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If founders treated their investors the same way they treated their employees

software.rajivprab.com

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Re: If founders treated their investors the same way they treated their employees

#161
post #147

Earlier quoted context omitted.

Options aren't a game. They're preferable to employees, for tax reasons. If startups gave employees shares, then employees would have to pay taxes on those shares, even though they're illiquid - so you're paying taxes on something you can't even sell! Options solve this problem well, by delaying the tax burden until the equity is actually worth something. If it ends up worth nothing, you don't exercise your options a…

I doubt that's the reason. Like some FAANGs do with stocks, can't you always deduct a part of RSUs as tax liability and add the remaining into the employee's account?

You can do this at a public company because the RSUs are liquid. They can be sold at market rate on the stock market, for cash, which is what's given to the government. The government doesn't want your illiquid startup shares.

Re: If founders treated their investors the same way they treated their employees

#162
post #76

Earlier quoted context omitted.

FWIW it's rooted in US tax law. Unexercised Incentive Stock Options (ISOs) are required to expire 90 days after an employee leaves. The way some companies get around it is that, after 90 days, they replace the expired ISOs with nonstatutory stock options which, as their name implies, are not recognized by the tax code. Tax code is complicated but NSOs are ultimately worth maybe 10%-20% less than "equivalent" ISOs. Bu…

> NSOs are ultimately worth maybe 10%-20% less than "equivalent" ISOs I'm at a company that gives NSOs. Can you explain what you mean when you say that NSOs are worth less than ISOs?

Obvious disclaimer: I'm not a tax specialist. You should not rely on tax advice found in an internet comment. I probably got some stuff wrong below.

When you exercise an ISO, it is not considered regular taxable income. It is as if you legitimately purchased the stock on the market for that price. No tax is due until you sell. If you sell immediately then you pay regular income tax on the gain. But if you hold it for at least a year, then you pay long-term capital gains rate, which maxes out at 20% (vs. 37% for regular income tax).

When you exercise an NSO, the gain is considered income and is immediately taxable at regular income tax rates, whether you sell it or not. If the company is not public, then you can't sell share to pay the taxes, so if you're going to exercise NSOs, you'd better do it either before the valuation has gone up much (in which case you end up paying mostly long-term capital gains tax), or wait until after IPO (and pay regular income tax). Since investing in startups is very very risky, exercising early probably isn't the right choice for most regular people.

Extra complication: The US has two tax codes that exist in a sort of quantum superposition. Each taxpayer must pay whichever tax bill is larger of the two. The above describes the regular tax code, but there is also Alternative Minimum Tax (AMT). Under AMT, ISOs are not special; they are treated like NSOs. But, the maximum tax rate under AMT is 28% rather than 37%, and doesn't kick in until higher income levels. So if you exercise ISOs before the company has gone public, but after the valuation has raised significantly over the exercise price, you might again have trouble paying the taxes. But if you manage to pay them, and you manage to hold for a year, your overall gain will probably be 10%-20% more than what you would have gotten with NSOs.

Extra extra complication: Let's say you exercise your ISOs before IPO and you manage to pay the AMT. Years later, you sell the stock. Is your capital gains computed based on the ISO exercise price, or the valuation at exercise? BOTH! Under regular income tax, you owe capital gains on everything since the exercise price, but under AMT you already paid for the gains between the exercise price and the valuation at exercise. If you don't want to get double-taxed you have to learn what it means to take a credit for a timing-based AMT adjustment. This is well beyond the point where Turbo Tax gets pretty unhelpful and you probably need to get a CPA, but in the Bay Area there are so many rich clients that a decent CPA will charge thousands (maybe tens of thousands) of dollars to do your taxes. Have fun!

All that said, if your plan is to exercise-and-sell in one action sometime after IPO, then I think ISO vs. NSO doesn't make much difference.

Re: If founders treated their investors the same way they treated their employees

#163
post #8

Bravo bravo bravo! This piece neatly encapsulates all the problems with ISOs. The biggest one is mentioned at the beginning - information asymmetry. I don’t really understand why most companies, especially small ones less than 100 people, can’t be transparent about their cap table with employees. I do think the culture around 90 day exercise Windows is changing. Here is a list of companies with extended windows [1].…

AFAIK the 90 day thing was more of a legal thing than something the companies themselves wanted to enforce?

