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Re:Boards are dangerous to founder/CEOs by hinkley on Tuesday November 23, 2021 @02:41PM (#29322324)
They don't have to value the company at $0 to fuck you over once you're gone. The current board can depreciate all of the shares by 50% and then issue themselves twice their original shares so they break even. Then do the same thing a couple of rounds later.

I haven't seen $0 but I knew a few people who got diluted to a joke. It doesn't take but a factor of 2-4 dilution of your outlook to drastically change your opinion of how you spent that time.

Re:Boards are dangerous to founder/CEOs by jasode on Tuesday November 23, 2021 @03:42PM (#29323221)
>They don't have to value the company at $0 to fuck you over once you're gone. The current board can depreciate all of the shares by 50% and then issue themselves twice their original shares so they break even.

Mark Zuckerberg tried a variation of that game to cut out Eduardo Saverin's shares when they changed the company from a Florida LLC to a Delaware Inc. Well, Saverin sued and Facebook lost that lawsuit; they settled. Saverin got ~4% ownership worth $5+ billion at the time.

https://www.businessinsider.com/exclusive-heres-the-email-zu...

Re:Boards are dangerous to founder/CEOs by Kranar on Tuesday November 23, 2021 @05:49PM (#29324546)
Facebook did not lose any lawsuit. A settlement is a far cry from a loss and judging from the outcome, it looks like Saverin got screwed over.

So basically, the board will try to screw you over; if you're not in a strong enough position to do something about it then you're out of luck, if you are strong enough to do something about it, then you might be able to recoup some of what you're entitled to.

Re:Boards are dangerous to founder/CEOs by distribot on Tuesday November 23, 2021 @07:09PM (#29325339)
Anyone know how Zuckerberg avoided the same thing happening to him?

Bezos was a 30 year old with a decade of experience in finance, I assume he was quite savvy. But Zuckerberg was a teen.

Re:Boards are dangerous to founder/CEOs by tdfx on Tuesday November 23, 2021 @10:05PM (#29326538)
As far as I can tell, Zuckerberg's true talent is being thrown into situations he has no life experience to handle and appropriately picking the right people to surround himself with and listen to.
Re:Boards are dangerous to founder/CEOs by disgruntledphd2 on Wednesday November 24, 2021 @07:53AM (#29329499)
>Zuckerberg's true talent is being thrown into situations he has no life experience to handle and appropriately picking the right people to surround himself with and listen to.

This seems to be falling apart for him right now, as a bunch of those people have recently left FB. But yeah, I generally agree with your main point, he does seem to be very good at this.

Re:Boards are dangerous to founder/CEOs by jacquesm on Wednesday November 24, 2021 @12:01AM (#29327059)
To steal their ideas and screw them over.
Re:Boards are dangerous to founder/CEOs by jerrre on Wednesday November 24, 2021 @05:04AM (#29328492)
that part is normally just silently implied...
Re:Boards are dangerous to founder/CEOs by ngcazz on Wednesday November 24, 2021 @06:39AM (#29328989)
Situations like work.
Re:Boards are dangerous to founder/CEOs by asdfasgasdgasdg on Wednesday November 24, 2021 @12:38AM (#29327218)
He had more power, because Facebook was an obvious rocket ship. So he could make better deals for himself when it came time to finance, and retain a controlling share in the company. If the board tried to fire him, he could just fire the board.
Re:Boards are dangerous to founder/CEOs by LudwigNagasena on Wednesday November 24, 2021 @12:14AM (#29327118)
He has the controlling stake in the company.
Re:Boards are dangerous to founder/CEOs by dbuder on Tuesday November 23, 2021 @09:43PM (#29326434)
They did it to others? They knew ownership and control was paramount and acted accordingly.
Re:Boards are dangerous to founder/CEOs by djyaz1200 on Tuesday November 23, 2021 @08:17PM (#29325881)
Shawn Fanning
Re:Boards are dangerous to founder/CEOs by andrewseanryan on Tuesday November 23, 2021 @09:02PM (#29326193)
Pretty sure it was Sean Parker but I could be wrong
Re:Boards are dangerous to founder/CEOs by djyaz1200 on Tuesday November 23, 2021 @10:05PM (#29326541)
One of the Sean's :)
Re:Boards are dangerous to founder/CEOs by CRConrad on Friday November 26, 2021 @09:45AM (#29350628)
Or Shauns.

(Oh holy fucking mother of Baa[l], only now it struck me that the name of the animatronic series by the Wallace-and-Gromit guys is of course a play on Shorn the sheep!)

