Legacy Pro Sports

Ryan Sherry


Brandon Siler, founder of LPS, was born in Daytona Beach, FL.  He moved to Orlando, Florida, at a young age, and attended Evans High School in the lower socio economic neighborhood of Pine Hills.  He graduated from Evans in 2004 with a 4.2 and committed to the University of Florida to play football for the Gators. In the 2004-2005 season he earned SEC Freshman Player of the year while maintaining a 3.6 GPA. In his junior year his Florida Gators went on to win the 2007 BCS National Championship and he elected to turn pro after that season. Brandon was drafted by the San Diego Chargers in 2007 and played 4 seasons with the chargers until his contract expired in 2011.  In 2012 and 2013, he played football with the Kansas City Chiefs.  After 6 seasons, Brandon decided to retire from the NFL and start the next chapter of his life.  

“Two years after I retired, I started to experience some of the negative effects that football had on my body.  After being a manager at a Fortune 500 company for two years, I decided that I would leave the company and truly seek a resolution to these problems.  I admit I was scared to leave a good financial situation and a great job, so I started to seek out assistance that would give me time to get back on my feet.

​​I was surprised to find out how much assistance was actually available to retired players.  You would think that would make me happy, but instead I became irritated and outraged that more players didn't know about it.  I didn't know rather to be upset with the NFL, NFLPA, or at myself. The process to get most of the assistance was extensive and the knowledge of this assistance, often times, was stuck inside of a thick book that we would not read in its entirety.  I needed to figure out a solution to this problem.  I wanted to help bridge the gap between player’s awareness and the leagues efforts. That's when I founded a company whose mission would be to serve that exact purpose.  

Legacy Pro Sports is an organization that helps former NFL Football Players prepare for life after the game, emphasizing on all the key elements to get one’s personal, financial, and medical affairs in order. I am not an agent, attorney, or a financial advisor.  I am a former NFL Player that has found my "calling" after football, and that's to change the way my brothers retire."

Brandon Siler

'04-07 University of Florida
'07-11 San Diego Chargers
'12-13 Kansas City Chiefs

Starting Life After the Game

Organization Co-Founder

Organization Co-Founder

Ryan Sherry is from Fort Myers, FL.  After attending Canterbury School, he received an athletic scholarship to the University of Florida. Ryan truly left a footprint on the UF campus.  He graduated from the Warrington College of Business Administration with an emphasis in Sports Management.  As a 4 year letterman on the Men's Tennis team, Ryan played a part in two SEC team championships (2003-2005), and he was the tournament MVP in 2005.  He made the SEC Scholar Athlete honor rolls in 2003-2005 as well.

In addition to his educational and athletic achievements, Ryan was nominated to the Student Athletic Advisory Committee (SAAC), where he represented the voice of UF student-athletes.  He is a member of Sigma Phi Epsilon Fraternity Florida Chapter, as well as Florida Blue Key: a student honor and service society at the University of Florida.

Following graduation, Ryan became an entrepreneur through creating, developing, and operating two popular nightclubs in SWFL.  After six successful years in the entertainment industry, he sold both businesses. Before entering the securities business and joining the Art and Science of Successful Planning, Ryan worked for his family's dental practices in the areas of business development and marketing.

Ryan's current focus is working with former NFL athletes developing claims filings for the NFL Concussion Settlement program and guiding those former athletes in the area of budgeting and personal finances; supporting them and helping them maintain a quality of life as they transition from one chapter in life to the next.