One Sunday in the early 2000s, Christopher Shucart sat down to a family dinner that would change the course of his life. He was 24 years old, and he’d worked in Naples for a year after graduating cum laude from Arizona State University’s Del E. Webb School of Construction. Though he enjoyed his work at a well-respected local construction company, he decided he was ready to take the entrepreneurial leap and set out on his own. In fact, he’d just handed in his notice. What happened next surprised him: When Shucart announced his decision at Sunday dinner, his father, James—a commercial real estate developer—suggested they try working together. “We could give it a shot on a three-year basis,” his father said, “and see how it goes.” The result? “Twenty years later, we’ve built this cool little company,” Shucart says. “It’s been terrific.”

Their cool little company—JCS Realty Group—has been behind some of the most visible properties in the Naples area, including the revamped Hitching Post Plaza near Lely Resort and the Port of the Islands development near Everglades City. In recent years, Shucart’s father has stepped back from the business as his son continues to push forward. “He gave me the tools to be able to take the company and move it to the next level,” Shucart says.

To that end, Shucart joined with fellow entrepreneurs Marty Kenney and Christopher Lee to form Naples-based CMC Hospitality. The group recently launched Central Square (formerly Victoria Square) in downtown Naples with four distinct venues: District, a cool craft cocktail lounge; Staff Only, a hip speakeasy; The Kitchen & Mini Bar with an outdoor tropical theme; and late-night destination The Alley.

Over the course of his journey, Shucart has learned valuable lessons both about being an entrepreneur and working with family. He shares his top two with us.

Respect Makes All the Difference

“Working with family has so many great benefits,” Shucart says. “Number one, you get to spend time with your family.” But that benefit can also be a drawback, he noted, as it can be difficult to separate the two when family and business are both in the mix. Yet Shucart said he’s lucky—he and his father have a great deal of mutual respect for each other, and that respect is key. “I 100% respect him, and he in turn respects me. I think that’s why there’s a balance between the two of us. If you can get to that level, it makes all the difference.”

Look at the Big Picture

Sometimes a decision that’s good for the individual isn’t always good for the family business, Shucart says: “Those are always tough decisions to work through. You have to look at it from the big picture, on a holistic basis, to make the right decision.”