Celebrating Men of Influence!

Proudly Honoring Our Community

We are fortunate to have so many influential men who share their dreams, advice, experiences, and inspirations with us to make a significant difference in our community. These extraordinary men are proven leaders and role models who have a passion for life and love helping others!

Larry Cheever, 101-Year-Old WWII US Army Veteran

BACKGROUND: Lawrence Cheever was born in 1920 in Jim Falls, Wisconsin. With help from son Rick and granddaughter Sarah Cheever, we learned. “He grew up with eight siblings on a 40-acre farm on the Chippewa River. Cheever finished 8th grade and worked at the family businesses with logging, boat rentals, and a convenience store until 1942. He was drafted into the US Army at 22. He trained at Fort Stewart in Georgia, where he had challenges with his captain over Sabbath observances and bearing arms as a conscientious objector. After repeated threats of court-martial, a major intervened. After hearing the facts, he was given the option of training as a non-combatant medic. From Fort Stewart, he was deployed to Casablanca in North Africa. From there, they went to Italy, France, and Belgium before ending up in Germany, where he saw WWII end.”

“While studying for his Nursing Bachelor’s in Science degree after his military service, he met Lois Bale, who he married between his nursing years. He practiced anesthesia at Grady Memorial Hospital in Atlanta before relocating to Savannah, Tennessee. There he and Lois had six children with, five boys and a girl. His younger brother, Warren, joined him at nursing school and went to work practicing anesthesia in Florida. His brother called Larry to work in Florida. Larry moved his family to Winter Garden, where he worked for 25 years. He built a house on 2.5 acres where he planted an orange tree grove and his garden. Then, as an anesthetist, he temporarily moved to West Virginia. He worked there until he was 70 when he decided to retire, spending the winters in Winter Garden and the summers in West Virginia.”

WHAT INSPIRES YOU: “I love looking at flowers and plants. I am always inspired by photographing nature, plants, flowers, animals, and interesting things I see.”

YOUR SECRETS TO SUCCESS? “Always trying to please God. I’m a Seventh-Day Adventist, so I have worked Sunday to Friday every week since I was a young child. My secret to longevity is that I have always been a vegetarian. I always relaxed doing long walks and gardening every day.”

YOUR FAVORITE MOTTO: “Waste not, want not.”When in Africa and during WWII, I saw a lot of poverty.“We taught our children always to clean their plates. At dinner time, we used to say, come and get it or we’ll throw it out!”

ADVICE FOR YOUR YOUNGER SELF? “As a teen, obey your parents and appreciate what your parents are trying to teach you.”

BEST ADVICE YOU EVER RECEIVED? “When returning home from the war, a lieutenant advised me to go back to school after the war, to get a college education and a professional career.”

ANYTHING ELSE: “I have always enjoyed traveling the world and visiting 48 states while meeting and talking to people of different cultures and experiences.”

Obed ‘Obie’ Samuel Diaz, K923 Radio

BACKGROUND: “I’m a Winter Garden guy. I majored in Musical Theatre and Acting at Performing Arts High School, leading to a 25-year radio career currently ON AIR with K923 and the Cox Media Group. I started working at a radio station during my junior year in high school. By the time I was a senior, I had become a radio producer. I host the Global Better Man brand to help promote the betterment of men. We host huge inspirational and educational events with guest speakers like Denzell Washington and Evander Holyfield. In addition, we broadcast our podcast show to men in over 80 countries. I’m a family man with a wife and four kids. The fourth is adopted.”

YOUR PASSION & WHAT INSPIRES YOU: “I have a passion for bridging people to Jesus and to discover real living. This is a continuous opportunity to help people with the challenges and opportunities in life. Once you find out you are in the matrix, you can start telling other people about it while sharing guidance, wisdom, and understanding to help us all live a better life.”

YOUR SECRET TO SUCCESS? “I remind myself that my special communications, musical talents, and other gifts were given to me for a purpose greater than me. So I try to use them to help, motivate and lead others.”

