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Picking Co-Founders the Army Officer Way

97 points by Chan_Yuk_Chi 5y ago

bambax 5y ago
I'm sure the US military is a formidable force; but despite this, the US as a country loses many (most?) wars it engages in. So the lesson to learn may not just be, how to build a good team on the ground, but: how to pick your battles wisely. A startup CEO isn't just a platoon leader: they are also a politician and a strategist. That's what makes it so difficult.
- chrisseaton 5y ago
  > I'm sure the US military I don't think this post is about the US military though. Uniforms look Singaporean.
  - GravitasFailure 5y ago
    From the author's bio, "Space Lawyer and Founder. Former Singapore Army officer. Sci-fi author in general." Though I suspect the uniforms in the third and fifth pictures aren't Singaporean or American.
    - jcranmer 5y ago
      The fifth picture, from its source attribution, is (Scottish, I think) Highland Territorials in a trench in France in 1914.
  - bambax 5y ago
    The post is about how we should learn about leadership from the military. The US army is the mightiest military force in the world. But that's not enough to win wars. Winning wars seems more interesting than having great teams.
    - chrisseaton 5y ago
      > But that's not enough to win wars. The blog post never says it is. > Winning wars seems more interesting than having great teams. It's ok to write blog posts about a variety of things, even if you think there's something potentially more interesting elsewhere.
      - bambax 5y ago
        Sure, but it's not like those things "elsewhere" are completely unrelated. It's implied that building great teams "military style" are a great solution to many problems, and are applicable to the corporate world. I would like to point out that having a great military force is not enough for what's important -- many times, it's not even needed!
        Chan_Yuk_Chi 5y ago
        This isn't an article about winning wars, and I'm not advocating that building great teams is a guarantor of success. This is a guide for those who have decided on their own that they want to focus on building a great team, because their personal assessment is that a great team is what they need to succeed.
- freedomben 5y ago
  > A startup CEO isn't just a platoon leader: they are also a politician and a strategist. That's what makes it so difficult. In the US, the head of the military is a politician (the US president). As a side effect of that the majority of high ranking officers are politicians as well, albeit playing a different game since it's the politicians they are trying to impress rather than the people.
- ryanmarsh 5y ago
  When you have the opportunity to train with non-US militaries one quickly learns a bit of gratefulness. Our officer and non-commissioned officers are far more professional, and our junior enlisted are far better trained. There are some exceptions. British Royal Marines and SAS really impressed me. So why does the US lose wars? Because we don’t let the military fight them to win. How else does a 21st century military lose to someone living in the sixth century? The officer corp spends 10x more time restraining soldiers than gassing them up. It’s difficult to fathom what we’re capable of (even with the law of armed conflict).
  - JamesSwift 5y ago
    I was never actually in the "armed" forces, but I did serve in the military, and I don't think the issue was lack of military force in Afghanistan. The problem was that we started off with overwhelming force, destroying civilian lives, and giving every opportunity for the taliban to generate anti-american sentiment in the process. It required a nuanced approach from day 1 and we didn't start that approach until day 300 (philosophically speaking). We needed to win the trust of the civilian population and we did nothing to secure that trust.
    - ryanmarsh 5y ago
      Exactly. This weird 21st century idea of military as gracious nation building conquerer is weird and we are not good at that. Note that, conversely, force on force "wars" are won very quickly. We should have left Afghanistan in 2002.
  - neffy 5y ago
    The US didn't lose the war in Afghanistan, it won that remarkably quickly. It lost the peace - temporarily at least. But personally I wouldn't be quite so quick to write off 20 years of somewhat liberalism, and widespread internet access, in terms of that nation's development.
  - WJW 5y ago
    > How else does a 21st century military lose to someone living in the sixth century? Part of the reason is this type of chronic underestimation of the enemy. The Taliban may hold some socially outdated ideas, but their use of digital communications and machine guns is absolutely not "from the sixth century". Rule 1 of warfare is to never underestimate your opponent. The main problem the US had was that from basically day 2 (day 1 being spent winning the conventional war) they were looking for a way to leave the country again and everybody there knew it. If you are not looking to annex the conquered territory indefinitely (which is extremely unpopular in western countries for PR reasons) then eventually you will have to leave and so your opponents only need to find a way to survive until then.
