The author of the Pragmatic Engineer once posted a list of his previous failed startup ideas. Nothing wrong with failing, of course, and it’s important to understand that it can take multiple attempts to find something successful.
However, it’s worth cautioning everyone to note how much his success revolves around newsletters, ebooks (as used as an example in this article), and the job boards that go along with his newsletter.
I generally like and appreciate Pragmatic Engineer content, but it needs to be taken with a grain of salt. The premise of this post is about starting a startup as a software engineer, but the example content is an information product (ebook) and the “startup” is just selling that ebook through content marketing. In fact this basically a cookie-cutter copy of the early 2000s self-help guru books where someone became successful selling books on how to become successful, but targeted at software engineers. This feels like someone read a Tim Ferriss book from the early 2000s and asked themselves how they could resell the same idea to software engineers.
The author does have some good resources explaining the internal processes at companies he has worked for (Uber), but lately a lot of his newsletter content is recycled from The Information and random Tweets. In fact, he had to retract a claim that he reported on recently because it turned out to be a completely untrue rumor that was circulating on Twitter, which he reported as a “scoop”. I suspect a lot of the quotes where he says “I interviewed an engineer at _____” might be just be sourced from random Tweets.
As with all content marketers selling advice, please take this all with a grain of salt. Some of the information is definitely accurate and actionable, but framing this ebook marketing story as “how to start a startup as a software engineer” is pure marketing spin.
The Pragmatic Engineer here :) And here is the list of side projects and their status I posted about you might have referred to [1]. I never posted about failed startup ideas.
As I wrote in another comment, this post is from late 2020, when I planned to start a startup, and when I had no idea I would be successful with my writing - it was maybe a month or two after publishing my first book. The context of this article was the skills I thought I'd use when going down the startup route.
On some assumptions of my recent writing:
> "I suspect a lot of the quotes where he says “I interviewed an engineer at ____ might be just be sourced from random Tweets"
When I write that I talked with someone at a company, it means I connected with them directly on various channels (e.g. over DMs, Signal, video call etc). I talk with lots of people, and incorporate some of these into the "The Scoop" articles and sometimes tweet about them (like this [2]). If I base something on a tweet, I'd share that. If I use something else as a source of information I share that as well.
If I come across things that are not true, I aim to correct it immediately (like this [3])
In my new career, integrity is the most valuable asset I have, and I aim to make it very clear when I share information that comes with directly talking with people, versus taking things from other sources.
> As with all content marketers selling advice, please take this all with a grain of salt.
Agree on this, and please see the context on when I wrote this article.
Thanks for the additional context. However, this is the exact issue I was trying to point out:
> this post is from late 2020, when I planned to start a startup, and when I had no idea I would be successful with my writing - it was maybe a month or two after publishing my first book.
The title of the article implies that the content is advice for starting a successful startup for a software engineer. It literally uses the phrase “a startup”.
Then you read the content and it’s about marketing an ebook. The fact that this was written only a month or two after getting some sales of your ebook is exactly the problem I wanted to point out: There is always a kernel of wisdom or truth inside of Pragmatic Engineer content, but I’m usually left feeling like the headline was hyper-optimized for maximum clickbait value, but the content doesn’t quite deliver what the headline promised.
In this specific example, I click because I wanted to read an article about starting a startup as a software engineer. Instead, I got basically a 1-2 month retrospective on marketing an eBook on HN that doesn’t even explain why the book took off, other than perhaps luck. That’s the type of disconnect between headline and content that degrades the sense of trust very quickly.
Thanks for elaborating. You're right: the title is misleading. I changed the title to reflect what I meant to write about: "Want to learn about entrepreneurship, as a software engineer? Sell something online".
And yes, your point is a valid criticism on "selling advice" without having been successful the space you write about. It's also a reason why I'm trying to steer clear on offering advice on running or scaling a business - since running my own business, ironically. I made one exception so far on this, sharing my thoughts on the term 'creator'. [1].
I also noticed how writing about business topics pulls in people who want to succeed in a similar way, and can go down the "publish self help content" in ways that you described. It's not appealing to me.
Appreciate the caveats on the publication! I'll also think of how to make it more clear to indicate my sources are direct and the information is "exclusive" without over using the "exclusive" part.
Thanks for responding and being open to some healthy discussion.
