Except they sold the company at a ~flat multiple over the valuation. If employees got RSUs, then at least they made say $65K after short-term capital gains (30%+). But if as options... no growth over the latest valuation's strike price, so nothing. $65K is not $200K and certainly not $2M.. and $0 is even worse.
FWIW, I'm a happy customer, am happy for the founders, and hope the new features keep rolling out through the acquisition -- our usage of Loom grows every month! The issue here is not the founders, but HR & VC. This is why joining companies with high valuations is a big risk as the VC's have already set inflated prices that ate your potential payout -- you earn on growth over the strike price at time of joining -- and these high markup companies have a lot of revenue to grow into.
At least once a year the company would be required to do a 409a valuation to set the FMV for those underlying common shares and thus the strike price for any options in the next year or less. The 409a valuation for common shares is pretty much always going to be significantly discounted vs preferred for a variety of reasons like lack of liquidation preference, lack of liquidity, etc. These discounts are often 50% plus, but the shares likely have a 1:1 economic value to other share classes in a sale, except the most recent preferred that get to use their preference.
Anyways the reality is going to be determined by each company’s details, but option strike prices at private companies are generally much lower than the current going price for preferred due to the discounts provided by the 409a valuation.
by the time of these $100M+ rounds for $1B unicorns to hire a lot of people, the 90% discount is long gone
and relevant to this case, often the investor will do a higher valuation (artificially minting a unicorn etc) for optics/vanity reasons, which eats an additional 1+ years of future growth, eliminating the relevance of a discount here
and for folks who many not have followed terms above: investors get preferred shares, with rights over these discounted common shares. These include things like veto rights over acquisitions, first money out ("if $200M raised, no one else sees any $ until that $200M is paid back"), and for high-valuation unicorn rounds, often something like a participation multiple ("guaranteed extra $100M profit, so no one sees anything till $300M paid"), high interest rate on convertible debt portions, etc. So beyond the obvious dilution hit of new investors, there are a lot of these gotchas that trade a bigger bank account for heightened exit value risks to employees.
I assure you they can get more creative than saying that the last preferred price was at $X, therefore our hands are tied and the common must be close to that. They can take into consideration the preferred preferences, the current state of the business, the time since the last round, etc. For example, the 409a value can keep going down and down if the value of the business is (defensibly) going down and down, regardless of the last fundraising round.
And totally agree wrt creative arguments being viable... Just not clear what ends up happening in practice. Ex: I can imagine a split between paper unicorns vs ones w revenue backing it up being closer to market, and those later ones often switching to RSUs. So genuine curiosity here.
Early employees would be lucky to get options worth 10-20bps of the company, so assuming $800M was distributed to shareholders after accounting for 1x liquidation preference that might only be $800k-$1.6M before accounting for dilution for the very earliest employees, and a lot less for everyone else.
Why do I think they didn't make much from vested shares? Simple preference math. While I don't know Loom's cap table, or how each round was structured, I think we can all agree that they gave shares to investors that at least had 1X preference. Given that the sale happened at a substantial discount to their last round valuation, it's likely that preferences ate up most if not all of the proceeds of the deal. There may have been a sweetener of some sort offered to the leadership team, and that may have been distributed to all existing employees, but that would have been independent of the cap table (they're not going to give a package to departed employees that exercised options).
Options from the last raise would be under water, but they operated for years before that raise. There are likely a lot of employees doing reasonably well.
So it's possible for employees to have joined after the new 409a when it was valued at 1.5bln and early exercised against that value.
Depends on the exercise price. Exercise price is lower than the preferred price that the investor paid. Due to the fact that investors get preferred shares.
409a can often be 20% of the preferred valuation.
In this case, since series C was 1.5bln and sold for $975m, then the preferred shares were bought during C would be made whole first (assuming the prior rounds were made whole first and there's enough left over for series C preferred) before those who exercised right after the valuation for common shares.
Edit: I forgot that preferred shares also come with liquidation preferences too, meaning that in a loss situation, later employees are highly unlikely to get something
Depending on liquidation preference clauses I don't think any employee outside the founders will make much from this sale.