I'm just speaking based on my interpretation. I think the "chalice" is a jeweled cup that seems valuable, but the poison is not what you would expect to drink. So, the deal seems like a big prize, but comes with hard-to-understand disadvantages that make it a poor choice. E.g. someone bought tumblr and tried to make it advertiser friendly by removing NSFW content. As soon as they did, the community that was still flourishing there abandoned it and they had no eyeballs to sell.
Not necessarily undo MS, but rather that the deal looks attractive but may actually not be any good. In other words, it could end up being one of those deals where a few years down the road MS has to write the purchase price off as a loss.
Given the opportunity though, it still seems like a risk well worth it.
Businesses rarely (if ever) fail because of an acquisition gone wrong. But a acquisition gone right can have great returns.
If Instagram flopped when Facebook bought it, Facebook would still be doing just fine. But since it did go well.. yeah.
So I believe that it's still probably in the investor's best interest if MS does the deal even if it's only like a 35% chance that it isn't a complete failure.
AOL would have been destroyed anyway. They were a dialup ISP who saw their time coming. They were smart to take their inflated stock price to buy a real asset.
Of course they mismanaged it and it should have been a reverse takeover like Next/Apple.
From the Oxford English Dictionary [0]:
"An award or honour which is likely to prove a disadvantage or source of problems to the recipient; the phrase is found originally in Shakespeare's Macbeth (1606), in a speech in which Macbeth flinches from the prospective murder of Duncan."
He's saying that managing TikTok might be more difficult than Microsoft can imagine. Here is the relevant part from the interview:
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As you are the technology adviser to Microsoft, I think you can look forward in a few months to fighting this battle yourself when the company owns TikTok.
Yeah, my critique of dance moves will be fantastically value-added for them.
TikTok is more than just dance moves. There’s political content.
I know, I’m kidding. You’re right. Who knows what’s going to happen with that deal. But yes, it’s a poison chalice. Being big in the social media business is no simple game, like the encryption issue.
So are you wary of Microsoft getting into that game?
I mean, this may sound self-serving, but I think that the game being more competitive is probably a good thing. But having Trump kill off the only competitor, it’s pretty bizarre.
Do you understand what rule or regulation the president is invoking to demand that TikTok sell to an American company and then take a cut of the sales price?
I agree that the principle this is proceeding on is singly strange. The cut thing, that’s doubly strange. Anyway, Microsoft will have to deal with all of that.
