Jan Plewes, CPA


Managing Director
Octagon Financial Services
McLean, Va.

As a tax and financial adviser to professional athletes, I enjoy working with them and helping them manage their wealth. Their issues are not unlike yours and mine, really, only on a larger scale. They need to learn to budget their money, be committed to savings and investments, and focus on their career.

I’m a managing director at Octagon, a full-service sports agency and sports consulting business. We handle athletes from just about all sports: tennis, basketball, football, baseball, hockey and others. In just about every sporting event, we have a client in it somewhere. So we’re always pulling for them and wishing the best for them. In the longer term, I enjoy seeing clients reach retirement with a nice portfolio. I love that part of our business, and I do love sports, too. I grew up with five brothers and had to learn to love sports if I was going to hang in there with them!

I’ve lived in the D.C. area or Maryland most of my life. I graduated from the University of Maryland, got my CPA and worked in public accounting for just a couple of years before I started working with Octagon. I’ve been here for 23 years now. My husband, Steve, and I live in Gaithersburg, Md. We have three children, with the oldest recently married and the youngest just having graduated from high school. My husband has his own financial planning business in Gaithersburg.

I took my first accounting class in college, and I caught on pretty quickly and liked it. So I pursued it as a degree and found I really enjoyed working in the tax area. When I started working at Octagon, it was primarily to do tax work for the athletes. Their returns can be tricky because they’re required to file in every state in which they earn income, so you can have 10 or 15 different states for one client. This past year, we had a couple of very large and complex tax cases that we took to IRS appeals and which were settled favorably for the clients. It can get rather complicated. For example, for nonresidents of the U.S., we have to determine how much of their endorsement income is required to be reported in the U.S. and how much of that is considered royalties. Some royalties are exempt by treaty. Those are the kinds of things that really fascinate me.

Athletes face a lot of peer pressure to spend money and to live a certain lifestyle. We try to keep them from focusing on that and just look at how much money they can put away today, because we know that they’re going to retire when they’re still young. A lot of people want to take advantage of athletes because they have a lot of money. Sometimes family and friends bring them investment ideas—schemes, you might even call them. Or somebody says something in the locker room, and it sounds to them like a great idea. And the client says, “Oh, well, I’ll just put a little money into this, a little money into that.” But these things rarely work out. Often, they’re not executed well or the investment is not sound.

The athletes can benefit from good, solid guidance. Moses Malone, for example, has been very diligent about investing. He was one of the first basketball players to come straight out of high school into the professional leagues. He’s been really successful, and I think that’s because he’s listened to solid advice. He’s been a terrific client for us.

As you might expect of a sports agency, we have a lot of former athletes here and just some very fit people. I’ve been a recreational runner for 18 years, including one marathon. My other hobbies are cooking and wine tasting. It’s always fun to try new recipes and wine with friends. I’ve also been very active in my kids’ schools. I was president of the elementary school PTA for a year, and for the past two years I was the parent volunteer coordinator at a high school of more than 2,400 students.

We had a client in the French Open recently. We have lots of TVs around the office, and so we turned on the match and watched it while we were working. We can stand around and talk sports a little bit during the day, and in fact, it’s important that we do. And it’s fun.


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