The UK is much better in this regard as the HMRC has rules for approved option schemes - I have EMI shares in my current employer

Re: If founders treated their investors the same way they treated their employees

#164

The last time I got hired into a startup with options, they didn't tell me what percentage of equity the options represented, they just said, "You get 50K." I didn't even ask for any more details because their choice to give numbers instead of a meaningful metric made me think to myself, "OK, so I'm deciding whether to take this based solely on salary, and anything else is just a future bonus, not a deciding factor."…

I never even think about options. They're a non-factor when deciding to work at a startup or any company. I don't even know why they bother to give them out. As an alternative to tiny options they could opt to give people a bonus on acquisition or IPO or find some other incentive to keep talent. I'm honestly more interested in 401k contributions.

Re: If founders treated their investors the same way they treated their employees

#165
post #152

Earlier quoted context omitted.

Same happens in big cos when sometimes hundreds or more engineering years are scrapped purely because of internal political wars or “reorgs”

That's precisely my point. Startup work is not any more meaningful or everlasting than work at a big company. GP claimed PMs at big companies only come up with meaningless work but I think the work is meaningless almost everywhere. Every human needs purpose but pouring yourself into something that is very likely to have so little permanent impact seems foolish. I think there is a desperate call for balance in life wh…

I disagree - it’s just way harder to come by any meaning in the corporate world than it is in startup. Startups have to assign meaningful work to everyone they hired or they die. Not so for big (or even medium) corp so they have to play the “work life balance” card so you don’t blow your brains out from boredom. Ofc that also means big cos are more welcoming to people who didn’t want anything to do with their work in the first place and just in it for the paycheck (nothing wrong with that) and it’s always a spectrum.

Re: If founders treated their investors the same way they treated their employees

#166
post #134

Earlier quoted context omitted.

The problem is that some people need money and can't say no. That's why anybody works for minimum wage... The executives and investors and FAANG engineers have all made good money and seen decent RSU terms, you can't pull the wool over their eyes. Someone who is just getting into tech may be allured by a 50k salary and "1 MILLION OPTIONS!!!!" (There are ten trillion in the option pool). I think engineers would do wel…

I've seen startups willingly train their new employees to think about equity in broken or meaningless terms. Early in my career I sat through a discussion of equity with a VP of engineering where they explained that our options would always be priced ~$4 on acquisition and $12 on IPO. The finance people would always just make it work that way regardless of the number of options in the pool and the total valuation. I…

yup. we went through a down round at a previous company. if i were to exercise my options, I'd be immediately down 50%. some "incentive."

Re: If founders treated their investors the same way they treated their employees

#167
post #66

Earlier quoted context omitted.

Main reason: it's more fun. I could be a cog in a giant corporate machine, or I can have a measurable impact where I work. I can stay in my lane and do my specific job tasks, or I can run around putting out fires and helping wherever help is needed. I mindlessly build the specific design product handed me, or I can guide my own work in accordance to the needs of our customers and the business. I can follow policy and…

>I could be a cog in a giant corporate machine, or I can have a measurable impact where I work. I think that point can support working for either a big company or a small company depending on what type of impact you are looking for. I've worked for startups in the past and have had a huge impact on the startup but almost no impact on the outside world because the startups just weren't tackling very visible problems.…

> I think that point can support working for either a big company or a small company depending on what type of impact you are looking for.

For a lot of people, "I want to have an impact where I work" is more about their own ego and sense of importance than about impact on other people's lives. This is not a value judgment, by the way - wanting to feel like more than just another faceless disposable drone is a valid desire.

Re: If founders treated their investors the same way they treated their employees

#168
post #161

Earlier quoted context omitted.

I doubt that's the reason. Like some FAANGs do with stocks, can't you always deduct a part of RSUs as tax liability and add the remaining into the employee's account?

You can do this at a public company because the RSUs are liquid. They can be sold at market rate on the stock market, for cash, which is what's given to the government. The government doesn't want your illiquid startup shares.

Can't you postpone the tax to be paid to when actual tradable equity will be delivered?

Re: If founders treated their investors the same way they treated their employees

#169
post #3

Valid reasons to work for a startup: - You are a cofounder. - You have little experience and you are using this to break into the industry, and get experience on many different technologies ("wear many hats"). - They are working on a very specific problem or using a specific technology that you strongly desire to work on and it's difficult to do it anywhere else. - You want to work a certain way (remote, on the beach…

I mean, making a lot of money in salary is a very valid reason if they actually pay you a lot of money in salary (it does happen).
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