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#90 - Sailing

#90 - Sailing

Sailing
Price: Chapped Lips & Wind Blown Hair

If you think a sloop is a rapper, feel ketch is played with a baseball and glove and believe that yawl is a greeting in the southern American states you are likely not rubbing shoulders with the Rockefellers. If however, you are unfamiliar with rap music, believe that ballpark franks are uncivilized and refuse to associate with Confederate sympathizers, you already know that standing topside in Chesapeake Bay is the perfect summer pastime. If you lean more to the latter than the former you are aware that sailing is among the stuff that rich people love

While port, starboard, stern and bow make the average person’s head spin, these are among the first words out of a trust fund baby’s mouth once the proverbial silver spoon is removed. Rich people that do not learn to sail are as out of place as an Amish couple at a swinger’s party or a West Virginian at a wedding where the bride and groom are not related, it’s awkward for everybody. That said these social anomalies are few and far between. Just as every working class American should have a chicken in every pot and a car in every garage, the rich will continue to have a blue water cruiser in every bay and a mooring ball in every harbor. More important, to the rich, than actually sailing their luxury yacht is ensuring that they have the most conspicuous slip at the marina. There is hardly any point in commissioning an 89 foot Oyster yacht if nobody knows it is yours. While size is important, sailing ships are one of the few places that a sense of humor is acceptable in wealthy circles. Witty monikers like Alimony, TARP, and Golden Parachute all convey a playfulness that only money can buy.

The question, as always, is how can sailing help you to befriend the fabulously wealthy without becoming their indentured servant dishing up caviar on the high seas while the aforementioned Alimony is heeling in 45 knot winds. While anyone with a PhD in English literature can land a crew job on a yacht off St. Maarten, it takes a special type of sycophant to ingratiate themselves and secure an aft berth on a month long cruise of the Mediterranean.  To start, learn a few key words like regatta, Maxi class and Top-Sider boat shoes. Next, learn how to tie a bowline, a cleat hitch and a reef knot and know when to use them. Finally, purchase a vintage copy of Slocum’s Sailing Alone Around The World. To bring it all together, plant yourself at the most Jimmy Buffettesque pub in the port reading this month’s copy of Yacht World circling classifieds larger than 45 feet. In no time, you’ll be talking about ports of call in the BVIs with an overweight boat owner wearing the latest Tommy Bahama linen pants and Helly Hansen waterproofs. Word of advice there’s no such thing as a starport jigpole!

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#83 - Flying First Class

#83 - Flying First Class

Flying First Class
Price: Your First Born, Their Pocket Change

Flying isn’t natural. As they say, “If God had meant you to fly he would have given you wings”, Icarus learned this the hard way. Of course, when they said this, they were probably referring to economy class where the masses are crammed into uncomfortable seats with sweaty, broad shouldered, obese individuals who want to talk to you about their 2-star vacation or persistent skin rash that is likely contagious. If this situation is the bookend to your holiday or business trip, you are probably inclined to agree that mankind is better off on terra firma. While the rich certainly prefer the comforts of a private jet, when push comes to shove, a lie-flat seat with noise-reducing headphones, personal media players, fine dining, full bar and a curtain to separate you from the plebs makes commercial flights tolerable.

For the masses that feel they have won the lottery because they managed to “score” a seat in an emergency exit row, there is a belief that the seats on the other side of the curtain are prohibitively expensive because of the roominess and luxury. Rich people know that, while 40” of seat pitch is comfortable, the real reason to sit in first class is that one does not have to associate with people that can’t afford the finer things in life. After all, the food, personalized service and comfort are table stakes in the lives of the wealthy. First class seating is one of the few places that legitimize class segregation, making it extremely attractive to the rich. Having a boarding pass that reads 2B with a flute of champagne in hand is a wonderful reminder that while money can’t buy happiness, it can help you choose your misery which does not include spending time with individuals who think a timeshare is a good investment.

Naturally, if you want to make good with the wealthy the first option is to secure yourself a seat in first class. This can be done in a few ways; buck up for the extra few thousand dollars every time you fly, try to sweet talk the ticketing agent into upgrading you on every flight or start sleeping with a flight attendant. Of course, if you could pull off the latter two options with any level of consistency, you would likely already be on the road to success and riches and able to execute on option A. As back-up,the art of conversation to kick start a discussion with your wealthy counterpart will work wonders. Give your new friend an opportunity to dazzle you with their in-flight experience. Use informed inquiry about flying Emirates or United’s P.S. service while jet setting between the left and right coast and sit back and listen. Make this work and you may never have to hear the question “fish or chicken” again. Enjoy the friendly skies!

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#79 - Black Credit Cards

#79 - Black Credit Cards

Black Credit Cards
Price: Compulsive Spending

Every month Americans buy a few thousand dollars worth of toys ranging from plasma TVs to designer handbags. These are important to the average person because they symbolize another step towards achieving their five year plan one luxury item at a time. Thanks to the magic of financing and low APRs, these same people pay only a small percentage of what they charged to their credit card, roll over the remainder and promise themselves that they will pay off the balance next month. That might be true if it weren’t for the semi-annual sale at Neiman Marcus or the twenty dollar Crate & Barrel gift card that morphed into a new couch, throw, cushions, coffee table and rug for 40% off, justified by the personal promise to take lunch to work and only drinking one latte a day for the next six months! As a result the average household carries about $8,000 in credit card debt. For the rich, things are a little different. A black, invite-only credit card is a subtle, yet effective, plastic symbol of status and success and like they say, “once you go black you’ll never go back.”

