What’s the most exotic place you’ve gone fishing?

It’s not exotic, per se, but it’s about a mile off of the Rockaways, bobbing around with Captain John McMurray in the wee hours of the morning in November a couple years back. You could see the Wonder Wheel on Coney Island in the distance. 

We’re sitting out there in New York Harbor, it’s maybe 6:30 in the morning. The sun’s about to come up, schools of baitfish everywhere, and all of a sudden, two humpback whales come bursting out of the water right next to the boat with their mouths wide open, bunker pouring out of them.

The captain, who’s a tough-as-nails Coast Guard vet, screams at me, “Holy Mackerel!” (well something like that) as the whales crash into the water, and the splash literally gets us wet on the boat. It was that close. We proceeded to catch four 40-pound plus stripers live-lining menhaden before 8 AM. Then, just as we were about to head in after a great morning, a 20-foot thresher shark swims right under the boat. And I’m looking at this like, “Where the hell are we? Coney Island is right there, and this is like National Geographic!”

How’d you become a Tottenham Hotspur fan?

For the longest time, I thought watching soccer was akin to watching grass grow or paint dry. But a few people I trusted were rabid soccer fans. I decided, okay, I’ll give it a try.

Around that time Bill Simmons wrote a brilliantly funny article addressing my exact predicament: an American looking to get interested in English Premier League soccer. He broke down the 20 EPL teams at the time, comparing each to an American equivalent in basketball, hockey, baseball, and so on. He mentioned who their celebrity fans were, fun facts, and what kind of vibe the team had. 

The Spurs writeup cast the team as a sort of modern-day Brooklyn Dodgers … the lovable, scrappy underdog who had some magical moments but could never really get it over the finish line. I liked that story, and I have to say, ever since I became a fan, they have had their best runs of form in quite some time.

What common trap do entrepreneurs fall into when they’re starting a company?

I can’t say this with a tremendous amount of authority, because I’ve only really started one company in my life, but sometimes I think folks take on investors too early. Proving out your business model a little bit isn’t a bad thing. 

It may be an old-fashioned way of thinking, but when you look at all the current unicorns, none of them are making money. It’s all based upon these future promises of value. In some cases that’s proven to be a brilliant strategy … Amazon, Google, Facebook … you name it, but it is such a rarity.

If you’re looking to build something of value, something sustainable that can create jobs for people and support families, you have to prove pretty quickly that you can make money. More tech entrepreneurs need the discipline of not having money in the bank and the pressure of going out and making it. 

A musician you enjoy but have to defend in public.

Well, most of my recent musical leanings have come courtesy of my teenage girls, so I get fed a steady diet of Top 40 pop. I’m ashamed to say that sometimes I find some of it to be pretty damn good. It ends up on my playlist, and I then find myself at the gym popping on Sia, who’s my recent go-to.

Harry Styles is royalty in our household. Shawn Mendes is big too. I know all of the words to a lot of the songs. I might need to defend that in public. 

Parents’ worlds revolve around their children. You can’t help it. So, the kids basically dictate my understanding of pop culture right now. 

I am terrible at all the nice conversations folks have around the office about what everyone is watching and reading. That said, I can have an informed debate about the merits of Drake vs Post Malone.

You’re the new owner of the New York Islanders. Congratulations. What’s your first move?

I hate to say it, but it’s getting them out of Brooklyn and back to Nassau Coliseum. The old barn is where the Islanders belong. Barclays Center is just not built for hockey.

I grew up with that team from the first year. We had season tickets in 1972 and drove from Connecticut to the Coliseum three times a week for every home game. The team sort of picked us. The owner, Roy Boe, was a Stamford, Connecticut-based businessman who my dad knew professionally.

I don’t think we could afford them ourselves, but Mr. Boe gave us season tickets for the first few years at no charge. Those early Islanders were terrible. They set records for the worst NHL team that ever played. He just wanted people to show up, and we did. Then we started paying for the tickets because we got hooked.

Over the next decade they became one of the most successful sports franchises ever, winning four straight Stanley Cups. What a magical ride that was. The NHL at that time was just madness. Just picture everyone in the stands smoking cigarettes, throwing beers at the players as they came in and out of the locker room. Fights every game on the ice, the fans going bananas. It would get so loud, you thought they were going to literally blow the roof off the barn. It was great.

Favorite restaurant on Martha’s Vineyard?

I’d say the Chilmark Tavern. I like Jenna, who runs the place, and it’s less than a mile away from the home we rent, so it’s our local haunt. Every time I’m there, I feel very comfortable.

My family’s gone to Martha’s Vineyard every year for the last 20 years, and I used to go when I was a kid. I can honestly say it hasn’t changed too much, other than it’s more crowded and it’s a little wealthier. It’s kind of a pain to get to the island, which helps. If it were more convenient, you’d see three times as many people.

My first memory of the Vineyard was the summer that Spielberg was filming Jaws. The movie crew was handing out t-shirts to the kids, and I didn’t take my Jaws t-shirt off for about six months. I saw one of the mechanical sharks too.

Another favorite Vineyard restaurant is State Road, which has been through a number of iterations, but was famous back in the ‘70s for having wild parties in the basement. That was the whole Belushi, Aykroyd, Bruce Willis crowd. In fact, one of the houses that we swim at all the time now is still in the Belushi family.

Describe your perfect backyard.

It’s definitely got a good grill. And it’s been landscaped by my wife Jeannine, who has an exceptionally green thumb. 

A place where I can pick a few fresh vegetables and some berries, and where I can just enjoy the blue sky. It doesn’t have to be big. I love our little backyard in Brooklyn. It has all of those things.

Season one of your podcast just got the green light. What’s it about?

I’ve always toyed with the idea of city fishing stories, something like “the urban angler.” Urban Angler, truth be told, is the name of a high-end fly-fishing shop in Manhattan. Great name, excellent store.

I was lucky enough to grow up a stone’s throw from Long Island Sound. My grandfather was a lobsterman and a fisherman, not as a trade, but he took it pretty seriously as a hobby. So, I’ve been saltwater fishing my whole life. I love exploring the beaches and fishing holes of NYC, and it makes for inspired gift ideas. One of my favorite wall decorations at home is a watercolor striped bass by then 14-year-old Aida Fraser, a gift for dad on his birthday.

There’s no place I’d rather be than where land meets water. A fishing pole in your hand makes it extra special. But that place, anywhere in the world where you meet the ocean, that’s where I want to be.

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