He's the Sports Tax Man
A native of Brooklyn whose grandfather emigrated from Italy — a heritage he takes much pride in — Robert Raiola, CPA, grew up watching and playing baseball. While he admits he didn't have the chops to play in the big leagues, he was able to capitalize on his love of sports with his current role as director of sports and entertainment at PKF O'Connor Davies. With 20 years of sports and entertainment accounting experience, Robert's clients include professional athletes, high-profile coaches, broadcasters, models, musicians, entertainers and comedians.
Building a National Following
About five years ago, Robert ventured into new territory by establishing a presence on Twitter as @SportsTaxMan. "Twitter has helped me expand my brand and be a thought leader in the area," Robert says. National Public Radio (NPR) caught wind of the tax tips and facts he was sharing on Twitter and interviewed him about the tax repercussions athletes would have to consider for certain deals. They ended the podcast with a very appropriate song: "Tax Man" by The Beatles.
Media recognition has helped Robert attain more than 52,000 followers on Twitter. But has this translated into more business? "A mother of a second-round draft pick in the NFL said, 'Based on your Twitter feed, you really know about taxes, and I want to talk to you about representing my son.' One call and one meeting later, we were hired," Robert said. "I've gotten a bunch of new clients because of my Twitter feed."
Robert co-authored the book Winning Tax Strategies and Planning for Athletes and Entertainers, published by the AICPA, and has provided sports tax advice and information for ESPN, CBS Sports, Sports Illustrated, the Bleacher Report, Yahoo! Sports, The Washington Post, The New York Times, Bloomberg and local sports news. "People care about who wins and loses [in sports], but they are also interested in athletes' wages and how they are impacted by taxes in different states," he says.
Becoming a Trading Card
Robert grew up collecting Topps baseball cards, so imagine his surprise when they reached out to him about creating his own trading card. It was like a dream come true. "Back in January [2016] … they said, ‘We are big fans of your work and we want to feature you on a trading card.' It was an honor to be part of the [sports card] set. I was flattered," he says. Robert's card is part of Topps' Allen & Ginter line.
Advocating for His Clients
For privacy reasons, Robert won't reveal who his clients are, but he doesn't shy away from providing commentary on tax issues affecting the sports industry. For instance, Robert publicly criticized the City of Cleveland for taxing an athlete who did not have physical nexus in the city. "If you're a player, you really need to have a CPA who is familiar with the tax laws relating to professional athletes," says Robert.
There are other assessments besides income taxes of which athletes need to be mindful. Athletes and entertainers need to understand everything they"re paying for and why they are paying it. "It's not what you make, it's what you keep," he says.
Robert enjoys helping clients navigate the murky tax waters and make the best financial decisions. "This is my area. I know it well, and I think I do it well," he says. "We always hope that we get to enjoy going to work and love what we do. I really have a passion for what I do."