I'm going to use this ask to answer half a dozen others that ask the same think but on anon (Sorry folks, these past few days I'm being kind of flooded with asks).
I'm sure he will. Actually, when last november someone leaked that Automattic was reducing tumblr staff to 1/3rd of what it used to be, one of my first thoughts was that Matt was taking weight out of tumblr to be make it easier to sell. Automattic won't want to lose a lot of people if tumblr goes away, but obviously you can't sell a company without sending some people who knows how to handle it going in the deal. So yeah, I'm pretty sure that Matt has been open to listen to offers since that point, at least.
Now, the problem is... who would want to buy tumblr? For starters, you need a lot of disposable cash. See, I'm sure Automattic would pretty much give it for free at this point. But still, even with reduced headcount, I don't think the monthly running costs of tumblr are less than 3 or 4 million US dollars. Any company willing to purchase Tumblr needs to be able to safely burn that amount every month and willing to do it.
Then, to do what? Tumblr has gone under 4 different corporate overlords during its history. And none of them, at any point, has made money out of it. Tumblr is a big black hole of money that somehow has been kept alive for 17 years. So any company willing to purchase tumblr would need to think they are smarter than the rest and have a different plan that could work.
When Automattic purchased it back in 2019, Verizon was about to close it for good. That's why Automattic managed to get it for a token amount. Automattic thought it was smarter than Verizon, than Yahoo, than David Karp, and that it could get it to profitability. It didn't.
I'm not saying there isn't any chance of a sale. I see how a company that has a steady income and is interested in a massive amount of traffic could be interested. But at this point I wouldn't bet on it, and even if it happens, the kind of company who fits that description won't be something we would like to have around (programatic ads companies, online gambling, etc).
So well, possible? yes. Likely? I don't think so. A good solution? I don't think so.