adwww 5y ago
Co Founders are already quite often reasonably gung-ho risk takers. I think what's often lacking are attributes like empathy - I'm not sure trying to further militarise startups helps that.
- IG_Semmelweiss 5y ago
  I do thinl there is an element of empathy that has been stripped away from the military as it has modernized. The same is true for startups as they have modernised. Before, the commander was the first in and last man out of battle (the article's "lead by example") now we have smooth talking presidents sending young men to die in a suit and tie. Napoleon would have none of that. Likewise, whereas before startups genuinely tried to do good (google "dont be evil", staying out of China, game devs creating worlds like 2nd life etc); nowadays startups actively find ways to treat you as the product, to be sold to the highest bidder and you are just a number on some dashboard, that must be enticed to engage. See Google, Zynga, FB, etc . Empathy has gone missing and this is not a particular problem for startups or military. There are too many degrees of separation between the ruler and the ruled. Between the doer and the consumer. As that distance increases, we also lose connection to what matters. The incompetent are shmoozing themselves into power, and this phenomena is not specific to 1 part of society
- altrus 5y ago
  From the Article: What I actually learned is that if something is right, it’s right. Context makes a slight difference but fundamental principles hold true. There are laws of nature. The article isn't suggesting militarizing start ups - it's providing some context on which elements of the military officer selection process are transferable to the start up co-founder selection process. edit: clarity
- irq-1 5y ago
  Empathy is addressed as a negative: > ...the overfamiliarity problem. That one founder will become too comfortable, start taking liberties with the others that they would never dare to do in any other context, by virtue of the fact that ‘they’re all friends’. Dealing with our own and others immaturity, or lack of professionalism, in a caring and sympathetic way seems like a fundamental difference between the military and private life. The military kicks you out or keeps you down, and non-military groups try to help everyone grow while tolerating problems. I wonder what the military attitude would be to the common business idea of growing into the job, or learning on the job? (Or the Dilbert principle.)
rjsw 5y ago
Wondered if it was going to suggest this [1]. [1] https://en.wikipedia.org/wiki/Purchase_of_commissions_in_the_British_Army https://en.wikipedia.org/wiki/Purchase_of_commissions_in_the...
ryanmarsh 5y ago
I’ve found many parallels between combat leadership and business/leadership/dev/ops The principles of good leadership in “open ended” problem spaces seem to apply no matter the other variables. Too often personal emotional reactions to the military or war (often misconceptions) overshadow the lessons and they are dismissed. I’ve had people smugly dismiss these ideas because of where the lessons were learned.
- Chan_Yuk_Chi 5y ago
  Precisely this. I wrote this as a rebuke of assertions that lessons in the military are only valid in the military, and that they aren't useful elsewhere because "this isn't the Army."
icegreentea2 5y ago
The author goes out of his way (and I think it was a good call), not to call out "army things" that make for good co-founders, but to frame it as "these are qualities of good choices that were made obvious to me in an army context". Specifically: * Trustworthy * Professional * Competency What other (non-business) contexts could we frame this type of article as? I suspect team-sports will stick out as an example, but where else?
- deleted 5y ago
  [deleted]
- InitialLastName 5y ago
  For all of the flack that artists get, the "workaday" side of the arts (think orchestra members, studio musicians, professional theater casts and crews, film and cartoon studios) emphasize this like crazy. Talent can get you through an audition, but showing up reliably and on time, being comprehensively prepared, and performing at a consistently high level will keep you employed.
- Chan_Yuk_Chi 5y ago
  Team-sports actually was an example I used in an initial draft re: professionalism (the idea that you leave everything on the field when the game ends) but I ultimately dropped it because I was stacking one analogy on top of another.
jl2718 5y ago
