THE OLC LEADERSHIP TEAM
CHESTER WEBER:
Chester Weber is the most decorated combined driver in the U.S. He became the youngest member of the U.S. Equestrian Team at age 18 for the World Pairs Driving Championship. He moved to the Four in Hand Division in 1999 whereupon he has earned 21 National Championships and 10 medals at International Championships, including 6 Individual Medals and 4 Team Medals. The first of those individual medals was in 2008 when he won a Silver Medal for the U.S. in the Four in Hand FEI World Driving Championships, making him the first American to win a medal at that level. He also won England’s Royal Windsor two consecutive years, winning a personal congratulations from Queen Elizabeth in 2014. He has consistently held top rankings in the FEI system, including the number one spot. Weber has been recognized as USEF Equestrian of Honor twice and actively supports young drivers and equestrian sports. He represents athletes across all disciplines with seats on both the USET Board of Trustees and USEF Board of Directors where he provides strategic leadership for the development and support of horses and riders who represent the Unites States at the highest levels of international competition.
The Weber family was approached in 1990 about hosting a club-level driving competition and welcomed competitors onto their picturesque property, Live Oak Stud, for the first time that year. Live Oak International has grown year over year and is now the largest combined driving and show jumping tournament in the U.S. Chester Weber co-presides over this event with his niece, Chloe Reid, for what has become the largest spectator event in Marion County. After 34 years of hosting the event and a commitment to ensuring that there is something for everyone from a kids’ zone with play area and face painting to a food court and vendor area, it has now become one of the most anticipated family events in Ocala. More than 15,000 people come to enjoy the event on the grounds of one of the most iconic horse farms in Ocala and to see more than 200 competitors from around the world compete at the highest levels. Despite the draw of top international competitors, Chester remains true to his vision of growing the sport by including divisions for young athletes, allowing them the unique opportunity to compete alongside their international role models.
Weber serves on various boards in Ocala, Florida, including Empath Hospice of Marion County and Horse Farms Forever. The former is committed to ensuring quality health care in the local community and the latter to ensuring community development and preservation of the local equestrian culture in one of the largest and fastest-growing counties in Florida. With this growth comes need and in response to that growing need, Weber serves on the board of The Community Foundation which is dedicated to enhancing the quality of life in Marion County by facilitating charitable giving and supporting community giving initiatives. Weber is also very involved in supporting local churches and spiritual leaders throughout the region. Each December, he hosts a luncheon to recognize and support these leaders as they serve those in their respective spheres of influence. This event grows each year with the event in December, 2024 being the largest single gathering of spiritual leaders in Marion County to date. His commitment to Marion County is obvious with the support of each of these organizations and their initiatives.
After watching a friend have a poor experience with end-of-life care, Weber established Gratitude and Compassion which is the holding company for Roberts of Ocala, Coast to Coast Cremations, and the Caisson Team, all services dedicated to providing compassionate care to grieving families throughout Central and now South Florida. Weber is determined that individuals should be celebrated in their last days just as they are at the time of their birth and that their families should be supported with the same level of care, compassion and attention to detail at the end as they were at the beginning. As part of his commitment to celebrating life and creating living legacies, he established the Gratitude and Compassion Foundation which supports financial remembrances to organizations of importance to those who have lost people dear to them.
Weber is also known for his commitment to veterans and veterans’ services throughout Marion County. That combined with his experience as a world class equestrian created a unique opportunity for him in spring, 2024. In May 2023, the caisson platoon support for funerals at Arlington National Cemetery had been put on hold; that suspension was extended in November 2023. In early 2024, Weber was consulted regarding recommendations for safely rebuilding that program. Since then, he has played a key role in revitalizing the U.S, Army’s Caisson Detachment, training horses and riders, improving tack and equipment, and developing ongoing care and standards for the program which would ensure its success and longevity. Major Wes Strickland, Director of Communications for the U. S. Army’s 3rd Infantry said of him, “Mr. Weber’s work in assisting the Military District of Washington and the 3d U.S. Infantry Regiment’s efforts to rebuild the caisson program will help shape the organization long into the future. The next generation of caisson soldiers, and our veterans they carry to their final resting place, will forever be indebted to his determination and creativity.” Horses and riders trained by Mr. Weber were part of the ceremonies in January 2025 for former President Jimmy Carter and transported his coffin down Pennsylvania Avenue to the Capitol building. The caisson support for funeral services at Arlington National Cemetery was reactivated on a limited level in June 2025 and this offering will be increased as additional teams of horses and riders complete their training.
Weber has a background in the hospitality business which lends itself to attention to detail, service excellence and team building, all of which he employs in the enterprises described above and are key to his success.
CORIN CARACCIOLO
Corin Caracciolo is a wife, mom, and powerhouse sales leader with more than a decade of success in the pharmaceutical industry. Throughout her career, she has launched multiple groundbreaking products, consistently delivered strong results, and earned recognition for her performance and leadership. Yet beyond titles and accolades, Corin is passionate about the heart of leadership—creating spaces where influence becomes inspiration and inspiration leads to impact.
