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Tim O'Reilly: How I Failed (oreilly.com)
281 points by gruseom on Sept 16, 2013 | hide | past | favorite | 74 comments

I guess this is a recurring one:

I complained, but I eventually gave in. As we grew, it was harder and harder to maintain our informal processes. (I remember a real inflection point at about 50-60 employees, and another at about 100.) We gradually gave up our homegrown way of doing things, and accepted normal HR practices — vacation and sick days, regular reviews, annual salary adjustments — and bit by bit, I let the “HR professionals” take over the job of framing and managing the internal culture. That was a mistake.

The original process reminded me of Bryan Cantril's (bcantrill on Hacker News[1], creator of DTrace and VP of Engineering at Joyent) recent post on Leadership without Management: Scaling Organizations by Scaling Engineers[2], and of Yshan Wong's (former director of engineering at Facebook, and current CEO of Reddit) writtings on the topic[3].

[1] https://news.ycombinator.com/user?id=bcantrill

[2] https://news.ycombinator.com/item?id=6387649

[3] http://algeri-wong.com/yishan/engineering-management-process...

I wonder if there were companies that instead of growing as a single entity created early spin-offs to diversify aside without losing the core spirit. It's so common to see success become bloated and resist death by all commercial means necessary while newcomers bring something fresh to the table.

I've wondered for a long time if that's exactly why George Lucas intentionally created separate companies while he made all his movies (e.g. ILM, Lucasfilm, LucasArts, THX, Pixar). I wonder if there's either a good book that goes into detail about that, or if anyone on HN knows him close enough to ask him directly. :-)

It could be an implicit understanding of Dunbar's number - http://en.wikipedia.org/wiki/Dunbar's_number

Dunbar's number is interesting. His methods were not particularly scientific but his language was. It was a fairly formative paper for me when i was studying history of science.

I do think there is something in the number, but where it comes from is unclear.

I remember being told about some companies and government agencies built under 150, but never heard Dunbar's name. Thanks

You will probably find this book interesting:


There are a few other companies organized as "business cells", but Semco is relatively well-known.

Exactly! My favorite pop culture explanation of Dunbar's number is "What is the Monkeysphere?" by David Wong in Cracked.com (http://www.cracked.com/article_14990_what-monkeysphere.html)

In my humble experience, 50 employees is make or break for most companies. My theory is that it's because once you hit 50 people, you begin to get the "who's that" effect.

It reminds me of michaelochurch's posts on open allocation.

Well, for me, a consumer, O'Reilly failed in other regards.

1) It started producing mediocre books by the dozens. Gone are the days were the O'Reilly tomes (like the Perl books) were THE definitive books on a language.

2) It started promoting all sorts of half-though marketing/visionary crap (Thomas Friedman means Alvus Toffler style), on Open Source, Web 2.0 etc.

3) The Safari bookstore (which I was on and off subscriber over the years) had BS restrictions and a bad UI. I haven't even bothered to check if they provide a good tablet story nowadays.

Don't even get me started on the mediocre books. It's a shame, because there are still some very good books being produced with the O'Reilly name on them, but no longer can I trust them to be good because there's an animal on the cover.

The worst book I have bought in the past two years was O'Reilly's Building Node Applications with MongoDB and Backbone.

My quick, capsule review of that book: Piece of Shit. Bad example code, horrific continuity, next to no editing, it had everything needed to be lumped in with the crappy tech books. Ironically, the "Sam's Teach Yourself" Node.js book (which I had already gone through and was hoping to expand upon with the O'Reilly purchase) was vastly superior.

I wish I could get my money back, but I don't think Amazon does refunds for ebooks.

>Piece of Shit. Bad example code, horrific continuity, next to no editing, it had everything needed to be lumped in with the crappy tech books.

exactly the same can be said about their couchdb-book (first edition)

i have worse things to say about their "Data Source Handbook", the fact that they STILL sell it is unbelievable

but to be fair: the functionalJS book and DOM enlightenment (see http://domenlightenment.com) were quite decent. both books recommended.

While we're being fair, I'm currently working through the O'Reilly "Clojure Programming" book, and it is fantastic. The other Clojure books assume tons of Java knowledge, while this one takes a "coming from Ruby or Python" approach.