Imagine you sign up to be a startup founder at YC. It’s a salary job, and the pay is low, very low. The promotion schedule is pre-determined, almost invariant of your success. You develop a specialty and your team is assigned to you, rotating once every two years. Most teams only work on one problem, but if you are one of the very best, you get called to work on many small problems. There is almost no requirement for entry into the program except an extremely brutal training that keeps most people out of it. There are only two benefits. First, you get to be part of something that might change the world for everybody else. Secondly, you will gain respect, experience, and trust to start your own business when you get out. So there you are, on a team with a bunch of people you have never met before. You are now stuck together. If somebody is a problem, you deal with the problem because you can’t get rid of the person. There is a structure, but you’re all on the same path to those roles. All your grievances point to YC and not your team. You’re all getting screwed equally, but no matter how bad it gets, you all chose this, and you all depend on each other. You get a problem you didn’t choose. You might think it’s stupid. Too bad. Your team owns it now, and they depend on you. You succeed or fail together - nobody cares about praise or blame. Your team makes all the decisions. Nobody is looking over your shoulder. Nobody inserts their suggestions. You report only on a need-to-know basis. Nobody can tell you what to do. If you do something wrong, it will come back to you later in the report out, but not now. The only way to get rid of you is by trial of your peers for an ethical violation. So what it comes down to, is that you just do your job, and you don’t worry about anything else. You can and must work effectively with almost anybody in that situation.
- ARandomerDude 5y ago
  The world you just described is what Hollywood thinks the military is like. The actual military is very different from this.
  - jl2718 5y ago
    This is both true and untrue. I hate to say it this way, but, the vast majority of the military doesn’t do anything, so maybe you get a lot of blustering about nothing. The closer you get to combat, the more it is like this. I sat through hundreds of command briefings, and I can’t recall a single instance of tactical spot correction. That could be the basis of a command relief. Orders are superior to any rank.
quirkot 5y ago
I'm sorry. What? > "In basic training, we had to shout everything and repeat every instruction we were given." ... "So that one day, if we’re getting shot at or shelled, we’d repeat instructions we were given clearly so that the message could be passed down the line without the individuals passing it on having to think about it." The reason for repeating is maybe someday help a dude pass along a shout ... as opposed to confirming the accurate receipt and understanding of the order? Maybe the shout thing is a nice side benefit, but in no way is it the primary reason
- alisonkisk 5y ago
  Repetition helps generate accurate receipt and understanding.
etothepii 5y ago
I agree with the OP that trustworthyness is a key requirement for building a successful co-founder relationship. What I can't work out is how you would measure trustworthyness or (perhaps more importantly) how you would establish if you are good at measuring trustworthyness.
sdrinf 5y ago
I've seen, and read many, many of these kind of articles on how to evaluate potential co-founders (they're mostly generated as part of a shutdown, and I get it, there were a lot of feelings involved). I put forth the problem, that evaluation is actually the -relatively- easier part; finding startup cofounders who both operate at sufficiently high levels of competence, at skills that are complimentary to yours, and can operate a startup (ie operating under conditions of knightian uncertainty/Goal ambiguity/Isotropy) is the very, very difficult challenge.
notadev 5y ago
Since the author is using his Singaporean military service as the analogy, Singaporean-Malays need not apply. Their faith supposedly makes them an inherent risk, so they’re likely only eligible for low-level software developer positions, or maybe DevOps since that’s where most of the firefighting is.
- Chan_Yuk_Chi 5y ago
  I personally served with plenty of Singaporean-Malays. My first Officer Commanding was Malay. The idea that their faith renders them a risk is not a view we hold.
  - notadev 5y ago
    I suppose you are correct in pointing to their faith not being an issue, but their allegiances are still questioned by some. Why do Malays disproportionately make up the bulk of police/SCDF during NS? https://www.quora.com/Why-are-there-no-Muslims-in-some-sectors-of-the-Singapore-Army-and-Navy https://www.quora.com/Why-are-there-no-Muslims-in-some-secto...
m0zg 5y ago
This would carry a lot more weight if this "startup" at least had a functioning website. Or indeed if work in startups was anything like the army (which it is not - I've been through this). It's weird: I freelance now, and work almost exclusively with startups, and I observe that a nontrivial fraction of people are in it for the "allure". Such folks tend to write a lot of articles on Medium and Substack, post a lot on Twitter, too, and then... nothing. Case in point: one of my clients is currently busy discussing _OKRs_ even though they haven't raised the seed round yet, have no prototype, and what little code they do have is so thoroughly busted I can't even start working on it. No shortage of social media posts tho.

