. He found mentors, learned a lot, and grew in the role.
The Skip-Level Conversation That Started a Book
The next turning point came after he became a manager of managers. In a skip-level meeting, an engineer who was new to Uber told him they felt stuck. They had been trying to read the whole codebase and couldn't make sense of it. At their previous company, work arrived as Jira tickets. At Uber, people were telling them to create their own Phabricator tickets, which confused them. They asked how to get better and, more importantly, how to become a senior engineer one day.
Orosz said he knew how to answer that. By then everyone on his own team had been promoted at least once, and he knew how to mentor people. But this engineer already had a manager, and he felt it wasn't his place to step in. Doing so would have been "kind of uncool" toward that manager. His idea instead was a book he could hand to someone like this engineer, containing "my two cents" on what he had seen work, which they could take or leave.
He started writing that book while still at Uber and signed with a publisher. The book never got finished.
COVID, Layoffs, and a Break From Uber
He said that without COVID, "none of this might have happened." Uber went through layoffs. Its business was collapsing, and a quarter of his team was let go. He had to move the rest of the team to other groups, because their mission of building a wallet for drivers and others no longer made sense. He became demotivated and decided to leave Uber for a while and finish the book. That book later became The Software Engineer's Guidebook.
Like any good project, he joked, it was always "six months" from being done. Nine months into what he called his self-imposed "funemployment," he started asking himself what he was doing. His plan had been to finish the book, raise money, and start a startup, "something something platform engineering," essentially copy-pasting an internal Uber project into a company. He noted that many successful startups have done exactly that.
At that point he saw another option: write a newsletter that carried on the book's work. It "all clicked." He would write the newsletter he himself could never find to buy.
The Newsletter, and What Followed
He described The Pragmatic Engineer as a place for the advice, insights, and "open secrets" that were obvious to him and to some people already working in the industry. Many people didn't know these things. Even those who did had rarely seen them written down so clearly.
By his account, the newsletter got traction immediately, without any advertising. It became the top-selling technology newsletter on Substack. Four years later it passed one million subscribers in total, again with no advertising. Along the way, he said, he realised this was "something special."
The podcast grew out of the interviews he was doing for the newsletter. He had many good, lively conversations and felt it was a shame they weren't captured, so he started recording them. He said the podcast also became very successful.
The last missing piece, which he had thought about but never believed could happen, was bringing people together in person. He described the audience as people who care about the tech industry and software engineering, who don't like the hype, and who want to know what is actually happening.
Who Was in the Room
He asked for a show of hands. Most attendees worked as software engineers or engineering leaders. The room included people from San Francisco, California, the rest of the US, and outside the country. He mentioned speaking with attendees who had travelled from Singapore and Brazil. He said the field everyone works in is software engineering, which is "now turning into a little bit AI engineering as well — not a little bit, a lot, honestly."
What He Thinks Makes the Event Different
He named several things he considers special about the summit.
The speakers. He joked that the lineup is almost a "Pragmatic Engineer cinematic universe." Every speaker had either appeared on The Pragmatic Engineer podcast or worked with him on a deep dive, and he estimated he had met about 70% of them in person before the event. When people ask him how to become a speaker, his answer is roughly "first get in touch." He said it is rare to be able to listen to world-class people on a podcast and then meet them at a conference. He called it "a crazy idea" when they started. Many of the speakers are also authors, whose books were available on the fourth floor for signing.
The organizers. The event was organised by Statsig, a company known for experimentation systems and feature flagging. Orosz said it turns out Statsig moonlights as the Bay Area's single best event organiser, and he asked for a round of applause. He promised "delightful surprises" during the day, including a chance to build architecture out of Lego downstairs.
The attendees. He called this the most important factor and the reason the event works at all. He said they designed the event not to make a profit: ticket revenue roughly covers costs. Close to 2,000 people applied, and the organisers selected attendees carefully. They looked for builders, experienced professionals, and people who are optimistic about technology's future and curious about how to navigate it. He said that after going through the attendee list and talking to people that morning, he hadn't seen another event where everyone is there for the same purpose: to "move together, and move together faster."