To be clear: I am a subscriber and I do recommend The Pragmatic Engineer to a lot of people, although with some of the context above. Looking forward to watching the newsletter evolve over time.
Thanks - I keep evolving the publication; The Scoop is barely a few months old and was (still is) a bonus addition to the long-form weekly articles.
To quote or not to quote from other publications is an good question. Re-reading the last two Scoop issues, they both, indeed started with The Information quotes as you rightfully noted. I didn’t mark the information that was unreported outside my newsletter clearly either. The ones that were all based on directly talking with sources at companies - like the internal controversy on Slack access at Stripe, compensation rises and the Board's role at Adyen, the Meta PSC process as it’s playing out right now, the details on Google’s hiring freeze as confirmed with managers at the company, the Graphcore hiring freeze, reporting on the upcoming Apple hiring slowdown - and then sharing when Bloomberg shared information on the same two weeks later.
Here is an un-paywalled The Scoop issue from two weeks ago [1] where the first article was, indeed referring to The Information as a source, the second news referencing Bloomberg - confirming earlier reporting - and the next six scoops mostly from my own sources.
I don’t like the idea of calling out “exclusive” details, but I can also see how quoting from other sources can de-value this publication. Also, the reality as a on-person publication is there will be relevant news I won’t get to, but might still be relevant to share as a summary.
Hi PE, I have found something in how to counter overworked SEO. I started re-using the Google tool Google trends with a twist:
1 Pick the High Searched Term of your subject.
2 Pick an extremely niche unique term of your subject that gets low search hits.
Now combine them as a title to a post. Income wise one has two levers,
immediate bump which often is just as high as the long term tail when it accumulates and the long tail is the niche search term.
> A similar - though much more impactful - example was how Traf Icons saw over $250K in sales after MKBHD - a YouTuber with over 13M subscribers - made a video with over 7M views of him installing these icons
these post usually based around survivorship bias, that's assuming there was no prior relationship/agreement.
Thank you for writing this! This quite align with what I've recently experienced. I was looking at a number of Twitter accounts that tweets about how to get engagements on Twitter. Naturally, they pointed to their own account as a good example of what to do. But if you look closely, they tend to find success precisely because they talk and sell courses on how to be successful. Not exactly the best example.
One thing I've noticed about those Twitter accounts with huge number of followers in the entrepreneurship topic(or perhaps any topic) is that they tweet about just one thing consistently; Everything they tweet about, incl. memes are almost always about their 'thing'.
Twitter rewards that consistency by organically promoting such accounts under 'topics', I guess it's easy to classify the tweets if the account stays within topic.
The followers are following those accounts for that 'thing' too and consider the follower count to be an accreditation for their subject matter experience. This works great if FOMO is involved and Entrepreneurial advice has boat load of it.
Good for them, Their business and perhaps may be their followers too.
But I personally tweet about everything from mental health to linux kernel; When I feel like it and it's evident from that I have just ~500 followers with 13 years of Twitter account. I don't follow anyone as I don't trust the conformist feed algorithms, I have lists for subject matter experts which I follow according to my needs and I engage(like, reply) to the tweets from my followers using my custom tool.
I guess my account is an exact contrast for someone who wishes to be a successful Twitter marketer; Which is a shame considering I'm an indie too.
The difficulty with tech blogging in general, is that even the best produce at most one genuinely great, authentic piece per year.
So, if you want to be posting regularly, there is no choice but to recycle other people's insights, or produce less well-researched pieces, or to just repeat yourself a lot.
Recycling insight is one thing, but I was referring to the sense that a lot of the content feels like “reporting on reporting”. That is, an article telling me that The Information posted an article that said something.
The quotes are always properly attributed with links, but given that the original content is behind a different subscription I feel slightly sleazy for subscribing to a newsletter that basically summarizes and quotes from a different paid newsletter as a primary source. (I also subscribe to The Information, FWIW)
Just want to push back on the note that my newsletter "basically summarizes and quotes from a different paid newsletter as a primary source".
The last issue had the most number of The Information quotes [1] plus a bunch of original reporting and opinions.
The one two weeks ago had one such quote [2] and a bunch of original reporting.
I hadn't quoted The Information three months before, the last time I mentioned anything from that source was late April [3].