97 points by Chan_Yuk_Chi 5y ago

I'm sure the US military is a formidable force; but despite this, the US as a country loses many (most?) wars it engages in. So the lesson to learn may not just be, how to build a good team on the ground, but: how to pick your battles wisely. A startup CEO isn't just a platoon leader: they are also a politician and a strategist. That's what makes it so difficult.

chrisseaton 5y ago
> I'm sure the US military I don't think this post is about the US military though. Uniforms look Singaporean.
- GravitasFailure 5y ago
  From the author's bio, "Space Lawyer and Founder. Former Singapore Army officer. Sci-fi author in general." Though I suspect the uniforms in the third and fifth pictures aren't Singaporean or American.
  - jcranmer 5y ago
    The fifth picture, from its source attribution, is (Scottish, I think) Highland Territorials in a trench in France in 1914.
- bambax 5y ago
  The post is about how we should learn about leadership from the military. The US army is the mightiest military force in the world. But that's not enough to win wars. Winning wars seems more interesting than having great teams.
  - chrisseaton 5y ago
    > But that's not enough to win wars. The blog post never says it is. > Winning wars seems more interesting than having great teams. It's ok to write blog posts about a variety of things, even if you think there's something potentially more interesting elsewhere.
    - bambax 5y ago
      Sure, but it's not like those things "elsewhere" are completely unrelated. It's implied that building great teams "military style" are a great solution to many problems, and are applicable to the corporate world. I would like to point out that having a great military force is not enough for what's important -- many times, it's not even needed!
      - Chan_Yuk_Chi 5y ago
        This isn't an article about winning wars, and I'm not advocating that building great teams is a guarantor of success. This is a guide for those who have decided on their own that they want to focus on building a great team, because their personal assessment is that a great team is what they need to succeed.
freedomben 5y ago
> A startup CEO isn't just a platoon leader: they are also a politician and a strategist. That's what makes it so difficult. In the US, the head of the military is a politician (the US president). As a side effect of that the majority of high ranking officers are politicians as well, albeit playing a different game since it's the politicians they are trying to impress rather than the people.
ryanmarsh 5y ago
When you have the opportunity to train with non-US militaries one quickly learns a bit of gratefulness. Our officer and non-commissioned officers are far more professional, and our junior enlisted are far better trained. There are some exceptions. British Royal Marines and SAS really impressed me. So why does the US lose wars? Because we don’t let the military fight them to win. How else does a 21st century military lose to someone living in the sixth century? The officer corp spends 10x more time restraining soldiers than gassing them up. It’s difficult to fathom what we’re capable of (even with the law of armed conflict).
- JamesSwift 5y ago
  I was never actually in the "armed" forces, but I did serve in the military, and I don't think the issue was lack of military force in Afghanistan. The problem was that we started off with overwhelming force, destroying civilian lives, and giving every opportunity for the taliban to generate anti-american sentiment in the process. It required a nuanced approach from day 1 and we didn't start that approach until day 300 (philosophically speaking). We needed to win the trust of the civilian population and we did nothing to secure that trust.
  - ryanmarsh 5y ago
    Exactly. This weird 21st century idea of military as gracious nation building conquerer is weird and we are not good at that. Note that, conversely, force on force "wars" are won very quickly. We should have left Afghanistan in 2002.
- neffy 5y ago
  The US didn't lose the war in Afghanistan, it won that remarkably quickly. It lost the peace - temporarily at least. But personally I wouldn't be quite so quick to write off 20 years of somewhat liberalism, and widespread internet access, in terms of that nation's development.
- WJW 5y ago
  > How else does a 21st century military lose to someone living in the sixth century? Part of the reason is this type of chronic underestimation of the enemy. The Taliban may hold some socially outdated ideas, but their use of digital communications and machine guns is absolutely not "from the sixth century". Rule 1 of warfare is to never underestimate your opponent. The main problem the US had was that from basically day 2 (day 1 being spent winning the conventional war) they were looking for a way to leave the country again and everybody there knew it. If you are not looking to annex the conquered territory indefinitely (which is extremely unpopular in western countries for PR reasons) then eventually you will have to leave and so your opponents only need to find a way to survive until then.

adwww 5y ago

Co Founders are already quite often reasonably gung-ho risk takers. I think what's often lacking are attributes like empathy - I'm not sure trying to further militarise startups helps that.

