Sacks is skeptical of the Uber/Expedia cross-sell thesis, arguing Uber users have no intent to book hotels through a ride-hailing app, making the synergy rationale MBA hand-waving rather than real product thinking.
I don't think Uber customers want to be cross-sold on booking a hotel... when I use the Uber app, I just want to basically make a couple of clicks, set my destination, get my car, and then move on.” ⚑
Friedberg sees a financial rationale for Uber acquiring Expedia at ~4x pro forma EBITDA via cost synergies and cross-sell, with VRBO as an underutilized asset, but acknowledges significant AI-driven strategic risk to the business model.
You could see a scenario where you could increase Expedia's EBITDA by 75 to 100%, maybe getting it as high as $6 billion. And while Expedia's market cap trades at $20 billion... they're probably paying $26 billion for the company and they g” ⚑
Chamath argues Expedia's core business model — a UI layer on top of licensed third-party travel data — is structurally fragile in an AI agent world where tools like Perplexity can bypass it entirely, making a $30B acquisition a catastrophically bad capital allocation.
I cannot think of a more fragile business model than the UI layer on top of widely available data... it would just be a very bad capital allocation decision. Now, that's okay to get things wrong, but not for $30 billion wrong... $30 billion” ⚑