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

In this series of posts, Influencers explain how their career paths might have changed. Read all the stories here and write your own (please include the hashtag #RoadNotTaken in the body of your post).

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.

My own Kickstarter campaign, circa 1979!

Fred also gave me my first lesson in personal finance; he told me to deposit my seed capital in a safe money market account while I worked on my business plan for a restaurant (sans hot tub) because that's what I knew best. I walked into a local branch of a national brokerage and did exactly what Fred advised. And that’s when things went horribly wrong, but are at the heart of how I ended up where I am.

I didn’t know anything about investing, or risk, let alone the option strategy the broker enticed me with, with promises of being able to earn a lot. I had explained I couldn’t take any risk, so I just assumed this options strategy sounded like a great risk-free way to make more money for my hot tub venture. (Yes, I was that na?ve.)

The $50,000 eventually became $0. It was a very painful lesson in not being informed, and trusting people to be honest. But the experience ignited an interest in investing. So I decided I would try to become a broker too. You can read my whole story here, but the short version is that I not only became a broker, what I learned while studying for my exams was that the broker who put me in options had crossed the line by putting me in such a risky investment when in fact I had explained I needed the money to be safe. I got the $50,000 back (and repaid my debts) and a new career passion: helping people take control of their financial lives.

I am grateful I got ripped off. It led me to take responsibility for my own money, and led me to a career focused helping others avoid being ripped off. All because of a hot tub dream.

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