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Interview With The Agent: Rich Gray

Richard Gray is the founder and agent for Gray Area Sports Group. Although only licensed for a year, he has worked in basketball since 2010. He spent two separate stints with Priority Sports & Entertainment as an intern: the first in 2010 before attending law school at Washburn University at Priority’s Chicago office, and the second stint at Priority’s LA office during the summer of his second year. After law school, Richard spent two seasons in basketball operations with the Brooklyn Nets and three seasons in basketball operations with the New York Liberty. 

We were fortunate enough to have the opportunity to interview Richard about his industry experience thus far. Check it out below.

SAB: How did you get started in the representation industry?

Rich Gray: It was completely an accident, to be honest. After wrapping up my college basketball career, I quickly realized that playing professionally wasn’t in the cards. So, going into my final semester of undergrad I accepted an internship working for the Chicago Sky (WNBA). They used to share an office space with CSMG (later acquired by Octagon) when the late great Hank Thomas ran their basketball division. I happened to see Hank walk through the office with Dwyane Wade and Chris Bosh shortly after they became clients and that prompted me to walk over and ask him what he did in his line of work. He gave me a full run down of his job as an agent and what he did to get to that point. He talked about his early stages of grinding, receiving little to no pay and emphasized getting his law degree to show he was serious about his craft and gaining credibility. We have to remember, at that point, there was no exam in place to become a licensed agent.

Although it was partly due to the aesthetics of the job (plush office in downtown Chicago and being around the NBA), I was sold on merging business and basketball to carve out my path. That day, after talking to Hank, my decision was made. I spent some incredible stints with Priority Sports as an intern while I was in law school but that first interaction with Hank is what sparked everything.

What made you want to start your own agency instead of gaining experience with an already established firm?

It was really a timing thing and a really crazy story. Right after law school, instead of looking for a job on the agency side, I wanted to experience working for an NBA team. So, I spent a year with the Brooklyn Nets during the Billy King/Bobby Marks era as a basketball operations intern and then a season as a basketball operations “associate,” which is pretty much an extended internship with a few extra dollars. The experience with the Nets piqued my interest on the team side which led to a full time position in the video room with the New York Liberty, which I thought would lead me to a permanent role with the Knicks, since we were in the same facility. Well, first week on the job I bumped into Isiah Thomas who was just named President of the Liberty; and, without going deeply into the story, after having a conversation with Isiah and he finding out I was connected to some of his mentors back in Chicago as well as my education and background, he hired me as his special assistant in addition to my role as video coordinator/basketball ops assistant with the Liberty.

While working with Isiah I was able to work closely with Jaylen Brown in his draft process, Milton Doyle (former two-way player with the Nets) in his process and be a sounding board for Malik Beasley and his family during his second season when his agent lost his certification. These were all relationships through Isiah and I made the most of each of those opportunities by tapping into the experiences I had working on the team side and agency side and provided a high level of service. While I still help Jaylen and his team with projects, the first to inquire about me representing him was Milton Doyle. I had no intentions of officially entering the business at that moment. I actually helped hand pick his first agent, so when he asked if I would be interested in representing him, it caught me off guard, but I was up for the challenge.

I passed the agents exam and signed Milton Doyle [who I co-rep with Keith Kreiter]. At that point, I considered working for an agency, but after a lack of interest, my brother and I decided to take some of the revenue from our thriving Trivia Card business and we launched Gray Area Sports Group.

How do you set yourself apart from other agents with more experience when recruiting?

I use my journey and the experiences along the way as well as the quality relationships I’ve built in basketball to my advantage.

In the recruitment process, instead of focusing on what I lack in comparison to other agents, I lean heavily on how my past experiences will help me be a good fit for them. While with the Nets, I built up a great contact list with every other team we faced on game nights. GMs, Scouts, etc. I dropped off the opposing team credentials every game and made sure I introduced myself and followed up with everyone I came across, so the relationships I have are a major sell. I only have a handful of clients and I don’t recruit a bunch of guys, so the personal attention is there. I spent just about every day during the draft process with my client that I landed this year and I was on the phone on his behalf 100% of the time.

Can you tell us about some of the highs and lows from your first year in the business? What were some of the biggest challenges you faced and how you handled them?

Highs: (1) I was able to sign six players, all in different walks of their careers and they each had either a personal connection or a referral aspect to them. This lets me know that I’m doing things the right way and that I have made a good impression on people so far in my career. (2) Help one of my clients have a 180 during the offseason. We were able to get on better terms with the organization and help get his team option picked up when it looked bleak at one point. This was all due to an offseason plan we put in place.

Lows: (1) Listening to teams not think or feel as highly as you do about your clients. I struggled with not taking that personally at first. (2) Being made aware of some of the negative things that competing agents say about you during the recruiting process. It got pretty brutal. (3) Having a guy get cut or come up short of an expectation. It led to a lot of sleepless nights, and not because of fear of losing a client but feeling like I let them down.

When going through highs or lows, I try not to allow them to carry me. Never get too excited nor get too down on yourself. Enjoy the success but stay even keel and get back to work.

How has your legal background helped you thus far? Is this a route you recommend to aspiring agents?

There are a lot of different rules and nuances in the CBA. You have to learn it and be able to apply it at a high level. Front office guys are really smart and know the cap, so when you’re on the phone speaking through different scenarios, you have to have an understanding if you want to be taken seriously.

Even if they don’t get a JD, specialized clinics on sports law can be very beneficial.

What is one piece of advice you wish you knew when you started out?

You don’t have to have all of your ducks in a row to get started. Money, mentors or connection to prospects…none of that. There are guys in the industry that I started off with who started with nothing and they are thriving now. Treat people right and nurture those relationships.

Where can our readers follow you and keep up with your career?

On Twitter: @iamrichgray and the Gray Area Sports Group Facebook page.