Hacker News new | past | comments | ask | show | jobs | submit login
Ask HN: Best resources for non-technical founders to understand hacker mindset?
115 points by jamiecollinson on May 15, 2020 | hide | past | favorite | 105 comments
Background: technical founder wondering what reading to recommend to a business focused founder for them to grok the hacker mindset. I've thought perhaps Mythical Man Month and How To Become A Hacker (Eric Raymond essay) but not sure they're quite right.

Any suggestions?

(In case it helps an analogue in the mathematical world might be A Mathematician's Apology or Gödel, Escher, Bach.)

I have to admit, even I'm not sure what a "hacker mindset" is. As one technical cofounder to another, I think the most important thing is for you to understand the business side. Most importantly, how interpersonal skills matter and how emotions play out in a business setting.

Beyond that, a solid understanding of scientific approaches to understanding is the second most important. Being able to tease apart correlation and causation, and being rigorous about what you accept as real knowledge vs mere opinion or anecdote. The business world, and the tech world, has a lot of "opinion" that masquerades as fact. E.g. "well I did X and I'm successful so clearly X must work!"

> As one technical cofounder to another, I think the most important thing is for you to understand the business side.

But the OP isn't asking for help themselves, and has said nothing about needing help themselves. Maybe they already understand the business side?

Well, it could be a case of "My wife gets upset when I cheat on her. How can I make her understand that it's not a big deal?".

I am not saying that it is but I do think that Stephen Coveys famous "seek first to understand, then to be understood" quote holds a lot of truth. In order to communicate your own perspective on something to someone, you need to have a sense of how theirs differs to yours.

Sure, but then... what's the second step? Because that's what the OP was asking for here.

IMHO it's kind of against the Principle of Charity to assume that someone asking a question about how to do part N of a multi-part process, hasn't already figured out how to do the previous N-1 parts of that process. They must have, to get to the point where they're motivated enough to reach out for help with part N.

In programming terms: if I'm writing a compiler, and I'm asking about codegen, the Principle of Charity would suggest that I've already solved enough other compiler-writing problems that I have an input to feed to a codegen pass!

Ignoring the Principle of Charity in cases like this can lead to some really useless/unproductive advice.

For example, I've been writing a research decompiler for an ISA that has less embedded information than usual (e.g. no reified CALL/RET ops, just plain branch instructions.) It needs some weird heuristics to derive subroutines from coroutines, and to properly scope variables. This means that I can't immediately derive an interprocedural SSA form for the variables, in order to help calculate a dominator tree. So I want to ask people how to calculate a dominator tree from stack variables, because having something like that would help as an input into those heuristics.

But every "solution" on StackOverflow-like sites insists that the context of the problem—the assumptions it makes—are impossible/invalid. They try to mentally rewind to step 1 themselves, and then can't understand how I solved it (because I didn't write out the textbook worth of novel algorithms I used to solve step 1 in the problem description), so they don't even believe there is a step 2. Rather than just... attempting to help me with step 2. Which doesn't actually require any understanding of step 1, other than its outputs.

It's sort of the opposite of the XY problem. Rather than the parent problem X being best solved through a different strategy that avoids problem Y, people believe that the parent problem X itself is unreasonable, because they model an X that is solved through Y as requiring that the solution also flow through a previous sub-problem Z; and they think that Z is something that people just don't bother to do, so nobody could actually be asking in good faith about XY.

I've also suffered through this with doctors, who literally won't believe me when I list off the entire sequence of steps they would try and say that I've tried them to no avail. I only go to the doctor when I run out of ways to try to solve the problem myself, so if I'm here, it's because the problem is a zebra instead of a horse! A horse, I would have fixed on my own!

> As one technical cofounder to another, I think the most important thing is for you to understand the business side.

Totally on-the-point advice! The mind of a business-mate is often less ranged and logical than a techy-mate would prefer. So could be your biz patner's way of understanding and discovering what makes a techy mind tick.

If this is to improve understanding between you two, the best way is to agree on zones of responsibility and what it takes to come to trust in result. The hardest for biz folks is to relinquish control, while hardcore tech guys don't like to compromise. Somehow these need to balance.

> Beyond that, a solid understanding of scientific approaches to understanding is the second most important.

Are there any good resources for learning more about this?

any ABET-accredited engineering curriculum ought to do.

Sorry for the delayed reply. I actually graduated from an ABET-accredited engineering program. I was looking for something more along the lines of "learning how to learn".

For example, a scientific analysis attempting to break down what "understanding" is, or evidence-based techniques for gaining understanding more quickly.

"well I did X and I'm successful so clearly X must work!"

If they did something...and that thing was successful then by definition that thing they did...it works, right?

