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> The answer makes one good point, though: D'Angelo did invest his own money in Quora, basically buying sole control over the company.

The first clause (investing money) is a much less profound statement than the second clause (buying sole control).

In order to buy sole control, he set the valuation of the new shares at something that washed out the "A" round guys. That should be a giant red-flashing signal to everyone involved.



I'm a VC, and when I read the line "buying sole control" I assumed that the Series A investment from Benchmark is intact, and their shares still vote on any protective provisions granted to the preferred stock, but Adam simply bought enough stock in the Series B (in combination with his originally granted founders shares) to do two things:

1) represent a majority of all outstanding stock (both common and preferred). 2) represent a majority of all preferred stock.

If the preferred stock votes on all protective provisions in an all-for-one manner, then Adam would control the preferred voting, assuming #2 is true above. All-for-one means that all classes of preferred stock vote together as one group, and each share, regardless of class, gives you one vote. If the governance issues that affect the preferred stock are not setup as "all-for-one" voting, then the other likely situation would be independent class voting, in which case Benchmark and Adam would each get their own veto (Benchmark would control the voting of the Srs A and Adam would control the voting of the Srs B, and so they could each vote the other party down). If Adam really has sole control, then preferred voting would need to happen in an "all-for-one" manner.

My explanation is just an assumption based on that one flip line, but that's how it reads to me.


> then the other likely situation would be independent class voting

There is a third situation, which is that Benchmark walked away from the B. Given the value of an asset sale, they would not have much to lose.

> My explanation is just an assumption based on that one flip line

Yes noted, and I should have also noted in my post that it's quite possible the reporter confused "80% of B" with "80% of the company".


I'm not sure that actually happened, and is probably a mis-representation by the journalist. I imagine that investing a lot of his own money has got the board, uh, on board, and proven that he is very serious about the things he wants to do.

But I might be wrong.


I've recently started trying to understand how these dilution events occur. I was wondering if you could better explain what happened in this case so I could further my understanding.


Its fairly straightforward. There is 'money' and there is 'stock'.

Money funds day to day operations, pays salaries, power bills etc.

Stock determines ownership, and in most corporations governance.

Now day to day you spend money and ideally you also get revenue. If the revenue that comes in for any given month/quarter is more than the money going out that month/quarter then you are 'operationally cash flow positive' meaning that other than something like a big lawsuit or a promissory note coming due or some big financial event you can keep working and the lights on. It doesn't necessarily mean you can hire anyone or 'grow' or fund a PR campaign.

Then there is stock which represents ownership in the company, there can be multiple classes of stock which convey different rights, and there can be corporate bylaws which change how decisions are made while private vs public, but for the simple case we'll assume that 1 to 1, one share of stock is worth 1/(total-stock) of the company and exerts an equivalent amount of control. When you make a decision for the company you at the board level you effectively 'vote your stock' when you vote. If 50.1% of the stock votes one way that is the way the decision goes.

So lets consider a couple of scenarios:

Lets say the Company is :

   1,000,000 shares
   Investor A - 10% stock (100,000 shares)
   Investor B - 15% stock (150,000 shares)
   Investor C - 15% stock (150,000 shares)
   Founder A  - 25% stock (250,000 shares)
   Founder B  - 25% stock (250,000 shares)
   (everyone else in the company) - 10% remaining stock.
Now the two founders, if they agree they can get their decisions ratified by the board with one additional investor voting with them. The 'value' of the company is price-per-share * total shares. So lets say this company was valued at $10M so each share is 'worth' $10.

Now you need more money (revenues aren't covering it) so you try to sell more stock which is going to change the numbers around. Lets say you need $10M for the next 24 months and none of the investors want to invest any more money. You've got a crisis. But if you are also independently wealthy you can say "I'll put in the $10M but I'll take 2 million shares." So the 'totals' after that transaction are 3 million shares in total (up from 1 million) and as a strict percentage we've got:

   3,000,000 shares
   Investor A - 3.3% stock (100,000 shares)
   Investor B - 5% stock (150,000 shares)
   Investor C - 5% stock (150,000 shares)
   Founder A  - 8.3% stock (250,000 shares)
   Founder B  - 75% stock (2,250,000 shares)
   (everyone else in the company) - 3.3% remaining stock.
Founder B now has 'sole control' because they have enough stock to make any decision, vote their own stock, and have that decision be ratified.


You've got a crisis. But if you are also independently wealthy you can say "I'll put in the $10M but I'll take 2 million shares."

This is the bit I don't understand. Is the founder/investor essentially holding everyone else to ransom in such a situation, and saying they'll allow the company to go bust if the other participants don't accept a 2/3 cut in their voting power?

If so, how does a company or a co-founder protect against such tactics? I know about anti-takeover strategies like poison pills and so on in the corporate world, but I wonder whether they are really effective in the early stage rounds.


This is the bit I don't understand. Is the founder/investor essentially holding everyone else to ransom in such a situation, and saying they'll allow the company to go bust if the other participants don't accept a 2/3 cut in their voting power?

In this sort of scenario nobody is being held hostage. The situation is that more money is needed to keep the company operating, there are three ways of getting money, revenue from products, a loan, and selling equity (stock).

