042: How To Be A Sports Agent (Drew Pittman)

Drew Pittman

Did you know that the year after Jerry Maguire was released the number of certified sports agents in the US tripled?! It did. If you’re like many sports fans who have thought being a sports agent would be a really cool gig, you’re in luck! My friend Drew Pittman is here to give us the skinny on what it takes to make it as an honest NFL agent.

In this episode of How’d You Get Into That?, Drew tells us what it’s been like to be an honest agent in a not-so-honest industry, how he’s maintained his integrity and kept his priorities straight while still managing to be successful on his own terms. We talk about all of that and so much more…


Drew was born and raised in Texas, the land where football is revered and the favorite past time in nearly every household. It’s more than just a hobby, it’s a lifeblood of every community. And it was for Drew. His dad took him to his first big-time game when they attended the 1968 Cotton Bowl, one of the major college football championships.

Though he loved the game, Drew never had the physical skills to be a successful football player so he picked up a different sport, soccer (also called football in every other part of the world). And he played soccer all throughout college. His original intention was to graduate and move to Europe to play professionally, but he later decided against that and considered becoming a sports agent. He wanted to see players treated like people and wanted to help them both personally and professionally. There was also a time where he learned to install artificial turf in Denver, this gave him a different perspective and appreciation of sports field and the maintenance the undergo.

He didn’t become a sports agent after college, but it was always in the back of his mind. Instead, he worked for his father in the banking industry for 8 years and then he joined a friend’s business in commercial real estate. His job was to help banks get themselves out of bad commercial investments. He was savvy enough to see he was working himself out of a job and would one day be let go.


  • What are the key traits he looks for when representing a client?
  • How many agents are there and how many NFL players?
  • Does he believe this is his true calling?
  • How many years of research did he do before starting his firm?
  • What advice does he give someone considering becoming an agent?
  • What’s one thing he says he hasn’t been great at?
  • And so much more!

And at the age of 29 that one day came. He was released from his job and decided that was the time to go for his sports agent dream. He incorporated, sent in the money and the paperwork to the state of Texas and rolled up his sleeves. Drew says he had no money and even less sense when he started, but he went for it anyway!

There were definitely some lean years and a lot of trials along the way. He says for the first five years he got up every day knowing it could be his last day as a sports agent. He simply prayed for guidance and asked to be shown another path if he was meant to do something else. With the support of his wife and his two sons, they managed and today Drew’s firm represents anywhere from 30-35 NFL players along with a few coaches.

He’s incredibly grateful for the work he does and for the way he does it. Even though someone once told him he wouldn’t make it as an agent because he was honest and has integrity, Drew has proven you can be a successful and honest agent with values and morals. He attributes the years he spent exploring the industry as well as his finance degree and his time in the banking world as all keys to his success.

Please join me in thanking Drew for being such a great guest on the show today. Even if you aren’t a sports fan or have any inclination to work as an agent, he gives valuable lessons on how to create a life you love by staying true to your own value system, regardless of the industry standard. We appreciate you being here with us and we’ll see you on the next episode of “How Did You Get Into That?”. 

Tweetable: “A lot of being successful is having good business sense.” Drew Pittman


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