Yes, Clojure Programming is amazing.

I wish I could get my money back, but I don't think Amazon does refunds for ebooks.

There is a one-week window to return ebooks in the U.S.

1) I think the OSS landscape has simply changed. We used to have a handful of languages and frameworks with cryptic documentation, which O'Reilly books could coalesce in definitive bibles. Now you have new stuff coming out every day, github repositories all over the place, new tools, languages on top of languages... It's much harder to figure out what matters and what not. In that sense, O'Reilly is holding better than most other publishers, in what is probably a lost war (things will accelerate more and more, to the point where relevant point-in-time documentation will become impossible to produce in book format).

2) I agree on this. I wrote it down to the spirit of "American optimism" that us Europeans can find a bit distasteful, and sometimes it just seems too self-serving, fanning the flames of this or that technological phenomenon in order to sell more books. However, that's his job, and at least he tries to bring some open debate on the topics rather than leaving big players to come out with The Next Big Thing on their own.

3) All O'Reilly eBooks get automatically synchronised to your Dropbox folder in pdf, ePub and Mobi, which I think is a fantastic story for mobile (could do with better Kindle integration I guess, but Amazon holds the keys to that particular kingdom). I've never used Safari tbh, I'm not a fan of subscriptions.

What publishers do you recommend? I've been a real big fan of No Starch Press lately, though they don't have that many books yet. Syngress also isn't bad.

Manning[1], the Pragmatic Bookshelf[2], and Apress[3] have been the best in my experience. They cover relevant topics and technologies, the books are typically written by experts and written well, there are ebook versions of everything at reasonable-ish pricing, and sometimes you can get early access to books before their finished.

1: http://manning.com/ 2: http://pragprog.com/titles 3: http://www.apress.com/

I really like books from Manning publications. Their "in action" series are excellent.

If Syngress isn't bad then they've definitely improved. For a while they had some great security titles, but the mid/later half of the last decade they produced a lot of bad books. Terrible editing, repeating chapters used in different books, etc. I don't think Ive bought one of their titles in the last 4-5 year and I haven't regretted it.

It's really alien to me to judge a book based on its publisher. Whenever I need a book I check out reviews on Amazon or on programming sites to find the best in class. Is there a reason that it matters that I'm not thinking of?

It mattered a lot before. If you had no online reviews to go by, going into a book store and picking up an O'Reilly book was a reasonably good bet.

It doesn't matter so much now, and it also only worked because O'Reilly was a small publisher who had the benefit of being able to be really picky about authors and subjects. It doesn't scale when you want to get a large number of books out on subjects where you may have very little choice in authors. How many people are qualified to write a book about [insert random 5 months old javascript library of the week]? Often it might be a handful of people, several of whom won't be interested and/or are bad writers.

"failure #4: tolerating mediocrity" gives me hope for the future of the animal books. i never understood why tim tolerated books - in the quality range from mediocre to bad to scam (i.e.: http://goo.gl/XrZs3c) - which only sold because his name is on the cover, thus hurting his reputation and nullifying all his "... create more value than you can capture" talks. but well, if this essay is not only marketing (it certainly sounds a little bit like it) then there might still be some hope for the animal books. i own these books my career so i certainly hope they can turn this around.

In the 1990s every O'Reilly book (except for the extremely think ones like Sendmail or Unix Power Tools) used the awesome "RepKover" lay-flat binding which was later done away with. Guess that was a result of the "financial discipline" dogma. :-(

Nice to read a real veterans perspective rather than the usual "What I learnt since I started my business last Thursday". Tim admits what he got wrong but you know that he got so much right and built a sustainable business. Most of us have favourite O'Reilly book.

I was thinking the same thing. His hard earned thoughts carry much more wisdom than, "We should have followed the lean principles that we ignored. Whoops!"

agreed. HN often has too many "yet more oh-so-wise life advice from 20-something white male programmers living in an US city in 2013"-type articles.

Double-agreed: "20-something white male programmers" with great paid-for education and early access to capital...

