I doubt a Yahoo — or any company that is truly desperate for Tumblr’s hip demographic and gargantuan traffic– can get this deal done unless the money is just insane. Tumblr has a position of strength, and it’s founders have already taken a good deal of money off the table through secondary rounds. There’s no immediate pressure that I know of, and I’d be stunned if Tumblr founder David Karp wanted to be some has-been Web 1.0 company’s life raft.
And Facebook — unlike Twitter — has a publicly traded currency, which always makes acquisitions easier. Karp would actually know how much he’s selling his company for, unlike Kevin Systrom who got about $300 million less for Instagram than he’d thought by selling to a pre-IPO Facebook.
Ingram’s weakest point is the this-is-how-my-teens-use-it argument; always a tempting argument but one that should usually be resisted. This was the logic that lead VCs to pump more money into WebVan than any other ecommerce company save Amazon. But our wives want to pay more money not to have to go to the store! Not exactly how the average middle American housewife thinks. If we’re going by that reasoning Facebook should also buy Yo Gabba Gabba. My son can’t get enough of it.