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

software.rajivprab.com

261–270 of 278 posts

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

#261

Earlier quoted context omitted.

> ... now I stand I make low 7 figures from the equity on this last company (publicly traded now). Isn't that a "never need to work again" situation though? eg, you've effectively freed up your future to put time into whatever you want?

Low 7 figures to me would be between $1,000,000 and $3,000,000. I don't think that I would call that "never need to work again" money. It's between 10 and 30 years of my salary. A good lump sum to stash in the retirement fund. Maybe retire at 55 instead of 65, but definitely not "never need to work again" money.

It's entirely possible to relocate to a different country with a cheaper cost of living, universal health care, etc too. So, the limits of the US system should be taken as a given.

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

#262
post #14

Earlier quoted context omitted.

Depending on the size of the startup at the time you join, I found it fairly easy to negotiate an extension to the exercise window. Likely because so few people even bring it up.

I joined very early (~15 people total at the company) and have been unsuccessful negotiating an increase. I guess the lawyers have to get involved, board has to sign off, and that's tough. Or at least, that's what I've been told.

This is the ultimate YMMV scenario, and heavily dependent on how bad the company wants you. At the end of the day you need to be in a place where you can walk away from any deal that doesn't make sense. Unfortunately people looking for jobs at startups are usually somewhat desperate.

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

#263
I have a question on this. I am employed in a startup since the last 3 years. I already have 100k shares vested (5 year window, 3 years passed). I can buy them at a low strike price (What happens if I don't pay the tax but just buy the options? Will I lose my options because I haven't paid the tax?

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

#264

I have a question on this. I am employed in a startup since the last 3 years. I already have 100k shares vested (5 year window, 3 years passed). I can buy them at a low strike price ( What happens if I don't pay the tax but just buy the options? Will I lose my options because I haven't paid the tax?

In the US, any stock held past December 31 of the year in which it was obtained by exerciing an ISO (the most common kind of startup option) generates "income" according to the Alternative Minimum Tax (AMT).

AMT is essentially a completely different taxation system that runs in parallel to regular income tax in America. If the shares you exercise are worth a good amount, you will probably wind up paying AMT, especially if you live in a place with high state and local taxes.

After calculating your tax liability for both systems, you have to pay whichever is larger of regular income tax or AMT. Usually this payment, or part of it, comes due April 15th of the next year. Your company is not involved in your reporting and paying these taxes, but it's a federal crime to either misrepresent your income (which omitting the exercise from your filing would be) or not to pay the appropriate taxes.

If you haven't realized yet, a lot of this is complicated, so do your own due dilligence and/or work with a tax professional.

The AMT tax rate is 26% or 28%. The "income" considered by AMT for exercising and holding is equal to the difference between your strike price and the fair market value (FMV) of the stock on the day you exercised. FMV is based on a 409a valuation for companies that are still private. For public companies it's the market price for the stock on that day.

I'm not sure what you mean by your having "a low strike price (To make the math easy, I'll give a hyptothetical...

You have 100k vested shares with a strike price of $0.10. The company has done well for the past 3 years and now has a FMV of $3.10 per share. To exercise 100k shares, you would need to pay $10k. However, if you're still holding these shares on 1/1/2021, you will have an AMT tax liability due 4/15/2021 of ~28% * ($3.10 - $0.10) * 100k = $84k.

Now it's weird how AMT works, so the above number isn't exactly what you wind up paying, but it's close. In general, the case stated above implies you would owe a sizeable amount in taxes if you exercised and held the stock.

People do this if they're leaving a company and their options will otherwise expire, or if they strongly believe the company will IPO or be acquired soon. Exercising starts a clock on the stock you're holding. If you hold the stock for a year after you exercise, your earnings will then only be taxed at the long term capital gains rate (probably 20%) rather than the ordinary income tax rate (usually higher than 20%). Earnings are the sale price minus the strike price (what you paid to acquire the stock or your "cost basis").

