Buying an existing business has many benefits, but it also comes with its own set of bureaucratic challenges. Ralph Caprilozzi found this out first-hand when trying to buy the business he helped build. Caprilozzi grew up making wine with his grandfather and started working at Shelter Rock Winery when he was 19. The "winery" is a place for customers to make their own wine with help from experts. From stomping and squeezing grapes all the way to bottling, Shelter Rock lets people get a hands-on winemaking experience. People come back year after year to make their own barrels and be a part of a unique experience rooted in tradition.
Helping customers make their own wine has become second nature to the now 27-year-old Caprilozzi, but buying and running a business—even one he already knew well—was a challenge he needed help with. Luckily, Shay Nagarsheth, a Connecticut Small Business Development Center (CTSBDC) Advisor and winemaking enthusiast, stopped in to buy grapes. Together, Caprilozzi and Nagarsheth were able to navigate the complicated process of buying an existing business and rebranding Shelter Rock Winemaking.
The road to business ownership
Caprilozzi describes the process as a "rollercoaster," as he ran into one obstacle after another. His advisor was able to help him put together the documents one typically needs to get a loan: a business plan, projections, and a marketing plan. However, traditional banks were still not ready to take a chance on Caprilozzi. Was this the end of the road for his entrepreneurial dreams? Not if Nagarsheth had anything to say about it. CTSBDC advisors know the local lending landscape very well. He introduced Caprilozzi to smaller community lenders, who are often able to work with aspiring entrepreneurs that traditional banks cannot.
With CTSBDC's help, Caprilozzi was able to secure a loan from Community Investment Corporation—but even that had its challenges. Like many entrepreneurs, Caprilozzi was seeking an SBA Loan. When the federal government shut down in late 2025, his loan application was caught up in the backlog.
"Shay was imperative to the process," says Caprilozzi, who sometimes spoke with his advisor multiple times a week. From the basics of securing his own EIN number to making sense of the previous owner's financial systems, Nagarsheth was there to consult whenever Caprilozzi needed him—even a couple of days before Christmas.
Carrying on the winemaking tradition
Once the trials and tribulations of paperwork and loan applications were behind him, Caprilozzi could turn his attention to growing the winemaking business. "This year, he will produce more barrels than this place has ever done, and that's a testament to Ralph," says Nagarsheth.
Existing clients stayed on after the change of hands because they already knew and trusted Caprilozzi, and as word-of-mouth spread, new members started coming in. Caprilozzi says he has exceeded last year's number of barrel orders. That doesn't mean the challenges of being a business owner have ceased. An important HVAC unit failed; the forklift battery needed to be replaced; and some of his palettes were stolen.
"There's been so much to tackle as a newcomer," says Caprilozzi. "Shay's help has been invaluable."
Despite the challenges, he is excited to continue finding new ways to grow his revenue and welcome new people into the Shelter Rock community. "People are often intimidated by winemaking, but people have been doing it for thousands of years," says Caprilozzi. "It's a great way to stay connected to tradition, nature, and community." So, he hopes to host more small events to give people a taste of the process, perhaps without the need to commit to the nine-month process of making your own barrel from scratch.
With his deep knowledge of winemaking and continued support from CTSBDC, he is ready to turn each new challenge into another step forward. For Caprilozzi, business ownership is not just about carrying on what he helped build—it is about giving more people a place to gather, learn, and create something they can proudly call their own.
