Tristan Winston (left) and his sister, Kayla Winston co-own Endless Wins Vending, LLC. The business owners reside in Baltimore County. Photo credit: Chantell Williams

What does a seven-year-old and a twelve-year-old know about running a vending business? Tristan Winston, 7, and his big sister, Kayla Winston, 12, can tell you a thing or two about building one from the ground up. They are the proud co-owners of Endless Wins Vending, LLC.

“My brother and I wanted to start a snack business. We love snacks and wanted to show the world you can do anything you put your mind to,” Kayla said, mentioning another reason their business was created.

The business was legally established in late July of 2023, partly because the snack lovers wanted to earn their own money.

To help run Endless Wins Vending, LLC, Kayla pounds the pavement alongside her brother and mother, Chantell Williams, handing out business cards while inquiring about potential opportunities to collaborate with different establishments. Behind the scenes, Kayla filled the small business’ candy machine to prepare for delivery to their first client.

Kayla Winston (left) pours candy into a machine with Tristan Winston.
Photo credit: Chantell Williams

The entrepreneurs are excited about setting up the machine at Samuel Cain, Sr.’s business called Junior’s Barbershop, located in Essex, Maryland on September 16, 2023. He owns and runs a barber shop and beauty salon.

Cain mentioned that he found out about Endless Wins Vending, LLC when the brother and sister duo walked into his place of business. He ultimately decided to offer an opportunity for Winston and Kayla to get the start that they needed.

“I will support them by offering their services to my clientele in hopes that it becomes a successful business venture for them,” Cain said.

The entrepreneur could relate to early beginnings in business. According to Cain, he was given a start in business at an early age. He has been a successful business owner for many years.

“I wish the same for them, and will help them to achieve just that by setting up their vending machine at my place of business and hope that my clientele utilizes their products,” Cain said.

Endless Wins Vending, LLC can provide more than candy machines. Williams noted that Endless Wins Vending, LLC  is able to sell snacks, candy, beverages and pretty much anything that a business owner may request through their vending enterprise.

She added, “We are accepting inquiries about having machines and locations.”

Williams noted that the entrepreneurs can service the Baltimore area and Anne Arundel County.

Tristan and Kayla’s journey would have been impossible without Williams’ sacrifices that required extra time and resources. The ambitious mother feels that helping her children to start a business is worth her efforts. She stepped up to become the business’ manager.

“As a mom, I want to make sure that I am continuously paving a way for their future and to support them and their dreams,” Williams said.

The devoted mother has been driving her kidpreneurs around to purchase supplies for their grand delivery that will kick off landing a first win, but the Endless Wins Vending, LLC team is not sitting still.

They are in the midst of searching for additional prospective machine locations where clients or customers wait more than a 10 to 15-minute period. Williams stated that after inquiries are made, she sets up a meeting with the decision maker of an establishment to enable the Endless Wins Vending, LLC team to introduce their business services. The company’s proposal book provides information about a variety of vending machines with him or her. The Endless Wins Vending, LLC trio finds out more about potential the customer’s needs, then proceeds accordingly.

Both Kayla and Tristan feel good about showing other children that becoming business owners at a young age is possible. However, the pair already knows that marketing is a challenge of business ownership.

“The hardest part about starting a business as a child is getting the world, and your city, to know that your business exists,” Tristan said.

When Kayla is older, she would like to become an executive chef and own her own restaurant. She felt that having a snack business would jump-start her career in owning a business while allowing her to learn financial responsibility.

“The most rewarding part of establishing Endless Wins Vending, LLC is to see what you put your mind to, you’re able to do at any age. We hope to show the world that whatever you want to do, you can do it, no matter how young you are, no matter how old you are,” Kayla and Tristan Winston said.

Kayla, Tristan and their mother welcome more inquiries about Endless Wins Vending, LLC. Call Williams at 443-916-5458. Follow the brother and sister’s new entrepreneurial journey via

Click Here to See More posts by this Author