If Tim reads this:

Tim, you didn't fail. The industry has failed. For the past few-to-several years, books on technology have been obsolete by the time they are written- not just published, so you can't make money off of selling even digital copies of books. Developers read about the latest technology in project readme's (markdown formatted in GitHub), a wiki, one or more blogs, StackOverflow, and so on.

What else could your company do to stay relevant? I really have no idea. Posts on your site that come up in Google are often outdated, so O'Reilly to me is at most a place where developers that want to give talks and lectures can publish a book, which probably won't sell much. Maybe it will boost their resume or help them get more contract work? I really have no idea why people give talks and write books anymore. It seems like a waste of time that could be spent developing. Developing good code makes you relevant now.

I just feel sorry for the whole situation. I would have hoped will all of the publishing money from the 1990's and early 2000's, you'd own your own island, where you'd be on the beach drinking Coronas. But instead, the company has apparently tanked. That sucks. I liked the animal-covered books.

Good observation but I disagree, to some extent. Technical books that teach low-level knowledge and technologies will always become obsolete quickly. But books that enable the reader to understand deep concepts rather than shallow technologies have a much longer half-life. This is similar to the complaint that engineering school is always "behind the technology curve" which is nonsense. You don't go to school to learn technology, instead, you learn the basis underlying it. This latter knowledge changes much more slowly. A good technical book should aim to teach the same.

Relevant abstruse goose comic. http://abstrusegoose.com/531

Indeed. When do you think SQL and Relational Theory will be outdated? And, do you think you can learn that from a wiki or a blog?

Even deeper, something like regular expressions, how do they work?

Or shallower (sort of?) you can't sell a cookbook of "whats the regular expression in perl to match the first word of a sentance" because we have google for that, but you can sell a style guide type book like "Modern Perl" where you probably could google everything in that book, but it would take 1000 different searches and not have a common voice.

His company hasn't tanked. I think you might have skipped the part about how they've in recent years have put tens of millions in the bank. They are making more money now than what they did when the book publishing market peaked around 2000.

The article is not about the failure of his company, but about what mistakes he think he made along the way.

This essay left me unfulfilled, and I'm not sure why.

I was leery of taking so much time reading it. Most times when people write essays about "How I failed" they're full of self-promotional bullshit, the end of which is usually something like "I was just too awesome", or "We tried too hard" or some other pointless throwaway.

Here there's a fair bit of patting himself on the back, but Tim is honestly trying to get somewhere. Where, I don't know. In parts it reads like he's finally figured out that he was way too loosey-goosey with feel-good ideas that he wasn't ready to fight for. In other parts it feels like he's compelled to make lists of people or groups he should have treated with more attention.

In short, it needs an editor. I'm plowing through 3000 words where a better structure could probably cut that in half. Is there a thesis? Or is this just a mashup? I'm betting on the latter, but I'm still not sure.

I love the ideas Tim espouses but not because they make me feel all warm and fuzzy. I get the feeling this is his criteria. I love the ideas because they work, they have functional and financial value. Not sticking with them would be like not paying the electric bill because it was inconvenient.

I liked the essay and voted it up on HN. But I can't recommend it. It's rambling, it's honest, and it's missing the kind of structural and cognitive analysis that could have turned a thoughtful recollection into something more consumable and immediately usable. Sorry to be so negative. It just hit a weird spot with me where I know there's something really good in there, but I don't believe the author hasn't done the work of teasing it out for himself, much less the rest of us.

> In short, it needs an editor. I'm plowing through 3000 words where a better structure could probably cut that in half.

Ah yes, like an O'Reilly book...

Good luck with that. I worked in the editorial department and most of the copy edits were outsourced. There's a house style guide that's loosely followed at best, and other than that, this is what potential authors get for direction: http://oreilly.com/oreilly/author/intro.csp

That page hasn't changed or really been updated in a few years. Sigh. Moved on to greener pastures...

I wonder what happened inside. Did Tim know?

