When Jeffrey Oster finally admitted that his career Plan A would not materialize, he embarked on freshly created Plan B — far, far afield indeed from Plan A.
Nevertheless, this would soon allow him to happily pick up Plan A without quitting what turned out to be a successful, lucrative Plan B career.
Plan A? The trumpeter and flugelhornist aspired to have his own record label for his music. Plan B? He would become a stockbroker. As it turned out, the new financial advisor began by specializing in selling annuities.
One trait that both the professions of musician and financial planner require? “Fearlessness,” says Oster, a registered principal with Raymond James, in an interview with ThinkAdvisor.
The independent has about $100 million in assets under management with Raymond James. The bulk of his book is in annuities, but he also helps clients to invest in equities and mutual funds, and he manages money.
Outside Raymond James, Oster has AUM of about $50 million in fixed life insurance and the like, with no broker attached.
In the interview, the Alameda, California-based Oster, 64, argues that annuities “get a bad rap” because “a lot of representatives don’t necessarily know everything about them.
“You have to know your stuff and be passionate about it and be able to present it clearly,” he insists.
One of the top annuity producers in the Raymond James Insurance Group, Oster also maintains his other career: His own record label, Retso, churns out his original music to the tune of an album every two years.
Since 2003, he has released nine albums, the most recent of which, “Brothers,” was released in July.
In the 1980s, Oster struggled for seven years trying to go beyond playing Top 40 songs in a Los Angeles bar band. But in 1987, he changed gears completely when, at the suggestion of a friend, he decided to become a stockbroker.
After passing the Series 7 exam, he went to work for Independent Advantage Financial, an insurance marketing agency.
Selling annuities exclusively over the phone, he was named Salesman of the Year for six consecutive years.
Then it was on to Prudential Securities, where he became a senior vice president, again focused on annuities.
In 1997, he joined Raymond James as an independent advisor, at the same time launching a separate business working with insurance companies’ “orphan” policyholders.
As for the Danville, Illinois, native’s music career, that has expanded significantly. In 2017 and 2019, he performed with the band Flow at Carnegie Hall’s Weill Recital Hall. He plays club dates and festivals, too.
He also wrote and performed on a 2013 Pete Seeger album and played on a CD accompanying a 2017 book by Deepak Chopra.
ThinkAdvisor recently held a phone interview with Oster, who was speaking from a cabin he owns in Vermont.
Inspired by Herb Alpert, Miles Davis and Steely Dan, among others, he called his “quiet” music the perfect background for sending email — whereupon, he offered up a mellow phrase on his flugelhorn.
Here are highlights of our interview.
THINKADVISOR: How do you describe your music?
JEFFREY OSTER: I call it “Miles Davis Meets Pink Floyd.” It’s an ethereal, soulful, warm sound. Probably 80% of my playing on my records is flugelhorn.
I don’t do hip-hop or rap or heavy metal. It’s quiet music for wine and cheese, and working on your computer while sending out emails, or chilling at a dinner party. I should make an album: “Music for Emailing.”
What prompted you to become a financial advisor?
I’ve been playing the trumpet since I was 8. In 1979, I moved to LA to be the next Herb Alpert. I spent about seven years making 10 grand a year and starving. For a long time, I was a limo driver. I also sold office supplies on the phone.
One of the other limo drivers became a financial advisor with Integrated Resources. He said: “You’re good on the phone. Why don’t you become a broker?”
What went through your mind?