Re:Boards are dangerous to founder/CEOs by Cymen on Tuesday November 23, 2021 @04:17PM (#29323663)
I experienced dilution as a former employee of a startup. Teespring did a 13:1 down round a year or so after I left (2015?). If you weren't an accredited investor that could afford to invest in the round, you had 1/13 of your original shares after the round finished. I experienced both being pushed into AMT when exercising the options (they didn't offer early exercise) along with having 1/13 of my shares later on. No idea if I'll ever see any money out of the deal so I've chalked it up being a lesson learned -- many say to value stock options as $0 but they can have negative value.
Re:Boards are dangerous to founder/CEOs by jiveturkey on Tuesday November 23, 2021 @05:28PM (#29324356)
well to be fair, you should never exercise if it isn't early exercise. the odds are very much against you. I mean, by the odds you shouldn't early exercise either but at least you don't get hit by the AMT bullet.
Re:Boards are dangerous to founder/CEOs by redshirtrob on Tuesday November 23, 2021 @07:08PM (#29325324)
That's certainly not true. You should evaluate the investment just like any other investment and decide if you can afford to lose the money and stomach the risk.

Part of your evaluation should be consulting a tax professional to determine if there are any immediate, negative tax consequences. You're not guaranteed to get hit by AMT just because you exercise some stock options.

Re:Boards are dangerous to founder/CEOs by lumost on Tuesday November 23, 2021 @09:52PM (#29326480)
There are very few times where the finances work out for options. Most employees lack access to the necessary company financials to make an informed financial decision, there is a 100% downside risk and barring early stage founder equity stakes - it's unlikely that the equity will do better than getting lucky on a top stock pick.

I have yet to hear a single case of an employee purchasing their options when they left and thinking it was the right decision later on.

Re:Boards are dangerous to founder/CEOs by mavelikara on Tuesday November 23, 2021 @10:33PM (#29326682)
> I have yet to hear a single case of an employee purchasing their options when they left and thinking it was the right decision later on.

I know at least a dozen ex-colleagues of mine who fit this criteria. When the company in question exited, it created 400 millionaire employees.

Re:Boards are dangerous to founder/CEOs by ido on Wednesday November 24, 2021 @05:50AM (#29328748)
that's the problem with anecdotal evidence - you can't really tell for sure a company is going to become a massive unicorn often until very close to the point it does. I've worked at companies that raised many millions of $s and seemed very promising and a few years later went out of business. Who becomes a winner is also not always completely "fair" (as in it depends somewhat on circumstances/fortunate happenstance).
Re:Boards are dangerous to founder/CEOs by mavelikara on Wednesday November 24, 2021 @11:45AM (#29331945)
> you can't really tell for sure a company is going to become a massive unicorn often until very close to the point it does.

I don't contest this point.

> I've worked at companies that raised many millions of $s and seemed very promising and a few years later went out of business.

The only narrative I contest with my anecdata is drawing a universal truth from this experience of yours.

As a sibling comment said:

> Salt of the Earth folk love to share their stories of financial misery, but generally keep quiet about their embarrassment of riches.

Re:Boards are dangerous to founder/CEOs by ido on Thursday November 25, 2021 @01:50AM (#29338855)
I think it's the other way around - we comparatively hear a lot more about the successes than the failures. For every unicorn that made 400 people millionaires there are probably >1000 startups that either went out of business, never had a liquidation event, or never at the scale that rank and file employers got anything significant.

Obviously not literally "nobody", someone at some point joins google/microsoft/facebook/amazon/etc at an early stage and exists a millionaire many times over. Just like every week somebody wins the lottery. It's just not as likely to happen to you personally as the people selling you on joining their early startup would like you to believe.

Re:Boards are dangerous to founder/CEOs by mavelikara on Thursday November 25, 2021 @02:48PM (#29344387)
> I think it's the other way around - we comparatively hear a lot more about the successes than the failures

Not here on HN.

I was prompted to post on this thread after reading comment after comment about failures.

Re:Boards are dangerous to founder/CEOs by lumost on Wednesday November 24, 2021 @10:02AM (#29330612)
aye - latecomers to a company may have massive financial/product impact but have less equity when the IPO happens vs. those who were there initially and left after 12 months. On the other side the board and others can dilute early equity holders at their leisure.

At the end of the day you're really throwing money into a black box which may turn out to contain a trash can. There is more financial transparency in penny stocks.

I've personally had great success with RSUs, but those are ultimately part of your comp even if you discount them to zero - there is no requirement to put in additional money.

Re:Boards are dangerous to founder/CEOs by sgtnoodle on Wednesday November 24, 2021 @06:34AM (#29328963)
I won't claim that it's the expected outcome for most, but I've exercised options well into AMT territory on multiple occasions, and it seems to have worked out favorably to the point that I could probably skip the ping pong and shrimping boat phases and jump straight to mowing lawns for fun like Forrest Gump.