The Goal for the Day
Orosz said his aim was to make this the single best day attendees could spend in a professional setting. He wanted it to be a place to take in new ideas and talk with the speakers afterwards, and above all a place for attendees to connect with each other.
He told a story from the previous day's dry runs. He had joked that some friendship or connection made at the summit would lead to an incredible startup, and possibly a large tech company, within two to three years. The more he thought about it, he said, the more convinced he became that there would be more than one. He closed by encouraging attendees to say hello to the speakers, to take in the ideas, and especially to talk to one another and exchange contact details. Everyone in the room was there for a reason, he said, "and let's make this count."
Good morning everyone. Good morning San Francisco. This is pretty wild because I still remember how all of this started and I never had anything like this in my mind.
Eight years ago, I became an engineering manager at Uber and I was an engineering man. We had an apprentice management program which was really cool. They gave me a bunch of training. I connected with fellow folks who had no clue what engineering management is. But then I got a new manager, Shaolin, and she told me and I told on our first one-on-one, she said, "How can I support you?" And I said, "Look, Shaolin, I'll be real with you. Uber is new to me. Working inside a Silicon Valley company that is growing faster than any company in the history, that was back Uber. This is all new to me and I need support. I would like to learn from the best." And she said, of course, I'll connect you with folks, but she said, but why don't you get a subscription, get the best possible subscription that money can buy for any magazine, do your research and do that. And so I did, and the best I could find was Harvard Business Review at the time. They write really cool stuff about management, some people are nodding, but it didn't feel that it was talking about what I was doing inside tech, leading a team, working with technology things. The articles felt very generic, Eric.
And so I did what made most sense. I wrote them an email saying, "Hey, I'd write for you about engineering management, what it's like inside of Uber. Are you interested?" And I never received a response. Man, someone's kicking themselves up there.
And you know, I kind of went on. I got a lot of mentors. I grew. I learned a lot about these things. And then the next thing that happened is I became a manager of managers. I had my first manager under me and I asked for a meeting with my skip level, an engineer who was very starry-eyed, very new to Uber, and he said, "Oh Gergely, I feel a bit stuck. I've been trying to read the whole codebase. I don't understand. It's so different. At my old company we used to be given Jira tickets, now people are telling me I need to create my own Phabricator tickets. It's confusing. How can I get better and more importantly how can I become one day that senior engineer?" Because I was hired as an two I used super principal engineer kind of pissed. So there's a lot to unpack there.
But I was like, I've done this before. I could close my eyes. By that point in my team, everyone who was on my team was promoted at least once. I knew how to mentor people. I knew how to help them. But for this person, I figured this is not my place. They've got a manager. I shouldn't be the one spending, it's kind of uncool to my manager to do this. And I figured, would it not be nice to have a book that I could give to them just with my two cents that I've seen work? And you can take it or leave it. And so I started writing this book at Uber. I worked with a publisher but the book never got ready.
And then it just so happens COVID happened. Without COVID none of this might have happened. Uber had layoffs. It was a tough time. Our business was collapsing. A quarter of our team was let go. The rest of my team I had to reallocate elsewhere because our mission and vision did not make sense, building this wallet for drivers and others. And I got demotivated. And at that point I decided, you know what? Let me just leave Uber a little bit and finish this book that I've been writing, which later turned out to be The Software Engineer's Guidebook.
As with any good project, I thought it would take six months, but it's always six months ahead. Funny how that is, right? Software engineering, writing a book. And nine months into this self-imposed funemployment, I was like, what am I doing right now? My plan was finish a book, raise some money, do a startup, something something platform engineering, Ctrl+C Ctrl+V an internal Uber project and turn it into a startup. By the way, so many successful startups have done this, it's incredible. And that's the moment that I saw there's an opportunity to maybe just write a newsletter, carry on with my book. And at that point it all clicked. I was like, let me write this newsletter that I could never buy, that was not out there.