All linked issues are un-paywalled.
Point taken though on quoting from other publications and the perception a few such quotes can create in a paid publication, not to mention when these external quotes are how an issue starts. And especially when burying original or "exclusive" reporting from original sources.
I'm learning the ropes on this one as I go and will iterate on the format and the notion of "reporting on reporting".
I appreciate the links and sources, I’m not sure what OP’s problem is. I have a feeling they prefer opinion pieces, instead of insights into reported news.
There's unique authentic content and then there is expanding what is already known with a voice. Something that I refer to when I reflect on this is https://xkcd.com/1053/
Yep, after thinking about this and trying my hand at being the first "engineer" at a pre-product fit startup, I decided that this kind of thing is fine and even sensible advice for people who just want to run a successful business, any business at all, but just very much isn't for me. I like thinking about how to scale up software, not how to get more engagement. I'm just a better fit for more established companies that have a product with some amount of existing flywheel and need to keep it working, improve it, and expand it.
I think the advocacy for these content based businesses would honestly make more sense directed to people whose direct interest is in business and marketing who just need to learn how to do some simple "low code"ing to turn their ideas into businesses. I don't think most of us here got into the programming game to start blogging and book-writing businesses!
Edit to add: I do really like The Pragmatic Engineer by the way! I'm glad the author is interested in this kind of business, because I benefit from it. It just isn't the right sort of thing for me to work on. Different strokes for different folks.
Unfair. The blog post is pretty clear that it’s a recap on things learnt about entrepreneurship and not, as you label it a “startup”. It is most certainly not inviting its readers to embark upon that business pursuit. I think the advice is clear: go sell something, anything, on the side and you’ll be amazed what you learn. Now bring those learnings back into your actual business aspirations.
It's not surprising. Information products are often the easiest to produce, lowest risk-to-reward, and often valuable enough people will part with money just to see if you have some information they don't. It's sort of like FBA used to be when alibaba arbitrage was still new.
It's so, so, so much harder to start a SaaS product and get an MMR that covers minimum expenses. It has very little to do with talent, because SWEs are talented enough to make an app, but more about getting properly funded and often times how well you can get foreign developers to work for you so you can move quicker. Solo development still happens occasionally, but only rarely anymore. SaaS products have necessarily gotten even more complex and the "one man job" type niches are filled to the gills with failed projects.
Yeah this seems to be a common trend? It's easier to make money by capturing some small group of attention and getting them to pay you. In the best form of this you get interesting podcasts/writing that can be really great (Ben Thompson, Sam Harris, Bari Weiss, Yascha Mounk, Scott Alexander, etc.), but the more common form seems to just be mediocre content marketing, how-to, and self-help crap.
I'm the author of this article. Please note that 2020 should be added to the title, as I wrote it late 2020, after I left Uber and my plan back then was to start a startup some months later.
I had recently left Uber, and launched this e-book, and wrote this post with notes on what I thought might be useful skills as I go ahead with that startup.
Note that I did not go ahead with founding a startup, so most of this post should be taken as "skills I thought would have been useful if I launched a venture-funded startup."
I do think you can learn things better if you have some skin in the game. Specifically, learning about entrepreneurship can be easier if you start a small venture, even if on the side.
Also, as PragmaticPulp pointed out, the title is misleading given my advice is based on a book launch, not a startup. I changed the title on the original blog post to "Want to learn about entrepreneurship, as a software engineer? Sell something online."
This guy puts a LOT of effort in marketing. Much more than the typical software engineer is willing to do. Twitter, substack, blog, youtube, SEO content, ads, he does it all.
Of course you'll be successful if you spend years marketing yourself and learning all the tricks of the trade. What most engineers want, though, is to do well online while spending most hours on interesting software projects and putting in a minimal marketing effort. I'm happy for the guy, but I'm pretty sure most people here wouldn't be happy if we had to do his job.
I think there's something to be said for effort to outcome ratios being the limiting factor.
This is why making something you genuinely enjoy can be the best approach. Because the reward you get is the satisfaction of having done it and the money you make plays a much smaller role.
Some of the most successful people I know had the initial reaction of "oh this is getting too much attention I should stop" when their things initially became popular before leaning into the interest and making businesses out of them.
There's a reason common start up advice is "solve a problem that you have."
