Totally!
What you’ll hear from DAF folks is
“we have to sell everything we get in when we get it” -> not true, managed by disclosures
“Our job is managing volatility of the donated assets, so getting volatile assets would be bad for the fund, or possibly not allowed” -> not true, managed by disclosures
“DAFs are disliked because of asset stuffing, and on the down” -> true as to the first part. On and off legislative pushes centeraround getting 2-ish% a year as a mandatory donation, so you could be ahead of the curve on an ‘ethics’ basis with this as a rule.
“It’s impossible to value illiquid stock so we can’t get a proper deduction” -> not true, you can get an outside valuation, or see below on the secondaries
The scheme I’d suggest on a call would just be: find a friend who did well from your cohort, or pitch some of your VC allies that have helped on the board, see if anyone is willing to give it a try in the 10mm or so range. You’ll then need to find someone who wants this stock in the secondary market; this would be either the key partnership or the key staff you hire, and another reason to bring in the VCs here. You’d be able to accept any donor with stock that has a value in the secondary market.
One of the things we looked at was psychology on give now / give later, most founders are planning on mooning, and therefore want to give later. This lets them split the difference a little - deduction at current secondary prices, but they could hold off on selling and get more out to charity if the stock does well.
On valuation, to my mind the easiest path is finding a secondary buyer, then you’ve got an independent price.
We even ID’ed an Exec Director who wants to do this, and would be great! My contact is in my profile.