The broken thought-process there is mostly about when you take a shotgun approach that involves many different things that could all individually pan out (or not); or which could all be multipliers for one-another (or not.) If, in the end, you succeed, you end up believing that everything you tried was a necessary part of your success. When, in actuality, you might have succeeded despite some of those approaches, rather than because of them. They might have been actively harmful to your success, but just not harmful enough to overcome the other successful things you tried.

In another instance, people who try one main thing (e.g. applying to a particular college) but who succeed entirely through no effort of their own (e.g. through nepotism), will end up thinking that what they did mattered.

"The broken thought-process there is mostly about when you take a shotgun approach that involves many different things..."

This sounds like quite the qualifier...which is fine, but I think it's important to take your response/reasoning into a much more narrow hypothetical.

I mean, we're talking about advice for running a startup here—an entrepreneur would be an idiot to not do everything possible to give themselves multiple independent avenues to success (e.g. do multiple forms of inbound advertising; attempt product-market fit with multiple markets; etc.)

I've worn a tiger-warding talisman around my neck for years, and so far I haven't been attacked by a tiger.

Is it fair of me to assume that this talisman works, and that I can safely climb into a tiger enclosure?

I would think unless and until you have tested that hypothesis (wearing of the talisman in a tiger rich environment) it's an invalid conclusion.

Now if you have successfully avoided tiger enclosures and subsequently not been attacked by any tigers, (regardless of what you are wearing) that method probably works ;)

No, it could have worked for a reason independent of the thing.

It certainly worked for them. But results are not typically indicative of risk, so anyone doing X may doom themselves by doing something that doesn't work in their special context.

Do you know of any resources (books preferably) on learning to understand the business and emotional side that you are referring to?

“The Innovator’s Prescription” (Clay Christensen) explains the Innovator’s Dilemma better than the original book and introduces jobs-to-be-done with the milkshake story.

“Creativity Inc.” (Ed Catmull) explains how Pixar manages people & throws in a few insights from mature (post Apple firing) Steve Jobs.

“Managing the Design Factory” (Don Reinertsen) explains how to prioritize projects and analyze a business for bottlenecks in order to minimize cost of delay.

Thank you. I am already reading Creativity Inc. at the moment and I am greatly enjoying it. I will check out the others as well.

Maciej Ceglowski has a good bit in one of his idlewords posts about how the "what makes hackers tick" genre is full of pieces that are really "how to be someone just like the author". There's probably nobody that remark applies to more than ESR, and ESR is probably not someone you'd want to work to resemble more closely.

So, in reality, if you want to understand your technical cofounders, it is probably not a good idea to take ESR seriously when he says that you should find a "real" Unix (your technical cofounders are, actuarially speaking, almost certainly macOS people), hand-write lots of HTML, or "serve" th "tribal elders of open source". And the idea that "attitude is not a substitute for competence" among hackers is both funny on a variety of levels, and also a singularly bad note for understanding software developers you work with.

The Mythical Mammoth doesn't have any of these problems, and is a great book, and one worth reading simply so you can have a sense of what building software actually entails (Dynamics of Software Development is another older book that has aged somewhat well --- as have all of Joel Spolsky's posts on Joel on Software; in fact, I'd probably start there). But while this stuff will help you understand the work that's happening on your team, it probably won't do much to help you with the mindset of your team members.

There probably isn't a substitute for just talking to your cofounders, a lot, and asking lots of questions.

Mythical Mammoth is a delightful correction.

I had to wiki ESR, I'd needed to remind myself who he was.

And, tptacek, guess whose name I stumbled upon while I was reading his wiki page? Incidentally, I think that section of the wiki is poorly written. I'm left even more confused due to lack of context.

I agree; obviously, I didn't write it. Feel free to delete it.

A few tips:

Lots of hackers are introverts. They are wired differently from founders and ceos (who have gravitated towards a life full of constant interactions with people). Hackers don't mind being "in the zone" for hours at a time to work on a problem. Sometimes this means coding, but sometimes this just means having enough quiet time to just sit an think while they turn a problem over in their mind. This is required.

Another side to the introvert thing -- I believe "open plan seating" is a fundamental disconnect between extroverted decision-makers and introverted knowledge workers. It is not surprising to me that productivity has skyrocketed for problem-solvers working from home.

Another tip is to ask "what do you think?" then listen. Then wait even longer and listen some more. The absolute best business people I've worked with were masters of this. The worst would already have made decisions and questions were just checkboxes.

(this works everywhere in life, but is particularly relevant to the really smart people at the top of the tech tree)

also, hacker doesn't mean criminals who break into computers. Go with the original meaning (well, the one after carriage driver)



> It is not surprising to me that productivity has skyrocketed for problem-solvers working from home.

Do you have a source with data to back that up? The early indicators of the efficacy of WFH that I've seen have been pretty mixed.

