The first English speaker to settle permanently in what would become San Francisco was William A. Richardson, first officer of the British ship Orion, who enjoyed the Comandante's fiesta at Presidio in 1822 so much that he jumped ship, changed his religion, and married the Comandante's daughter, Mara Antonia Martínez.
Luckily for him, 1822 was when Mexico became independent from Spain and permitted trade with foreign vessels inaugurating the era of the "hide and tallow" trade in California that vastly enriched ranchers and Richardson.
He applied for, and received, a land grant in Yerba Buena Cove, built a house, and lived happily until 1841. At that point he moved to Sausalito and sold his Yerba Buena house and land, and proceeded to take financial advice from the wrong people. He died a pauper, a frequent fate among San Francisco founders.