YOUR FAVORITE MOTTO: “Your Life is an occasion! Rise to it. -- Do something with your life while making advantageous things happen in all the spaces you take.”

ADVICE FOR YOUR YOUNGER SELF? “Invest! Look for exciting new opportunities like Apple and Amazon.”


YOUR BEST KEPT SECRET? “I'm actually not a professional at anything in this life. I just have the personality and drive to help make others feel included and valuable.”

ANYTHING ELSE? “My Winter Garden favorites are Axum Coffee, Rosalie’s French Café, and the Winter Garden Farmer’s Market. I've had open-heart surgery twice. I fought and won a battle against alcoholism. I love country music. It makes sense to me as it embraces family, faith, and hard work. I started Sons of Thunder, a local fraternity here in Winter Garden that's now over 600 men strong. Like the Better Man brand, we encourage men to help each other through guest speakers at special events and through mentorships. Some men feel defeated, while others are champions. We help each other by sharing challenges, advice, and opportunities. I’m grateful for what I have, yet I try to stay humble. I always try my best to do what I can to help affect the world!”

Jim O'Brien, Mayor of Windermere

BACKGROUND: “I am a native Floridian, born and raised in West Palm Beach and married to Kristin O’Brien, and father of two children Jacob, 21, and Emily, 15. I hold a Master’s Degree in Education and Counseling and have worked in non-profit Management, Programmatic Service Delivery, Philanthropy, Grant Management, Emergency Management, and Disaster Recovery. I am currently serving my third term as Mayor of The Town of Windermere and Sr. Disaster Recovery Consultant for CDR Maguire Emergency Management. I previously served on the Windermere Town Council for four consecutive terms.

YOUR PASSION & WHAT INSPIRES YOU: “I am passionate about building and preserving our Town for the benefit of our children. I am inspired by my family and those around me. I love to build consensus and find compromise, two things that we have lost in most forms of Government. I enjoy finding common-sense solutions to complex issues. I am inspired by those who are not afraid of failure. They are some of the most successful people I know. I am always amazed by those who serve others with total abandon. The early history of our Country and the vision of our forefathers always inspires me. I also love to know how things work, especially behind the scenes.”

YOUR SECRET TO SUCCESS? “Surrounding myself with the best people possible. Successful leaders are never afraid of hiring and teaming with people smarter than themselves. Always seek to learn from and respect the past while playing a long game. Seek to do everything with integrity and transparency.”

YOUR FAVORITE MOTTOS: “Get Busy Living or Get Busy Dying! Work the Problem! Don’t spend time worrying about who gets the credit! Integrity Matters! When the horse is dead, dismount! Democracy is a fragile experiment that must be carefully tended.”

ADVICE FOR YOUR YOUNGER SELF? “Don’t be afraid to say no. Work to truly listen to others. Know your strengths and weaknesses, and don’t be afraid to embrace them.”

BEST ADVICE YOU EVER RECEIVED? “There are no throw-away people. Begin with the end in mind. Work to be solution-based.”

BEST KEPT SECRET? “It might not be a secret, but I am terrible at recalling names. If I could do anything, I would be a jet pilot.”

Michael Smart, Owner - Smart Mobile Detailing

BACKGROUND: “I’m originally from Boston. My family moved to Florida when I was in 5th grade. I graduated from West Orange High School in 2014. My first job was at “Classic Car Wash” in Winter Garden. After graduating, I became a Georgia Police Officer in 2016. I truly loved serving the community. I’m grateful for my time as an officer. At the end of 2020, I managed a car wash in the Atlanta area. I have always loved detailing cars. I learned to do it when I was a teen. Managing a car wash with a full detail center allowed me to really became a student of the trade taking my skills to a professional level. In July 2021, God called Mary Sloan and I to move back home to Winter Garden and start our own business. We opened Smart Mobile Detailing in 2021, which has been a tremendous blessing to us.” 