I've tried a few things that I genuinely enjoyed and I wish I haven't, they were also problems I personally had.
Now I think the best question to ask before building anything online is: "can I sell this to people?" If the answer is no or maybe, then consider it a hobby.
Unfortunately sales is not solved by building things I love.
This isn't the same thing. All of those things are part of the overall effort to engineer some kind of software artifact, which is what I enjoy doing. A meeting trying to come to consensus on an approach or to prioritize competing work or what process we should be using to avoid production issues or keep documentation up to date is not the same thing as running a twitter account or experimenting with different headlines or copy. Both kinds of work are very important, but the first kind is what I enjoy doing and the second kind feels like pulling teeth to me and that makes me bad at it.
That is a good point. That said there are many "non-tech" meetings you have to endure at organizations. However I concede that the amount of time for those is much less than the time spent on the marketing side of a business.
Yep, I won't work anywhere that doesn't have a good marketing department that I'm not involved in. Marketing is super important, usually more important than what I'm doing, but I'm not the right person to do it.
I think everything you're saying is exactly right. I think most developers wouldn't be happy doing what needed to be done to be successful (mostly the emphasis on marketing).
I never know what to think about these posts. As I've mentioned in other comments or posts around similar topics, I've had a successful eBook and still do. But when I'm asked for advice, I'm not really sure what to say. It just feels like dumb luck sometimes, honestly.
Certainly a combination! Here’s a study I think every child should be taught, where they created artificially compartmentalized worlds for new music. They found:
1) many songs had almost no downloads in any world. They were “truly bad“, and avoiding that is the skill
2) amongst the non-bad, different song is went viral in different worlds. That is the luck.
I wrote a Show HN post, then crossed my fingers... and with luck, the post ended up upvoted, and eventually on the front page of Hacker News.
I genuinely have no idea how that happens. Everything I've submitted falls immediately off the front page and gets zero comments.
At first I figured it's just because it was my blog (hello imposter syndrome), but I've also posted old classic articles from others that usually get a heap of comments, and they too got nowhere.
I'm guessing HN front page is either dumb luck, or requires some deep SEO voodoo that's beyond me.
> or requires some deep SEO voodoo that's beyond me.
Timing and somewhat clickbaity titles.
By timing I mean if the last item in /newest is like 30 min ago, don't bother, it'll go to the second page too fast to get traction. If it's like 2h ago, then post.
And by clickbaity titles I don't really mean "you won't believe what happens next" kind, but to use your submissions as an example, "You Can't Sit on the Sidelines and Become a Philosopher" is the only one I would click on. The other 10 didn't make me curious one bit.
Interesting - normally I never look at /newest, but after reading your comment I had a brief look. And apparently some users post 4-5 links in quick succession. At first I suspected they were bots, but apparently said users simply decided to post a few links today. Not the typical submission pattern I would have expected.
The other day I saw someone explain how they made a habit of posting interesting news they saw at the end of the day. I imagine that user might be doing something similar.
> as of this moment we even have stories with 3 votes in [the front page]. At the same time I've seen some stories go unnoticed with 9 votes in the "new" section.
I've submitted 11 things on HN. Three things were my content, three I'd seen posted here before that got a lot of comments but hadn't been posted for a while, and the rest were just random things of interest.
Had much more success submitting stuff to reddit. So I guess I'll stick to the comment section on HN :)
11 is not that much. Out of my 442 submissions, only 35 reached the front page and had significant activity (>= 20 points and >= 10 comments). That's an 8% chance of reaching the front page without optimizing anything (apart from the interestingness of the submissions themselves).
Looking through your submissions, all of those are such interesting topics. It’s a shame there isn’t time and space for all the interesting topics that must be being submitted all the time.
I wanted to hear more about the “is there a demand for this?” part, as choosing a suitable niche is one of the most important tasks before starting any kind of online venture.
Finding a middle ground between “what do I want to do” with “what people want” and “which specific niche still has some space available” is a tricky task.
One simply shouldn't even think about doing any real product work without pondering about and validating this choice, as a bad one can pretty much invalidate all the solid work done afterwards.
> Finding a middle ground between “what do I want to do” with “what people want” and “which specific niche still has some space available” is a tricky task.
… made even trickier when the hopeful founder is a self-admitted weirdo.