And that's what The Pragmatic Engineer is. I just started to write the advice, the insights, the open secrets that were clear to me and clear to some of you who are already working in here. But a lot of people didn't know, or even the people who did know, they didn't see it written down as clearly. This newsletter immediately got massive traction. There was no advertisement involved, nothing. And it just grew. It became first the top-selling technology newsletter on Substack. It then, four years later, crossed 1 million subscribers in total, who are subscribing again without any advertisement.
And during that path I realized this is something special. I started to do a podcast because I did a lot of interviews with people and I always felt it was a shame that we had some really good conversations with folks, really animated, and it was never captured. And the podcast also became just really, really successful. And the last part that was missing, that I always thought about but I never thought it could happen, is this: us coming together, people who care about the tech industry, the software engineering. We don't like the hype, but we want to know what is actually happening, and get together. So this is how it all came together.
So hands up if you work either as a software engineer or as an engineering leader in the tech industry. Hands up if you're based here in San Francisco, if you're in California, if you're in the US, and if you traveled from outside of the US. Wow. You can see there's folks from all over the place. And I talked with someone who came all the way from Singapore, from Brazil. Thank you for all of you.
This is why this event is so special. We are all working in tech, mostly in the software engineering field that is now turning into a little bit AI engineering as well. Not a little bit, a lot, honestly. And there's all of us from across the world. These ideas are bringing us together.
The other thing that makes this event very, very special is the speakers. I was joking that it's almost like the Pragmatic Engineer cinematic universe, because all the speakers are people who have been either on my podcast, on The Pragmatic Engineer Podcast, or they did a deep dive with me, and I think 70% of the speakers I met in person before this event. Some people are messaging me, how can I be a speaker, and I was like, well, first get in touch. But I realized this is very special. It doesn't really happen that you're listening to a podcast with some amazing world-class people and you can also meet them at the conference. And this was a crazy idea when we started, but we made it happen thanks to these speakers. They're not only on the podcast or writing deep dives, but a lot of them are outstanding authors. You can get their books down on the fourth floor and you can also walk up to them and ask for them to sign those books as well.
Another thing that makes it really, really special, and this is turning into an event I've never seen before, is the organizing team. Statsig is a company known for their experimentation, their advanced experimentation systems and feature flagging and many, many more things. But turns out they moonlight as the Bay Area's single best event organizer. So let's give them a huge round of applause for this event. You'll see a lot of delightful surprises throughout the day, from building architecture with Legos downstairs to a lot of thoughtful things scattered across the event.
And finally, the thing that makes this the most special, and the reason this only works, is you. It's all the attendees. When we did this event, we turned everything upside down. This is not an event where we wanted to make a profit. We're actually just breaking even with the tickets and those costs. We had closer to 2,000 people apply to attend and we were very careful in selecting folks who we think are builders, are experienced professionals, are people who are optimistic about the future of technology and also just curious to figure out, how am I going to figure this out. And this is all of you. Having looked through both the list of attendees and also talking to you today just before, I haven't really seen an event where everyone is just here for that one thing, to move together and move together faster. So let's give a round of applause to all of you who showed up here today. Thank you.
My goal today is to make this the single best day that you can spend in a professional setting. A place where you will soak in new ideas, where you can talk with the speakers afterwards as well and get their takes, connect with them, but more importantly connect with each other.
I was joking yesterday when we were doing the dry runs here that I bet that today there will be a friendship formed or a connection made that will lead to an incredible startup and potentially a massive tech company in two to three years. And I was kind of joking about it. The more I thought about it, I'm pretty sure there will be not just one, there will be more. So throughout the day, I encourage you to not only come and say hi to the speakers and connect with them, and not only to take in the ideas, but talk to fellow professionals, exchange contact information. Every one of you here is here for a reason. And let's make this count.
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