Ryan Chadwick is busy. Even when he’s doing what you might call his equivalent of relaxing, you can see it in his eyes—the wheels are turning. Something is in the works.

Today, he’s dealing with major happenings at three of his restaurants. (He and his three partners, childhood buddies from summers on Nantucket, own nine of them, among other brands and establishments).

“I started a small ice delivery company on Nantucket to put myself through college,” Ryan says, an eye glancing downward to his ever-buzzing phone. “When I graduated from school, I thought I wanted to wear a suit and work in finance. But every day at the office I kept dreaming of going back to that ice company. I got laid off two weeks before September 11th. When that happened, everything was turned upside down. So for me, I thought, ‘What am I going to do?’ I'm going to go back to the ice company on Nantucket. From that day on, I've never worked for anyone else.”

Around the time Ryan started his delivery business on Nantucket, two other young entrepreneurs were starting down their own path, and creating quite a buzz on the Nantucket waterfront.

“Around the same time when I was in Nantucket starting the ice business—doing the summer house thing during college, packing eight guys in a three bedroom house and trying to smuggle kegs in from Hyannis—I remember when Shep and Ian had a little powerboat down in the Boat Basin,” he said. “They used to have these parties down there, they’d invite people for drinks, and they were selling stuff out of the back of the boat. It was very on brand at the time. I always thought it was great.”

Just like Shep & Ian were building their brand on the water, Ryan was building his brand on Nantucket and beyond. “I constantly pivoted in my business and turned something into something else,” he told us.

That ice company on Nantucket turned into a grocery delivery company on the island, which in turn grew to a delivery company out in Aspen. A laundromat was added (fun fact: Ryan was the first guy to offer wash and fold service in Aspen).

And then, he got into food. “I started a hot dog stand in Aspen called Frank's. We sold hotdogs, lobster rolls and sausages out of a street cart. That was my first food and beverage business. The lobster rolls are a big hit. My uncle in Maine is a lobster fisherman, so I have some seafood in my background.”

All of that led him, and us, to Montauk. “We opened Grey Lady Manhattan first, second was Grey Lady Aspen, then Grey Lady Nantucket. So, when it came time for the fourth location, we chose Montauk—if you drew a line from New York to Nantucket, you crossed through Montauk,” Ryan tells us.

For a restaurant with a nautical vibe, there are few places better on the water in Montauk.

“We’re on a marina, and at the time I was living on a sailboat that we had docked out back. Plus, it made a lot of sense for the brand. We'll buy fish fresh each week. Gosman’s Fish Market is four doors down from Grey Lady. They'll deliver it on a hand truck, just wheel it down the wharf. We've worked with them ever since we opened. They're good people; true Montauk locals.”

For a person who appreciates hard work—which Ryan most certainly does—the Montauk docks are the place to be. And as we sit about a five-iron’s distance from the Atlantic and watch the fishing boats pass by, despite everything he has going on, Ryan is surprisingly laid back. (Be it in his own unique way.) “It's a lot of work, but I don't mind working,” he says with a smile on his face.

“Some people call me an entrepreneur. Some people call me a workaholic to a fault, where all I do is work. I don't vacation. Most of my weekends involve being on the phone, or a laptop, or some sort of business. It's a lot of energy to put out, but I find that I enjoy it. Work is my hobby.”

But, like golf, building ships in a bottle or cleaning the Augean Stables, Ryan’s hobby happens to be quite challenging. “What's really hard about the restaurant industry is there are a lot of things that can go wrong versus things that can go right. So for me, I've been able to fix things—whether it's actual things, like an ice maker or plumbing, or something like permitting, or press and marketing—on the fly,” he said. “If you're someone that's a problem solver, you can succeed in this business. And I've been able to replicate that. It's hard, but I have a really good team that works just as hard as I do, if not harder. Without them, I wouldn't be able to expand as much, or as fast.”

It can’t all be go go go though. And even a guy like Ryan has to slow down every now and then. “I grew up in Maine. And I don't have any businesses in Maine…yet,” he adds, the word ‘yet’ eliciting a wry smile. “So when I go back there, it's like going home. I'll sit on the beach, and my family's still there. So for me, if I want to disconnect, I just go there. That's what I call my vacation time.”

He pauses, and looks out at the water. The phone buzzes. “Then I'll check in and it usually scares the hell out of me because I'll have a hundred unread emails,” he laughs. “I also spend a lot of time in The Bahamas, spearfishing and freediving. But I'm trying to build a conch farm in the Bahamas, so I'll probably turn that into work, too.”

Whatever Ryan is up to next (he just started a trolley company and lobster shack in the Catskills) we bet it’ll work. And if it doesn’t work, we can guarantee he will.