[1] He was initiated at a very young age by his uncle Piero to a political career, siding with the Guelphs and sent on a mission in 1368 to Milan with the Visconti.

Driven out of Florence in 1372 circa, he found refuge in Germany, where he fought against the Grand Duchy of Lithuania under the insignia of the Teutonic Order and remained there until 1381.

During his absence in Florence, following the uprising called Tumulto dei Ciompi, his house was destroyed and set on fire and he suffered confinement far from the city.

In 1389 he went to Milan to negotiate with Duke Gian Galeazzo Visconti, who was intent on subduing Florence.

[1] During his tenure, Florence prospered in the arts and studies, promoting the growth of the university, which was later taken over by the Medici.