Hmmm... I don't have proof, just anecdotal. And of course, everyone who likes working from home will mention that their productivity is up (self-selection).

One of the most important is the Managers vs Makers schedule: http://www.paulgraham.com/makersschedule.html

I'd also recommend Peopleware

Let me sum up all possible books about understanding the "hacker" (terrible word by the way, because of multiple meanings, which meaning are we talking about?) mindset, to a management perspective:

1) True "hackers" value knowledge over money.

2) True "hackers" value doing things once and doing them right, no matter how long that takes. (Compare to the business mindset of "we need it now", or "we needed it yesterday")

3) True "hackers" value taking ownership in their work, that is, whatever they work on becomes an extension of themselves, much like an artist working on a work of art.

4) True "hackers" are not about work-arounds. If/when work-arounds are used, it's because there there's an artificial timeframe (as might be found in the corporate world), and there's a lack of understanding in the infrastructure which created the need for that work-around.

But, all of these virtues run counter to the demands of business, which constantly wants more things done faster, cheaper, with more features, more complexity, less testing, and doesn't want to worry about problems that may be caused by all of those things in the future (less accountability) -- as long as customer revenue can be collected today.

You see, a true "hacker's" values -- are completely different than those of big business...

And business people wonder why there's stress and burnout among tech people...

I’m not a hacker if I’d rather hack together something quickly, even if it’s a bit hacky? That would seem to violate your #2 rule for “true” “hackers”. Or if I like hacking my way through a problem instead of doing it the expected way? That would seem to violate #4.

And I’m not a “true” “hacker” if I want to make money?

I thought I was a hacker. But if this is what hackers are, I’m pretty ok with being voted off the island.

You're still a hacker. The parent comment is conflating engineers (by which I mean, like the kind of people who design bridges and critical infrastructure - not just the title given to anyone who can code) with hackers. Think of it this way. Almost all engineers are hackers, but the majority of hackers are not engineers.

Tons of hackers don't give a flying fuck about the "right way" to do something. Hackers are just the people who decide to apply their personal agency and creative talents towards building, altering, breaking and fixing things. There is no unifying motivation for doing so (though admittedly, curiosity is more common than money as a motivator), nor any standardized way of engaging in the process.

I pretty wholeheartedly agree with your 2nd paragraph.

Regarding your first, I have similar concerns about this gatekeeping of “engineers”. Civil engineers and the like have much more stringent regulations and much more weight put onto correctness, but they aren’t required to prize correctness-for-its-own-sake, or think of their work like art, or be doing the work for its own sake rather than money.

I’m pretty confident that attempting to ascribe a unified motive to any group is a mistake.

> 3) True "hackers" value taking ownership in their work, that is, whatever they work on becomes an extension of themselves, much like an artist working on a work of art

There's something to be said about owning your work, but I have to disagree that unhealthy attachment to work products is a universal attribute of technical founder hackers. It's not a kid, it's a thing that was supposed to be the best use of the resources and information available at the time.

I must have confused this point with vanity and retention in projecting my own counterproductive anti-patterns.

Prolific is not the objective for a true hacker, but not me but a guy I know mentioned something about starting projects and seeing the next 5 years of potentially happily working on that project, too.

I don't think there is a hacker mindset. We don't all have the same experiences or motivations for why we build, tinker, break, and fix. We just all happen to do that stuff. Some of the most impressive "hackers" I've ever met were old HAM radio enthusiasts with thick country accents who live in the middle of nowhere. Those folks have almost nothing in common with the extremely educated liberal developers in SF. But both groups collect knowledge and apply it in the real world in creative ways.

So being a hacker is a practice, and in some cases it's a lifestyle (when you orient your life around hacking). But it's not a mindset. Some folks are compulsive hackers, some are methodical, some are opportunistic, others are hackers out of necessity - but they're all united by what they do, not how they think.

> But both groups collect knowledge and apply it in the real world in creative ways.

so maybe use your hacker mindset to deduce this is the mindset then?

Well there are patterns in behavior, but I don't think it's enough to qualify as a singular mindset (with mindset defined as "the established set of attitudes held by someone.") Plus, the piece you quoted could just as easily be used to describe artists.

If I had to define hacker attitudes, I wouldn't use information collection and application as the standard. Some people carefully select subjects study them in depth, and others just passively pick up information through exposure to experts, and others collect knowledge as a by-product of trying random stuff and failing at it. Hackers (and non-hackers) don't necessarily need to prefer one method to the other. And everyone, even non-hackers collect information - so that's not in itself a special attitude of hackers. The application part is more unique, but how is that different from what artists do?

If I had to choose particular attitudes that would enable someone to practice as a hacker, it would be:

- high tolerance for failure and unexepected behaviors, or even joy in failure under certain circumstances.

