this post was submitted on 23 Feb 2024
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Remember when Spez said it was "It's time we grow up and behave like an adult company"? Apparently, that means paying himself $193 million and single-handedly tanking Reddit's profitability right b... (www.npr.org)
submitted 8 months ago by [email protected] to c/[email protected]
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Remember when Spez said it was "It's time we grow up and behave like an adult company"? Apparently, that means paying himself $193 million and single-handedly tanking Reddit's profitability right b...::undefined

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[–] [email protected] 1 points 8 months ago (1 children)

Its a huge headache for startups sometimes. I had team members I wanted to compensate but just giving them the equity would have been an imediate big tax bill on a non-liquid, and speculative, asset. There's ways to massage it (like vesting) but he will absolutely have that taxed.

Is there an equivalent of the sell-to-cover withholding strategy for stocks that aren’t publicly tradable?

[–] [email protected] 1 points 8 months ago

I don't see why you couldnt, but you'd need a buyer. Like if you had a funding round you might include in part of your use of proceeds a small buyback/ sell to cover like you're talking about. If the company was doing the sell to coverthats definitely easier cash wise than a bonus but not 0.

All these rules make total sense, they're just hard for really early companies. The lawyer calls alone on this stuff start to add up in a hurry and if you skip them you may have just screwed the people you want to help and muddied things for any future raise.