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An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee

ospflor63.stanford.edu

31–40 of 44 posts

Re: An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee

#31
post #8

Earlier quoted context omitted.

I'm going to check this book out. But I've always had one nagging question about vesting I haven't found a good answer for. Say you have a bunch of shares vesting over 2-4 years. Is it possible (or realistic) to make an arrangement that in the event of an acquisition or liquidity event that your stock becomes full vested? Even if its been less than the full vesting period?

Acceleration usually comes as single-trigger or double-trigger. Single-trigger is what you are talking about: when all of your options vest immediately upon acquisition. It could be argued that this is unfair to those that have worked their full time to earn their full options grant. Usually, in this arrangement, a certain percentage of your shares are subject to the trigger (so, 25% vest immediately, for example). I…

So in the case where you don't have accelerated vesting, what happens to unvested options in an acquisition? Do they get converted to options in the equivalent dollar amount of stock in the acquiring company on the same vesting schedule? (Obviously subject to negotiation, YMMV etc etc...)

Re: An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee

#33
Hey there's something I'm a bit confused about. The text talks about how when you receive stock as an employee you pay income (gains) tax over them for which they might not have the cash. Does this also hold for other stock holders like the founders?

When the FMV has increased, do founders also have to pay taxes for their shares?

Re: An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee

#34
Great guide overall – a couple of clarifications, though. The first sentence of the Ownership section seems to confuse ‘authorized’ with ‘issued and outstanding’ shares. The amount of shares authorized must be in your corporate charter and requires shareholder approval to change. From that pool of authorized, the board can then issue shares which then become the ‘issued and outstanding’ shares. If you add in the amount of shares that could be issued if all securities convertible into that class of stock were converted (e.g. convertible debt, options, warrants) then you have fully diluted issued and outstanding. Also, as someone pointed out, ISO vs. NSO has nothing to do with employee vs. advisor: ISO’s are incentive plans/options that are designed to meet certain requirements in order to allow favorable tax treatment.

Re: An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee

#35
post #33

Hey there's something I'm a bit confused about. The text talks about how when you receive stock as an employee you pay income (gains) tax over them for which they might not have the cash. Does this also hold for other stock holders like the founders? When the FMV has increased, do founders also have to pay taxes for their shares?

To avoid this, vesting founders would presumably file an 83b election within 30 days of receiving the shares (mentioned in the PDF.) Then, they only have to pay tax when they sell the shares. And if they held on to those shares for over one year, this would be a smaller, capital gains tax.

Described in more detail here: http://www.grellas.com/faq_business_startup_004.html

Re: An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee

#36
post #35
post #33

Hey there's something I'm a bit confused about. The text talks about how when you receive stock as an employee you pay income (gains) tax over them for which they might not have the cash. Does this also hold for other stock holders like the founders? When the FMV has increased, do founders also have to pay taxes for their shares?

To avoid this, vesting founders would presumably file an 83b election within 30 days of receiving the shares (mentioned in the PDF.) Then, they only have to pay tax when they sell the shares. And if they held on to those shares for over one year, this would be a smaller, capital gains tax. Described in more detail here: http://www.grellas.com/faq_business_startup_004.html

What is the definition of 'date of grant' in this sentence:

Procedurally, an 83(b) election must be made within 30 days of the date of grant.

Is it when the vesting schedule says you vest?

Is it when the vesting schedule says you vest, and the stock is physically sign over?

Re: An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee

#37
post #31

Earlier quoted context omitted.

Acceleration usually comes as single-trigger or double-trigger. Single-trigger is what you are talking about: when all of your options vest immediately upon acquisition. It could be argued that this is unfair to those that have worked their full time to earn their full options grant. Usually, in this arrangement, a certain percentage of your shares are subject to the trigger (so, 25% vest immediately, for example). I…

So in the case where you don't have accelerated vesting, what happens to unvested options in an acquisition? Do they get converted to options in the equivalent dollar amount of stock in the acquiring company on the same vesting schedule? (Obviously subject to negotiation, YMMV etc etc...)

With an acquisition I went through, none of the unvested options (after acceleration) turned into anything (meaning those remaining shares were never issued/created). However the acquiring company put forth their own stock incentive plan in hopes of retaining employees.

Re: An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee

#39
post #35

Earlier quoted context omitted.

To avoid this, vesting founders would presumably file an 83b election within 30 days of receiving the shares (mentioned in the PDF.) Then, they only have to pay tax when they sell the shares. And if they held on to those shares for over one year, this would be a smaller, capital gains tax. Described in more detail here: http://www.grellas.com/faq_business_startup_004.html

What is the definition of 'date of grant' in this sentence: Procedurally, an 83(b) election must be made within 30 days of the date of grant. Is it when the vesting schedule says you vest? Is it when the vesting schedule says you vest, and the stock is physically sign over?

Well that just scared the crap out of me. Fortunately, the rest of the net believes that you have 30 days from the date of purchase.

Re: An Introduction to Stock & Options for the Tech Entrepreneur or Startup Employee

#40
post #14
post #2

This (extremely well-written) document has made the HN front page at least once before. I think this is a testament to how useful this information is for entrepreneurs. I didn't have time to read it in full last time, glad it's back again.

There's actually a couple of errors on the first two pages. Where can I submit errata?

Also, the author (myself) reads Hacker News, including this comment. :)
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