I met him once in person, but never heard him talk about the editorial process. We went through an office reno in my time there that eliminated cubicles and most offices and created a one-room "collaborative" workspace--for people who all worked with headphones on. I see what was intended, but without more editorial structure (i.e., distinct acquisition, development, and production levels with accompanying procedures and staff), the book-producing process--and accountability for missteps--was a blur. A distinct contrast was O'Reilly's contract with Microsoft Press: Those books received special handling as opposed to O'Reilly-branded titles, and MS provided massive amounts of documentation for editors to use, as opposed to the O'Reilly mantra of "preserve the author's voice." It was, at best, a confusing place to work for someone with a background in traditional book publishing.

> We started Safari Books Online as a joint venture with our biggest competitor ...

If you do not know about Safari Books Online [1], do yourself a favor and check it out! You pay a smallish monthly fee, and get access to digitized books. Want to learn about XZY tech, just head over to Safari Books Online and read the latest and greatest books, pick the chapters you want, and move on. Most university libraries will have access agreements, so this will most likely be free, or ask your company about a corporate membership!

I am not affiliated with them, just a very happy customer. This is the perfect use case for me, since I typically will read tech books only once, never looking at them again, and just google from that point on.

[1] http://www.safaribooksonline.com/

Many schools (I go to a tiny tech school in Hoboken, NJ) offer subscriptions to their students. There's some pretty neat titles on there. Be sure to check if you're a college student.

The problem is, they're not putting out the best books anymore, and I find myself going there less and less. Right now, I think I'd rather have access to Manning's titles, even though there aren't nearly as many.

There's something that just... isn't there anymore with most of the oreilly books.

Just checked and I see 173 Manning titles listed on Safari Books Online right now.

I should say manning's MEAP program, of which I have been buying a few recently and don't believe make it to safari.

I have the lowest priced account on this, and I probably don't use it all that much, but it's useful (especially when you're in support) as a kind of insurance policy for those times when someone goes, "One of these has stopped working - fix it", and your first thought is to reply, "What the hell is one of those?", and your second thought is, "I'd better find a book on whatever the hell one of those is."

As much as he's done great things, there's a bit of "O'Reilly promotes neoliberalism and business as the only answer," the kind of thing that should ideally go away at some point in free/open/participatory society.

c.f. O'Reilly as "The Meme Hustler" (in the words of Evgeny Morozov): http://www.thebaffler.com/past/the_meme_hustler

Jaron Lanier makes the case a bit better.

I'm not sure Lanier goes after O'Reilly as strongly and directly.

Morozov's article is a complete roast of O'Reilly. Though certainly entertaining in style, the real gem of the The Meme Hustler is Morozov's basic theory of PR: Those who control the "discourse" (the words and phrases used to describe and name new phenomena in books, magazines, blogs, newspapers) have incredible influence across industries — especially when there's little opposition. As a niche publisher in the esoteric (but simultaneously important) field of bits and bytes, O'Reilly has capitalized on this and has faced little criticism from other industries.

Politicians and Fortune 500 CEO's face pushback to their BS all the time, sometimes initially led by Critical Studies departments. This Baffler article was one of the the few times I've seen a technologist explicitly called on his ideology (beyond the profit motive).

I suspect Mr. O'Reilly wasn't too pleased about it.

Perhaps in such a society, the case against that proposition would just need to be made in more convincing fashion?

Like the teaser ads leading up to a reality TV show's new season, this confessional "tell all" is probably part of the promotional rollout of O'Reilly's new conference series: http://cultivatecon.com/cultivate2013

This is a well-written and articulated article. It is as much a teaser ad as picking 3 chapters out of 15 of a consistently good book and making them available for free. I mean that, even if making them available for free is part of the promotional plan, writing them was genuinely done for the content.

Edit: Another way to look at it: Don't you get value out of it by reading it even if you don't attend the conference ?

I've got about 84" of my office shelves devoted to O'Reilly books and while Tim may be able to see failure in hindsight, the only thing I want to convey to him is my thanks ... I wish my failure was so grand.

O'Reilly strikes me as the company that could "disrupt" the dreaded academic publishing industry.

They have solid experience in classic publishing and online publishing and a culture rooted in openness. They also have the brand to attract enough peer reviewers and the like.

And they know how to "fill the gas tank" via conferences if they want to go that route so maybe they should just prototype a couple of academic conferences and see how it goes.

They write some great ads over there at O'Reilly.