- Gains pleasure from novelty (learning new things, having new experiences, finding new applications of things). As a result, most hacker types place more value on things that are obviously flawed, but novel and unique vs things which are perfectly executed but familiar.

I think that second point differentiates hackers from at least some artists (ie, Chefs usually prefer to stick to establish culinary pattersn, musicians playing in a symphony find beauty in the same piece that has been played for hundreds of years). Other experimental artists who do seek novelty (noise music, etc) are basically hackers IMO.

Edit: but to my original point, if you have neither of the attitudes I identified, but do hacker stuff anyhow - you're still a hacker. Those attitude patterns don't take precedence over the actual reality of hacking. There just common in people who continue to do it over their lifetime.

I'm with the people asking "why."

There is almost no real reason for a business side founder to "grok" a hacker mindset. If hackers/developers are the business' customer, then the business owner just needs to find ones to talk to.

Forgive the directness but what I hear in the way the question above is framed is that there is actually some communication misalignment between the tech founder- who considers himself to have a "hacker mindset"- and the business founder, and the "hacker mindset" is a crutch the tech founder is using to protect against some fear or concern being probed by the business founder.

If that is the case, the solution is to drop the defensiveness and just talk about it, not point to some resource as though it is an authority that business people have to worship offering tenets for them to adhere to. A new business only has a chance to succeed if the founders succeed in building a relationship that permits each other to fail and recover, and where they grok each others' mindsets, not some caricature that Eric Raymond made up.

Happy to be completely wrong.


I don't think I agree with this. I think what the poster is looking for is how to help the more businessy founder understand the engineers that (s)he's necessarily going to be hiring and working with. That strikes me as a perfectly sensible and worthwhile goal and one that will probably help their start up have a healthy culture in its early months/years.

Yeah, could be, but if that were the problem, my guess is that the question would be different. How do I help my business founder understand what to look for and value when hiring, etc.

The issue is that OP question is an answer to the real question, which goes unasked.


How do you even define a 'hacker mindset' anyway. It seems too hard to really pin down a definition so I'm not sure it's worth the time anyway.

The word "hacker" has been re-purposed so many times.

IMO hacker culture includes but is not limited to computer engineering and science. It is about being so curious about a domain of knowledge that you end up learning it in its little details, and as result, you can bend that domain to your will. Hackers are often working on experimental stuff that have little to no commercial value but are still valuable in their own way. You can read a bit about computer hacker culture in the Jargon file.

Examples of (people I consider) hackers are (YouTube channels) Applied Science, cnhlor, and styropyro.

> You can read a bit about computer hacker culture in the Jargon file.

The Jargon File is an artifact of "hacker culture" as it existed in the 1980s and early 1990s. I would hesitate to recommend it nowadays -- it's rather dated, and could lead an unaware reader to some false impressions.

The single most important thing that made me understand the hacker mindset as a teenager was the Jargon File. And the publications and conference videos of the Chaos Computer Club also had a great influence on me, as well as Clifford Stoll's The Cuckoo's Egg.

Read books by hackers, watch conference talks. And ofc get to know hackers, go to hack spaces. Keep an open mind and be curious. That's a good starting point to see how hacker culture really is. It's mostly about unorthodox curiosity and having fun with machines and systems. Think of children playing with toys, who grew up and never stopped playing with toys.

Don't waste your time on pop culture presentations of hackers, like movies or reading articles about "great" hacks or hackers, it's misleading and not going to transform your mind to think like a hacker in any way.

Most technical people you work with, even in early startups, will not be "hackers" in any way, shape or form. Hacking doesn't usually equate to doing things that tend to make businesses lots of money. Sometimes it does, but not usually.

Yep, I think hacking became kind of a buzzword in the new economy. Facebook deciding to name their corporate grounds to "1 Hacker Way" is such an example of how tech companies have appropiated the term to mean something that doesn't really have anything to do with the hacker mindest. They just think it's cool and it attracts young talents. It's part of their brand marketing and hiring strategy.

The only connection between Facebook and hacking I can think of is that their software may have relied on "dirty hacks" and crutches in the past to make it work.

Hacker culture by nature is very anti-corporate, anarchistic and against subordinating everything under the dictatorship of profit maximization.

If the OP thinks "hacker mindest" equals being on a path to create the next big app or service, you are being mislead big time.

> Hacker culture by nature is very anti-corporate, anarchistic and against subordinating everything under the dictatorship of profit maximization.

Yes! I came this close to recommending "Steal This Book" by Abbie Hoffman for that exact reason. But I got the feeling that was not exactly the type of hacker that OP was looking for...

Worldview indoctrination is a fun game, I suppose. A mix of fiction and biography is probably about right:


Douglas Copeland's "Microserfs"

Neal Stephenson, "Snow Crash" and perhaps especially "Cryptonomicon" (the early randy chapters and anything about Eiphphyte in particular)

Real Genius (the film).


