CN#9. The Pragmatic Engineer: IT newsletter with a high-earning audience

FREQUENCY: Usually twice a week (paid). Monthly (free).

NEWSLETTER TYPE: Professional, Engagement

PURPOSE: Helping software engineers and managers by uncovering solutions to software challenges at big tech and high-growth startups.


SUBSCRIBERS: 220,000 free and paid

WORD COUNT: 4,572 (shortened, free version)


SUBJECT LINE: Real-World Engineering Challenges #7: Choosing Technologies


The newsletter uses the independent newsletter hosting platform Substack. The templated designs are simple, readable and functional with a Helvetica-like sans serif font.

Author Gergely Orosz adds a bold first line or word but there’s little other attention to formatting. There are wholly functional, sometimes hand-drawn graphics illustrating software engineering processes. No pictures for the purposes of lightening or adorning.


There’s a welcome from Orosz, who straight up offers a Cyber Monday 20% discount offer on paid membership, an invitation to read reviews and an all-important deadline for the offer.

Orosz is a former senior software engineer with Uber, Microsoft, Skyscanner and Skype, based in the Netherlands.

This newsletter is No 7 in a series of “real-world engineering challenges” in which case studies from tech companies are interpreted. There are 4 in this issue and we kick off with a helpful summary. Already you’re getting a sense of how much value is about to be delivered.

In this free monthly version you’re getting a monster 4,500 words of deep, well-researched analysis, so an engaged reader is probably wondering what other riches await in the paid offering.

The first study is about how engineers chose a particular solution over another for Trello, a task management app. The content is about the nature of the service problems being addressed and the decision-making of the team involved.

As a non-IT person serving a general newsletter audience, I won’t go into detail on the editorial, other than to record that the reader gets 650 words on this study before hitting the paywall.

Commit to a subscription and you’ll get more, which the author previews, telling you how unexpectedly cheaper the Trello solution is to operate, and details of a subsequent problem that cropped up. All very tantalising if you’re engaged.

Next, there’s a nice touch where mechanics of the article’s construction is shared.

Orosz outlines the questions arising from the source article, and explains he approached the author with questions, got certain answers, but not everything he wanted. This makes the reader feel like the writer is batting for them and doing his best.

The pattern repeats 3 times throughout the newsletter with the meat of the case studies provided but extra details hidden.

After the case study commentaries there’s Takeaways, summarising the key points, moving into more mainstream observations that a CEO or more general reader (like me) would understand, such as:

➕ When changing technologies, make sure you solve for a large enough pain point.

➕ When building a new project, think about future pain points.

➕ When changing technologies, do it one step at a time, if possible.

The newsletter ends with 15 featured jobs from The Pragmatic Engineer’s website job board, and an invitation to hirers to join a group to find engineering talent looking for new opportunities.

Here are some examples of the coverage in other editions:

➕ How Facebook is deciding which engineers to fire

➕ Resiliency in distributed systems

➕ How Uber is measuring engineering productivity

➕ Internal politics for software engineers and managers

➕ Ways staff and principal engineers get stuck (and how to get unstuck)

Orosz has added a further string to his bow with The Scoop, a bonus series of newsletters for paying subscribers on news-related developments in Big Tech.

The latest asks why Elon Musk is being so cruel to Twitter software engineers.


Orosz sources information from blog posts, articles and insider contacts and then follows up with questions to the authors and other experts. He works on several newsletters in parallel.

Sources are attributed and linked to an original blog post or article and the source author’s personal profile.

There's a painstaking approach to regularly creating high quality, in-depth copy.

Not a native English writer, he employs an editor to improve readability. He even posts draft articles on Twitter to get others to improve them - not something I've ever seen journalists do.


The Pragmatic Engineer is the top performing technology newsletter on Substack, ranked by total number of subscribers.

A subscription is $15 a month or $150 a year for two (sometimes three) articles a week plus the archive and access to documents and templates on a range of software engineering career-related subjects. The free version gives you one article a month.

