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Setting aside the intrinsic risk of blockchain to the endowment itself, which you address, what about the inverse (risk of the endowment to the blockchain)?
Do you think the existing investors in the platform as a whole would be inclined to support these accounts? If not, what would the result be if investors actively seek to negate rewards that the endowment delegates seek?
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Thanks for the reply! These are good questions.
In real life, endowments and real-estate donations are often given with constraints on how the gift can be used by the recipient, so if large amounts of funds for the endowment were to be donated by someone on the Steem blockchain, it might be prudent to try to stipulate terms on the sorts of voting and content-creation behavior that are permitted or prohibited.
As to whether the blockchain community would be welcoming, I guess it depends on a variety of factors, but the endowment would need to navigate the same landscape as anyone else on the blockchain. As long as the votes and posts are geared towards promoting useful content, I'd hope that they'd be supported, but this is an important factor for consideration, because it clearly adds some uncertainty to the idea. (This is one of the concerns I have had with downvotes in general. It's not really limited to the endowment idea. For example, what if a major music label decided to launch a downvote campaign against all people who post competing music-videos...)
It's also interesting to think of what might happen if someone did start voting to counter the rewards of a school with 10 or 20 thousand active students or more (and their families and alumni). Might that academic community respond by buying more Steem and launching a "bidding war"?
I have to say that I don't know, but those are interesting and important questions for anyone who might consider pursuing a strategy like this.
This is similar to what I speculate as well:
https://steemit.com/steem/@inertia/creating-demand-for-steem-power-vote-negation
I do think we have seen that happen in practice with some of the "flag wars" of the past. One time I remember in particular, I was assuming that Steem's value was going up because two parties were both powering up to downvote each other. It's ironic that when that happens, the competitors strengthen each other by bidding up the value of their stakes.
OTOH, sometimes the target doesn't fight back, but instead they pack up and leave. That's harder to do when they're tied to an on-chain endowment, though.