In addition to her corporate success, Corin is an entrepreneur, real estate investor, and community advocate. She is deeply involved in local initiatives, from supporting the American Cancer Society to speaking at women’s events. Fueled by a vision to bring world-class leadership development to her hometown, she co-founded the Ocala Leadership Conference to ignite growth, elevate voices, and equip leaders with the tools to make lasting change. Her goal is to create more than just an event—it’s a movement designed to transform the way Ocala leads, connects, and inspires.
Corin also believes true leadership begins at home. As a devoted wife to her husband Bryan and proud mom to Bennett and Collins, she finds joy in cheering from the sidelines at her children’s games, traveling the world with her family, and turning everyday moments into meaningful memories. Her life and work are rooted in the same values: faith, grit, and the power of intentional influence.
MARK CUMMINS:
Mark D. Cummins is a decorated U.S. Marine, TEDx speaker, best-selling author, coach, and leader who partners with people to reach their full potential. A John C. Maxwell Certified Leadership Coach and President of MDC Life & Leadership Development Co., Mark has spent over three decades training leaders across business, sports, government, and non-profits.
His creative communication style is rooted in his Doctoral Thesis on Multi-Sensory Communication, helping him connect content with people in life-changing ways. In addition, Mark serves as the Lead Pastor of Church of Hope in Ocala, Florida.
Mark is the author of the book IronParents: Training Kids To Go The Distance and has long hosted the Live2Lead Conference in Central Florida, where he invests in developing business and community leaders.
A lifelong competitive athlete, Mark has excelled in powerlifting, countless 5Ks, half-marathons, and marathons, and is both an IRONMAN™ Triathlete and Boston Marathon finisher.
Mark and his wife, Linda, have been married for 36 years and together raised two daughters, Emily and Katie. As a family, they call themselves “Team Cummins”, united by a shared passion for faith, family, and making the world a better and brighter place.
CHARISSE RIVERS
Charisse Rivers – Financial Storyteller, Retirement Architect, and Champion for the Next Generation
Charisse Rivers grew up understanding that a little hope—and a lot of heart—can change the course of a life. Today, as the founder and CEO of Zinnia Wealth Management, she brings that same spirit to retirement planning. Charisse doesn’t believe in cookie-cutter portfolios or quick-fix products. Instead, she leads a team that takes a 360-degree view of every client’s financial world, crafting retirement plans as unique as the people behind them.
Her passion for education and empowerment shines through on her nationally syndicated show and podcast, Retirement Coffee Talk, where she mixes common-sense financial advice with real conversations and inspiring guests from Jason Aldean to Tim Tebow to Candace Owens just to name a few. Retirement planning, she believes, should be approachable, empowering—and yes, even a little fun.
Beyond the boardroom and the broadcast studio, Charisse’s heart beats for giving back. She founded The Grilled Cheese Foundation to honor the kindness her family once received and to pay it forward to the next generation. Through the Foundation, Charisse is empowering underserved children to discover their passions, nurture their talents, and build the confidence they need to thrive and shape the future they deserve. By funding activities like dance, sports, music, and college scholarships, the Foundation helps young people unlock their potential and pursue dreams they may have once thought were out of reach.
Charisse Rivers is more than a retirement planner. She’s a builder of futures, a voice of encouragement, and proof that with the right plan—and the right heart—you can design a life you love well beyond the nine-to-five.
Live by Design, Not by Default.
BRYAN CARACCIOLO:
Husband, Father, Serial Entrepreneur, Developer, and Visionary Leader
Bryan W. Caracciolo is a dynamic entrepreneur, real estate developer, and business leader whose career spans over two decades of building and transforming businesses across multiple industries. Known for his bold vision, relentless work ethic, and commitment to creating value for communities, Bryan has established himself as an accomplished business professional.
Early Life and Athletic Background
Born and raised in Ocala, Florida, Bryan learned the values of hard work, resilience, and determination from an early age. A natural athlete with a passion for competition, Bryan pursued football throughout his youth, ultimately earning the opportunity to play at the collegiate level for the University of Central Florida (UCF). His time at UCF, playing for the Knights, not only sharpened his discipline and leadership skills but also instilled in him the mindset to think big, push boundaries, and never back down from a challenge.
Rise in Orlando’s Nightlife & Event Industry
While still a teenager, Bryan’s entrepreneurial spirit took center stage. At the age of 19, he became one of the largest nightlife promoters in Orlando, a city known for its vibrant entertainment scene. His natural talent for marketing, strategic partnerships, and understanding consumer experiences allowed him to thrive in this competitive industry.
By the age of 22, Bryan had gone beyond event promotion and became the owner and operator of multiple nightlife entertainment venues. These ventures were not just successful businesses; they were a testament to his ability to create memorable experiences, build strong teams, and manage large-scale operations. Bryan’s success in Orlando’s nightlife laid the foundation for the business acumen and fearless approach that would define the rest of his career.