Failure #7: The Founder needs to STFU:

Your customers at the end of the day define your business, because they spend the money that enables you to continue. While you believe you have great thoughts, as a commercial entity you do not have the luxury of such things because the market speaks louder than your own ego.

I like Tim, a lot, but at the end of the day he vainly spoke as O'Reilly media and not as Tim (a guy who has some smart things to say but is independent from a company) and that has an impact. If Gates spoke as MS HMFIC about vaccinations he would get roasted in the market, but Tim never divorced himself from the company and thus made the company suffer for his own personal conceits. If you're a sole propietorship then you can afford such luxury, but Tim had a larger vision for the company yet confused himself with that vision.

"The Founder needs to STFU: Your customers at the end of the day define your business, because they spend the money that enables you to continue. While you believe you have great thoughts, as a commercial entity you do not have the luxury of such things because the market speaks louder than your own ego."

You have someone that understands the market way better than you do, as his extensive track record supports.

Who are you to talk to him like this? I mean the insulting part "Shut the fuck up".

I admire this person because I have a company and I know how incredibly hard is to do what this man has done, he is talking about the real problems that real companies have. You talk about luxuries as if what this person has was given to him in a silver plate.

"Tim never divorced himself from the company and thus made the company suffer for his own personal conceits"

When you have a company your company always suffers from your personal conceits, whenever you realize it or not. For example if you made a company your beliefs about "what the market wants" will be as subjective as Tim's, only that probably Tim's will be better adjusted to reality, because he has proven that he is good at it and you don't.

Everybody believes to be more objective in his decisions that others, like everybody believes to be more intelligent than everybody else. It is very easy to see the straw in someone else's eye.

What is your point? That nobody is perfect?

I have "UNIX in a Nutshell" and "Essential System Administration" (the better 1st and 2nd Editions, not the 3rd which was ..eh) to thank for my career.

What disappointed you about the third edition? I don't know the previous ones. I imagine they were probably more concise?

This is a really nice, reflective post that represents a lifetime of lessons. I'd encourage people to read it carefully.

Tim O'Reilly changed the trajectory of my life and probably countless others how self-taught themselves using the famous O'Reilly books into a job or often much more.

> Financial discipline matters. It really matters.

oh god yes. money is like a blind spot to me - but this line speaks to me best in a whole article that reeks of good advice.

thanks Mr Oreilly.

Money likes to flow. It feels "good" to let money flow. Using discipline is at odds with almost every natural instinct that most people have. When a windfall heads your way it is easy to think it is endless. Treating them with respect is probably the best business lesson an entrepreneur can learn.

That's the part that stood out for me. O'Reilly Media has highly profitable conferences and every new book adds to a backlist. It should not have cash flow problems, and, properly run, it doesn't.

That must have kept Tim from taking on the HR challenge and other lesser problems on his list.

I only get advances on delivery of milestones. I sure that was a key reform, based on what he wrote regarding late and un-delivered books.

It's encouraging to read this having read Stephen Few's blog post "O’Reilly Media Has Lost Its Soul"[1] earlier this year about his troubles publishing Information Dashboard Design through O’Reilly Media and choosing to publish the second edition without them and how difficult they made it.

[1] http://www.perceptualedge.com/blog/?p=1521

This, considering that he succeeded so wildly - not just in building a successful business, but in making the culture of the software industry so much better.

For me, as a perpetual employee that would love to run his own business one day (and is working towards that), this is quite an insight, but I'll bet it's hard to do it another way:


The only raises we had were merit raises, as you improved your skills and impact. You were expected to manage your own time, with no set hours, and the only responsibility around vacation time was to make sure that no balls got dropped.

Eventually, I hired an employment lawyer to review my draft, and he said, “That’s the most inspiring employee manual I’ve ever read, but I can’t let you use it.”

I complained, but I eventually gave in. As we grew, it was harder and harder to maintain our informal processes. (I remember a real inflection point at about 50-60 employees, and another at about 100.) We gradually gave up our homegrown way of doing things, and accepted normal HR practices — vacation and sick days, regular reviews, annual salary adjustments — and bit by bit, I let the “HR professionals” take over the job of framing and managing the internal culture. That was a mistake.


