[2] Hewes supported himself from the age of fourteen and earned enough to pay for his education including entry into Phillips Academy, Andover and Yale College.
During his second year at Yale he joined his savings with a small inheritance from his father investing the monies in galvanized iron houses that were shipped to California.
Seeing San Francisco as a promising metropolis of the Pacific Coast he began a small-scale business of earth-moving as the city was leveling sand dunes and filling streets.
[3] He grew the enterprise to reclaiming the harbor, blocked by hundreds of abandoned ships from the gold rush, to level and fill the area where much of San Francisco's business district now stands.
Hewes was invited to be a part of the Big Four (Central Pacific Railroad) but declined due to the financial risks, over his lifetime he gained and lost several fortunes.
Called Anapauma, "a place of rest", it was a massive sheep ranch over 800 acres (3.2 km2) with a large portion eventually converted in vineyards which later died off from blight.