When a Unicorn Startup Stumbles, Its Employees Get Hurt

The management pushing the stock and painting a rosy picture while behind the scenes the ship was sinking.

The employees putting everything they had (and then some) into a single stock from their employer.

I don't know if there was criminal behavior involved but an imbalance of information was in play that cost the employees everything and then some.

Indeed. Smart, young companies are refusing preferred share investments and are willing to keep their valuation lower because of that. It's true that you're selling a larger portion of your future for less money in many ways, but you protect the founders and original investors as well as the employees too.

Huge growth is important but it's also important to be smart about it. Selling a part of your company for a bit less if often better than mortgaging the common shares.

> that employee would still have had to personally fork over the amount needed to purchase the underlying shares

Then what is the difference over just buying the shares outright as opposed to exercising options?

My understanding has always been that exercising options means getting a benefit (the shares) which has a value (the strike price) and you subsequently pay tax on that value.

You have not yet actually made a guess you've just kept asserting that "a lot of money" is "a lot of money" and I agree. A lot of money is a lot money. I just think that modulo nobody is actually seeing a lot of money from start-up employee equity.

I remember clearly when I was in a similar situation with the sale of a company I helped start in 1999. All this gain on paper which required (because of the Alternative Minimum Tax rule) that I pay taxes on gains I had not realized. And then later realizing an actual loss. And the decade afterwards of getting $3,000/year that I could claim against my taxes.

The only reason I'm not still claiming my $3,000 a year is that we had some gains that could be offset by those losses in 2007 and 2008. Of course there are the much higher fees to have your taxes prepared.

I agree with the Times that it is the non-executive employees who get the worst of it, both because it may be the only investment they have (other than their 401k) and they may not have any experience in managing risk.

For example, the article mentions, and my own experience mimics, that the executives are in a bind when it comes to discussing company performance and prospects. Legal risks abound if they mislead and existential risks abound if they demoralize the company. It would be especially problematic when the company has started the IPO process as Good had.

Then there is the greed factor that comes in on everyone's part. The board turns down an $825M offer because they feel it is their duty, given they expect the company is worth more than that. Employees don't cash out some of their holding at $3/share expecting a bigger IPO lift. Both angry because nobody came from the future to tell them, hey this is the best offer you are ever going to get for this stock, take it. And so they "ride" the value down and get angrier and angrier but its hard to know at whom.

When this happened to me, I was holding 10,000 shares of Sun stock that had been $60 a share in 2000, that was going down and down and down. It later reverse split 3:1 (so down to 3,333 shares) and sold for $9.50 a share to Oracle or about $32,000. I was really angry at myself for "losing" so much money. Of course it wasn't that I had "lost" the money, I never had it, it was all on paper, I just hadn't converted at the time because I was hoping to convert when it was even "more". Or put another way, my greed kept me from selling something which could have paid off my mortgage at the time.