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Is having a board of directors full of VC big shots to answer to that different from having a boss?

I listened to a Changelog podcast the other day featuring Sytse Sijbrandij (GitLab CEO) and he mentioned having to run stuff by his board and I was like woa, even someone as obviously self-made as @sytse has a boss.

I'm starting to think that only by bootstrapping (or taking very little investment, at least) you really do work without a boss. Not sure if the YC path that pg promotes in this article fits that.

(I'm thinking about this a lot lately because my company is currently at this crossroads. We raised a little, turned that into profitable growth, but we could raise more to grow faster.)

EDIT: meta-level comment: it's kind of weird how we managed to create a world where nearly everybody has a boss. CEOs answer to the board, who answer to shareholders, who work at investment funds that have bosses and shareholders and LPs of their own, and down the rabbit hole it goes. I wonder if there's any general way out of this, different from "bootstrap a SaaS" which is a little specific to be good general advice.




Even if you are totally self funded you still are accountable to your customers. For software companies this might not be so bad, but many small business owners will tell you they make extremely demanding bosses


> Even if you are totally self funded you still are accountable to your customers

2 main differences:

1) your customer's requirements are pure (usually) - "please add a frammel button so I can manage my widgets better". Your boss's requirements are less so - "please satisfy corporate by attending this compliance training".

2) you can fire any customers who you don't like. Not so your boss.


> 2) you can fire any customers who you don't like. Not so your boss.

I know what you mean, but I think there's an alternate way to look at this.

Every time I've moved jobs, I really look at it as firing my boss. The process is pretty much the same as firing someone:

* First, I voiced my concerns and gave my boss a chance to improve.

* When he wasn't improving, I began searching the job market to find his replacement (my future boss).

* After a few interviews, I found a replacement that was a really good fit for the role of "my boss".

* I let my old boss know that his performance had not improved enough, and I was forced to let him go, but I wished him all the best in his future endeavors.

* I gave my new boss a start date, and so far everything is going great.


Except you don’t get to keep the job. Firing your boss means changing your job, firing your customer does not.


Adding to that, unless they’re your only customer, firing one customer means you’ve only lost a % of potential future income. Firing your boss, and quitting your job altogether-unless you’re moonlighting, getting passive income elsewhere or accepted an offer before quitting-most commonly means losing 100% of future earnings until signing onto the next job.


> "please satisfy corporate by attending this compliance training".

Compliance training is about legal requirement. A little extrapolation suggests it is going to be things that your bosses are only asking you to consider because they are legally mandated. If they were going to be considerations anyway, why mandate them?

A lot of stupid things businesses do are to satisfy legal requirements that the business thinks is stupid. That one isn't the boss, it is the government.


Compliance training is about legal requirement.

That's the thing -- oftentimes your Boss thinks that X is a "legal requirement". When really it's "so-and-so is bugging me to cram this down your throats saying something about 'legal' and I'm too busy to even bother googling to find out whether it's really so. Plus even if I did some basic research I might have to actually think about it for a minute or two - and you know how much I hate that. So to save myself time, I think I'll just cram it down your throats."

My favorite X in this category: drug testing. (Contrary to popular belief, it's almost never an actual legal requirement - even if your company is getting state or federal funds.)


This is technically true, but as a solo founder, you're even less equipped than a large company with a legal and compliance team to determine what's actually a legal requirement and what's not - and what legal requirements are imposed by industry groups like PCI instead of the government but are no less binding in practice if you want to run a certain sort of business, and what sorts of things are in the grey area of "the law only speaks about this broadly, but nobody chooses a specific implementation other than X in practice, so in theory you could innovate but you're on your own," and what sorts of things aren't legal requirements on their own but do save you if you get into legal trouble for other reasons, and so forth.

Remember that solo founders are widely encouraged to incorporate in Delaware just because it's the least legal risk. One state! Out of fifty, and several non-state entities! There's no legal requirement, and you can absolutely incorporate in your home state or many other places, but the advice is that if you want to focus on what your business does best, don't spend time thinking about any states' corporate law other than Delaware's, which is well-explored. If that's the bar, basically all other forms of compliance are well above it.