The downside of exercising now is 1) you have to pay cash to exercise, 2) you will generate a tax liability without necessarily having a way to sell your stock, and 3) if the price of the stock falls, the AMT you paid winds up being an even greater percent of the value. There is a way to receive credit on future tax bills for previously paid AMT tax that wound up like this, but it's complicated and best to be avoided.

The upside is mostly to obtain the a lower tax rate on the eventual sale. Most employees still with the company who didn't exercise their stock early don't exercise it until they plan to sell it.

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

#265

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 think engineers would do well to know that you are a COST CENTER to the business and the people who run it. They need you to make their product so they can make money but they hire you begrudgingly. I don't agree. Engineers are sometimes a cost center, but they can also be a profit center. You can help revenue by decreasing expenses by automating something or noticing how the business is wasting money w/r/t tech…

I can’t remember where I read this essay but it went along the lines of: no one is really interested in reducing costs, they’d much rather increase revenue, the reason being that the larger your budget the more important you are on the totem pole and reducing your (already approved) expenses doesn’t make your budget larger.

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

#266
post #262

Earlier quoted context omitted.

I joined very early (~15 people total at the company) and have been unsuccessful negotiating an increase. I guess the lawyers have to get involved, board has to sign off, and that's tough. Or at least, that's what I've been told.

This is the ultimate YMMV scenario, and heavily dependent on how bad the company wants you. At the end of the day you need to be in a place where you can walk away from any deal that doesn't make sense. Unfortunately people looking for jobs at startups are usually somewhat desperate.

Fair. I think the company wants me pretty badly, and knows I'll likely stick around because I'm still vesting. So there's no incentive for them to grant an exercise window extension at this point.

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

#267

Earlier quoted context omitted.

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…

You got everything right, but in my experience TurboTax handles the AMT credit just fine. I personally recouped 6 figures of credit carried over across multiple years, and TurboTax always automatically calculated the usable credit every year, and when I ultimately sold the exercised shares it also properly computed the different AMT cost basis, allowing me to recoup even more that year due to the higher spread. I wou…

I guess it's gotten better. I remember a time when they asked you to please just enter a number for your timing-based AMT adjustments without even giving you a hint what that is. Admittedly that was a long long time ago.

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

#268

Earlier quoted context omitted.

One should exercise at the earliest possible convenience. If I'd exercised on day 1 when I joined a startup, I wouldn't have owed tax because I wasn't getting a discount, but a locked-in price. So when I exercised after the value increased, I then owed tax. I've seen it suggested that one should exercise on day 1. But that doesn't have to mean you pay for them immediately (after all, you don't get to keep them immedi…

Or one should never exercise at all until an acquisition or an IPO happens. I've seen too many people exercise stock options trying to minimize tax implications down the road, only to see them eventually leave the company for any number of reasons and they end up get heavily diluted to almost nothing in future rounds. All that money basically down the drain trying to chase long term capital gains vs regular income ta…

You're definitely correct. "Convenience" is emphasized. If it's not convenient to exercise, don't; wait until a liquidity event.

This makes me curious: what's the total typically required to purchase one's options (not including the potential tax implications)? Does it vary wildly from a couple thousand to tens- or hundreds-of-thousands? Lottery ticket money, or significant fractions of annual income?

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

#269

Earlier quoted context omitted.

>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 d…

It's a more salient feeling. I worked at a school for a while, and you can have deep impact on a handful of lives. It doesn't scale, but you can really feel the effect.

On the other hand, if I submit a patch to Chrome that makes it 0.00001% faster, it's a much bigger impact -- millions of hours saved -- but it's an impact you can only see in aggregate statistics. No individual will even notice the effect, so it's much harder to see or feel. It's more abstract. You have to be pretty analytical to get the same level of satisfaction, even if you've done more to benefit people overall.

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

#270

The oft-cited quote is that it's very, very, very rare to make money working as an employee at a Startup. The farther you are away from the founding team, the harder it is. And 99 times out of a 100 even the founding team doesn't make anything, if there's an upside exit at all. If you want to work at a startup as a non-founder employee, go into it knowing that you're taking the risk and getting little of the potentia…

Your last sentence is key. I think it was a way of financing enterprises some centuries ago. Why is it no longer accepted?
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