Steven Levy's Hackers: Heroes of the Computer Revolution. All the elder gods are here.

Cliff Stoll, The Cuckoo's Egg.

Maybe you could say a bit more about why you’re asking. In some cases others would be right to suggest that you find material relevant to business for yourself.

The one case that I can think of off the top of my head that might apply to this situation is if there are disagreements re:product refinement/feature set/bug prevalence. (Basically, “why doesn’t this work as seamlessly as X?”) In that case you might do well to find the MVPs (and later iterations) of famous startups.

Wild guess here. Think of your problem/goal starting from the other end.

(crass generalization) non technical people tend to see the "idea" they have isolated out of the sea of possibilities as the important thing.

Now that this important idea has been identified I just need someone to stuff some "supports" under it and we are done!

top down

From the other direction, great ideas are a dime a dozen. Enormous amounts of (outwardly invisible) time have been spent exploring the landscape these "supports" would need to sit on the down to the bedrock. There may be things that are just to obvious to consider explaining why that particular idea is not worth the effort. Maybe it is boring or sub optimal or infeasible, or just dumb.

A hacker (what ever that means anymore) would be more apt to consider what they had on hand and where they were and most importantly, how they could inject some cleverness into the building of their supports, then climb up and see where they had gotten themselves.

bottom up

All obvious gross simplifications for illustration purposes.

If you are endeavouring to address a disconnect, first of all kudos to you for making the effort.

Two paths that could help are

Better illustrator of "the idea". The everyday marketing of the idea to the masses is not going to help here. You would need to demonstrate the value added that would make what ever reluctance there is be set aside.

The other is experience what is causing the reluctance; get some blisters yourself.

A lot of us technical folks think the "hacker mindset" is an unfortunate, childlike simplification of what we do. I personally prefer solid engineering to "hacking".

I strongly encourage you to make your non-technical folks aware of good engineering practices, instead of this "everyone needs to learn to code and have special snowflake hacker skills" mindset that has so permeated the industry.

I'm a "hacker" in my free time, doing projects to tinker, have fun and learn. At my job I am not a hacker. I am an engineer. I engineer solutions to corporate problems. It's not that interesting.

True spherical hackers in the vacuum want to be undisputable experts in complex topics and as this often mixes with sheer egoism, they like to flex with this knowledge and remind others how unsophisticated others are. But ideal spherical hackers are rare. Moreover, smart people like to learn new stuff not only about the tech side of things, so if they sniff you're trying to manipulate them, they'll pay you back with the same coin and you'll get a team of cynical snarky devs. If you want to become a leader for them, you'll have to earn their respect (again, a lazy attempt to earn it by slipping how you know some python will dump your rating that very moment, as that would be seen as a cheap manipulation). A leader for them can be a super knowledgeable jerk (e.g. Linus) or a super humble guy who sends the message "you know more than me, so I'll step out of your way". In other words, if you really want to step on their ego by telling them what to do, you'd better be an undisputable expert, or expect a delayed counter reaction.

The turn of phrase "true spherical hackers in the vacuum" is quite clever and entertaining, but I submit that it is unlikely to be grokked by someone who does not already have familiarity with hacker-isms/culture. :)

(And of course they likely wouldn't understand "grok" either").

Tbh, even I don't understand "grok" :)

>... recommend to a business focused founder for them to grok the hacker mindset.

From 1000 ft, what's different between the two? It's all about solving problems.

The business focused founder sees a problem, a business/market opportunity. He/She needs to figure out how to solve it, how to come up with a way to satisfy that market. If a product exists, how do they get that product into the hands of the customer. If the product doesn't exist, how to get it into existence and then get it into the hands of the customer.

The hacker/developer/whatever sees a problem and He/She tries to develop a product that satisfies that problem based on the requirements they're either given or suss out themselves. The hacker mindset is an insatiable need for knowledge. How to do a thing. How to make a thing. How did others make a thing. Don't business people think that way, also? Probably one big difference might be that the hacker mindset shares knowledge. Business people are more protective of it. (Generally)

I would add that most folks who go into business are motivated primarily by seeing the dollars appear, while most "hackers" I know are primarily motivated by the rush they get when they've understood the new problem/solution.

That's painting with broad strokes obviously and a person can be motivated by both. But that's the axis I would draw the distinction on.

It's not that hard. Try to build / construct something. You will soon discover a layer of detail that you never anticipated. And then some more.

Hackers / programmers are trained to be cognizant of these details and complexities that aren't obvious on first glance.

Heck sometimes this weighs us down. I'd rather have someone ignorant and brave on my team. :)

The book "Coders At Work: Reflections on the Craft of Programming".

It is not a technical book.

It'll be as good as anything : ).

