Shasta Longley

Business Owner
Double SS Holding Group LLC
Ocoee, FL 34761

Shasta Longley is the owner of Double SS Holding Group LLC and a respected professional whose career spans public safety, regulatory compliance, and the trucking industry. With a strong foundation in safety, risk management, and operational oversight, she brings decades of experience to her work as a business owner and commercial driver. Her professional background includes certifications and training in fire prevention, occupational health and safety, and compliance through the USF Health OSHA Training Institute, along with leadership experience across government, education, and private industry.

Shasta’s career path has taken her through a variety of public service roles before ultimately finding her calling in the trucking industry. She began her career as a correctional officer for Orange County before moving into code enforcement with the City of Orlando, where she served for 16 years and developed a deep appreciation for protecting communities and ensuring regulatory compliance. She later worked as a Compliance Manager at Valencia College, overseeing chemical hazardous waste management and safety data sheet programs. Her commitment to public safety also led her to serve as a fire inspector with the Osceola County School District and the Clermont Fire Department. In March 2016, after the passing of her husband, a Florida Highway Patrol state trooper, an opportunity from a former classmate introduced her to the trucking industry, where she learned the operational and back-office side of the business with Rams Trucking and Logistics.

In 2024, Shasta expanded her expertise by earning her CDL license so she could experience the road side of the trucking business firsthand and better understand the challenges drivers face. Today, she operates her own authority through Double SS Holding Group LLC, hauling flatbed and step deck loads that include construction equipment, building materials, military vehicles, and electrical equipment. The work requires significant physical strength and skill, including tarping, chaining, and securing heavy cargo—tasks that make this specialized form of hauling less common for women. Having traveled across nearly every state in the country except Alaska, Hawaii, and Maine, Shasta is passionate about showing that trucking can be a lifestyle, not just a job. She is equally committed to demonstrating that women can thrive and succeed in the industry while maintaining their individuality and femininity.

• CDL (Commercial Driver's License)
• Certificate of Completion, Electrical Wiring

• Ashford University - MBA, Project Management
• Ashford University - BBA, Public Administration
• Ashford University - AA, Non-Profit/Public/Organizational Management

• TNT Award (Traditional Non-Traditional Woman Award) from Orange County

Q

What do you attribute your success to?

I attribute my success to the mentorship I received from my classmate Jamel, who taught me everything I know about trucking. He really showed me the ropes and taught me how to eat - not just crabs, but filet mignon and lobster, as I like to say. He was someone who had done 10 years in prison, came out, turned his life around completely, bought a $700,000 home in Clermont, and never looked back. He had a learning disability but never took 'I can't' as an answer - he always either did it or tried. He was the one that really drove me to go farther with trucking and take it to the next level. He showed me that the sky's the limit and that you can write your own ticket in this industry. Even though he tragically got killed on the road in Pennsylvania in 2024, his memory and his lessons continue to inspire me. I also believe in keeping overhead low, saving for rainy days, and reinvesting in residual investments. I tell other truckers to manage their money wisely and run shorter loads closer to home when fuel prices are high. The key is financial discipline and understanding both sides of the business the office work and the road work.

Q

What advice would you give to young women entering your industry?

I want other women to know that you can do this work and still be feminine in your own way, still be beautiful, and still be yourself. You don't have to change who you are for this industry. The work I do is very physical and demanding - I have to tarp, chain, and strap things down - and you don't find a lot of women doing the particular type of equipment and trailer that I use. I've only run across one other woman doing flatbed work the whole time I've been out here. But anybody can do it - a woman can do it, a man can do it, you can adjust. I show people on my TikTok and YouTube channels what it's really like, from cooking on the truck to doing my hair weave in truck stop bathrooms, to showing what the showers look like. I want women to see that there's more to trucking than just trucking you can make it a lifestyle, you can make it inviting. It's hard work, but you can also still regroup and come back and be just who you want to be. When people say they can't do it, I tell them yes you can - look at what my mentor accomplished despite having a learning disability and a criminal record. The American dream is real when you're an owner-operator, and you can literally write your own ticket.

Q

What are the biggest challenges or opportunities in your field right now?

Right now, the biggest challenge is fuel prices approaching $6, $7, even $8 per gallon. I just paid $700 for diesel fuel the other day, plus another $40 for DEF, so $740 total for one fill-up. Before these gas hikes, a typical fill-up was around $450 to $500. With prices this high, I tell people to keep their overhead low and run shorter loads closer to home. You have to manage your overhead carefully, especially if you have families to support. The mountains also steal a lot of time and burn a lot of fuel - you run through tank after tank going through them. My strategy now is to try to stay below Tennessee, stay on I-40 and below, and try to stay out of the mountains. Another challenge is that a lot of guys are struggling because they get wrapped up in $150,000 leases for brand new trucks and get stuck at one company for five years with limited money. I advise people to buy used trucks if they can - even a truck with 500,000 miles that costs $10,000 or $12,000 can pay for itself five times over in just a month of loads. The opportunity is that when you own your own authority as an owner-operator, you really can write your own ticket and see the American dream. The sky's the limit, and there's no such thing as 'I can't make it' in this industry.

Locations

Double SS Holding Group LLC

Ocoee, FL 34761