I get that good hackers have an instinct to ask "Why?" or "Really?" at every step and to understand the whole system, and I have it too, but one thing I've learned with experience is you need to train yourself to put a stopping point on "Why?" if you want to get anything done at your current level of descent. You absolutely can go arbitrarily deep, nobody is goin to stop you, and there are all sorts of fences that have no reason for existing, but you have a limited amount of time to do whatever work you want to do and show results. Do you want to build the next great social network, or the next great form of corporate structure? You can absolutely do either - you can't do both.

(One caveat: there are a few things that are legal requirements or near enough thereto that only apply when you have more than a few employees. If you're a solo founder, you presumably can't create a hostile work environment for yourself, for instance. However, if you're a solo founder pursuing B2B deals and having meetings with companies, it might be worth being aware of what sorts of things your target companies consider hostile work environments and would cause them to not invite you back for the sake of their legal risk - and that's even more about the standard corporate view of the law than the law itself. So, you may not be able to get away ignoring these conventions even as a solo founder, after all.)


I have this for my small business. About 450 small "bosses" (clients). Because we don't answer to investors or board or anything we have what I call "alignment" with our clients.

Despite 400+ opinions, the pull on the team is one way: client needs.

My previous Companies has outside money, board, etc. That's three directions of pull.

We've saved a lot of time that way on investor management but our growth was limited by cash-on-hand.


Have you ever needed to fire a client? Or been in a situation where you have to juggle client needs that were non-compatible?


Fire client: less than 2%. But looks, losing only 2% to focus on the other 98. Well, you'll grow back.

Not-Compatoble request is a bit harder. But, with like 10+ prior years in consultant I'm generally able to direct thing to a multiple compatible solution.

Lots of research and customer development play for that.


And you are accountable to your employees. Take the board I have for example. It is a relief to know that if I’m not longer the right person they will replace me. If you are bootstrapped with 1000+ employees a board might be something you want even if you don’t need to do it from an ownership perspective.


I mean, at a certain point you're asking for ultimate power over everything and instead of attempting to become autonomous you find yourself attempting to become a supervillain


the zuckerberg route


now that they're a publicly traded company, there's no way Zuckerberg could ever downsize Facebook into an honest company without the shareholders throwing a fit or suing the company.


Ah! That's an angle I hadn't considered yet.

Was there a concrete point at which you and your co-founder agreed to accept a minority stake and therefore give up absolute control? Was it a hard call to make or, already then, a relief because of the employee accountability?


Having a board of directors over you doesn't always mean dropping to a minority ownership stake, or even giving up absolute control.

The board of directors is legally responsible for running the company, in practice through major company decisions and scrutiny, so you can take some relief from that if you're a CxO doing what you think best "day to day" but not entirely sure you really know by yourself. Your board will get the legal blame if it goes seriously wrong and you've kept them sufficiently informed and involved in key decisions.

But you can still have a majority ownership stake while appointing a board. In doing so, you keep ultimate control (as shareholders) but you won't often exercise it.

Having ultimate control might change the social dynamics, but shareholders are not responsible for the company, the board of directors is and they should know it. Shareholders have the power to pass resolutions which effectively override directors, but most of the time they don't. Even if they do, it's up to the directors to figure out how to do what the shareholders want in a responsible and defensible way.


That is a totally different situation. Your customers can't just do whatever they want to you whenever they want. A board coalition with more than 50% of the shares can. They can say anytime they want, "we want out, your job is now to sell the company at the least possible loss". I have had this happen at a place where I worked.


It can if you only have one customer. The issue is monopsony.


I'm replying to a comment that specifically said "customers" in plural. If you are in a situation with one customer, then really, you're not even talking about a company-and-customers relationship anymore, that's more like a consulting or contracting relationship and is a whole different ball of wax.


I'm sorry customers are no boss.


yeah, this has always been the dumbest of takes. When I have an issue at Amazon, is Bezos picking up the phone? Hell no. Even at places where the "customer is always right", all that means is the customer is the boss of the hourly wage slave. The CEO doesn't give a damn. And this results in so much ugly behavior here in America, where customers think they can throw drinks at fast food workers and have an adult tantrum.

