IBM to buy HashiCorp in $6.4B deal

First of all your percentage of ownership is unrealistic. I joined in November 2019 and got a grant of a few thousand RSUs that fully vested before I left, and that I still have most of, plus I bought some shares in a few rounds of our ESPP when that became available -- as of today I have just under 5,000 shares. HashiCorp has nearly 200 million shares issued, so I own a hair over .0025% of the company. Really early employees got relatively big blocks of options but nobody I knew well there, even employees there long enough to be in that category (and there were very few of them still around by December 2021), was looking at "fuck-you money" just from the IPO.

Second, the current price isn't the whole story for employees. I had RSUs because of when I joined so the story might have been different for earlier employees who had options, but I don't think it differs in ways that matter for this discussion. As background for others:

* On IPO day in December 2021, 10% of our vested RSUs were "unlocked" -- a bit of an unusual deal where we could sell those shares immediately (or at any later time). Note "vested" there -- if you had joined the day before the IPO and not vested any RSUs yet, nothing unlocked for you. (Most of the time, as I understand it, you don't have any unlocked shares as an employee when your company IPOs -- you get to watch the stock price do whatever it does, usually go down a lot, for six months to a year.) * At a later date, if some criteria were met (which were both a report of quarterly earnings coming out and some specific financial metrics I forget), an additional tranche of vested shares (I think an additional 15%) unlocked -- I believe this was targeted at June 2022 and did happen on schedule. * After 1 year, everything vested unlocked.

At the moment of the IPO the price was $80, but it initially climbed into the $90's pretty fast. At one point, during intraday trading, it actually (very briefly) broke just above $100.

So, if you were aware ahead of time that the normal trajectory of stock post-IPO is down, and if you put in the right kind and size of limit orders, and if you were lucky enough to not overestimate the limit and end up not selling anything at all, then you could sell enough shares while it was up to cover the taxes on all of it and potentially make a little money over that. I was that lucky, and managed to hit all of those conditions while selling almost all of my unlocked shares (I even managed to sell a small block of shares at $100), plus my entire first post-IPO vesting block, and ended up with enough to cover the taxes on the whole ball of already-vested shares, plus a few grand left over. Since then, I haven't sold any shares except for what was automatically sold at each of my RSU vesting events.

For RSUs not yet vested at the IPO, the IPO price didn't matter because they sold a tranche of each new vesting block at market price to cover the taxes on them when they vested -- you could end up owing additional taxes but only, as I understand it, if the share price rose between vesting and sale of the remaining shares in the block, so you would inherently have the funds to pay the taxes on the difference. (And if the price fell in that time, you could correspondingly claim a loss to reduce your taxes owed.)

There were a fair number of people who held onto all their shares till it was way down, though, and had to sell a lot to cover their tax bill in early 2022 -- I think if you waited that long you had to sell pretty much all your unlocked shares because the price was well down by tax time (it bottomed out under $30 in early March 2022, then rose for awhile till it was back up over $55 right before tax day, so again, if you were lucky and bet on the timing right, you didn't end up too bad off, but waiting till the day before April 15 was not something I bet a lot of people felt comfortable doing while they were watching the price slide below $50 in late February). I even warned one of the sales reps I worked with, while the price was still up, about the big tax bill he should prepare for, and he was certain I was wrong and that he would only be taxed when he sold, and only on the sale price. (He was of course wrong, but I tried...)

The June unlock was pretty much irrelevant for me because by that point the share price was down under $30 -- it spent the whole month of June after the first week under $35. The highest it went between June 30, 2022 and today, was $44.34. The entire last year it's only made it above $35 on three days, and only closed above $35 on one of them. I figured long-term the company was likely to eventually either become profitable, or get bought, and in either case the price would bump back up.

I was thinking about cutting my losses and cashing out entirely when it dropped below $30 after the June layoffs, and again in November when it was below $20, and then yet again when I left the company in January of this year, but the analyst consensus seemed to be around $32-34 through all of that so I held on -- kinda glad I did now instead of selling at the bottom.

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