Businessman, family man, avid golfer, and friend to everyone he meets

David and Sandra Guess on their wedding day, October 25, 2014

Guess doing what he loves to do...swing the golf club

Guess riding in the boat with Bentley

Guess and Josh new Paducah Firefighter hire

Guess, Sandra, and daughter Shannon

Sandra, Lindsey, Josh, Guess and Shannon

David Guess is a bit of a self-made man. He’s a graduate of Paducah Tilghman High School and former student at Reidland Elementary and Middle Schools. Guess transferred to Paducah City Schools in the ninth grade. He said, “We moved to the city when my mother got a job at the plant. She told me we needed to be closer because it was too far to drive to Reidland.” 


“Moving to another school in the ninth grade was tough.” said Guess. “I still remember the first person I met was Evan Miller when he came and sat by me in the gym. Evan was everyone’s friend.” This encounter with Miller may be one of the reasons everyone likes Guess. He’s that friend that will come sit by your side if you’re sitting on the bench alone. He’s ‘the buddy bench’ guy. He's one of those people that never meets a stranger. To this day, Guess has friends from the playgrounds at Reidland Elementary School to his years at Murray State University. He's fast friends with everyone he meets. 

Today, Guess is a successful business owner with both residential and commercial properties. In fact, in 2017 Guess and his wife Sandra purchased the Hipp Building from Dick Walker and the Gene Hipp Estate. Guess said, “I didn’t realize how big it was.” The 55,000 sq. ft. building is located on Jackson Street across the road from Red’s Donuts. 

As of 2020, the couple completed renovations on 10,000 sq. ft. of the building for the Kentucky Transportation Regional Real ID office and Children’s with Special Healthcare Needs. Both organizations are very important to our community. 

Beginning October 1, 2020, all US citizens will need a ‘real I.D. compliant’ driver’s license, US passport, US military ID, or other accepted identification to fly within the United States.  The Children’s with Special Healthcare Needs, formerly located in downtown Paducah has since moved to the Hipp Building. The Kentucky government program helps children with needs such as hearing loss, autism, or other health-related issues.

Guess’ entrepreneurial spirit comes naturally. His dad and stepmom. Paul and Alice Guess owned Paducah Supply. After Guess graduated from Murray State University with a degree in business, he worked in the family business, as well as built houses until his dad sold it and retired at the age of 52. After which, Guess expanded his part-time business, David Guess Heating and Air, into a full-time, prosperous endeavor in 1992. 

In addition to Guess’ thriving heating and air business, he owns numerous properties including an apartment complex with 30 apartments all within Paducah city limits. He also has rental property in Reidland and around Kentucky Lake. 

Guess said, “Sandra and I like to buy 100 year old properties with brick exterior, original hardwood flooring, and wide crown molding that may need  to be  completely stripped-down during the renovation process or just need only minor repairs.” The couple really enjoys working together on these projects. They’ve been told they “make a great team.” 

Another venture that Guess started was an online business for contact lenses. He’s the owner of clearviewcontacts.com and has the help of his mother and stepdad to run the business. Guess’ mother manages the day-to-day operations and his stepdad, Dr. John Strakal, a retired optometrist, helps in his specialized area. 

A businessman is Guess’ profession but his true love is his family. Guess has two children that are both accomplished and a joy to be around. His son Josh works for the Paducah Fire Department and is married to Lindsey, a dental asisstant. His daughter Shannon is a doctor of pharmacy and is married to Daniel, also a pharmacist. Shannon and Daniel live in Bowling Green, Kentucky.

In a few days, Guess and his wife Sandra will be celebrating their sixth anniversary. Out of the devastating yet historical ice storm 2009, a budding romance started. Amidst the chaotic natural disaster, the two were introduced for the first time. Sandra made the statement that she wasn’t on Facebook but found out Guess had a Facebook page and went home that evening and created her first page. The couple married on October 25, 2014. “God has blessed us more than we deserve,” said Guess. 

Guess is an advocate for animals. He has a rescue Yorkie named “Bentley'' that appears to go with him everywhere, including boating trips on the lake. In addition to his dog, the family has two outside cats, Winston and Riley. 

The couple has a several outside interests. They do like to travel. Adventures range from tropical paradise locations to snow-covered mountaintops. Taking lake trips with friends or 'hanging out at each others’ homes' is one of their most favorite activities. It’s simple and Guess said, “maybe boring” but “God has blessed us with great friends. The Tilghman guys I talk to almost daily are Mike and Gary Leneave and Gil Arterburn. We’ve been friends for 35 years. We have each other’s backs.” said Guess. 

In addition to the vacations, Guess is an avid golfer, in fact, he said, “If I could play golf each morning and finish at dark, seven days a week, stopping only to eat, I would...but that’s not happening.” He does get to play with his regular group of golf buddies most weeks and he and Sandra participate in couples tournaments. It’s definitely one of his passions. 

Early January, Guess made a commitment to run for another term in the Paducah City Commissioners’ race. He is a former two-term commissioner and is ready to throw his hat in the ring once again. “I have been the one working on the inside of government operations and also the guy on the other side of the counter attempting to get things done with meeting roadblocks.” Guess sees this election as one that he can invoke change and make a difference in the lives of Paducah citizens. 

Guess said he wants to bring more jobs to our area and streamline government operations. He wants to make Paducah ‘business friendly.’ Guess’ background fits nicely with his goals for Paducah. He has several solid businesses and lots of properties. It makes sense that this would be his platform. Go with what you know. 

If you’ve been interested in city government over the last 20 years, Guess served two terms in 2002 and 2006. He said, “My first run for city commission was at the age of 38. Some remember me as the guy that won by ONE vote one term. So yes, every vote does count.”

Having Guess as a friend is a true treasure. He’s the guy that you can always count on to help out a friend, neighbor, or complete stranger. It’s those golden boy looks with the ocean blue eyes. He’s the guy that will sit by you on the ‘buddy bench’ if you’re alone. Everyone needs a friend like Guess. He's the guy you can count on in a storm..even an ice storm.