"Peter Seibel interviews 15 of the most interesting computer programmers alive today in Coders at Work, offering a companion volume to Apress’s highly acclaimed best-seller Founders at Work by Jessica Livingston. As the words “at work” suggest, Peter Seibel focuses on how his interviewees tackle the day-to-day work of programming, while revealing much more, like how they became great programmers, how they recognize programming talent in others, and what kinds of problems they find most interesting.

Hundreds of people have suggested names of programmers to interview on the Coders at Work web site: www.codersatwork.com. The complete list was 284 names. Having digested everyone’s feedback, we selected 15 folks who’ve been kind enough to agree to be interviewed:

Frances Allen: Pioneer in optimizing compilers, first woman to win the Turing Award (2006) and first female IBM fellow Joe Armstrong: Inventor of Erlang Joshua Bloch: Author of the Java collections framework, now at Google Bernie Cosell: One of the main software guys behind the original ARPANET IMPs and a master debugger Douglas Crockford: JSON founder, JavaScript architect at Yahoo! L. Peter Deutsch: Author of Ghostscript, implementer of Smalltalk-80 at Xerox PARC and Lisp 1.5 on PDP-1 Brendan Eich: Inventor of JavaScript, CTO of the Mozilla Corporation Brad Fitzpatrick: Writer of LiveJournal, OpenID, memcached, and Perlbal Dan Ingalls: Smalltalk implementor and designer Simon Peyton Jones: Coinventor of Haskell and lead designer of Glasgow Haskell Compiler Donald Knuth: Author of The Art of Computer Programming and creator of TeX Peter Norvig: Director of Research at Google and author of the standard text on AI Guy Steele: Coinventor of Scheme and part of the Common Lisp Gang of Five, currently working on Fortress Ken Thompson: Inventor of UNIX Jamie Zawinski: Author of XEmacs and early Netscape/Mozilla hacker"

Since it's actually about you and for that one guy, you should just tell him what it is that is set in your mind.

The thing about it though, is that mindsets are not readily transferable. They are basically worldviews which are formed slowly and because of their foundational place in cognition are remarkably resistant to change.

One challenge is technical debt. To start to understand it, find a tool that he uses regularly (assuming such a thing exists). Maybe it is Excel. Now have him solve some kind of problem with it. And then schedule a meeting with his friend the following week to review his spreadsheet. Then add requirements that his spreadsheet must handle. Tell him he must hurry so that those requirements are complete before his meeting. Ensure that there are too many requirements for the spreadsheet or that there isn't time to properly reorganize it.

In the meeting, explain to his friend that he has been the mastermind of this spreadsheet design. Have him first demo the calculation features of the spreadsheet. The have him walk through the design, show the formulas in the cells, explain his naming scheme.

The goal of this exercise is to demonstrate why engineers seem to be so concerned about their code organization and technical debt. Which is that they have their name on any mess they make in the code, and they have to maintain it as it changes. Without ever having done that part of it, it is difficult for a business person to really understand the developer's point of view.

I think you need to make it clear that you are a maker and your limitations are more in the realm of physics -- what can work and what won't work.

Business people tend to be more social-oriented, people-oriented. And one of the pitfalls of that is that most such people think if you just make the right friends, find the right words, push the right emotional buttons, you can make magic.

And sometimes that's true. But sometimes what they want is a case of "Something cannot be both heavy and light at the same time. I can be light and large -- like a cloud -- but it can't be both heavy and light. Pick one."

I do a lot of studying of social things and I hate people who are manipulative. A lot of people with serious social skills are manipulative.

In short, many of them lie when it's convenient because they don't want to deal with negative emotions or whatever.

So I would have them watch the Jim Carrey movie "Liar, Liar." and challenge them to use their social skills to tell the actual truth in a more acceptable manner instead of fudging.

I would also recommend negotiating books. Hard skills when it comes to dealing with people helps make it possible to be both honest and diplomatic.

The Mind and Heart of the Negotiator is research based and very meaty.

Getting to Yes is also research based, but a quick, easy read.

"The Jargon File" might be a good place to start. From there, maybe read one of The Cathedral and the Bazaar, The Soul of a New Machine, or Hackers: Heroes of the Computer Revolution.

I read Fire in the Valley when I was young and it impacted me, although there might be a better book that's similar. I might also recommend something by Jaron Lanier or Stallman if you don't might being a little political.

I've been collecting things in an Arena channel, "Use, Misuse, Rugged Consumerism, etc." that might be helpful in seeing one aspect of what such a mindset might be.


A 'Hacker' is just a technically literate 'Hustler'. There are likely more books or resources for developing a hustler mindset you can find. It's a more generic mode of thinking and can apply beyond just technical.

Founders need to be technical about something. The idea of a "non-technical" founder is nonsense. I have seen it and they were basically a VC with expensive friends just creating a job for social reason to get them out of the house.

