On pro-rata basis most of these secondary liquidity events as apart of raises are not "retirement" level of liquidity - it's just "safety net" level of liquidity. So I think they would probably not be considered "sizable".
I'll give you nice-guy points for turning it down - that's a very principled position to take when that much money is sitting in front of you and all you have to do is say "yes"
I think your intuition on #2 is right - pro-rata across the board or even if the amounts are small enough, offering to do it as a "series B bonus" line item in payroll is not out of the question. 10% seems on the high side but sub 5% it's probably do-able.
I agree with a lot of what you've written - I understand if you want to stay anonymous but would love to talk to you about this more if you are open to it!
I had no intention of posting this to HN (someone I don't know posted it!) and also didn't expect more than the 10 people I shared it with to actually read it - no vote bait intended! I'm happy to take your feedback on a better title that is less baity and more apt.
I'd be asking the same question, it's a fair criticism. I wrote this expecting 10 people to read it and I wrote it as a part of a writer's feedback group. I'm just a random guy who has worked at a lot of startups, nothing special!
I could not agree more - I still have no idea why 90 days is the standard. It also exploits people who are ignorant about equity compensation more than people who are not - which I think is even worse.
I don't know if I agree - but I'm open to being wrong. I can't recall many scenarios where I thought someone was a strong fit at 3 months but a terrible fit at 12 months. I can probably think of a couple of scenarios for 3 months and 6 months, especially with slower time to value roles like leadership positions.
Right now 3 months is within my risk tolerance - and there is another side to the cliff that folks don't talk about too often, pre-cliff people will generally be less transparent with negative feedback for fear of being fired before the cliff hits. I'm ok with giving up a bit of equity and polluting the cap table if it increases transparency faster. Maybe the lower risk bet would be a 6 month cliff but I believe 12 months is too long to hold the equity hostage.
We allow early-exercise too but I (possibly, incorrectly) assumed that this was the standard for newly incorporated startups - at least within the last 2-3 years it has become significantly more common.
"secondary sales restricted only by a short right-of-first-refusal period"
I really like this as well, I've always found it confusing when private companies are anti-secondary for former employees especially. I'll look into adding something like this to our stock plan, ROFR protects against any hostile take over weirdness and I'm confident we could add something like this to make it relatively easy to sell on secondary under a certain % threshold.
I was being generous - if there are 3 cofounders and you let one of your early employees get in the 2-3% range - it might be closer to 10x - but you're right that the majority of the time it's between 20x and 50x, sometimes even more dramatic than that for solo founder scenarios
Thank you for letting me know about this - I searched for other tender offers or liquidity for employees of WeWork and couldn't find anything (and the 2 former WeWork employees I know joined in late 2019 / 2020 - so they had a pretty terrible experience)
I will re-work that section so that it's factually correct
