Потом он завёл собственные лавки и

Потом он завёл собственные лавки и сумел пройти путь до купца первой гильдии, крупного предпринимателя и городского головы.

Результаты (английский) 1:

Then he has built his own shops and managed to pass the path to a merchant of the first Guild, a major businessman and Mayor.

Результаты (английский) 2:

Then he started a own shop and managed to go all the way up the first guild merchant, prominent businessman and the mayor.

Результаты (английский) 3:

then he got his own shop, and managed to walk to the first merchant guild, a businessman and urban head.