Anyone comparing a customer to a boss has had the luxury of never having a terrible boss.


customers are much easier to fire than a boss.


you can fire SaaS customers. happens all the time.


> Even if you are totally self funded you still are accountable to your customers.

Rentiers are an exception.


I think that this is a natural consequence of organizing your economy around "Capital" instead of people.

A fascinating alternative has been proposed by Yanis Varoufakis in which financial markets are eliminated, but labor and commodity markets remain: i.e. you can only own a single (variable value, single vote) share in 1 company at a time (usually a company you own are employed at); that share is tied to you as a person like a library card (you can't give it to someone else). Essentially all enterprises become cooperatively owned by the people who WORK for the enterprise. People have accounts with the Central Bank of their nation, etc... This stuff is pretty straightforward to do since banking is almost entirely automatable now.

But that's far too egalitarian to catch on with the current state of affairs. :-)


I think it is the opposite - it is a consequence of which system has better long term surviveability.

Companies survive because they don't die. That seems trite, I know. The consequences of it are important, as the equation is one where no matter how well you do, avoiding death is what matters.

SHL at Gumroad is a great example. SHL was encouraged to quit by the VCs when Gumroad was not a clear unicorn[1]. SHL chose not to let Gumroad die, and Gumroad lives.

The problem with all the ideas like the one Yanis Varoufakis proposes, is that they will almost certainly do well in good times, but companies survive because they don't die, and any system like the one you mention will lead to more dead companies.

That's a big claim I know, but imagine a situation where a company has 20 people - 4 sales and 8 support (secretaries, returns, admin) in the office and 8 people who work in fulfillment - a warehouse and lets say deliveries. Times get tough, and they are forced to have a vote on who needs to be sacked - how do they vote? 12 of the 20 work together, do you really think they will vote to have their friends in the office sacked?

And would they even get to that point? Why would anyone ever vote to lose their job? And what about pay rises? How do you negotiate pay rises when everyone votes? In a multi-division company, lets say 3 divisions, would everyone vote to take a lower pay than people in a more productive division? Would hiring be run along profitability lines, with one division growing large, or prestige/some other political goal like maintaining voting block power?

Capital has clearly aligned goals that round to "don't die". Capital will be assigned in productive areas, pay rates will be higher in more valuable divisions (AWS vs Amazon Warehouse workers) and kill off products that aren't working (See Google).

At the meta, system level, there is also alignment. Capital can be reassigned to different companies, aligning the individual players with the system overall. That is why Blackberry was valued below its cash on hand at one point - capital was reassigned as Blackberry was more likely to blow through the cash than grow. A system where shares can not be reassigned has no system level optimisation which saves the system, even as individual companies die.

The same is not self evidently obvious or clear in collectivist systems, and always needs a series of extra steps to overcome self interest to be possible, none of which are convincing over longer timeframes.

Any collectivist system would only need a very small bias towards something other than optimising profitability to have long term terrible consequences. Homo Sapiens had a tiny advantage over Neanderthals and other Hominids, and we are here and they are not. The casino advantage in most games is < 3% and think how much money they make.

Collectivist business ideas will have all the same problems of politics, combined with the ability to die completely, which Governments do not suffer outside of war, as they have a taxation monopoly.

[1] https://sahillavingia.com/reflecting - "Some of my investors wanted me to shut down the business. They tried to convince me that my time was worth more than trying to keep a small business like Gumroad afloat, and I should try to build another billion-dollar company armed with all of my learnings — and their money."


It’s funny you say our current system enables companies to “not die” in hard times. In reality, during hard times corporate socialism is used to ensure companies’ survival wherein the taxpayer bails our big companies. I see no reason why similar corporate socialism couldn’t be used in a different system.

It’s also interesting you think capitalism allocates capital effectively. I would argue the opposite, that it aims to concentrate wealth into the hands of the few. How many life saving startups die while Apple has hundreds of billions of dollars of cash? How many brilliant people are born into poverty and can’t enact their ideas, while Bezos buys his sixth house?


Is it really that surprising though? Reciprocal altruism is a part of human nature. We give other individuals stuff they want so they will give us stuff we want. At the end of the day the economy and financial system are just a big layer of indirection in the process. Now whether you call your bosses "customers" or "managers" or "the board," at the end of the day it doesn't surprise me that much that everyone answers to someone.


