Tax Planning Strategies for Pro Athletes and Professionals, with Robert Raiola
Robert Raiola

Robert Raiola is the Director of the Sports and Entertainment Group and has over 20 years of sophisticated tax experience in both the public and private sectors. He provides tax planning strategies and business consulting to high net worth individuals and their families in the sports and entertainment field. Robert is widely known as the “Sports Tax Man” and has a following of approximately 50,000 on Twitter where there is a lively exchange of various sports, entertainment and tax topics.

What you’ll learn about in this episode:

  • Robert’s background and how he knew he wanted to be in the sports entertainment industry
  • How Robert keeps up within the fast-paced industry of sports and all the laws in different states
  • How Robert rose to become an expert in the sports industry and building his platforms
  • Best opportunity Robert received due to his marketing strategy
  • How Robert educates his clients and athletes around finances through social media and as a client relationship
  • The lack of education for high-profile athletes around their finances
  • Importance of understanding the taxes broadcasters have to pay from state to state
  • Different requests that Robert used to receive as tax write-offs
  • Challenges California pro sports teams have to maneuver to bring in top athletes at the top dollar
  • Benefits of getting money up front and not into your salary as a pro athlete
  • How much lobbying goes on within the state government form pro franchises to try to shape the tax laws
  • The two states Robert believes are the best states for pro athletes
  • An example of why a gross paycheck may not be the best net paycheck
  • How much time Robert spends on Twitter
  • An overview of how Trump's new tax laws change how expenses are written off
  • Advice Robert would give to upcoming graduates about

Additional resources:


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