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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

#531
post #496

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

This is a sad story: 90-day exercise windows are employee hostile, they should be much longer, especially when the company isn't public. However, and I don't know how to put this more kindly, but I can't help but wonder if you understood how options work while employed at the company? A simple technique to avoid having to quickly come up with a lump sum is to set aside enough money to excercise your options as you ac…

Yeah, it wasn't the case that I couldn't have come up with the $34k at all, it's that it was asked of me in the first place given that I'd already put in far more than $34k of extra hours and had no shares to show for it.

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

#532

Earlier quoted context omitted.

> None of the thousands of extra hours I worked (I kept track) counted for anything Yep, that's exactly what your management was counting on.

I worked my ass off at a startup, sleeping under the desk, weekends. The usual. At one point I needed a break and informed them that I was taking a break. Two months cycling through Europe. When I came back, they'd moved and I had the best cubicle reserved for my return. They missed me but only because I forced the issue.

It sounds like you realized you needed a break before it was too late (i.e. "burnout"), which is obviously good. But why did you return to this grind?

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

#533
post #24

Earlier quoted context omitted.

This advice is often given but it's easier said than done. Let's say you work at a unicorn for 3 years and in that time it goes up 10x in VC fantasy land valuation. On paper you have a lot of money and the company reasonably might go public a couple years after you leave. Let's say you're granted about a year's salary in shares when you first join so you've vested $100K for a round number. When you leave that equity…

The whole premise of a startup in any stage hiring a technical employee and granting them $100k worth of stock options will never happen. Typically you are granted X number of options. You are never told what the outstanding # of shares are and typically the shares themselves are valued in pennies. The idea is you think to yourself "well, it's 10k shares worth about $5k at the current valuation, but if they IPO and i…

> And the likelihood of a startup valuation increasing 10x in 4 years (typical vesting schedule) after dilution is extremely extremely unlikely to the point that it is time wasted even entertaining the outcome of such a scenario

You don't care about relative growth with options, just the difference between strike price and sell price. A '10x' growth of 0.01 to 0.10 only gains you 0.9 per option; a 2x growth of 5 to 10 gives you 5 per option.

Which is also why looking at your grant as '$100k worth' is silly. Look at how many units you have, and how the price might change, not what the strike price is right now.

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

#534

Earlier quoted context omitted.

> None of the thousands of extra hours I worked (I kept track) counted for anything Yep, that's exactly what your management was counting on.

I worked my ass off at a startup, sleeping under the desk, weekends. The usual. At one point I needed a break and informed them that I was taking a break. Two months cycling through Europe. When I came back, they'd moved and I had the best cubicle reserved for my return. They missed me but only because I forced the issue.

Sorry it sounds like the Stockholm syndrome.

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

#535
post #24

Earlier quoted context omitted.

This advice is often given but it's easier said than done. Let's say you work at a unicorn for 3 years and in that time it goes up 10x in VC fantasy land valuation. On paper you have a lot of money and the company reasonably might go public a couple years after you leave. Let's say you're granted about a year's salary in shares when you first join so you've vested $100K for a round number. When you leave that equity…

So I never understood - it seems like it would cost you 200k to buy something worth a million. Arent there people/institutions out there that would cover the 200k cost in exchange for maybe 300k worth of stock?

Unless there's buyers for that stock lined up, what you're buying is only worth a million on paper.

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

#536

Earlier quoted context omitted.

You do realize that this is the exact premise of risk and reward? That company could have been the next Google, Facebook, Amazon, etc, and in those 800-ish days you would have given up for weekends over 8 years you could have earned more than all of your ancestors probably have ever earned in their entire lives. All in a fraction of your single life. And yet, we still get posts like this one, and comments like yours,…

I think the point is employees under estimate the risk involved. I could make a start up that pays people in literal lottery tickets but I'd be unable to hire anyone because prospective employees can easily see it's a bad deal. Not the case for start ups.

I was thinking yes, but then no?! I bet you could hire a bunch of people with lottery tickets!

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

#537

Earlier quoted context omitted.

Given how few startup companies actually make it, treating it as zero is the only sane and rational thing to do.

Right, because it's better to be paid $X/year and have 0 stock options than it is to be paid $X/year and have Y stock options, and no sane person would prefer the latter or negotiate for a Y large enough to be worth something even if the startup doesn't "make it" but is sold for 5x less than they tell you the IPO is going to be. And a company that has already got $200M invested into it is just as likely to fail to gr…

Given loss aversion and human talent for rationalising their sunk cost, do you really think you'll be able to accurately value those options? Treating them as worth 0/ε is a good heuristic, it'll give you the right decision basically every time.

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

#538

Earlier quoted context omitted.

Others may messed it up, but Intuit lobbies to keep things that way. Here's their lobbyist's disclosure form. It says "Oppose IRS government tax preparation" right there in Box 16. https://soprweb.senate.gov/index.cfm?event=getFilingDetails&... Their SEC disclosure says essentially the same thing. Grab it from here: http://investors.intuit.com/financial-information/annual-rep... Specifically, on page 10 of the 2016 v…

Who's eligible for free tax preparations?

There is an income threshold: $64,000 for 2016, which the IRS says covers ~70% of tax payers.

If you make less than that, the "Free File Alliance" let you submit a simple federal return for free using their software. They may try to upsell you on various things and may charge for a state return too.

Above that threshold, your only free options are the paper forms or the "Free Fillable Forms" online. The latter option is really simple. It will copy some numbers from place to place and does some basic math, but beyond that it is very similar to filling in the paper form--it won't help you optimize your return or anything like that.

More here: https://www.irs.gov/uac/free-file-do-your-federal-taxes-for-...

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

#539

This has caused me some level of sadness in the past. I worked for a startup (started 6mo after founding with only 20 people and stayed for 8 years to 200+ people and 50million in revenue). During a number of phases, I worked for months at a time giving up weekends, late nights, holidays and even vacation time to get product out the door and beat the competition. I racked up 50k options, mostly all for less than a do…

If you are working for a small company, be a founder, not as an employee. Many folks mistake small companies as startups. Startup is a place where exponential growth happens. From what I see, this is a just a small company which had regular growth. Run if you don't see exponential growth.

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

#540

Earlier quoted context omitted.

I worked my ass off at a startup, sleeping under the desk, weekends. The usual. At one point I needed a break and informed them that I was taking a break. Two months cycling through Europe. When I came back, they'd moved and I had the best cubicle reserved for my return. They missed me but only because I forced the issue.

It sounds like you realized you needed a break before it was too late (i.e. "burnout"), which is obviously good. But why did you return to this grind?

Interesting work and stock. I was partially vested and I could/should have looked around.

Don Knuth said something (about TeX): never spend more than 2 years of your life on something. I've broken that rule several times but I'd counsel following it on startups, especially someone else's startup.

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