The one who puts up with the risk doesn't have a boss.

- Investors don't have a boss.

- A founder/CEO who owns 100% of a private company doesn't have a boss. But (s)he is putting up with very high risk, betting on self, and living with the consequences.


Great way to put this.


> it's kind of weird how we managed to create a world where nearly everybody has a boss

It’s a feature. Cycles get rid of hierarchies and individual corruption.


I don't understand why you didn't get more upvotes. This is a great angle (that aligns somewhat with Sytse's comment further up) that I hadn't considered yet. It's also a good counterpoint to the "having a boss is not natural" idea.


It's not that weird when you consider that most of us are descended from agriculturalists, where that pattern has prevailed since the dawn of civilization (proper).

Hunter-gatherers have patterns we can also describe as hierarchical as well, but it's meaningfully different.

Given the cultural, and possibly even genetic, coevolution of this strategy, bosses are going to be 'sticky'.


Ultimately the customer is at the top of the org chart, although one may be many abstract levels removed from their aggregate "management" decisions -- by intervening "middle managers" like the CEO, the board, and VCs. But certainly, in a smaller entrepreneurial venture, one feels the pressure from that ultimate boss more acutely.


On the contrary: the customer is a resource to be sought, managed and exploited.

The boss ultimately dictates how this is to be done. Businesses fire customers, pivot the business to seek better ones, abuse/shortchange/swindle their customers all the time.

There are Bureaus of Consumer Protection, but no Bureaus of Boss Protection.


Perhaps you understood me too literally. I mean the customer as boss in the abstract sense — not as if they are making literal management decisions. Customer as metonym.

When you seek product-market fit, or decide which features to prioritize for development, you are in effect seeking to satisfy this boss. When you make pricing decisions, you’re likewise being guided by the constraints of your target customer base. The customer can ultimately shut you down, firing everyone, to stretch the metaphor. Can you fire the customer? Sure. But you always need a customer of some kind, and as a going concern you ultimately serve at the pleasure of that (aggregate) customer, and not the reverse.


Having a panel of bosses is emphatically worse than having a boss.


Everyone has a boss - whether it’s their customers or someone else.


Physics is the final boss.


> EDIT: meta-level comment: it's kind of weird how we managed to create a world where nearly everybody has a boss. CEOs answer to the board, who answer to shareholders, who work at investment funds that have bosses and shareholders and LPs of their own, and down the rabbit hole it goes. I wonder if there's any general way out of this, different from "bootstrap a SaaS" which is a little specific to be good general advice.

This is one of the many points Kaczynski makes in his argument that “the Industrial Revolution and its consequences have been a disaster for the human race.” The complete lack of true autonomy seems inherent to the system.


Do you really think most individuals in hunter-gatherer societies had true autonomy? Or serfs in feudal Europe? In fact, if you have accumulated some degree of financial independence I'd argue you can have much more autonomy today than just about anyone pre-industrial revolution.


Of course, if you’re capable of retiring and not working for the rest of your life, you can be very autonomous. You can also be autonomous if you are a lord in feudal Europe, because in these situations you’ve ascended to a position where other people work to satisfy your material needs. Which is really no autonomy at all because you are reliant on the rest of society to continue to literally work for you.

Money abstracts this away, but if you achieve “financial independence”, that just means you have accumulated enough wealth tokens that you can indefinitely have enough to exchange for things that someone actually had to go make. You’re “autonomous” in the sense that you’re utterly dependent on an entire society that agrees with the practice of doing work in exchange for fiat currency. But the Pharoahs were also utterly dependent on a society that agreed with the practice of doing work because if you didn’t, the pharoah’s bureaucrats wouldn’t keep your land irrigated and you would starve to death.

But autonomy as a person who actually does work is another thing entirely. Industrialization introduced time clocks, shift work, Taylorism, and all kinds of stuff that eroded that autonomy.


> Do you really think most individuals in hunter-gatherer societies had true autonomy?

Actually, yes I do. It depends on which hunter gatherer society, but there is some indication from Sumerian scripts that before statecraft came a laisser-faire world, where people did not need to respond to a higher power, because one could always choose to bugger off to somewhere else.