The itches I want to scratch are not the kind most people have.
Over the past decade+ I've been here I've read something akin to "Ideas are cheap. Execution is everything" over and over, but I have yet to come up with an idea that would have even modest appeal. Ideas don't seem cheap.
'1st time founders talk about product, 2cnd time founders talk about channel'.
If you go to the Drug Store and look at the variety of aisles, note that the products don't change much.
The channels to those spots on the shelf are locked down hard. New products into that space are usually by companies who control distribution.
What happens when a crack dealer shows up on the corner in someone else's turf? They get shot. Well, you're not going to just walk into some market without being a target.
Hence the dilemma.
Products that have natural breakthrough aspects already have a big advantage.
There are so, so many cool physical products that would exist but don't because channels are locked down by big players.
Also another note - the author's attempt at digital advertising seemed to be a big glib! Throwing $40 on Twitter won't get you much. Most of it has to do with the ad and the target market.
The author definitely has some natural marketing skills, due to their obvious ability to narrate a story and capture attention with this article I'd recommend he leverage that in some way, possibly with a YouTube ad of some kind to try things out.
I guess it is probably 1000 words a day on average. I don't know whether the book have plots, graphs and other illustrations.
It is fast writing, but doable. It requires knowing the subject in advance well--that's a given--consistency (starts and stops double the time, the longer one writes, the easier it becomes), and to copy and paste here and there paragraphs and articles that one has written and saved through their career--there are many "additional_material.txt" in my folders.
Thanks. The book ended up as 61,000 words - which is not that much compared to all-text books - but lots of pages of resume examples. A "normal" 200 page book could have up to double the number of words (100-120K words). Just want to add that detail, as a "normal" 200-page book in two months would be much more impressive.
I originally aimed for a ~40 page book - a PDF initially -, assumed it will have a few chapters at most. As I started writing and pulling in more advice from recruiters and hiring managers, the chapters added up.
In what is pretty usual for projects you do the first time, I under-estimated the scope, as well as the time it will take. My original budget for time was a month. Not too different from some software projects in a completely new domain :)
I joined a startup 7 years ago as the first employee to build an open-source distributed database and have been working as a chief engineer since then. I write a lot of code, but most of the time I'm actually doing something other than code:
I visit customers to show our product proposition and listen to their requirements, write articles online to introduce our product, participate in meetups to talk about the technical architecture, operate the community to attract contributors, talk to ISVs or other companies about product integration...
Many of them are not programming, but why I still have to do these? I think even we have a good enough product, if nobody knows about it, it is nothing. We must try our best to improve the awareness of our product.
By the way, doing these things also make me grow faster, become more focused and even better at programming. So if you are a Software Engineer, please have a try, this is another kind of fun :-)
Rob Walling's book, "Start Small, Stay Small" was full of great advice for exactly this demographic. Some of the advice is kind of dated at this point... what would people recommend these days? It's still probably worth a read, because some of the advice is fairly timeless.
It's nice to get a pretty good, well thought out set of advice in one place that you can easily scan, bookmark and refer back to. I don't find video very good for that.
I have an alternative for B2B that worked not too bad for me as a typical introvert sales-averse SE: working a few years in customer support, pre-sales and solution engineer, ideally all three at the same time (in B2B obv.). Then you’ll hopefully have a good grasp of the sales process, how to make a good demo, how is organized the typical medium big company, which will help both close deal and build relevant features by talking to the relevant persons.
Then by knowing both how to build software, how works a typical company and how to sell, I was ready when an opportunity showed up.
I got bit by this same "I want to run a business" bug in the past, but I've been much happier since I concluded that it's actually better for me personally to do engineering work on successful products that I believe in.
> If you're considering starting a company: sell something online first to get a better feel of all the other things you'll need to focus on top of building a product. This experience has only made me more excited about doing something from scratch
This article did not read to me as Tim Ferris for X. Nothing that couldn't be read elsewhere, but to me not blameworthy or anything.
Generically: Don't make your important product to get out there the first product you try to get out there. So business structure first, then important product or service.
Kinda confused. What ended up working in the long run in terms of their marketing? Am I wrong to think they left that out and only mentioned the success of their marketing for launch?
Is this an actual saying? It made me think of Twin Peaks (season 3) where one character runs a conspiracy, conservative radio show and sells golden shovels that his listeners proudly display.
