Why I Joined the Dark Side

Six months ago I decided to quit my job at Morningstar, where I was an exchange-traded fund strategist, to become a financial advisor. Three months ago I told my boss. Six weeks ago I left.

While I enjoyed my role as editor of the Morningstar ETFInvestor newsletter, I couldn't see myself doing the same thing three years down the line. What I wanted to do was work for myself. Not to make lots of money (though that would be nice), but to be free to say what I want, do what I want, and work only with the people that I want. I was unsure how to achieve this, but I knew I wanted to manage money.

In late December, “Elvis” made a case that I could be a very successful advisor. I disagreed, pointing out that an advisor with good people skills and zero investment knowledge will make gobs more money than an advisor with mediocre people skills and actual expertise. For this reason the business overwhelmingly attracts salesmen, hustlers, hucksters.  It's an open secret that many advisors are so ignorant they couldn’t justify their services for free.

Despite my skepticism and harsh assessment of advisors, I couldn't get the idea out of my brain. My 29th birthday was coming up and the opportunity cost of striking out on my own was rising fast. I knew that at some point I would be making enough money that my risk-averse nature would overwhelm my budding entrepreneurial streak. And the more I thought about it, the more appealing the job seemed. Not only did it fulfill my need for autonomy and passion for investing, it was a challenge. Could I succeed in spite of the sales-y nature of the job? Could I run a business in a manner consistent with my values? I wasn't sure.

My lucky break came in January, when “Warren” broached the idea of me managing his money. I was stunned. I had emailed back and forth with him for a couple of years at that point. At first I wasn't sure he was serious, but that quickly changed as we talked. Despite a big age gap, Warren and I became good friends. I was comfortable quitting my job for him, and I had never met the guy (we eventually did meet). So here I am.