Failure #4: Tolerating mediocrity

We ended up building a culture where managers too often compensated for the failings of employees by working around them, either working harder themselves, hiring someone else to fill in the gaps, or just letting the organization be less effective.

As an employee, observing these indicators should probably push you to change to a better situation.

Michael Lewis talks about how students used Liar's Poker as a how-to guide in the preface to The Big Short. (Both are excellent books; he's a talented writer.)

I think StackOverflow is probably the true "spiritual" successor to O'Reilly (especially the animal books).

SO : O'Reilly :: web : print

I see not many here are commenting on the Treat your financial team as co-founders.

Or, "We even discovered several cases of fraud! That goes back to my point above about the importance of a crack financial team — one of their key jobs is to have strong controls in place."

Yeah, it is very sad this and also my and your comment got no feedback at all. My opinion is skewed, because I work in controlling, but most of these guys are sometimes so focused on "growth" and other myths that they forget to build an actual business.

"I complained, but I eventually gave in. As we grew, it was harder and harder to maintain our informal processes. (I remember a real inflection point at about 50-60 employees, and another at about 100.) We gradually gave up our homegrown way of doing things, and accepted normal HR practices — vacation and sick days, regular reviews, annual salary adjustments — and bit by bit, I let the “HR professionals” take over the job of framing and managing the internal culture. That was a mistake."

I worry about this with my own "company". I have two different projects right now, one that brings in money and I'm starting to add people to, one that has a couple of people and might soon bring in money. I see them separate only in so much as the people of the second one aren't interested in the work of the first one at this time. There will be opportunities in the future to merge the two.

I started working for myself because I hated working in modern office culture. I was always interested in being more than just a code-monkey. I wanted to understand the business and work practically and efficiently to create good value for our clients. I saw that a lot of programmers where architecture astronauts and a lot of project managers were unchecked salesmen and I thought I could be the best of both worlds by being honest with both the customer and myself about what could and couldn't be done. I didn't want to delay releases just because I was more interested in scratching an intellectual itch than getting the work done. But I also didn't want to over-promise on deliverables knowing that it would lead to an even bigger argument in a month's time when we didn't get 6 months worth of programming done.

And I got sick and tired of my health issues, fundamentally created by my overly demanding employers, being treated like they were a personal problem that I shouldn't bother them with. I'm sorry, you keep me in the office overnight, I'm not coming in on time the next day. It's not "unprofessional" for me to fall asleep in a meeting in which I'm not even expected to participate the day after you dumped last-minute changes on me, changes I know you kept to yourself because I overheard you on the phone talking about it and how you knew it would be easier to convince me to stay if the situation seemed dire. The chemical depression I experienced as a result of the poor nutrition, lack of sleep, and lack of sunlight you imposed on me through feeding me at my desk and holding my job over my head was fundamentally your fault, as was the resulting complete lack of productivity. You can't work someone 100 hours one week and expect them to be as fresh as a daisy the next.

Ahem, sorry, got lost there for a minute.

The last thing I want to do is be responsible for creating a business that becomes the very thing I despise. But I won't be able to oversee everything. I'm going to have to hire people who will be responsible for hiring more people. The fundamental structure of the company will have to be built on the understanding that treating employees with respect is not just a phrase for the promotional material.

The problem is that it's a whole litany of problems. You can't just focus on the vacation time or core hours or snacks and games in the break room. Frankly, even when I was in my early 20s I didn't care for snacks and games at work. I wanted to work at work and play at home. It's hiring practices, it's how you communicate with your customers, it's how you organize work, it's who you hire for work, it's the sort of work you do, it's 100% of everything that a company does, and if any one part of it is out of whack it's going to corrupt it all.

In O'Reilly's example of his "Rules of Thumb" manual, he hired the wrong lawyer, a lawyer that was only interested in viewing the problem through the lens of common corporate lawyering. He needed a lawyer that was just as devoted to recreating the work place as he was and understood that it was his (the lawyer's) job to protect that environment, not completely destroy it just because it wasn't easy to protect it.

And it scares the shit out of me. How many of my former employers started their own companies because they hated working for their own former employers? How do I avoid being ultimately responsible for someone's terrible work-life balance?

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