> If you leave the company, your options will expire if you don’t exercise them. Let me repeat that: if you leave the company, your options will expire if you don’t exercise them. The exact timeline of how quickly they expire depends on option type and company policy, but the termination window is commonly as short as 90 days. So, exercising your options enables you to actually own what you helped build.<p>This is why I choose to not work for companies that do not have extended exercise windows -- and IMO neither should you.<p>[1]: <a href="https://blog.samaltman.com/employee-equity#:~:text=2)%20Most%20employees,employee%20gets%20terminated" rel="nofollow">https://blog.samaltman.com/employee-equity#:~:text=2)%20Most...</a>.<p>[2]: <a href="https://github.com/holman/extended-exercise-windows" rel="nofollow">https://github.com/holman/extended-exercise-windows</a>
I'm planning on exercising some of mine (in the post-resignation 90 day period) via EquityBee. I don't want to lower my own cash reserves now due to a looming recession, but do believe the company has upside. EquityBee (and a few other companies, like vested, all of whom I think are legitimate) gives me money to exercise the options in exchange for ~30% of the shares should the company go public, plus repayment of the original loan. It's a win-win for me. The worst outcome is I make no money; the best is that I keep 70% of my shares without paying for them. They even pay AMT.
I gave my Wife money to exercise her ISO's(startup before IPO) for her first 1.75 years of shares when the company valuation hadn't changed. Her company went public and the stock jumped and then crashed, I think the current price per share is lower than her exercise price so she is underwater and the money I gave her is worth less as shares vs. cash I originally gave her. Really a huge bummer as this job up-ended our life and she has absolutely nothing to show for 3 brutal years of hard work. I guess the only thing is wait it out and see if the shares recover.
I worked at a unicorn startup for about 1.5 years. It started to become clear to me that I probably wasn’t going to make a comparable income to what I was making before in a public company so I left. I exercised my shares. A year later they went public through a SPAC. the shares got a hair cut through the SPAC ratio. Total comp was still really bad but shares were locked up for 6 months or so (maybe longer I don’t remember). I couldn’t sell them and now that I can the total value is under $4,000. I paid over $1k exercising them which felt like an insane bargain.<p>Maybe it will work out better for some of you though. I feel like if you are not extremely passionate about a startup and you are not one of the original founders… great place to learn and build your career but don’t think it will make you rich
This article uses your net effective tax rate to calculate the taxes on the bargain element -- 32.25% on someone earning $150k in California. They should be using your _marginal_ tax rate for that calculation, which would be 24+9.3=33.3% on the first 170050-150000=$20,050 of the bargain element, 32+9.3=41.3% on the next 215950-170050=$45900, and 35+9.3% on the rest.<p>Or, much easier is to use a calculator like the one they link[3], and calculate your total taxes on your current earnings, calculate total taxes on the earnings if you were to exercise, and then subtract.<p>I calculate $81,599-$38,038 = $43,561 in additional taxes, rather than the $41,893 they said.<p>I agree with the author's take on ISOs:<p>> It’s a bit complicated – and dry – so if you have ISOs you should probably talk to your tax person<p>My opinion on ISOs is essentially that for some middle ground between "few enough ISOs that you don't trigger AMT" and "so many ISOs that the potential tax savings are more than big enough to pay for a financial professional", it's not worth it to try and exercise ISOs early.<p>AMT on ISOs will complicate your taxes for years to come: in some circumstances, you can recover some of the money you paid as AMT on the ISOs in future years -- essentially, ISO bargain element is a specific category of AMT-taxable income which gives you an AMT credit for future years, which you can recover with form 8801 [4]. For several years after my ISO exercise, I was able to eat away that credit by paying the AMT tax amount when it was _lower_ than my standard income tax.<p><pre><code> 1. https://taxfoundation.org/2022-tax-brackets/
2. https://www.nerdwallet.com/article/taxes/california-state-tax
3. https://smartasset.com/taxes/income-taxes#H3aXczXUcM
4. https://www.irs.gov/forms-pubs/about-form-8801</code></pre>
This is a fine article. It covers a lot of the decisions one must consider when considering stock options. I just think it's a little abstract for folks who haven't lived the experience.<p>I actually tried to enumerate the scenarios. When I hit five variables I realized the advice would be mostly worthless. That's 32 separate outcomes, some of which are pretty subjective, e.g. do I think this is a viable company?<p>Nevertheless, I've been down this road a few times. I have some wins and losses. I think this article misses an important point: Exercising is not an all or nothing proposition.<p>For example: If I join a startup and leave after a year, the difference between my strike price and the 409a price might be non-zero. I can still exercise a percentage of my options to avoid AMT. Maybe I can't exercise all of them without triggering AMT, but chances are I can exercise a fair amount.<p>If I'm offered an early exercise, I don't have to do 100%. I can do a number that fits my budget. I just have to make sure I file my 83b election form.