> I wrote a Show HN post, then crossed my fingers... and with luck, the post ended up upvoted, and eventually on the front page of Hacker News.
Well it doesn't help when HN quietly shadow bans your posts. I have been a member of HN since 2013 and have barely submitted like 10 posts over this time. I only comment where I think I can contribute but recently I have realized that HN has shadow bans my posts.
Once I wrote a comment on HN about slippery slope of self hosting apps which I host and people seemed interested. So I decided to write a substack article about it and post it on HN. Guess what, HN shadow banned it because I am not supposed to submit stuff that I wrote but submit things I found on internet interesting.
Then recently I shared a reddit post on an Upwork scam and HN shadow banned it too. smh..
Is your first paragraph a quote or your own comment? I usually post a ">" in front of quotes from articles or other users.
I've seen posts I put up get lots of votes, go to the top position and stay there. I've also seen others go up, then drop off. It stands to reason if someone reports something for a site guidelines violation that it would weigh the article. However, I'm not sure that's how it really works.
You could reference Dang's comments about things like this for more insight. I wish we had the source code of HN to inspect, but then again it's written in a custom language, so I'm not sure I'd understand it!
Either way, this place is usually awesome and they do a good job policing it in a way that it has stayed awesome for a really long time. That's not to say some individuals here and there aren't burned by it. It's just letting go of it that is important. I don't think anyone here has time for long term grudges. If they did, they aren't worth the effort thinking about them.
This place isn't going to make or break you or your idea. The only thing that can do that is you! Good luck and I hope you do well with the writing!
sorry the editing got messed up, this is what I meant to write:
> I wrote a Show HN post, then crossed my fingers... and with luck, the post ended up upvoted, and eventually on the front page of Hacker News.
Well it doesn't help when HN quietly shadow bans your posts. I have been a member of HN since 2013 and have barely submitted like 10 posts over this time. I only comment where I think I can contribute but recently I have realized that HN has shadow bans my posts. Once I wrote a comment on HN about slippery slope of self hosting apps which I host and people seemed interested. So I decided to write a substack article about it and post it on HN. Guess what, HN shadow banned it because I am not supposed to submit stuff that I wrote but submit things I found on internet interesting.
Then recently I shared a reddit post on an Upwork scam and HN shadow banned it too. smh..
thanks for your comment. It's not about grudges but more about the anecdotal experience of the article. There are times when people would post how their post on Reddit helped them get their first sets of users but in recent time, even Reddit wont let you post your own stuff(self-promote) in majority of subreddits. So when there are road blocks like these, it becomes really hard to showcase your work you put so much effort into.
Title: "Want to Start a Startup, as a Software Engineer? Sell Something Online"
Post TLDR: it's hard to do it, but it's possible.
Takeaway message: "If you're considering starting a company: sell something online first to get a better feel of all the other things you'll need to focus on top of building a product."
Or to ask the reverse: in case of layoffs that are kept secret who is benefiting from secrecy:
the users/consumers, the employees, the investors, the founders?
However, it’s worth cautioning everyone to note how much his success revolves around newsletters, ebooks (as used as an example in this article), and the job boards that go along with his newsletter.
I generally like and appreciate Pragmatic Engineer content, but it needs to be taken with a grain of salt. The premise of this post is about starting a startup as a software engineer, but the example content is an information product (ebook) and the “startup” is just selling that ebook through content marketing. In fact this basically a cookie-cutter copy of the early 2000s self-help guru books where someone became successful selling books on how to become successful, but targeted at software engineers. This feels like someone read a Tim Ferriss book from the early 2000s and asked themselves how they could resell the same idea to software engineers.
The author does have some good resources explaining the internal processes at companies he has worked for (Uber), but lately a lot of his newsletter content is recycled from The Information and random Tweets. In fact, he had to retract a claim that he reported on recently because it turned out to be a completely untrue rumor that was circulating on Twitter, which he reported as a “scoop”. I suspect a lot of the quotes where he says “I interviewed an engineer at _____” might be just be sourced from random Tweets.
As with all content marketers selling advice, please take this all with a grain of salt. Some of the information is definitely accurate and actionable, but framing this ebook marketing story as “how to start a startup as a software engineer” is pure marketing spin.