IG_Semmelweiss 5y ago
I do thinl there is an element of empathy that has been stripped away from the military as it has modernized. The same is true for startups as they have modernised. Before, the commander was the first in and last man out of battle (the article's "lead by example") now we have smooth talking presidents sending young men to die in a suit and tie. Napoleon would have none of that. Likewise, whereas before startups genuinely tried to do good (google "dont be evil", staying out of China, game devs creating worlds like 2nd life etc); nowadays startups actively find ways to treat you as the product, to be sold to the highest bidder and you are just a number on some dashboard, that must be enticed to engage. See Google, Zynga, FB, etc . Empathy has gone missing and this is not a particular problem for startups or military. There are too many degrees of separation between the ruler and the ruled. Between the doer and the consumer. As that distance increases, we also lose connection to what matters. The incompetent are shmoozing themselves into power, and this phenomena is not specific to 1 part of society
altrus 5y ago
From the Article: What I actually learned is that if something is right, it’s right. Context makes a slight difference but fundamental principles hold true. There are laws of nature. The article isn't suggesting militarizing start ups - it's providing some context on which elements of the military officer selection process are transferable to the start up co-founder selection process. edit: clarity
irq-1 5y ago
Empathy is addressed as a negative: > ...the overfamiliarity problem. That one founder will become too comfortable, start taking liberties with the others that they would never dare to do in any other context, by virtue of the fact that ‘they’re all friends’. Dealing with our own and others immaturity, or lack of professionalism, in a caring and sympathetic way seems like a fundamental difference between the military and private life. The military kicks you out or keeps you down, and non-military groups try to help everyone grow while tolerating problems. I wonder what the military attitude would be to the common business idea of growing into the job, or learning on the job? (Or the Dilbert principle.)

rjsw 5y ago

Wondered if it was going to suggest this [1]. [1] https://en.wikipedia.org/wiki/Purchase_of_commissions_in_the_British_Army https://en.wikipedia.org/wiki/Purchase_of_commissions_in_the...

ryanmarsh 5y ago

I’ve found many parallels between combat leadership and business/leadership/dev/ops The principles of good leadership in “open ended” problem spaces seem to apply no matter the other variables. Too often personal emotional reactions to the military or war (often misconceptions) overshadow the lessons and they are dismissed. I’ve had people smugly dismiss these ideas because of where the lessons were learned.

Chan_Yuk_Chi 5y ago
Precisely this. I wrote this as a rebuke of assertions that lessons in the military are only valid in the military, and that they aren't useful elsewhere because "this isn't the Army."

icegreentea2 5y ago

The author goes out of his way (and I think it was a good call), not to call out "army things" that make for good co-founders, but to frame it as "these are qualities of good choices that were made obvious to me in an army context". Specifically: * Trustworthy * Professional * Competency What other (non-business) contexts could we frame this type of article as? I suspect team-sports will stick out as an example, but where else?

deleted 5y ago
[deleted]
InitialLastName 5y ago
For all of the flack that artists get, the "workaday" side of the arts (think orchestra members, studio musicians, professional theater casts and crews, film and cartoon studios) emphasize this like crazy. Talent can get you through an audition, but showing up reliably and on time, being comprehensively prepared, and performing at a consistently high level will keep you employed.
Chan_Yuk_Chi 5y ago
Team-sports actually was an example I used in an initial draft re: professionalism (the idea that you leave everything on the field when the game ends) but I ultimately dropped it because I was stacking one analogy on top of another.