Generally revenue isn't a real choice, if it was there then the question wouldn't come up. A loan is trickier, a large loan wants some sort of collateral and if you don't have assets that the lender would take as collateral you are looking at an extortionate interest rate if you can get a loan at all. Worse it adds a re-payment schedule that adds to the burn rate. That leaves selling stock.

So how much is the company "worth?" and what percentage of it would an investor want to buy in order to participate? These are fuzzy numbers, you can say "well sales are X and as a multiple of sales its worth Y" or "the addressable market is Q and these guys capturing 10% would be worth P" but really it comes down to if you believe or don't believe the business is a going concern. It is the place startups go to die, because if they can't convince someone to trade dollars for stock, the next step is bankruptcy.

But if someone is willing to invest they will do so "on their terms" which is to say they will give the conditions under which they will invest. They write this out formally in something called a term sheet. It talks about shares outstanding before the transaction, the transaction itself, and the resulting ownership percentages and valuation post transaction.

So nobody steps forward, next step is bankruptcy. Someone does step forward, well now you have a choice.

A lot of funding agreements have a 'participation right' which basically says Investor A who has 10% has a 'right' to participate in any funding to keep their percentage at 10% or sometimes 10% of the round. So in our example Founder B says I'm setting the terms at $5/share and I'm buying 2M shares for $10M with a post money valuation of $6.66 per share. Then Investor A is offered a chance to participate at that price, so they figure out how many shares they would buy at $5/share such that their ownership would remain at 10% after the transaction. Or they decline. It is their choice. And they may decline because they think its not a good deal, or they think the company is toast anyway and they have already written off that investment as a loss.

Their choice is same voting power in a non-existent entity (bankruptcy) or 1/3 the voting power in a continuing entity. The latter is better than nothing as they say.

If so, how does a company or a co-founder protect against such tactics? I know about anti-takeover strategies like poison pills and so on in the corporate world, but I wonder whether they are really effective in the early stage rounds.

The board votes on whether or not to do the funding round or turn the company assets over to the creditors (bankruptcy) You protect against this scenario by making sure the company is always more valuable as a going concern than as piece parts. The board can try to negotiate a 'better deal' which is to say reduce the percentage stake the new investor is getting in order to approve it, but if they are not participating then that is not a compelling argument.


Thanks for providing such a comprehensive answer to such a basic question. I understood this in the abstract, but your explanation addressed the strategic interests of every participant so well that it improved my understanding enormously.


Poison pills are "triggers" in which new shares can instantly be added to the company, in order to hinder a hostile takeover.

For example, if someone with 20% shares is trying to sweep up to 51%, a poison pill can come into effect when someone gains 40% ownership of the company, which would then give shares to existing board members, etc. This creates new shares and dilutes shares, but it also dilutes the person's shares who is trying to do the hostile takeover.

You could ask, "Why would anyone ever need to insure against this?" but it happens. Publicly traded companies can represent a massive wealth in assets, which can be stripped away, sold, and cashed out as dividends.

If a company's share price is getting abnormally low, there is a risk that someone could see the assets as being worth more than what it would cost to do a hostile takeover.

For example: Chuck Conway did it with KMart back in 2002 when the company declared bankruptcy. They sold off thousands of the Kmart stores for their land.


> If so, how does a company or a co-founder protect against such tactics? I know about anti-takeover strategies like poison pills and so on in the corporate world, but I wonder whether they are really effective in the early stage rounds.

If it's between founders, you work out how you want these situations to play out and then you see a lawyer to form a contract that will bind you.


So in this scenario, does it also mean that the shares are now worth less too? As in they are now worth $3/share ($10M/3,000,000) whereas before they were worth $10?


if you re-did the maths with the same guy buying 1,000,000 shares at $10 a share then they'd still end up with a controlling share in the business (and the business would indeed be worth $20M since it was worth $10M before and now has an extra $10M in cash, meaning that shares would still be worth $10 each).

so i'm not sure why the original example needed to place an odd value on the newly issued shares. as far as i can tell, it just muddies things.

i wrote this on rights issues, which is kind-of related (works through a similar kind of argument, except this time framed so people keep the same fractional shares) - http://acooke.org/cute/EnersisEnd0.html [edit: just fixed url] (i'm no expert, i was just interested in that particular case in the chilean press recently).

in short: you don't need to screw anyone over. it can just be that the person putting most money in ends up with most of the ownership.

the two key points are: (1) people need to agree on the company's value before; (2) the company gets the cash (and so its value goes up). of course, that cash won't sit in the bank - but it's the company's responsibility (and the investor's hope) that it is spent in a way that increases the value of the company.


After the new $10M in cash it is $20M/3,000,000, so they are worth $6.66/share


Edit: yes the value goes down of the shares, but the calculation 'post money' is $10M + $10M / 3m shares so 6.66 $/share.


Both the way the OP question was asked, and your answers are fantastic.


"In order to buy sole control, he set the valuation of the new shares at something that washed out the "A" round guys. "

That's a significant over-simplification of what happens in this type of situation. There are all type of scenarios, and I've certainly been at a startup in which the founders have ended up with <5% of the company after investors came in with a significant round of $$$ required to grow the company - they certainly didn't consider it a "giant red-flashing signal" (they approved the deal, after all) but instead, a huge raise that led the company to a $1Billion+ valuation.




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