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He had visited important counting houses in Europe in 1788 and was a friend of Filippo Filicchi, a renowned merchant in Leghorn, Italy, with whom his firm was a major trading partner.
The appearance of the Great Comet of 1744 gave him, then a schoolboy at Geneva, a permanent bias towards astronomy; he diligently prepared, however, for a mercantile career in counting-houses at Geneva, Leghorn, and Genoa, and visited Rome in the jubilee year (1750).
Later on, Sibley moved with his mother to Fayetteville, North Carolina where he received his education and apprenticed as a bookkeeper in the counting house of John Winslow.