jl2718 5y ago

Imagine you sign up to be a startup founder at YC. It’s a salary job, and the pay is low, very low. The promotion schedule is pre-determined, almost invariant of your success. You develop a specialty and your team is assigned to you, rotating once every two years. Most teams only work on one problem, but if you are one of the very best, you get called to work on many small problems. There is almost no requirement for entry into the program except an extremely brutal training that keeps most people out of it. There are only two benefits. First, you get to be part of something that might change the world for everybody else. Secondly, you will gain respect, experience, and trust to start your own business when you get out. So there you are, on a team with a bunch of people you have never met before. You are now stuck together. If somebody is a problem, you deal with the problem because you can’t get rid of the person. There is a structure, but you’re all on the same path to those roles. All your grievances point to YC and not your team. You’re all getting screwed equally, but no matter how bad it gets, you all chose this, and you all depend on each other. You get a problem you didn’t choose. You might think it’s stupid. Too bad. Your team owns it now, and they depend on you. You succeed or fail together - nobody cares about praise or blame. Your team makes all the decisions. Nobody is looking over your shoulder. Nobody inserts their suggestions. You report only on a need-to-know basis. Nobody can tell you what to do. If you do something wrong, it will come back to you later in the report out, but not now. The only way to get rid of you is by trial of your peers for an ethical violation. So what it comes down to, is that you just do your job, and you don’t worry about anything else. You can and must work effectively with almost anybody in that situation.

ARandomerDude 5y ago
The world you just described is what Hollywood thinks the military is like. The actual military is very different from this.
- jl2718 5y ago
  This is both true and untrue. I hate to say it this way, but, the vast majority of the military doesn’t do anything, so maybe you get a lot of blustering about nothing. The closer you get to combat, the more it is like this. I sat through hundreds of command briefings, and I can’t recall a single instance of tactical spot correction. That could be the basis of a command relief. Orders are superior to any rank.

quirkot 5y ago

I'm sorry. What? > "In basic training, we had to shout everything and repeat every instruction we were given." ... "So that one day, if we’re getting shot at or shelled, we’d repeat instructions we were given clearly so that the message could be passed down the line without the individuals passing it on having to think about it." The reason for repeating is maybe someday help a dude pass along a shout ... as opposed to confirming the accurate receipt and understanding of the order? Maybe the shout thing is a nice side benefit, but in no way is it the primary reason

alisonkisk 5y ago
Repetition helps generate accurate receipt and understanding.

etothepii 5y ago

I agree with the OP that trustworthyness is a key requirement for building a successful co-founder relationship. What I can't work out is how you would measure trustworthyness or (perhaps more importantly) how you would establish if you are good at measuring trustworthyness.

sdrinf 5y ago

I've seen, and read many, many of these kind of articles on how to evaluate potential co-founders (they're mostly generated as part of a shutdown, and I get it, there were a lot of feelings involved). I put forth the problem, that evaluation is actually the -relatively- easier part; finding startup cofounders who both operate at sufficiently high levels of competence, at skills that are complimentary to yours, and can operate a startup (ie operating under conditions of knightian uncertainty/Goal ambiguity/Isotropy) is the very, very difficult challenge.

notadev 5y ago

Since the author is using his Singaporean military service as the analogy, Singaporean-Malays need not apply. Their faith supposedly makes them an inherent risk, so they’re likely only eligible for low-level software developer positions, or maybe DevOps since that’s where most of the firefighting is.

Chan_Yuk_Chi 5y ago
I personally served with plenty of Singaporean-Malays. My first Officer Commanding was Malay. The idea that their faith renders them a risk is not a view we hold.
- notadev 5y ago
  I suppose you are correct in pointing to their faith not being an issue, but their allegiances are still questioned by some. Why do Malays disproportionately make up the bulk of police/SCDF during NS? https://www.quora.com/Why-are-there-no-Muslims-in-some-sectors-of-the-Singapore-Army-and-Navy https://www.quora.com/Why-are-there-no-Muslims-in-some-secto...

m0zg 5y ago

This would carry a lot more weight if this "startup" at least had a functioning website. Or indeed if work in startups was anything like the army (which it is not - I've been through this). It's weird: I freelance now, and work almost exclusively with startups, and I observe that a nontrivial fraction of people are in it for the "allure". Such folks tend to write a lot of articles on Medium and Substack, post a lot on Twitter, too, and then... nothing. Case in point: one of my clients is currently busy discussing _OKRs_ even though they haven't raised the seed round yet, have no prototype, and what little code they do have is so thoroughly busted I can't even start working on it. No shortage of social media posts tho.