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This Top Raymond James Annuity Broker Runs a Record Label, Too

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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?

I didn’t want to play “Proud Mary” to six people with their backs to me on a Tuesday night at some bar; I didn’t want to be a cover band musician. I wanted to save enough money to do music and hire other musicians and producers.

So, you went into financial services? 

Yes. In 1987, I got my Series 7 [license]. I became the top salesperson at a company that specialized in the direct marketing of annuities and single-premium life insurance.

They did investor newsletter inserts to get people to call for free booklets and cassette tapes.

What happened with your music?

For a year, I was still playing Top 40 music at the clubs till 1:30 in the morning. I’d get up at 7 and cold-call the Beverly Hills phone book till five at night, then go work at the clubs. But all that got too tiring.

Do playing music and working as an FA complement each other in some way?

My financial services direct marketing skills are completely applicable to running a record label of my own music, which I do.

A lot of the skills I learned selling annuities and insurance completely apply to the music business: How do you make a compelling call to action? How do you set up a website that [drives] people to listen to the music and [send payment] for one of your songs?

What’s one key trait needed for both professions?

Fearlessness is important as a musician. It’s important as a financial planner, too. You have to know your stuff and be passionate about it and be able to present it clearly. You have to be good at it.

I have very deep knowledge of the money business, especially about annuities and insurance. Not a lot of people do, and frankly, that’s why annuities get a bad rap — a lot of representatives don’t necessarily know everything about them.

What’s your philosophy about selling annuities?

You can explain annuities as building a bridge between the money under the mattress and [guaranteed lifetime income]. 

But the only way it can work is if it fits the client and is good for them.

As an independent with Raymond James, do you sell variable annuities?

Yes, but way less of them now. It’s more fixed indexed annuities with lifetime income riders. Those are very popular, and for good reason: Where else are you going to get a 5% payout that not only will pay you now, but for the rest of your life?

What’s been a high point of your annuity business?

I got my biggest client in about 1989, a small five-figure annuity — now they’re at almost $30 million. Not because I turned their $10,000 into $30 million. 

But as time has gone by, the relationship has maintained and grown.

Are your clients aware of your music career?

Yes, I don’t hide it. Mostly I don’t meet clients face to face: I’m a voice on the phone. 

So for [many], the first time they saw me was when I was on [the TV show] “America’s Funniest People,” because I also did some stand-up comedy when I was living in LA. I did the Comedy Store and other clubs. I came in third in the Funniest Person in the Valley contest. I wear that proudly.

I entered the Funniest Stockbroker contest at Stand-Up New York. I didn’t win anything, but it was cool.

How do clients react when they learn about your concurrent career in music?

I’m not shy to tell folks I play music. In fact, I have several clients who are musicians. Not every musician is poor. Even the ones without a lot of money don’t know what to do with [what they have]. 

I especially have relationships with musicians that might just be getting started and need help. I’m happy to do that. There’s a lot of gratification that comes from it. 


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