The Road Not Taken: How Losing $50,000 Became My Biggest Gain

Far from aspirations that would lead a reporter to refer to me as “a force in personal finance,” my career is the result of a hot tub dream gone bad.

My goal in my 20s was to open Rockridge Springs, a hot tub/café in San Francisco’s East Bay. That didn’t exactly work out, and that’s exactly why I am who I am today.

I spent seven years after college as a waitress at the Buttercup Bakery in Berkeley, CA. It was the sort of place where everyone there — staff and customers —were friends. We talked. We listened. We cared about each other. Everyone there knew my dream was to open a friendly neighborhood hot tub operation.

One day I shared with a beloved customer, Fred Hasbrook, that my parents told me they couldn’t loan me the $20,000 I needed for my startup. Fred listened quietly as he polished off his breakfast. When he finished, he didn’t just leave a tip. He gave me a $2,000 check and commitments from other diners/friends that totaled $50,000 (the equivalent of nearly $150,000 today). Along with a note: This is for people like you, so that your dreams can come true. To be paid back in 10 years, if you can, with no interest.

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