Leader of the Band

Like many musicians, Oster’s success has not come without struggle. In the mid-1970s, he moved to Los Angeles with the goal of becoming the next Herb Alpert. Instead, he began driving a limo, pitching his songs to clients. Mel Tillis, the country singer, actually published one of his songs. Over a 10-year period, Oster played in clubs, hotels and lounges, never making more than $12,000 a year. He sold office supplies, played at weddings and lived in a $150-a-month apartment with a Murphy bed that pulled out of a wall. Ramen noodles were a staple — with eggs and broccoli added when times were flush. He used cash advances from one credit card to pay off another.

Finally, says Oster: “After 10 years, I was tired.”

A limo driver friend who had become a stockbroker suggested Oster try financial services. Oster had been selling office supplies to his friend’s branch, and he had recognized Oster’s knack for sales. “Dude, I never graduated college. I never took a financial class in my life. You’ve got to be kidding,” Oster told him.When his friend began driving a Corvette, Oster decided to explore the possibility. In 1987, after studying for the Series 7 exam during band breaks, he passed the test and got his license.

Oster worked several years for Independent Advantage Financial, which sold fixed and variable annuities through endorsements in investment newsletters. Later he was attached to Prudential Securities, joining Raymond James Financial Services in 1997.

“When I quit the band and started financial services full-time, I told myself I would do original music at one point, hire the players I wanted to have play, be able to play a club I wanted to play at, that one day money would not be an obstacle” says Oster. “It took me until 2003 to get to that place.”

When Oster first e-mailed Ackerman that year about joining forces, Ackerman told him, “I’m not cheap.” Oster’s response: “Cost is only an issue in the absence of value,” a sales line classic. “Every e-mail I’ve ever written, every website I’ve created, is about getting a response,” says Oster. “It’s all about creating a value proposition and creating effective messages that trigger a response.”

Today, Oster continues to build both businesses. Going forward, he hopes to grow his assets and release a record every other year.

One of his biggest fans: Dick Averitt, chairman and CEO of Raymond James Financial Services. “Jeff has taken a very complicated subject, the annuity, and done a great job of helping clients understand how it’s best used,” notes Averitt. “Perhaps it’s his ability to understand complex matters, like musical rhythms, pattern and tone, and make them clear. I don’t think his talents are mutually exclusive.”

On his website, Oster writes: “Because I have enough financial resources now, I’m not trying to sound like whatever’s selling now. I’m just going for stuff that sounds good and makes me feel good. And that’s an incredibly freeing way to work.” At the moment, Oster is at work on his third record.

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Freelance writer Ellen Uzelac is based in Chestertown, Md.; the former West Coast bureau chief and national correspondent for The Baltimore Sun, can be reached at [email protected].