People keep not understanding or appreciating this point. This is precisely what Uber is in the middle of doing right now too, and to some extent probably what Spotify did, and the future value of those two is by no means clear or stable.

As long as they can can prop up the valuation for a short time, they can capitalize shortly after an IPO and externalize the losses on unwitting millions of people who came to own some unicorn stock because they were auto-enrolled in the 2055 retirement mix of some bottom scraping asset manager that charges high fees on a portfolio with loose definitions of what it can invest in.

There have been winners and losers on the tech IPOs of the past 5yrs. I'm curious how you differentiate the losers from the winners since some of the tech IPOs have done quite well.

(although, to be fair, Blue Apron is an obvious case of the next groupon.)

This is actually pretty wrong. Most likely they knew the real valuation was closer to $1, and so similar to the trajectory of a missile that goes up first so it can coast down, the IPO valuation is propped way up, to give plenty of room for it to fall during the lockup period and still be overvalued.

Making ~4x the (approximate) real valuation (which is already probably way higher than what they paid per share to invest) probably meant a significant return. Kind of like private equity strategy from inside a start-up.

I’m sure that employees with relatively low amounts of options plus a lockup period, needing to use their own money to buy the stock, with some more recent employees at relatively bad strike prices by comparison, did get screwed over.

Which is why you never, never accept options-based equity as compensation, and never accept an ultimatum between a competitive salary + low equity vs. less than market salary + higher equity. The lottery winners for whom these arrangements worked out should not factor into your judgment. And likely any experienced engineers should be requiring bonuses, meaningful severance, comprehensive insurance and a host of other forms of compensation.

Lot of them even bought more at that price thinking how low can it go.

Not really, search google for apron, and only one of the results is blue. Most common aprons are white, and black, so those would have better brand recognition.

No