This is a fabulous article and I only want to add a tiny little bit of additional context:
* Exits north of $100MM are rare, and a $400MM exit is rare indeed; virtually any such exit will be from a famous company. Valuations are at least somehow tethered to sales, and companies that justify mid- 9-figure exits can usually consider IPO... as an example of how rare that event is.
* In most sectors of the industry there are rule-of-thumb valuations based on multiples on sales. An enterprise software company aiming for a $150MM acquisition is expecting 4-8x, and needs to be achieving 18MM (optimistically) to 40MM (conservatively) sales to do that. You can reconcile this estimate by asking for current sales, this year's "number" (in a well-run company, everyone knows the number), and then asking "what's going to happen to scale the number up".
* Last time I had to think pragmatically about VC, a round that took participating preferred shares (in which the VC takes their money off the table, then takes their percentage off the table) was an indication of a weak round; if they're shooting for the moon, you're entitled to hold that against them.
* Finally, remember that if you quit, the equation changes again. When you leave, you can execute your vested options, but that costs money. Perhaps nobody in the company is less protected than former employees: investors have contractual provisions to protect their money, and employees are given retention grants, but former employees can be written right out of the deal. I've seen it happen.
My very first job was at a startup and I was all excited to get stock options. Later, I heard from a colleague who had bought his options from a previous company which had been bought recently: he had a call with the CFO who had to explain that, no, there wasn't anything left for the options he had bought. So, the $5k or so he paid for it were worth nothing at all.
That's when I learned to lean more towards the "options are worthless unless you're a very early employee in a high-potential startup".
(when I think about this, it saddens me a bit how cynical my first jobs have made me)
Having friends who had the same experience, that's been my attitude as well, but since I have a knack for sounding like I know exactly what I'm talking about even when I don't, let me candidly say that this attitude cost me a low but significant amount of money when my last employer got acquired. I didn't exercise my options.
I don't regret it, because the money I'd've spent to exercise helped get me through year #1 at Matasano, but if it hadn't, I might be upset.
former employees can be written right out of the deal
Can you elaborate on this? How does this work? As a holder of a lot of common stock in an increasingly VC-dominated company, this is interesting to me - surely if I buy my shares, I have that proportion of the company with the same rights as any other common stock holder? What about a "normal" acquisition deal could change that?
You can bet that the founders and VC's (or other institutional investors) own a super-majority of the shares. Therefore, they can simply write the rules to give themselves whatever they want. For even more fun, sub-groups of VC's can team up to force out founders or other VC's.
One way this is typically done is to increase the share count by 10X, then sell these new shares for 10 cents on the dollar to a sub-group of new investors.
As an existing shareholder, you MAY have the right to buy into such a deal, but only if you are a "qualified investor", meaning that you have substantial liquid wealth. Otherwise, you'll be left sitting on the sidelines.
Even in a "normal" acquisition, the current shareholders will have to vote on the deal, so it's not uncommon for the large shareholders to cut lucrative side deals with the buyer that give them much more profit than the average shareholder.
This all sounds plausible but note that the owners don't even have to intend to screw you out of your equity to screw you out of your equity. All that has to happen is for the company valuation to come in under the value of liquidation preferences, or for the deal to be so tight that much of the return is structured as an earnout for existing employees.
One mistake in the above: the right to participate in future financing rounds has nothing to do with qualified investor status, and everything to do with whether your agreement guarantees it. Good CEOs will often make sure all their investors are given a chance to participate (because it's the right thing to do and reduces the chance of one class of lawsuits) but it's only a guarantee if your documents say it is.
I was locked out of an investment round at one company because of qualification status. I'm pretty sure being meeting the accredited investor standard actually does matter, at least if you're not an employee and the round involves an exchange of money for financial instruments.
If your agreement had guaranteed you investment rights you would have had them. Since it didn't, it was at their discretion, and they could have used many different criteria to make that decision. Now as a general rule, when you have an option in the matter, you don't want non-accredited investors in your deal. But assuming that accredited status grants follow-on investment rights (or that lack of them prevents it) as a rule is wrong.
Did Facebook's Eduardo Saverin get 5% of Facebook back because he was singled out? If more stock holders were pushed out, would Saverin not have gotten 5% back?
VC and founders, holding preferred shares, take money off the table first. If things get tight, later VC's may take 2+x preferences. Deals can be structured that return cash to the VC, wipe out the rest of the equity, and leave existing employees grants or bonuses for retention; this latter deal element is an incentive extended by the acquiring company, not an entitlement owed shareholders.
The later investors just barely made their money back, so the employee options were (probably) worthless as well. Google issued new retention to make up for the fact that the employees got squashed, but not every acquirer is so generous.
Is it normal for founders to have preferred shares? In our case the founders all have common stock (albeit a lot of it), and in fact it came with more restrictions than normal common stock, namely a 3-year restricted stock period similar to an option vesting period.
Dunno, but note that founders often hold board states, and VC has an incentive to make sure they can take some money off the table, else they can make it harder to complete the best deal VC thinks they can get, in the name of holding out for an actual return.
That's very normal; founders usually have mostly common, and sometimes have extra restrictions. The other commenter is right, though - anyone with influence in a transaction typically comes out better, and founders are often in such a position.
I can't tell you the best or even the most modern ways, but one of the simpler ways I've seen this done is a massive dilution where key owners (investors, founders) have anti-dilution clauses coupled with new grants and acceleration for current employees. This works even if the liquidity event is so massive everyone involved is recouping well past their preferences.
My impression is that options agreements and grants that offer any real protection against being screwed once the company lacks any incentive to keep you happy are few and far between. If you don't _know_ you're protected from such things, you're undoubtedly not.
* Exits north of $100MM are rare, and a $400MM exit is rare indeed; virtually any such exit will be from a famous company. Valuations are at least somehow tethered to sales, and companies that justify mid- 9-figure exits can usually consider IPO... as an example of how rare that event is.
* In most sectors of the industry there are rule-of-thumb valuations based on multiples on sales. An enterprise software company aiming for a $150MM acquisition is expecting 4-8x, and needs to be achieving 18MM (optimistically) to 40MM (conservatively) sales to do that. You can reconcile this estimate by asking for current sales, this year's "number" (in a well-run company, everyone knows the number), and then asking "what's going to happen to scale the number up".
* Last time I had to think pragmatically about VC, a round that took participating preferred shares (in which the VC takes their money off the table, then takes their percentage off the table) was an indication of a weak round; if they're shooting for the moon, you're entitled to hold that against them.
* Finally, remember that if you quit, the equation changes again. When you leave, you can execute your vested options, but that costs money. Perhaps nobody in the company is less protected than former employees: investors have contractual provisions to protect their money, and employees are given retention grants, but former employees can be written right out of the deal. I've seen it happen.