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The Good, The Bad, and The Ugly of Startup Options (2019) (themargins.substack.com)
25 points by luu 4 months ago | hide | past | favorite | 9 comments

I'm sorry to be negative, but reading that wall of generalized vague text lost me 2 minutes of my life. Couldn't it have come with some hypothetical numbers or scenario tables to contain even the least bit of useful information to take away? It basically expanded the phrase "startups are risky payouts" into a page of someone's blah mental theories.

> No firm will realistically show you their cap table, or tell you the number of outstanding shares

I don't think this is very true. I can't imagine getting an offer without knowing the total number of shares.

It's usually true, companies won't make it easy.

Part of the reason is that the "cap table" is usually a mish-mash of disorganized Excel spreadsheets after several rounds.

jwz had to battle Netscape HR to see those numbers.

But Delaware-registered companies must on request.

My comment wasn't quite clear enough I think. I don't think you will see a cap table, but you should see total outstanding shares. And my comment was probably more true for startups in the traditional sense and not the 10-year-old, $10B 'startups' like Airbnb.

And yet it is true.

Not based on offers I or anyone I know has gotten. Who would blindly take options without knowing what percentage they make up?

Virtually everybody who isn't in a strong negotiating position (so almost all employees.)

Knowing the percentage isn't all the meaningful since there will be dilution later, or more classes, liquidation preferences, etc.

Your second sentence is very true, but not part of the quote I am disputing ("[companies don't] tell you the number of outstanding shares").

Some things to watch out for:

#1 Be wary of late stage private companies offering large ISO grants, these grants are absolutely worthless as long as the valuation does not exceed FMV (fair market valuation) at time of grant.

#2 (ISOs) Start date FMV is not grant date FMV, I got burned by taking an offer at a startup where the implied valuation of the ISO options shot up dramatically after my start date, 400x by the time the board met and issued options after my start date(the companies valuation only went down from this peak).

#3 (ISOs) Make sure that the exercise window is a few years after you leave the company, given alot of large unicorns take 7-10 years to go public you don't want to get into a situation where you join a company, its valuation shoots up, and are either let go or take another job and are forced to exercise 100's of thousands of ISOs(in 30 to 90 days) leading to a mammoth tax bill which gains may not be realized(think weWork and its dramatic collapse) and you are still on the hook for this come tax time.

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