Technical need not mean "code". It could be a medical expert working with a wide array of people to build something. Or a tax-expert. Or an employment expert etc.

Founder is what "product manager" should be. Instead it seems "product manager" is just some glue person at a large organization who is usually not great at accessing optionality and time and money costs.

The answer's simple. You're looking right at it!

Don't give them Mythical Man Month or Eric Raymond or any of that stuff: dated and esoteric. My interpretation of your post is basically that the business founder is going to be (involved in) hiring, and will be working with several software engineers soon. And you want to help them understand what makes the engineers tick: the sorts of things they find interesting, the sorts of ways they talk about it.

So that's easy. Tell them to look at HN, pick an article with a technical theme that's getting a lot of attention. Read the article, and then read the comment threads.

What are you hoping for the business focused founder to get out of this exercise?

The reason I ask is that in my experience the "hacker mindset" is a very nebulous thing. There's sort of a "hacker ideal", but in practice actual developers, white/blackhats, makers, etc. come from all sorts of backgrounds, have all sorts of ways of thinking about problems, and are motivated by all sorts of different things.

Are you hoping for the business founder to better understand how to effectively work with technical people?

Harvard's CS50 Intro to Computer Science. Available on various platforms like edX and YouTube.


Direct link to "Computational Thinking - CS50's Computer Science for Business Professionals 2017" - https://www.youtube.com/watch?v=Q2f9h_-_Fv4

Paul Graham's Makers vs Managers - http://www.paulgraham.com/makersschedule.html

Wow that was very enlightening. I had been wondering why meetings used to bug me, and now I have no issue. Oh did I mention I am a manager now, I scheduled this in an appropriate time slot. I cannot wait to get back to hating meetings.


The Psychology of Computer Programming

by Gerald M. Weinberg

Written in 1971, and still completely relevant. Topics include egoless programming, intelligence, psychological measurement, personality factors, motivation, training, social problems on large projects, problem-solving ability, programming language design, team formation, the programming environment, etc.

I don’t have any suggested reading material but my rule of thumb is to just assume that anything which appears simple to build is about 10x more complex for “reasons”. The simpler a feature is to use, the longer it will take to develop. And any major change in scope/priority adds 2x to the original timeline.

If you want to understand the details behind these general statements, you’ll need to spend the next several years in the trenches delivering dozens of technical projects.

I think many here (and maybe you too) would find the opposite valuable.

How to understand the business/sales/marketing/leadership/political mindset. Without cynicism.

I don`t watch these videos for entertainment, but this person has gained a little notoriety for this gig he started after his grandmother with dementia was scammed.


I was left agasp by some of the language (some is NSFW) and techniques ised by the scammers, but you would be the grandmother with dementia (non-technical user) vs someone who will say/do anything for money.

I've found the book "New Kingmakers: How Developers Conquered the World" really instructive on this point.

It focuses on the "rise of the developer," if you will, as an influential decision-making and budget-holding role within a company. It also includes lots of perspective on appealing to developers and avoiding marketing and business jargon.

As a nontechnical founder myself, it's been really helpful.

Watch DEFCON and Hackaday talks? Not so much a mindset but insights into how people think and what people find interesting (to have been selected).

"Masters of Doom" is a pretty demonstrative and entertaining bit of non-fiction that walks through the early days of id Software. Though not a manual or how-to, or anything like that, I'd recommend it to a non-technical founder or manager because it does a great job evoking the thrill of creation/breakthrough that is pretty central to the "hacker mindset".

Maybe "Hackers & Painters: Big Ideas From The Computer Age" by Graham. As a bonus, some of the chapters are business-oriented.

"Coders: who they are, what they think and how they are changing our world" by Clive Thompson, 2019. I think this is exactly what you are looking for.


I really enjoyed this interview with Larry Wall (of Perl fame), and I come back to it from time to time. He does a great job illustrating the hacker mindset that you mentioned https://www.youtube.com/watch?v=aNAtbYSxzuA

For me the mindset means a lot of different things.

1. Go beyond what people tell you. Discover your own truth.

2. The love for tinkering.

3. The idea that what you bought is your own and you can do anything with it.

4. To use something in a way that is completely not how it is intended.

5. Deep reverse engineering dives.

6. The guilty pleasure of picking digital locks.

I think I've books in all those directions.

I would recommend Steve Levy's: Hackers: Heroes of the Computer Revolution: 25th Anniversary Edition.

Hacker mindset to me is the predictable ability to swap between divergent and convergent thinking at will to discover optimal paths to desired outcomes regardless of means, context, biases, etc. — frequently just for the fun of it, to learn more, to be intentionally different, etc.