Launched in August 2021, within a month the newsletter had 15,000 free subscribers and an annual recurring revenue of $62,000 from 500 paid members, a number that doubled to 1,000 by October 2021.

Now with 220,000 total subscribers, revenue numbers are no longer disclosed. However, applying a 2%-3% free-to-paid conversion rate, the estimation of 4,400–6,600 paying subscribers and $660K-$990K of annual recurring revenue can’t be too far out.

Substack takes 10% of revenue and in addition there are Stripe credit card processing charges.


There are no sponsorships, affiliates or third-party ads. The goal is full independence, funded solely by subscribers. Orosz says while advertising is enticing it compromises independence.


Growth has been entirely using free sources and Orsoz has no marketing budget.

Free Subscribers

The top traffic source is Substack’s recommendation engine (launched April 2022) which delivers 70% of new subscribers.

New subscribers to Substack newsletters are offered similar newsletters, with the opt-in process made close to frictionless.

Next is the author’s original blog, driving about 15%.

The 15% balance comes from Twitter, LinkedIn, the Substack app, Hacker News and YouTube.

Social media is therefore providing a minority of subscribers despite Orasz’s substantial followings on Twitter (178,000), LinkedIn (93,000), and YouTube (54,000).

The conversion rates (the proportion of click-throughs that lead to a sign-up) for these platforms are as follows: Youtube 10%, LinkedIn 8%,Twitter 5%, Hacker News 1%.

Paid subscribers

The lesson here is that self-built platforms are higher converters to paying subscribers than social media.

The top channels for paid subscribers are “by far” the author’s owned properties, The Pragmatic Engineer Blog and

Among social media, Twitter drives the highest number of paid subscribers.

Next comes Substack, delivering half the number of paid subscribers as Twitter.

LinkedIn and Google each delivers just less than the number of subscribers who come from Substack.

Orosz says: "Much of my credibility when starting the newsletter – and still the #1 source of paying subscribers – is my engineering blog.

"This is curious, as most Substack authors consistently mention Twitter as their main subscriber source – but it’s not true for me.”


The authentic testimonials prove the tangible value The Pragmatic Engineer provides. Software engineers want greater knowledge of their subject, leading to better job prospects and higher salary expectations. Here’s what they say:

“What I've learned in just a single post increases my value as an employee at any company.”

“I've learned more from reading this newsletter than from any class/course I've ever taken.”

“I have been around tech for 30+ years. The knowledge you will pick up WILL increase your market value.”

“If you are a senior+ level engineer, this is one of the most invaluable resources you can have, and is worth every penny.”


The Pragmatic Engineer looks like an overnight success, but as Ray Kroc, who built McDonalds, said: “I was an overnight success all right, but thirty years is a long, long night.”

Gergely Orosz hasn’t waited that long but ran an unmonetized blog for 6 years before he launched this venture. Existing knowledge, traffic and goodwill are the foundation stones of the exploding success of the past two years.

However, there are other big drivers:

  1. The provision of tangible value through detailed professional knowledge that leads to a better job and higher salary for readers.
  2. Owning an editorial space mainstream media ignores and few others cover. Not many journalists could replicate the depth of engineering knowledge on show here, and few software engineers are willing to research and write consistently.
  3. Commitment to excellence through quality writing and accuracy. Orosz researches, follows up, keeps probing, polishing. The newsletters are engineered rather than written.
  4. Availability of source information in a new and evolving industry. Software engineers already share knowledge but value is added with curation, interpretation and analysis.
  5. Heightened reputation from years of consistent writing leads to authoritative industry admirers becoming contacts providing insider information.
  6. A high earning target audience offered a tax deductible personal learning and development tool.
  7. A clear objective: “I want to make it easier for engineers to grow, week after week.”
  8. Being a nice guy.

Final word to the author: “I don’t just have these conversations to gather sources and information, but where I can – and it’s easy enough to do – I also offer my two cents on professional situations.

"I tend to get questions on negotiating packages, career progression, or requests for a second opinion on a situation in a large tech company, or a startup. You can reach out to me.

Read The Pragmatic Engineer here.

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