While it is unknown whether Ammi Phillip was entirely self taught, or had interacted or been taught by other artists in the Colebrook, Connecticut area, there were such painters whose work Phillips might have seen growing up. Rueben Moulthrop, Nathaniel Wales, Uriah Brown, and Samuel Broadbent are all artists traced by documents to the area, and stylistic elements of their work can be seen in Phillips's early paintings. He enters the documentary record as an artist himself in 1809, at the age of 21, with advertisements in both "The Berkshire Reporter" and a Pittsfield, Massachusetts, tavern proclaiming his talent for painting "correct likenesses" distinguished by “perfect shadows and elegantly dressed in the prevailing fashions of the day.” Although Phillips also advertised his talent for "fancy painting, silhouettes, sign and ornamental painting", he soon specialized as a portraitist. Phillips was recorded in the diary of Dr. Samuel Barstow of Great Barrington, Massachusetts, dated October 6, 1811, mentioning small portraits he had commissioned of himself and his wife. Phillips's work satisfied the local standard, and within two years he was receiving regular portrait commissions from community leaders in this area of western Massachusetts. Phillips's earliest recorded portraits are that of Rev. and Mrs. Ephraim Judson and Gideon Smith of Stockbridge, Massachusetts in 1811. Gideon Smith was an innkeeper, and displayed his portrait in his tavern, implying that instead of a struggling painter trying to make ends meet, Phillips may have been quite business savvy.