He was first known to fame in the old Natchez, which was not a clipper at all and was even rated as slow while carrying cotton from New Orleans to New York.

But Captain Bob took this full-pooped old packet ship around the Horn and employed her in the China tea trade.

The voyages which he made in her were all fast, and he crowned them with the amazing run of seventy-eight days from Canton to New York, just one day behind the swiftest clipper passage ever sailed and which he himself performed in the Sea Witch.

Incredulous mariners simply could not explain this feat of the Natchez and suggested that Bob Waterman must have brought the old hooker home by some new route of his own discovery.
Captain Bob had won a reputation for discipline as the mate of a Black Ball liner, a rough school, and he was not a mild man.

Ashore his personality was said to have been a most attractive one, but there is no doubt that afloat he worked the very souls out of his sailors.