I'd like to know what to do with ~10 000 euros, right now. Where should I put it so it doesn't lose its value and keep a bit with inflation ?<p>edit for a bit of context: Western Europe, renting, unlikely to be able to buy/invest into a house/flat, looking at gold ingots, not the nerve for crypto.
It's perhaps worth noting that this the article is very US-centric. I'm in the UK, and I've never had an opportunity to exercise options that didn't come alongside an offer from the company to buy the shares. And in my experience, it's rare to exercise and hold. Even if you do, you can sell enough shares to cover the tax and keep the rest.<p>My current employer has (and uses) the right to repurchase any shares I hold at the current "fair market value" if I leave the business. That's also fairly standard for privately-held companies, it seems.
I help work on Compound (<a href="https://withcompound.com/" rel="nofollow">https://withcompound.com/</a>) (author of the essay also works at Compound).<p>We help tech employees manage their finances and specialize in equity compensation.<p>Our essay on equity and taxes may also be useful to those looking to better understand stock options: <a href="https://manual.withcompound.com/equity-guide-for-employees-at-fast-growing-companies" rel="nofollow">https://manual.withcompound.com/equity-guide-for-employees-a...</a>
Right now you want to be vesting in a promising company that is well funded and has revenue streams coming in. We are in the early days of creating the new winners of the next bull market.
I don't care about options. Let me see the money. Then I can buy shares in whatever company I want or invest in an index fund, managed fund or ETF.
I'm currently at a unicorn SaaS startup. I have 11,500 ISOs, about 7000 of which I've vested and exercised (I've got about 1.5 years left till I'm fully vested). My strike price is $1.50, which to me is a bargain, especially since there was a tender offer last year of around $14. There are ~70M outstanding shares.<p>Other stats: $60M ARR, 120% NRR last year, almost 100% YoY growth during 2021, raised $110M at 40x revenue last year, high NPS, company still has over $110M in the bank, TAM is in the tens of billions, current market penetration is <5%, planning to go public at $200M ARR. So the potential upside is huge.<p>Work environment is great, I have a great boss and a decently challenging/significant role. I'm a senior engineer making around $170k/year.<p>I'm curious what you all think - is it worth the risk of staying until I vest? The alternative would be to join a public software company and increase my salary significantly (which would help so much right now - we need a larger house for our kids).
The big thing to avoid is exercising at a high price, paying all your taxes, then watching the shares plummet the next year, and eventually selling at a loss and winding up with only the maximum carryover cap gains loss every year after that.<p>So the worst outcome is that your strike is $1.28 you exercise at $3.13 (costing you $80k + $40k in taxes or whatever -- it gets worse the better the stock is doing, which is one of many reasons why early exercise of options is risky but good) but you're stuck in a holding period while you go public, then when you exit that period you're at $0.50 or something like that, and you've passed over into a new tax year, and you have no cap gains to offset the losses on the stock.<p>This happened to a lot of employees at dot com companies in the 2001 collapse.
Startup equity will always be worthless for 99.9% of people, and the second it's worth something more, it will be lawyered away from you. So from a business perspective, you should never work at a startup if you're not a founder.<p>dvs: please convince me otherwise