Also, I have heard stories of former employees that didn't exercise their options or cashed out early, and I wouldn't say regretted it, but reflected on the fact that the stock did a lot better than they predicted it would.

Salt of the Earth folk love to share their stories of financial misery, but generally keep quiet about their embarrassment of riches.

Re:Boards are dangerous to founder/CEOs by bagels on Wednesday November 24, 2021 @12:53AM (#29327282)
I purchased options. Some didn't pan out. Some did. Was an early employee on all of them, purchase price was relatively low, and I don't regret any of them.
Re:Boards are dangerous to founder/CEOs by jiveturkey on Tuesday November 23, 2021 @07:50PM (#29325667)
If you aren't getting hit by AMT, the company is not growing fast enough and you should not exercise. If you are getting hit by AMT, the chances are you are out the exercise cost plus the AMT.
Re:Boards are dangerous to founder/CEOs by redshirtrob on Tuesday November 23, 2021 @08:04PM (#29325790)
I've done exactly what you're saying I should not do and it worked out very well.

My point is that these hard and fast rules don't leave any room for nuance. Consider, as I mentioned in another comment, you don't have to exercise 100% of your options. Exercise whatever makes you comfortable. Maybe that's one under the number that would push you into AMT.

If zero is your comfort level, then so be it. But get to that conclusion by doing a little thought and evaluation, not applying an arbitrary rule.

Re:Boards are dangerous to founder/CEOs by jiveturkey on Tuesday November 30, 2021 @06:24AM (#29391004)
Preface: humans are really bad at assessing risk. Also, you can't help but be biased in the decision process. Most people want a chance at the golden ticket. Especially after all that hard work we put in! We deserve a payout! What was I going to do with the $10,000 anyway, really? It won't break me.

The people that can make a reasoned and well considered, as impartial as possible judgement about it don't need to be told to do so. In fact, a statement that one should never buy the options can and mostly will (rightly so) just be ignored by such people.

But, judging by the number of people that have NO CLUE about how it works, need only the tiniest thing to grab onto to make the wrong decision. There is zero need to recommend "well consider your risk". If you have to ask, then my advice is always as I gave it: not to skip it as a rule, but if you re-read you'll notice all I said was, the odds are not in your favor and you "should" just leave the options behind. I think there is a subtle but important difference. Maybe I'm splitting hairs, if so, sorry.

You're actually arguing survivor bias as being some kind of counter argument! You are in the pretty small minority, I do hope you understand that.

Tell me, how do you feel about COVID vaccine? Shouldn't we just be allowed to make up our own mind about it? If masks and vaccines work, well the scientific set can wear masks and vaccine up. The anti-vax crowd can do as they please and die. We don't need the government to TELL US what to do, do we? No one gets out alive anyway, amirite?

What is your recommendation on COVID? Evaluate the risk and decide for yourself? Surely you prefer Florida's or Texas' take on COVID to California's then?

I now come full circle: humans are really bad at assessing risk.

Re:Boards are dangerous to founder/CEOs by hinkley on Tuesday November 23, 2021 @07:36PM (#29325565)
> You should evaluate the investment just like any other investment

Except it's not like any other investment. It's an investment that you are too close to. You can't think 100% objectively about an investment that you're too close to. For many people the solution is unambiguous: If I can't be objective about a decision then the answer is automatically 'no'.

Re:Boards are dangerous to founder/CEOs by redshirtrob on Tuesday November 23, 2021 @07:52PM (#29325684)
There are lots of things I'm close to that I need to think objectively about. Maybe I don't hit your ideal of 100%, but I do my best. Investments is one area. The health and well being of my children is another. You can never have perfect objectivity. You do the best you can. GP's advice is too rigid and therefor not very good.

FWIW, I'm speaking from experience. Had I taken GP's advice and "never exercise unless it's early exercise" then I would have missed out on a lot of money.

The other thing to keep in mind is you don't have to exercise 100% of your vested options. If you're too nervous or don't trust your own judgement, maybe go for 10%, or whatever makes you comfortable. There's a lot of room between 0 and 100 here. Go ahead and explore it.

Re:Boards are dangerous to founder/CEOs by low_common on Tuesday November 23, 2021 @04:16PM (#29323645)
How does share dilution work? Does that mean issuing more shares? How does depreciating shares happen?
Re:Boards are dangerous to founder/CEOs by hinkley on Tuesday November 23, 2021 @07:40PM (#29325598)
It's not a publicly traded company so the paper is worth exactly as much as the people who hold most of the paper decide it's worth. They need some sort of majority to vote to change the rules, and since the employees with unexercised shares control exactly 0.0 repeating percent of the company, you're going to lose that vote.

It's a democracy where the wolves vote that the sheep will be dinner.

