Small Fleet Summit: What to know before becoming an owner-operator

Owner of J and R Transfer speaks about risks and opportunities

(Photo: FreightWaves)

This fireside chat recap is from FreightWaves’ Small Fleet & Owner-Operator Summit.

FIRESIDE CHAT TOPIC: What I wish I knew before becoming an owner-operator

DETAILS: Entrepreneurship is a challenge in any industry, and creating your own trucking empire is not an easy task. Often it starts with that first truck. Former lease purchase owner-operator Wayne Cragg, who is on a bike ride for trucker health awareness, chats with Josue Ramos about the learning curve of becoming an owner-operator.

SPEAKER: Ramos is the owner of J and R Transfer LLC and OzX Logistics LLC.

BIO: Two years ago, Ramos inherited the carrier business from his father, who has been an owner-operator for the past 20 years. His background in trucking led him to start his brokerage business in late 2018.

KEY QUOTES FROM RAMOS:

“I wish I would’ve known more about the risks, the current landscape [and] just how hard it is to actually get good drivers. The list goes on — there’s a lot that I wish I knew.”

“I told myself that no matter what happens, I’m going to try to overcome it because where there’s problems, there’s opportunities. And there’s a lot of problems in this industry.”

“It’s a blessing to see that the brokers, the shippers, the manufacturers and the population in general [are] starting to open their eyes to what truckers go through, what business owners go through. And they’re starting to realize the importance of taking care of the individuals who actually move freight who basically keep the wheels turning.”

“The odds are against you out here, but my favorite part about the industry and trucking is it’s tied to everything. Every single business you can think of, it’s tied to it. And the demand will always be there. No matter what economy, no matter what’s going on in the world, trucking will always be here.”

Click here for more FreightWaves articles by Alyssa Sporrer.

Daily Infographic: Owner-Operator Fast Facts

The perspective of a female owner-operator

Modernizing insurance will keep small fleets’ wheels turning

GSCW chat recap: Is the COVID-19 supply chain sustainable?

Upcoming FreightWaves Events
Compliance

Brokerage Compliance Symposium

The day before F3. Every compliance issue you face - fraud exposure, carrier liability, FMCSA rules, cargo theft, insurance gaps - navigated by attorneys and operators defining best practices in a changing industry.

October 26, 2026
The Signal at Chattanooga Choo Choo • Chattanooga, TN
Register Now
Awards

F3 Awards Dinner

The night before F3. FreightTech100 companies honored. FreightTech 25 and Shipper of Choice winners revealed live. Cocktail reception into dinner and live music - 300 industry leaders in one purpose-built room.

October 26, 2026
The Signal at Chattanooga Choo Choo • Chattanooga, TN
Register Now
FreightTech

F3: Future of Freight Festival

Industry-defining keynotes, rapid-fire technology demos, and industry leaders networking in experiences across Chattanooga - plus the inaugural F3 Awards Dinner featuring the FreightTech and Shipper of Choice reveals.

October 27, 2026 – October 28, 2026
The Signal at Chattanooga Choo Choo • Chattanooga, TN
Register Now
Compliance Brokerage Compliance Symposium Oct 26 • The Signal at Chattanooga Choo Choo • Chattanooga, TN

The day before F3. Every compliance issue you face - fraud exposure, carrier liability, FMCSA rules, cargo theft, insurance gaps - navigated by attorneys and operators defining best practices in a changing industry.

The Signal at Chattanooga Choo Choo • Chattanooga, TN Register Now
Awards F3 Awards Dinner Oct 26 • The Signal at Chattanooga Choo Choo • Chattanooga, TN

The night before F3. FreightTech100 companies honored. FreightTech 25 and Shipper of Choice winners revealed live. Cocktail reception into dinner and live music - 300 industry leaders in one purpose-built room.

The Signal at Chattanooga Choo Choo • Chattanooga, TN Register Now
FreightTech F3: Future of Freight Festival Oct 27 – Oct 28 • The Signal at Chattanooga Choo Choo • Chattanooga, TN

Industry-defining keynotes, rapid-fire technology demos, and industry leaders networking in experiences across Chattanooga - plus the inaugural F3 Awards Dinner featuring the FreightTech and Shipper of Choice reveals.

The Signal at Chattanooga Choo Choo • Chattanooga, TN Register Now

Alyssa Sporrer

Alyssa is a staff writer at FreightWaves, covering sustainability news in the freight and supply chain industry, from low-carbon fuels to social sustainability, emissions & more. She graduated from Iowa State University with a double major in Marketing and Environmental Studies. She is passionate about all things environmental and enjoys outdoor activities such as skiing, ultimate frisbee, hiking, and soccer.