A couple of questions would be:
* At what speed is the industry going to embrace self-driving / "augmented driving" in trucks? I'd imagine a driver would still be required at the wheel in case of emergencies for the foreseeable future. What new skills would truckers have to learn?
* Given the environmental impact of trucking (self-driving or not), what are some interesting propositions that climate change startups could come up with? Do any players in the value chain even care about climate impact? Clearly, given the cut-throat nature of the business, there would necessarily need to be a revenue impact otherwise no one is going to use the proposition.
* I find the insurance part more interesting that the factoring part. Given the generally poor service quality of insurance companies, I'm wondering if there is a possibility of a "Lemonade" like insurance company in this space? Lemonade started out as a home insurer I believe. What is the killer proposition for an insurance company in this space?
Lots more thoughts come to mind. Again, great writeup, thanks!