Re:Boards are dangerous to founder/CEOs by throwawaythekey on Wednesday November 24, 2021 @12:32AM (#29327188)
Employees with full (exercised and vested) shares at my company don't have any voting power until after an exit event. The paperwork these days is truly ridiculous.
Re:Boards are dangerous to founder/CEOs by gnopgnip on Tuesday November 23, 2021 @08:29PM (#29325977)
The board and officers still have a fiduciary duty to minority share holders. Even if they can vote the company is worth zero and issue 100x as many shares, a court can say the company wasn't worth zero and they need to compensate the former owner.
Re:Boards are dangerous to founder/CEOs by ganeumann on Tuesday November 23, 2021 @09:16PM (#29326280)
While this is theoretically true, I think you would be hard-pressed to find an example of someone suing and winning.
Re:Boards are dangerous to founder/CEOs by jacquesm on Wednesday November 24, 2021 @12:04AM (#29327073)
I know of several such cases, but it's costly, and usually a good idea to decide whether or not you want to pursue something like this involves the cost (and stress) of a lawsuit over an extended period of time, and to ensure that that is outweighed by the upside of winning the case.
Re:Boards are dangerous to founder/CEOs by MagnumOpus on Wednesday November 24, 2021 @06:34AM (#29328962)
Hard pressed? Ed Saverin is a very well known case. He sued Facebook after his co-founder Zuckerberg diluted him out and settled for multiple billions. But then, it was a unusually straightforward case because Zucks put his malicious intentions in writing.
Re:Boards are dangerous to founder/CEOs by mleonhard on Wednesday November 24, 2021 @03:18PM (#29334624)
Could an employee union balance out the power of the board? They could attend board meetings and veto deals that harm the employees via strike or mass resignation.
Re:Boards are dangerous to founder/CEOs by anamax on Wednesday November 24, 2021 @10:47PM (#29338049)
Unions don't necessarily get board observer status, let alone board seats, AKA a board vote. Having a board vote isn't the same has having a veto over every possible decision.
Re:Boards are dangerous to founder/CEOs by mleonhard on Friday November 26, 2021 @06:45PM (#29355519)
You seem to be replying to a different comment.

> Having a board vote isn't the same has having a veto over every possible decision.

My comment did not imply that a board vote grants veto power. I suggested that the union could "veto deals ... via strike or mass resignation". This means that the union decides on a maximum dilution and agrees to strike or resign if the board makes a deal that dilutes employee positions more than the maximum.

> Unions don't necessarily get board observer status, let alone board seats, AKA a board vote.

My comment did not mention anything about board seats. The board would grant the union permission to attend board meetings, lest the board inadvertently trigger a strike or mass resignation.

Next time, please read the comment carefully before replying.

Re:Boards are dangerous to founder/CEOs by anamax on Friday November 26, 2021 @10:58PM (#29357263)
Take that up with the person who wrote "[The union] could attend board meetings and veto deals that harm the employees via strike or mass resignation."

Board meetings are for board members, so I gave that person the benefit of the doubt.

My mistake.

Re:Boards are dangerous to founder/CEOs by mleonhard on Sunday November 28, 2021 @01:05AM (#29366592)
You seem to be attacking the weakest part of my idea and ignoring the strongest parts. Apparently, there is a new word for this: dunking [0]. Please stop.

Your replies go against the guidelines [1]:

> Be kind. Don't be snarky. Have curious conversation; don't cross-examine.

> Please respond to the strongest plausible interpretation of what someone says, not a weaker one that's easier to criticize. Assume good faith.

> Please don't post shallow dismissals, especially of other people's work. A good critical comment teaches us something.

[0] https://news.ycombinator.com/item?id=29352131

[1] https://news.ycombinator.com/newsguidelines.html

Re:Boards are dangerous to founder/CEOs by antoniuschan99 on Tuesday November 23, 2021 @04:09PM (#29323568)
How does one go about learning about these things. HN crowd definitely leans towards the technical side myself including.

Btw. The blog is very informative and have subscribed.

Re:Boards are dangerous to founder/CEOs by hinkley on Tuesday November 23, 2021 @07:34PM (#29325545)
> How does one go about learning about these things.

A very good question that I don't have a good answer to. Management likes that there's a steady stream of new people who don't know that there's a bunch of tricks that get used and so everyone learns them the hard way.

Re:Boards are dangerous to founder/CEOs by anandrew on Tuesday November 23, 2021 @04:29PM (#29323805)
Could you explain more? Because this sounds like it should be very illegal. My understand is that shares represent partial ownership of the company. So what gives one set of shareholders the right to reduce others' ownership share?

In fact, why don't the boards of all companies do this? Devalue everyone else's shares so they become the sole owners?