Might be interesting to do a few hours of pair programming too; i.e. implement and ship a small feature

Ghosts in the Wire, Kevin Mitnick

Made me realise that many just do it because they like the challenge.

Steve Wozniak’s biography, “iWoz”. He perfectly explains how to combine off the shelf parts in novel ways so that 100% of R&D is focused on closing gaps unique to the business problem at hand.

Perhaps "The Innovators" by Walter Isaacson. If nothing else, it introduces the reader to many of the pivotal people in the history of computing.

I see how everything works. Humans, businesses, societies, machines, myself - everything. And I use that to have fun.

Paul Graham's Hackers & Painters?

Halt and Catch Fire seasons 1 and 2.

ER is blacklisted in tech community. Finishing GEB is no easy task.

I recommend hackers and painters by pg.

The book written by the guy who runs this site.

Skims on the painting part, I thought, but it makes for an interesting insight into the personal philosophy of someone who values both creativity and logic.

Many of his ideas are universal (probably why I'm here!). Others don't port so well (or are specific to his experience).

Well worth the OPs time, given the question.

Joel on Software is also a fantastic read. More concrete in talking about specific aspects of a software developers' working experience, and ideas towards technology in general.

A mentor of mine suggested I should read it alongside Hackers and Painters.

I can't thank him and his friends enough, frankly...

I liked Founders at Work by Jessica Livingston, but it isnt clear what you mean.

Eloquent JavaScript, even if you only go through the first few chapters

read Hackers by Steven Levy. one of the best histories of 70s and 80s era of computing. gave great feel for how programmers think

Elements of Programming Interviews (jk)

The Hacker Manifesto

The Anarchist's Cookbook

Industrial Society and Its Future (the Unabomber Manifesto)

Zen and the Art of Motorcycle Maintenance

> I've thought perhaps Mythical Man Month and How To Become A Hacker (Eric Raymond essay) but not sure they're quite right.

Please don't recommend Eric Raymond's work to people.

> technical founder wondering what reading to recommend to a business focused founder for them to grok the hacker mindset

What does "the hacker mindset" mean to you?

If you ask me: The most important thing about a hacker mindset is that it must exist outside of technology. A hacker mindset is not a "techy" mindset, it's something far more sublime, and is portable across different fields.

Hacking is about creativity and problem solving, but not in a formalized way. That doesn't always involve computers and related technology. Hacking should be fun, regardless of what industry or specialization it manifests in (which doesn't always translate well in business settings).

That isn't something that you're going to inject into someone by recommending them read a book. They have to seek it out for themselves. Without curiosity, hackers do not exist.

If they're going to be able to understand the mindset without having experienced it themselves, you might as well just share my comment here with them. If it sinks in, great! If not, I don't believe a few hundred pages of prose will have a different outcome.

Please review and stick to the site guidelines here. Note this one: "Eschew flamebait. Don't introduce flamewar topics unless you have something genuinely new to say. Avoid unrelated controversies and generic tangents."


What's wrong with ESR's work? I know the man himself can sometimes be controversial, but many of us came up on his works like The Jargon File, Cathedral and Bazaar, etc.

The Jargon File is almost entirely the work of others, in particular Guy Steele. ESR's contributions to it were largely self-serving, e.g. the addition of terms like "anti-idiotarianism" which had little usage outside right-wing political circles (including ESR himself, of course), and he hasn't updated it at all since the early 2000s.

> Please don't recommend Eric Raymond's work to people.

Why? Do you have some problem with his advice on how to ask questions[1]?

[1] http://catb.org/~esr/faqs/smart-questions.html

> Why?

Because promoting ESR's work to people has the unfortunate side-effect of elevating ESR's prestige.

See https://news.ycombinator.com/item?id=15513086 for more on why ESR is bad.

> Do you have some problem with his advice on how to ask questions[1]?

No, I think he's a bad person and we do our entire industry a disservice by continuing to elevate his status.

Find better heroes, should you even want heroes.

It does our industry an even-greater disservice to base prestige on great works rather than on character. We can get past the halo effect, if we try.

If I recall, there's a Buddhist proverb, where a pig is held up as a good example of enlightenment: it will happily pick truffles out of mud, taking the truffle and leaving the mud behind. It doesn't develop an opinion on the mud in the process; the truffle grew from the mud, but the mud isn't relevant to the truffle. It doesn't venerate/privilege/respect the mud—but nor does it find it disgusting. It's just mud. Irrelevant. Not food. The truffle, clean of mud, stands on its own. The truffle is a necessary part of a creature's mental model, insofar as it experiences hunger; but the mud is not.

You think the side-effect of elevating ESR's status outweighs the value of the ideas themselves?

It does. Especially since there are a lot of hackers in the world who can articulate the same ideas better and with less racism.

Guidelines | FAQ | Lists | API | Security | Legal | Apply to YC | Contact