About Kendall Tipper

Kendall Tipper is a Jacksonville, Florida-based entrepreneur and the founder of Tipper Transportation and Jacksonville Black Car Limo Service. A U.S. Army combat veteran who served in Afghanistan, Kendall carried the discipline, leadership, and commitment to service developed during his military career into the world of entrepreneurship.

Since entering the luxury ground transportation industry, Kendall has grown his companies from a small local operation into an established transportation provider serving clients throughout Florida, Georgia, and beyond.

From Military Service to Entrepreneurship

Before entering the business world, Kendall Tipper served approximately six years in the United States Army, including combat service in Afghanistan. His military experience helped shape an approach to leadership centered on discipline, accountability, preparation, and service to others.

After leaving the military, Kendall eventually turned his focus toward entrepreneurship and the secure luxury transportation industry, where those same principles became part of the foundation for the companies he would go on to build.

Military Service

  • United States Army combat veteran

  • Approximately six years of military service

  • Combat service in Afghanistan

  • Army Commendation Medal

  • Two Army Achievement Medals

  • Afghanistan Campaign Medal and NATO Medal

  • Personal Security Detail training and experience

  • Leadership and operational experience

Entrepreneurship

  • Founded Tipper Transportation in 2018

  • Founder of Jacksonville Black Car Limo Service

  • Grew from one vehicle to a 19-vehicle luxury fleet

  • Expanded the organization to more than 25 employees

  • Experience serving high-profile clientele and major events

  • Specialization in secure luxury ground transportation

  • Jacksonville, Florida-based entrepreneur

Building a Luxury Transportation Company

In 2018, Kendall Tipper founded Tipper Transportation in Jacksonville, Florida. What began as an entrepreneurial venture in chauffeured transportation grew over the following years into a larger luxury ground transportation operation.

Today, Kendall's companies operate a diverse fleet that includes luxury sedans, SUVs, executive Sprinter vans, and group transportation vehicles. Through Tipper Transportation and Jacksonville Black Car Limo Service, the businesses serve corporate travelers, private clients, special events, airport transportation, and other chauffeured transportation needs.

The companies have also had the opportunity to provide transportation for high-profile clients and major events, while building their reputation around professionalism, discretion, security, safety, and service.

Tipper Transportation

Founded in Jacksonville, Florida in 2018 and built around secure professional chauffeured transportation and personalized service.

Jacksonville Black Car Limo Service

A luxury black car and chauffeured transportation brand serving Jacksonville and clients throughout the region.

Leadership & Philosophy

Kendall's approach to business is shaped by many of the principles developed during his military service: preparation, accountability, attention to detail, and responsibility for the people who depend on him.

In the luxury transportation industry, that philosophy translates into an emphasis on professional chauffeurs, well-maintained late-model vehicles, client privacy, security, safety, reliability, and a consistently high standard of service.

For Kendall, transportation is ultimately a service business—and the experience a client receives matters just as much as the vehicle that arrives.

Let's Connect

For professional inquiries, media opportunities, industry partnerships, and business-related correspondence, connect with Kendall or get in touch through the contact page.

© 2026 Kendall Tipper | Jacksonville, Florida