500 years after The Apocalypse decimated the world, North America is a wasteland. Backwards people reduced to using 1680s technology at best, early Bronze Age technology at worst. There are only a few powerful nations in the continent, and raiders, marauders, slavers, cannibals and mutants stalk the vast stretches of wilderness in between major settlements. If you go out of a town, unarmed, you're guaranteed to got robbed and killed if you're a man, and robbed and enslaved if you're a woman. Slavers are even seen as honorable businessmen, not cruel monsters (for example, in Midwest Empire, 90% of people own at least one slave). Vicious animals are also there, and will happily eat any trader or merchant they see.
Around the late 30s of the 26th century, a new company is founded called Interstate Caravans. It starts out as a small trading company, with only about 30 employees, but it eventually wants to expand, connecting the East Coast and West Coast, like the Silk Road of ancient days. My question is, how could they go about this?