The Wynning Experience is an event planning company owned and operated by Allyson Massie Wynn. The company, started in 1996, “was always something I wanted to do.” said Wynn. A 1982 graduate of Paducah Tilghman High School, Wynn has worked countless hours building her company. “People usually just see the result of an event, the fun part. They don’t see the making of it, the stress, long hours, meetings, on and on…”
Three defining words ‘Plan. Design. Implement’ confidently expresses Wynn’s Winning attitude. After 20 years in the business, she’s courageously battling this ‘new normal’ brought about by COVID-19. Being a successful entrepreneur and a veteran event planner, the business “has its highs and lows - you take it in stride,” said Wynn.
Since the first shuttering of businesses,“COVID-19 has totally changed the way we do business. Until March, the focus was on in-person large-scale events for corporate clients. The first to shut down were the large, sponsored, in-person events. All the 2020 events started to go away one at a time until they all were eventually canceled.” The pandemic flipped Wynn’s virtual solutions business on its ear and immediately pivoted from an ‘as needed’ basis to 100 percent virtual.
Before Wynn became a successful Chicago businesswoman, a community in far western Kentucky was responsible for her upbringing. “I will forever appreciate growing up in a small town along with the ability to enjoy teenage years without mobile phones, social media, and selfies. Tilghman brings back so many happy memories” said Wynn. 'Hanging out with friends’ was one of the best remembrances of days gone by.
One of Wynn’s dear friends from high school, James Teague, passed away last year. Teague was a person that everyone liked. In school, he was this tall nice-looking kid that loved sports, particularly basketball, befriended everyone, and never had an unkind word. Teague received his Bachelor of Science degree from Chicago State, an MBA from the University of Phoenix, and achieved one of his lifelong goals of becoming a professor at Broward Community College. He lost his battle with brain cancer leaving behind a wife and two children. Teague was 54 years old.
Wynn was very active in high school. Her extra curricular activities included the drill team and the Tilghman Bell. The Tilghman Bell is the high school newspaper founded in 1913 and is still published today. In fact, there’s an online version at tilghmanbell.com. The newspaper, produced by the journalism class, covers news, sports, arts and entertainment, and commentary. It’s here where student expression is encouraged. Wynn was crowned the 1982 Basketball Homecoming Queen by the Paducah Tilghman basketball team. During her years in high school, Wynn had many friends and Teague was one of her dearest.
After graduating high school, Wynn attended the University of Kentucky and graduated from Western Kentucky University with a degree in Public Relations and Psychology. Her first move after graduation was to Nashville, Tennessee and within the first couple of months, she met her future husband, Raymond. “I was working at First American Bank and he would probably never admit it but would come to the bank to flirt with me. He would sometimes bring his friends; it was funny,” smiled Wynn.
When the two met, Wynn’s husband was a student at Meharry Medical College. After working in the banking industry, Wynn went to work at Meharry Medical College as a researcher and fundraiser. After working at the college, Wynn landed a job with a pharmaceutical company as a sales representative. During this time, she and Raymond married and moved to Rochester, New York. It was in New York that opportunity came knocking and Wynn accepted a job as a special events coordinator and her dream of owning a business was written in the stars. “My family has owned businesses for as long as I can remember so perhaps it was just a natural fit. As they say, nothing beats a failure like a try.’ explained Wynn. Now, 20 years later, the business is still going strong, just pivoting.
Wynn has worked on large-scale projects such as the Essence Music Festival, Billboard Music Awards, Oprah Live Your Best Life Tour, and the National Football League Super Bowl. In addition to her business, she published an e-book ‘So you Want to be an Event Planner.” It’s an insider’s look at the event planning industry, the first of a series of books to come.
Wynn and Raymond have two sons: Bradford, 26, a business consultant in Atlanta and Nigel, 24, a senior analyst in Chicago. Other than being with her husband and two sons, Wynn enjoys collecting art, fine dining, traveling, and being involved in community-based organizations.
“I love to travel and have racked up a few miles and a few stamps in my passport,” said Wynn. She prefers warm weather destinations. In fact, the family’s last vacation was south of the Yucatán Peninsula. “Belize was amazing. Beautiful people, wonderful food, relaxing, no traffic, one of our best vacations.”
As Wynn reflected on her successes, she said, “It’s important to surround yourself with people that care about your successes as much as you do.” When asked to describe her perfect day, she said, “Coffee, getting through my things on my to do list and talking with my family.”