Our Team

Over more than three decades in financial services, Chip May has honed his skills to help individuals, families and business owners navigate the many phases of life, while never losing a love of connecting with every client on a personal level. An avid outdoorsman, Chip grew up in Overland Park, KS and attended Kansas State University, where he received a degree in Feed Science and Technology. He started May Financial Solutions, and his career in financial services, in 1987. Chip earned his Master of Science in Financial Services (MSFS) from the American College of Financial Services, located in King of Prussia, PA, in 2005.

Chip has enjoyed a wonderful family life since marrying his wife Lisa in 1987 and welcoming their two children, Trevor and Courtney. Chip and Lisa were delighted to become grandparents upon the birth of Courtney and her husband John’s first daughter Analeigh in 2021. Chip received his pilot’s license in 2010 and he flies his Cessna 210 regularly, both recreationally and professionally as a volunteer pilot for Angel Flight, an organization that transports patients to medical appointments. He loves to stay active in the community and has served in the Boy Scouts of America, as a member and former president of the Arlington Sunrise Rotary Program, and as a charter member and past president of the Mansfield Chess in the Schools, Inc. program. You can often find Chip engaging in some outdoor activity, whether it be kayaking, hiking, fly fishing, bow hunting or shooting at the Arlington Sportsman’s Club.

Since joining May Financial Solutions in 2010, Katie Hutto has become an integral part of ensuring that operations run smoothly and clients get the individual attention they deserve. A native of Austin, TX, Katie moved to Fort Worth in 2006 to attend Texas Christian University, where she received a degree in psychology with a double minor in business and criminal justice. The daughter of two finance professionals, Katie initially did not intend to follow their career path, but after being introduced to Chip post-graduation, she realized that joining his team was a perfect way to blend a familiar field of work with her love of connecting with people. While Katie and her husband Keaton frequently visit family and friends in Austin, they call Fort Worth home and enjoy spending time with children Hagen and Adey, as well as their dogs Jerry and Blaze. Katie loves to relax by cooking up recipes new and old, reading, enjoying live music and traveling to new places. 

As soon as he signed on to the May Financial Solutions team in 2015, Kyle Castilaw hit the ground running, and his love of tinkering made him the perfect person to put the pieces of clients’ financial puzzles together to come up with a personalized solution. Kyle grew up in the Golden Triangle region of Southeast Texas and attended Stephen F. Austin State University, where he received a degree in music education. After working as a sound engineer, home theater specialist and elementary music teacher, a series of discussions with Chip, who was a longtime family friend of Kyle’s wife Kelly, led him to pursue a career in financial services. Kyle and Kelly live in Arlington with their hilarious son Landon and loveable mutt Shadow. When he’s not at work, Kyle enjoys 3D printing props like helmets, weapons and entire suits of armor, as well as hanging out with his weekly Dungeons & Dragons group, gaming and reading.

As Director of Operations, Lisa May provides invaluable support to the entire May Financial team. A native of Texas, Lisa attended Texas Tech University, where she received a degree in education. She uses both her organizational and administrative skills to help with internal processes and marketing efforts each and every day and she’s always ready to lend a helping hand. In their spare time, the Mays love to travel the world together, especially to places like Glacier National Park in Alaska, Banff, Canada and Yellowstone National Park.

A former television news reporter, Jill Riggs brought her skills in communication and engagement to the May Financial team in August 2022. She first became familiar with Chip, Katie and Kyle as a client, having been referred by her parents and aunt and uncle, who are all longtime clients themselves. You can typically find Jill writing and creating, whether it be newsletters, emails, social media posts or other projects. She grew up in Grapevine, TX and her love of reading and desire to write for a living led her to the University of Missouri, where she graduated in 2009 with a degree in broadcast journalism. She started her career in the beautiful city of Burlington, VT and then moved to Indianapolis, IN, where she worked as a reporter for nine years. When they're not chasing their identical twin boys Austin and Owen around, Jill and her husband Nate love to travel to National Parks, attend live concerts and watch all of the Oscar best picture nominees every year.