> These guys have unlimited money, why are they still transporting with regular couriers?

Commercial shipments don’t work like when you receive a package from Amazon. The terms of the freight, including the point at which ownership is handed off, are negotiated terms. An $11.4 million contract would have this negotiated and agreed upon. Depending on how it’s structured, the shipment may not have been the shipper’s responsibility at all after it left the warehouse.

> I can't imagine their insurance is too happy about it either.

Insurance would take the risk of the transport method into account. The policy would say what transport methods are covered and the allowed methods would be used to calculate the risk of loss.

I usually have two options. FOB origin, where I assume ownership when the item leaves the seller’s dock. FOB destination is more expensive, but the seller maintains ownership until the item is delivered to my choice of destination.

https://en.wikipedia.org/wiki/FOB_(shipping)

I always pay for FOB destination when ordering high value items. I bought two 250kVA UPSes from Eaton and one of the pallets tipped over on the truck.

The 2% I paid for FOB destination meant Eaton delivered another 250kVA UPS at their cost. Unsure if Eaton was made whole by the shipper or not.

This, exactly. There's a pretty good chance this is all on the buyer, by contract.