An early and very successful American portrait painter, he was born in Windham, Connecticut into an established Yankee family who recognized and encouraged their son's obvious talent.

He was sent at the age of sixteen to study art in Hartford with Joseph Steward, a retired minister who did painting. Waldo did some sign painting and then opened a portrait studio in Hartford. He met John Rutledge of South Carolina who invited him to go there to paint commission portraits, and he was so successful that the profits financed three years of study in England with Benjamin West and John Singleton Copley. Under West, he got much exposure to other American artists and to those especially skilled who were members of the Royal Academy.

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