You know a high roller when you see one. If the loyal entourage, sweet ride and phat apartment aren't clear giveaways, the unflagging confidence and unmatchable stories are. An international high roller brings that status to the next level, leaving a trail of debauchery and mayhem across the globe, with an ever-changing group of companions and hosts.
For the purposes of this article, the definition of an "international high roller" is someone whose jet-set lifestyle takes him or her all over the world in continuous style. You want this kid's life. And unfortunately, this article is as close as many of us will come.
One senior has lived this life for almost eight years. Having grown up abroad in Southeast Asia, Leo* came to the U.S. in high school to attend a boarding school outside Santa Barbara, and then came east to Tufts. During his school years, he has traveled with frequency to Whistler, Miami, Bali and beyond. Many of Leo's most extravagant memories took place on a trip to one of the 32 countries he has visited.
"My parents have always encouraged me to travel because my dad loves to travel," Leo said. "When I was a kid my parents would always take us to random countries. We loved doing that."
Since he has lived primarily in the U.S. since the age of 14, Leo has had the opportunity to forego many trips home in favor of taking radical trips with his friends.
"My parents would pay $1,500 for me to come home during a break, so they would rather I go have fun with my friends [for that amount of money]," he said. "They realize I'm in college and they know I'd rather go have fun with my friends and travel. A ticket to anywhere else in the world is cheaper than it is home."
Leo likes to take advantage of many airlines' round-the-world tickets, which enable him to stop anywhere along his route home, for what is usually a nominal fee.
"If anything, I'd just have to pay $100 to change it so I can decide to stop in Amsterdam or Paris ... I can basically choose where I want to stop," he said. "I can choose seven or eight destinations around the world on an around-the-world ticket that costs the same as a roundtrip ticket to Jakarta."
That's exactly what Leo did last year when he used a trip home as an opportunity to visit Paris, Amsterdam, Frankfurt, Istanbul, Singapore and Dubai. "I get to go visit old friends I grew up with, some friends from boarding school scattered across the country," Leo said. "I always just happen to get to visit all these people because they often live in these international hubs."
When he's not escaping the U.S. for a round-the-world trip or a getaway to his vacation compound in Bali, Leo is finding ways to enjoy his time in the U.S. "All my money goes into weed, snowboarding and my car," he said. "And I eat out every day. Oh, and computers."
Leo spent $1,200 on lift tickets alone last year, and managed to exceed $4,000 in snowboarding expenditures. "I drop so much money on snowboarding," he said. "It's not just lift tickets. It's hotels, transportation, food, going out to bars, equipment."
The food alone results in major charges, as Leo's appetite is insatiable after a long day of snowboarding. "You spend a lot of money on food," he said. And certain resorts, such as one he has frequented at Lake Tahoe, have onsite casinos.
Leo learned a lesson in how quickly costs rise when on spring break in Miami this year with a large group of friends. "The first night our tab was a grand," he said. "It was a phenomenal night. There were 10 of us, with a four-bottle minimum. We ended up getting the bottles, and then of course there were girls with us, so the guys had to pick up a little of the slack."
After recovering, he and his friends spent the day on a $5-million catamaran for a booze cruise. The vessel boasted three soundstages, with an open air, "chill, lounge-y house," Leo said. "You go downstairs, there's drum and bass, hip-hop, Questlove. It was awesome." Leo felt the $75 cover a worthy fee for the "phenomenal" music and "amazing" boat.
"The most ridiculous thing we did was the 12-hour rave at Ultra," Leo said. "It was insane. Every DJ you have possibly heard of was there playing throughout the day." The rave started at noon and went until midnight, with "the best of the best" in mixing represented, according to Leo.
He and his friend enjoyed the first week so much they decided to extend the trip another week. "I needed a vacation from my vacation," he said. "I just needed to burn out for a week." The fact that Leo would be shacking up in his friend's apartment in Coconut Grove by the Ritz Carlton, complete with 275-degree balcony views, made the decision that much easier.
As for his car, a Three-Series BMW convertible, he calls his additions "very frivolous." These additions include rims, lowering his car, a "very nice, but very inaccessible" sound system and a remote starter.
But the things that most exemplify Leo's high roller lifestyle reside in his home country. "The ridiculous things are all in [my home country]," he said. "From [the capitol city where I live] you can just hop over to some private islands where they have cool peacocks roaming the island." One such island has an ornate reef surrounding it with tropical fish and clear waters, where Leo fishes and dives, relishing the time he can "chill out on the island."
One "perk" of living where Leo does is the fact that there is little police enforcement, due to corruption and a lag in technology. Leo recalls trips on the highways near him in a friend's Ferrari doing 160 mph, loving "racing around at three in the morning without having a worry in the world."
*Name has been changed. This person's identity and the veracity of his statements have been confirmed.
