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Six Questions With Willis & Woy Sports Group Contract Advisor Ashley Millerick

The following “Six Questions” short interview with Ashley Millerick, NFL Player Agent with Willis & Woy Sports Group, was conducted by Belmont University Law School student and aspiring sports/entertainment agent Mark J. Burns. Connect with Ashley on Twitter and Linkedin.

Ashley Millerick is an NFLPA certified Contract Advisor working with Willis & Woy Sports Group.
Ashley Millerick is an NFLPA certified Contract Advisor working with Willis & Woy Sports Group.

1. You have your law degree (Texas Tech, ’12), and you’re also certified as an agent with the NFLPA. How much of your time is spent practicing law versus acting in your capacity as an agent?

I’m not acting as a lawyer on a daily basis. However, there are a lot of aspects of the business that allow me to use the knowledge I gained throughout law school. I use my legal skills most often when dealing with contract negotiations. They are also useful when putting together marketing and endorsement agreements for clients. In addition, when players or their families contact me with their personal issues, having a law degree helps resolve some of their issues quickly and succinctly.

2. When did you first realize you wanted to become a sports agent? As a follow-up, why did you decide to pursue that career?

I realized I wanted to be an agent after my first summer interning with Jordan [Woy]. I saw that the sports agent business was very competitive and difficult. However, after getting to work with Jordan I was motivated by his success as an agent. The agent business is nearly impossible to enter on your own as a young, new agent. People underestimate the expenses of being an agent and difficulty of forming the relationships necessary to be able assist players as their agent. Once I had proven myself to Jordan, he took an interest in my career and mentoring me. I then knew that I was in a very exceptional position and had a great opportunity in front of me. Once I had a full time position at Willis & Woy and I was working side by side with Jordan, I decided to concentrate specifically on pursuing a career as an agent.

3. How has social media helped you in your career progression?

I’m active on social media and it is helpful with keeping up with transactions and breaking news stories that are happening in the NFL. It is also beneficial in getting information out on our clients and company.

4. You work at Wills & Woy Sports Group in Dallas. What has it been like learning from Jordan Woy, an agent who has worked in the industry for 25-plus years?

One thing I have observed in this business is that there are a lot of agents who are very good at recruiting players from a sales side. However, there are very few agents who have vast experience on the business side of negotiating contracts, dealing with front offices executives and truly knowing the ins and outs of being an agent. Jordan is one of the select few who know that side of the business and getting that insight from him is invaluable.

5. What is the most difficult part about being a female agent in the male-dominated sports agency industry?

I don’t feel there are any major difficulties I face due to being a woman. There is the obstacle of overcoming the stereotype that being a sports agent is only a male’s job. On the other hand, I feel there are several advantages to being a woman in a male-dominated industry. In a mainly male profession you do standout and tend to be remembered since you are one of few women. You can bring a female prospective to advising player clients that I believe can be very helpful.

6. In 140 characters or less, what advice would you give to aspiring sports/entertainment business professionals who want to work in the agency world?

It is a tough business. You have to have passion and focus. There are highs and lows so you have to be ready for the successes as well as the rejections.

By Darren Heitner

Darren Adam Heitner, Esq., is a preeminent sports attorney and the founder of Heitner Legal, P.L.L.C., a Fort Lauderdale-based law firm specializing in sports law, contract negotiations, intellectual property, and arbitration. He earned his Juris Doctor from the University of Florida Levin College of Law in 2010 and a Bachelor of Arts in Political Science, magna cum laude, from the University of Florida in 2007, where he was named Valedictorian of the College of Liberal Arts and Sciences. Admitted to practice in the state bars of Florida, New York, and the District of Columbia, as well as multiple federal courts, Darren also serves as a certified arbitrator with the American Arbitration Association.

As an adjunct professor, Darren imparts his expertise through teaching Sports Law at the University of Florida Levin College of Law and Name, Image, and Likeness (NIL) at the University of Miami School of Law in the Entertainment, Arts, and Sports Law LL.M. program. His scholarly contributions include authoring several books published by the American Bar Association, such as How to Play the Game: What Every Sports Attorney Needs to Know, and numerous articles in prominent publications like Forbes, Inc. Magazine, and Above the Law. His thought leadership in NIL has earned him recognition as one of the foremost experts by The Wall Street Journal, USA TODAY, and On3, and he has been lauded as a “power player in NIL deals” by Action Network and a “top sports trademark attorney” by Sportico.

Darren’s passion for sports law led him to establish Sports Agent Blog on December 31, 2005, initially titled “I Want To Be A Sports Agent.” The platform, created as a New Year’s resolution, has grown into a cornerstone of the sports agency community, offering in-depth analysis of industry trends, legal disputes, and agent-player dynamics. His commitment to the field is further evidenced by his representation of numerous athletes and sports agents, as well as his prior role as an Adjunct Professor at Indiana University Bloomington, where he developed and taught a course on Sport Agency Management from 2011 to 2014.

Darren’s contributions have been recognized with prestigious honors, including the University of Florida’s 40 Under 40 Award, the University of Florida Levin College of Law’s Outstanding Young Alumnus Award, and designation as the best lawyer in Fort Lauderdale by Fort Lauderdale Magazine. He remains an active voice in the sports law community, sharing insights through his weekly NIL newsletter and his X posts, engaging a broad audience on legal developments in sports.