The Day I Almost Lost All My Money To a Man in a Well Tailored Suit

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My last year in high school I landed a competitive summer internship, where upwardly mobile high school seniors and college undergrads would be exposed to the world of business with the support of mentors and accountability.

While I wasn’t thrilled about working at an insurance company, I was ecstatic about wearing heels, working on Wall Street, and pulling in a cool $10/hr in an air conditioned building while my not-so-rockstar friends had to brave New York City’s summer heat as camp counselors with unruly children or head burger flippers in polyester uniforms at Burger King.

Even though I didn’t want to show it, I was pretty impressed with myself. In fact, I was super impressed. My mentors loved my contributions to the team, I was improving my writing skills and I “did” lunch with fellow interns almost every day.

During one of our power lunches, I mentioned to one of my intern friends, Delanie, that I wanted to begin investing- since, well, I was, of course, a Sheryl Sandberg in the making. Working around executives was beginning to rub off on me and I wanted to lean in—all the way. I just didn’t want to look like Wall Street, I wanted to play like Wall Street.

“I have a financial investor friend that can help you,” Delanie said.

A few days later, Delanie, told me to meet her financial friend at a local Subway at 5pm.

I arrived at Subway early so I could get focused and get calm. In my purse, next to my lip gloss, I had a check for $1,000, the total amount of money that I had saved up to that point. Everything was filled out, with the exception of “pay to the order of.”

As I waited for my financial advisor, I sat there, again, in awe of my maturity.  I was grooming myself for financial excellence. I saw myself and my financial advisor working closely together—with deep “meeting of the minds” encounters, where we poured over financial statements and he showed me how he made me a millionaire.

When I finally met my financial advisor, a man that I had neither spoken to or met before, something didn’t feel quite right.

My financial advisor was a very handsome man— young, tall, and with impeccable taste. His suit was well tailored and he smelled delicious.

After a few pleasantries, he went straight for my checkbook.

No folder with my name. No discussion about my life or my goals. No spreadsheets.

“So how much money do you have?” he asked dryly.

“A thousand,” I replied sheepishly.

“With you?” he dug.

“Actually, no I don’t. I left my checkbook at home.” I lied.

When my well-tailored thief got up to leave Subway, I knew that I had avoided something big, but I didn’t realize how big it was until I went home and told her about what happened.

“Kara, you can’t trust anybody with your money!” my mom explained.

“But he was wearing a suit, Mom,” I replied.

Then she broke it down Antiguan style, so I could really understand: “You no know nottin’ ‘bout life. A well-dress teef—a di biggest teef”

Translation: You don’t know anything about life. A well-dressed thief is the biggest kind of thief.

It took another twenty years to fully understand how stupid I was about picking a financial advisor until I met James, my current advisor who I’ve kept for the next decade.

True financial advisors  value building relationships; they put clients before cash. They ask you questions about your risk tolerance, your life goals, and your values. Excellent financial advisors meet with you bi-annually to discuss your portfolio and make adjustments accordingly.

Before making a leap into the world of equities, make sure you have the right people on your team.  

If you need deeper work around healing your relationship with money or overcoming your blocks and fears, maybe it’s time for some m​oney therapy​.

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