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What I Wish I'd Known About Equity Before Joining a Unicorn

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Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#12

Should have been titled "... in the USA" as tax rules are very different in other countries. For instance, in France, you only owe money to the taxperson when you sell your shares, for a profit. If you sell for a loss, this is tax-deducible.

Doesn't apply to Canada, either.

Well, unless the options are for shares in a non-Canadian controlled private corporation.

Got bit by that little loophole in my late stage startup when facing options expiration...

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#14

As always the main rule you need to live by is value the equity at zero and you'll be (maybe) happy. Short of being a founder (and thus not really being offered equity) I have never treated these things as anything beyond a minor on paper "bonus". Given you'd be lucky to get anything more than 1% even as a first employee I find them next to worthless as early stage motivators. Which is how everyone seems to play it -…

Exactly what everyone should do. If someone is obsessed with these kind of topics I think he should start his own startup and be a founder/co-founder.

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#15
Let me save you some reading: bargain down the options and go for the increased salary instead. I suppose that's not true if you're planning on staying long enough until you can exercise them, but I've been very happy doing that at the last few places I've worked at.

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#17

Great post and I totally agree. I recently talked to my financial advisor about my current company and we went through all the numbers for various pricing scenarios (of a public offering) over the next 4-6 year, at various valuations. From his point of view, he encourages me to stay the course - quite the opposite from most of the tech friends I know (most usually don't stick around after a few years). On a side note…

JIRA is not that bad. It was pretty stagnant for a while but they've been improving it. I think JIRA is an invaluable knowledge capture tool, particularly when you're tracking down a difficult root cause and you want to keep a bunch of people in the loop.

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#18

Great post and I totally agree. I recently talked to my financial advisor about my current company and we went through all the numbers for various pricing scenarios (of a public offering) over the next 4-6 year, at various valuations. From his point of view, he encourages me to stay the course - quite the opposite from most of the tech friends I know (most usually don't stick around after a few years). On a side note…

I hate it because it feels incredibly crusty. Nothing seems to update without hitting F5, there's annoying amount of jargon and poorly named fields everywhere, and in my company it's also tied into everything from client billing to asset management, presumably because it's sold as something that does everything including breakfast, and all that noise seems to permeate into every ticket type (I can't search for a ticket type or field anymore, there are over 400 types so the autocomplete is useless, I just ask PMs to make them.)

Re: What I Wish I'd Known About Equity Before Joining a Unicorn

#20

Should have been titled "... in the USA" as tax rules are very different in other countries. For instance, in France, you only owe money to the taxperson when you sell your shares, for a profit. If you sell for a loss, this is tax-deducible.

The US really does have a lot of problems with their tax system to be honest.

For a country whose citizens outwardly hate tax, you'd think they would have one of the best, most straightforward, and fair tax systems in the world. But instead you have one of the most convoluted, loopholey, broken systems in the world.

Whereas in countries where taxes aren't as "hated" (Europe, Canada, etc) they don't pay a cent to file taxes, have less loopholes, it is less complicated, and overall fairer.

If I was an American I'd hate tax too, but you guys made it that way. Why does it still cost money to file taxes anyway?

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