Return to Ocala and Founding of BWC Construction
Despite his success in Orlando, Bryan always held a deep connection to his hometown of Ocala. Recognizing the growth potential and opportunities in the Central Florida market, he returned to Ocala to pursue his next big challenge. With a vision to build something lasting and transformative, Bryan founded BWC Construction. Under Bryan’s leadership, BWC Construction quickly grew into one of the largest general contracting firms in Central Florida, completing over 2 million square feet of construction projects and becoming a INC 5000 company. His ability to oversee complex developments, manage large-scale teams, and maintain a focus on quality has earned the company a stellar reputation. Over time, BWC Construction expanded its services and evolved into a full-fledged real estate development firm, delivering projects that shape and enhance the communities they serve.
Expanding Business Ventures
Bryan’s entrepreneurial portfolio extends far beyond construction. As a strategic investor and visionary, he has founded and operates a diverse range of companies, including:
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Brick City Hospitality Group – A company dedicated to creating high-quality hospitality experiences.
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Brick City Hospitality Parking – Providing professional parking and logistics management.
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Old Florida Lodge, Inglis – A rustic retreat offering authentic Florida charm.
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Old Florida Marina and Lodge, Yankeetown – A premier marina and lodging destination on Florida’s Gulf Coast.
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Old Florida RV Resort, Orange Lake – A popular RV destination known for its exceptional amenities and lakeside atmosphere.
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Main Street Realty and Development – A real estate firm focusing on residential and commercial properties.
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BWC Capital Group – A real estate investment and private capital company specializing in high-return development projects.
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Butler LOFTS, LOFTS on Main and 3rd – Innovative residential and commercial developments designed for modern living in Downtown Leesburg, FL.
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Ocala RVs – A leading RV dealership in Ocala.
In addition to these core businesses, Bryan oversees numerous holding companies that manage diverse real estate, hospitality, and development assets. His broad vision allows him to identify opportunities across various sectors, creating synergies among his businesses and ensuring long-term growth.
Job Creation and Business Impact
Over the past 20 years, Bryan has built organizations that have employed more than 500 people, with teams as large as 200 employees at one time. His leadership emphasizes building a strong culture, empowering employees, and creating opportunities for professional growth. Bryan’s ability to assemble talented teams has been a critical factor in the sustained success of his companies. Beyond job creation, Bryan’s companies have had a significant economic impact on the communities they serve. Through real estate development, hospitality ventures, and local business operations, he has helped drive growth, enhance infrastructure, and improve the quality of life for residents and visitors alike.
Successful Exits and Capital Raising
Bryan’s business track record includes several successful exits, where he has sold companies he founded for seven-digit valuations. These accomplishments reflect his ability to build businesses from the ground up, scale them strategically, and create substantial value for himself and his investors. In the realm of real estate investment, Bryan has raised over $100 million in funds in collaboration with partners and investors. This capital has been deployed across a range of projects, from residential developments to commercial properties and hospitality ventures. His proven ability to attract and manage investment capital underscores his reputation as a trustworthy and results-driven business leader.
Commitment to Community and Development
At the heart of Bryan’s professional journey is a deep commitment to making communities better. His development projects are not just about building structures; they are about creating environments that meet the evolving needs of people and businesses. Whether it’s constructing high-quality residential developments, revitalizing hospitality destinations, or providing recreational spaces like RV resorts, Bryan is dedicated to delivering projects that bring long-term value to the community. At home, Bryan finds his greatest joy in family life with his wife, Corin, and their two children, Collins and Bennett. Together, they enjoy the balance of hard work and quality time, building memories rooted in faith, sports, and community. Bryan is deeply committed to giving back, serving as a youth football coach in the community, where he mentors young athletes both on and off the field. His role as a husband, father, and coach reflects the values he brings into his professional life—leadership, integrity, and dedication to creating opportunities for others to thrive.
The Visionary Behind Ocala Leadership Conference
Most recently, Bryan co-founded the Ocala Leadership Conference, a premier event series designed to bring leadership training, personal development, and professional education to Ocala and the surrounding region. Recognizing that leadership development resources have been limited in the area, Bryan and his partners launched this initiative to empower local business leaders, entrepreneurs, and professionals. The conference will host world-renowned speakers, bestselling authors, and leadership experts, offering attendees the tools and knowledge needed to excel in both business and life. With Ocala’s rapid growth and its emergence as a central hub in Florida, Bryan’s vision is to make the Ocala Leadership Conference a cornerstone for leadership excellence across the state.
A Legacy of Big Thinking
Bryan’s journey is defined by his big-picture mindset and unwavering belief in turning bold ideas into reality. From being a young entrepreneur in Orlando’s nightlife scene to building a portfolio of thriving businesses, Bryan’s story is one of resilience, strategic risk.