YOUR PASSION & WHAT INSPIRES YOU: “My passion is that I truly love to serve others. I always have. Working with my customers every day and getting to provide for them is why I love what I do. My saying holds true, “A clean car makes someone smile, even if just for a day!”  My fiancé, Mary Sloan, is my biggest inspiration. She is my rock. We met in 6th grade at Bridgewater Middle. We were each other’s first boyfriend/girlfriend! Being able to provide the best life for her and our future children is what inspires me every day. We are getting married on June 25th, 2022!”

YOUR SECRET TO SUCCESS? “Grit. You need to wake up and go after what you want — Every Single Day! No matter what. Tired? Who cares? Body hurts? Who cares? I’ve had a side job my entire life. Starting at 12, I mowed lawns and cleaned pools to do whatever I had to do because I was taught hard work. My parents never settled for anything less, and I’m thankful for that. My dad is the hardest working man you will ever meet. He taught me what true grit is.” 

YOUR FAVORITE MOTTO OR QUOTE: “Excellence is not given, inherited, or accidental. Excellence is earned.”— Brad Lea. 

ADVICE FOR YOUR YOUNGER SELF? “Your character isn’t defined in moments of success or greatness. Your character is defined when you are put to the test, and your back is against the wall. How you respond, handle yourself, and maintain yourself are what defines and creates your character. Be humble in moments of greatness and be thankful in moments of hardship — those moments will make you great.”

BEST ADVICE YOU EVER RECEIVED? “All of your excuses are lies.”

YOUR BEST KEPT SECRET? “One of my favorite movies is Hamilton. You get hip hop and rap, history, and America all in one. How can you beat that?”

ANYTHING ELSE INTERESTING: “My wife and I attend church at Mosaic. If you see us, please say hello!”

James ‘Jim’ Crescitelli, Director of Operations & Programming -- Winter Garden Heritage Foundation

BACKGROUND: “I moved here to Central Florida in 1978 from Brooklyn. I loved taking photos of the Lake Apopka area with fields, horses, barns, and landscapes. I love the history of this area! History really interests and fascinates me. I have a degree in Art. I am a professional published writer.  I have a background in customer service. I ran a retail book store and a photography store from the 70s through the 90s. I’m very proud of our Winter Garden Heritage Foundation and our Historical Museum. Come visit us by the red fire engine and the yellow Chessie Caboose at 21 East Plant Street – it’s all free!”

WHAT INSPIRES YOU: “I love to hear and share stories about the people who have helped to grow and nourish our area over the past 100 years. I am fascinated by the history, architecture, events, and what motivated people to move and thrive here.”

YOUR SECRETS TO SUCCESS? “Be open and honest. Carefully listen to people so that you can learn something from each of them. I try to share my insights and knowledge comfortably with others while remaining open to their suggestions and perspectives. I’m a good listener. I listen and apply what I learn to improve my work and life.”

YOUR FAVORITE MOTTOS & QUOTES: “ I believe in the Latin phrase: Omnem crede diem tibi diluxisse supremeum. -- Live each day as if it’s your last! I’m a happy, optimistic guy. Every day is an opportunity for a new story to be written.

ADVICE FOR YOUR YOUNGER SELF? “Don’t be afraid of anything! I know many people are afraid of someone or something. You can’t do that. Always move forward! There’s always something you can do, read and learn. Be creative! Don’t ever let yourself be bored!”

BEST ADVICE YOU EVER RECEIVED? “My grandmother used to say, ‘Never forget who you are!’ She also said, “Save ten dimes and you’ll have a dollar. Don’t forget your roots and how well you were brought up. Be good to all people!”

YOUR BEST KEPT SECRETS? “I’m a good knitter. I find knitting is very calming and it’s a great chance just to sit and chill. I also have every single issue of Martha Stewart Living Magazine with over 325 copies.”

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