Best resources for non-technical founders to understand hacker mindset?

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!"

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.

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)

reading:

https://stallman.org/articles/on-hacking.html

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 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.

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.

Cheers.

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.

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.

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

Fiction:

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).

Nonfiction:

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.

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.

>... 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)

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.

https://www.are.na/zach-rose/use-misuse-rugged-consumerism-e...

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.

https://try.newrelic.com/rs/newrelic/images/The_New_Kingmake...

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.

https://www.edx.org/course/cs50s-introduction-to-computer-sc...

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

https://smile.amazon.com/dp/0932633420/

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.

https://kitboga.com/

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.

https://www.goodreads.com/book/show/44037236-coders

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.

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.