As for the all-stock deal, I think you hit the nail on the head with this:

"You have investors like Tiger Global, with positions in both companies, now essentially converting their Postmates stock into Uber, at a surprising premium. "

The question is how many more investors are like this? Since cash is king in startups if you want to merge two startups you own, why would you drain one of cash to do the merger? Just merge them and you still have stock in both. I imagine this was a deal born in the VC conference rooms.

On the broader topic, I think Uber is falling for the old "Railroads forgot they were in the transportation business" cliché. In this cliché you sagely demonstrate that you are not really selling the thing you sell, but instead a meta thing. But this is the wrong way to play that.

If Uber wants to say "we are a last mile-logistics company" then they should be OEMing their logistics services through GrubHub, DoorDash, Postmates. They could also find other companies that want to deliver things such as flowers, groceries, or booze. The smart play is to make someone else's back office their front office.

Uber's problem now is that you can't really name their customer or their market. Are they selling to people who want to go to the airport or people who want a tasty snack? How are these two markets synergistic? How do marketing costs associated with tasty snacks going to help rides to the airport?

The most limited assets in a company are Time, Talent, and Management Attention (Geoffrey Moore, I think) How is a "logistics" company going to apportion these resources to rides, tasty snacks, or anything else Uber suddenly thinks it should be "logisticsing"?

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I don't know how classic of an example this is, but one all-stock deal that I remember recently was when Disney acquired the majority of 21st Century Fox in an all-stock deal, and it looks like they outbid some Cash+Equity offers in the process (source: https://en.wikipedia.org/wiki/Acquisition_of_21st_Century_Fox_by_Disney).

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