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Financial Planning > College Planning

Leader of the Band

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Google Jeff Oster and you’ll find him on Amazon, MySpace, CD Baby, SoundClick, MP3, PayPlay, CD Universe — even Wikipedia, the online encyclopedia.

It’s unusual terrain for a financial advisor to inhabit. Then again, how many advisors do you know who are award-winning musicians?

An accomplished trumpet and flugelhorn player, the 50-year-old Oster has forged a path that has led to a remarkable intersection: successful careers in both music and financial services.

The vehicle: a big talent for sales and marketing.

Who: Jeff Oster, Registered Principal, Raymond James Financial Services, Alameda, Calif.How Oster explains his decision to become a financial advisor after playing in a bar band for a living: “I didn’t want to be 50 playing ‘Proud Mary’ at some dive bar in the San Fernando Valley with five people in the audience with their backs turned to me on a Tuesday night.”

A registered principal for Raymond James Financial Services in Alameda, Calif., Oster, with $350 million in assets under management, is a marketing machine. A direct mail wizard, he built his financial services practice by marketing to orphan insurance policy holders. Today, Oster’s biggest client, representing $20 million in assets under management, originated with a $10,000 annuity he sold in 1991. Oster is the agent of record on 5,000 annuities, which has resulted additionally in what he calls 100 “deep clients.”

Oster, meanwhile, has used the Internet to great advantage to market his music, chilled jazz that he defines as “Miles Davis meets Enya.” Oster, a one-time limo driver, stand-up comedian and bar band musician, says he began to rethink a musical career in 2003 when four songs he placed on showed up on the website’s Top Ten Downloads list.

“I was getting 40,000 downloads a month, so I knew I had something going on,” says Oster, who has played trumpet since he was eight. “Over the years, I never had any idea of what kind of music I would make on my own. This was where it started. Today, I just play what moves me, what I love, what sounds good to me. And I figure if I love it, maybe somebody else will.”

The songs also attracted Will Ackerman, the founder of Windham Hill Records. In late 2003, Ackerman and Oster made the “At Last” extended play recording followed by the full-length album, “Released.” The album won the 2005 Album of the Year and Best Contemporary Instrumental Album awards at the NAR Lifestyle Music Awards, voted on by broadcasters. The Oster/Ackerman composition “At Last” won the Best New Age Song award at the 2005 Independent Music Awards.

“True,” Oster’s new Ackerman-produced album, was in the mix for a Grammy nomination as Best New Age Album, but did not make the final cut.

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.

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].


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