It only works of course when there is excess food compared to the amount of humans, which is not a stationary situation as humans multiply to fill that gap.


Everyone works for someone else, but at a certain level both of organizational standing and (for lack of a better way to put it) moral fluidity, you become invincible.

CEOs only answer to shareholders insofar as they're expected to deliver a profit, which is actually very easy to do because most business "profit" is actually rent-seeking derived from resources (including intangibles) the business already owns. You have to be incredibly hubristic to fail as a corporate CEO. It's an easy job.

That's not true for small companies. Startups are harder, and startup CEOs are basically middle management within the "hive company" of venture capital. The true executives are the VCs who float from project to project, careers and fates diversified, and can peel their names off anything that looks like it's going to fail.

In big companies, though, most CEOs would do better not to show up, except once a quarter to give a speech or something. All they do is fire people, producing churn, and get in the way of the people who do the actual work. They can only fail if their egos get the better of them and they get so hubristic that they break something that used to be working. The same is mostly true of executives in general, although they have a little more vulnerability insofar as (a) if their bosses screw up, they may end up eating blame, and (b) if the CEO screws up so bad he himself gets fired, they'll probably also be replaced during the regime change.


Do you actually have any experience or even a remotely internal view of how much CEO actually matters in multi billion dollar companies? Or are you just making incorrect assumptions based on no actual knowledge and experience?


In 2000s, there was an ownership dispute between stakeholders of a major Polish telecom (PTC at the time, now part of T-Mobile). It resulted in the company having two sets of CEOs and board members for a couple of years, with all the chaos at the highest levels of the company that could result from it. And yet, the firm plowed on successfully, didn't lose market share and is to this day very healthy.

It makes you wonder how important those big wigs really are. In my current company (a big bank), from what I'm seeing the execs are so far removed from reality by layers and layers of middle-managers who distort and manipulate facts to their favor when reporting upwards, that what the execs think they're managing is really some kind of alternative-universe avatar of the bank. Essentially they're operating in a Matrix created for them by their army of underlings.


There was a nice story that made me realize that in John Brooks' "Business Adventures"

The one about electric companies colluding, where the execs kept telling their subordinates not to collude with competitors, while said subordinates thought it was some sort of inside joke and just kept doing it.

Funniest part is, the execs apparently did not know, while their subordinates thought they were "clearly" communicating they were.

The morale, to me, was that management, at any scale or level, really only has as much power as their subordinates let them have.

And that implicit meanings, in communication, are absolutely and deeply unreliable.


In nearly all mature, publicly traded firms, if the death of the CEO would cause a big disruption for the firm's future prospects, then it is not a well run business. The decisions required at 99% of these mature companies do not require Steve Jobs-esque foresight nor risk taking.


Precisely. These businesses exist to minimize risk, which includes personnel risk. Everyone should be replaceable, even upper management. (Which is to avoid the psychological costs of replaceability or of investing oneself into work one knows that plenty of other people could do-- that is not something companies concern themselves with.)


Not to jump in on this question exactly, but Rakesh Khurana wrote a very well-researched book about the market for corporate CEOs, finding that expectations are hugely inflated with meager correlation between CEO compensation and anticipated results.

https://www.hbs.edu/faculty/Pages/item.aspx?num=11408


At that level, you don't get the salary your work "is worth", because we all know that's a fictional concept. Dollar value is only well defined for finished products. For labor, it comes down to relative leverage, and as a CEO, you get whatever you can get, and your buddies are on your board and you're probably on their boards, so usually that number is quite high.

CEOs may not be smart in the IQ sense we nerds tend to worship, but they understand leverage and positioning, and they understand how to hack complex human systems for personal benefit, because it's what they did to get their careers in the first place.


If you had to do an analysis. What would you say is the difference between Balmer's and Nadela's Microsoft.


I'd probably argue that's an extreme example but, yes, many CEOs absolutely do make a difference in terms of establishing culture and setting direction and strategy. Certainly bad CEOs can do a lot of damage. And I expect a lot of people saying CEOs don't make a difference would be utterly lost if they were dropped into the position at a large company.




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