Depending on the card, the wealthy consumer elite are invited to apply for a black, sometimes carbon woven, card that offers numerous benefits that an average Visa, MasterCard or American Express just can’t provide. These include concierge services, personal assistants, financial solutions, airline and hotel upgrades, personal shopping services and while you won’t find it listed in the Benefits Booklet, using a Visa Black Card or American Express Centurion card in any retail establishment means rich people are greeted with “I want to know you” eyes by stunning men and women who would gladly accompany them to the Waldorf for lunch. Ultimately, this is why exclusive, invite-only cards were created. They are the 21st century equivalent of smoking cigars indoors and wearing jewel encrusted pinky rings and tie clips. For rich people, the concurrent introduction of anti-smoking legislation and the ability to flash exclusive credit cards meant not having to accessorize their outfits to showcase their outlandish wealth although ascots remain remarkably popular.

For the average person, there isn’t a hope in hell that they will ever meet the criteria for garnering such an exclusive piece of hologram embossed ABS plastic card. For starters, only 1% of Americans have a black card and the Centurion, as an example, requires spending in the range of $250,000 per year after the $5,000 one-time fee and $2,500 annual fee! Fortunately, there are numerous ways to creatively clear these hurdles; the simplest solution is the DIY method. Materials required; one can transparent black spray paint, one credit card, one roll transparent tape and one copy of the Wall Street Journal although any daily newspaper will suffice. Lay the card on top of the paper and spray one coat of paint every thirty minutes until your card appears invite-only black. Flip card, apply tape to the magnetic strip and signature area and repeat. In no time you will be using your homemade black card and well on your way to impressing your wealthy friends. As a warning, if you plan to use your new black card as a retail pick-up line, check the return policy before  impressing the well proportioned clerk at Saks by purchasing that Rolex and asking her to dinner. While membership does have its privileges, faking it will do in a pinch!

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#78 - Opera

#78 - Opera

Opera
Price: Miniature Binoculars

Does being confined to a chair in a dark room, unable to eat, drink or speak while angry people berate you in a language you do not understand sound like an ideal night out? For most, this sounds like the worst vacation ever and one reason that visiting Afghanistan, Venezuela and Guantanamo Bay rank low on Condé Nast Traveler’s list of dream destinations. For rich people, this is called opera and the biggie sized German or Italian woman wearing the Viking helmet is a Diva rather than an interrogator.

The love of opera runs deep. Rich people love to talk about the architecture of the opera house, exotic sets, magnificent costumes, vocal size and range, Puccini, Strauss, Verdi and of course Mozart. A rich person from a good family can wax poetic for hours on the bittersweet tragedy of La Bohème, the comedic genius of Così Fan Tutte and the scandal of I Pagliacci. Given their knowledge and deep love of opera, you may wonder how the rich manage to grasp the plot and subtleties of productions conducted in a foreign language they neither speak nor understand. The simple answer is they don’t! The performance is a thinly veiled prelude to the most important part of any opera, the intermissions. Intermission is the perfect opportunity to enjoy a full meal, champagne and allow sycophants to compliment a rich person’s refinement, class, taste and sophistication. Watching this can prove more entertaining than the opera itself.

If you are more interested in life imitating art than the art itself, opera provides ample opportunities to mirror your own hopes and dreams. The annals of operatic discourse are rife with tales of sugar daddies fawning over young women and beautiful countesses falling for dashing men with ambition and optimism lacking only social status. If you are an aspiring sugar baby, male or female, your work is cut out for you. A conversational knowledge of Tristan and Isolde or The Barber of Seville that extends beyond Bugs Bunny or Seinfeld plus the ability to bat ones eyelashes should suffice. Either of these love stories may ingratiate you with your cultured courtier and with luck you’ll be enjoying lump crab cakes, roasted filet of beef and amaretto cheesecake at the Grand Tier restaurant faster than you can say “in te ravviso il sogno ch’io vorrei sempre sognar!” loosely translated as “I see in you the fulfillment of all my dreams!” Fitting isn’t it?

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#76 - Tartan Print Pants

#76 - Tartan Print Pants

Tartan Print Pants
Price: Wool Itch Where You Want It Least 

If eggnog, mistletoe, tinsel, Grandma’s flask and the lingering scent of pine needles sounds familiar, you know the holiday season is upon us. In many households, Dad’s tattered and occasionally revealing terrycloth robe has contributed to psychological trauma during the holidays, in other homes it is Mom’s “blackened” turkey that has scarred the children’s memories. For the children of rich people, the ghost of holiday trauma manifests itself as the donning of tartan print pants. These holiday favorites are thought to strike the perfect balance between formal and festive but in fact walk the line between hideous and ridiculous, more so for families without a hint of Scotsman in their storied lineage. 

Traditionally, tartan prints have bound clans and identified kinsmen to one another through the intricate patterns designed exclusively for their family name. As the Scottish boast an unrivaled history of war, the tartan played an integral role in identifying the unrecognizable fallen warriors of battle. Today, far from the vaunted lochs and moors of Culloden and Bannockburn these same tartans, as pants not kilts, represent cliché advertisements and the mark of a healthy net worth. For the wealthy it is a subconscious announcement that they are loud, proud and can make any item fashionable by spending excessively. In fact, there are fashion historians who believe the grunge movement in Seattle and today’s explosion of plaid prints at leading American clothiers can be traced back to a tartan cummerbund worn during holiday festivities hosted by the Vanderbilt family on December 19, 1872. This brash display spawned a “fashion” revolution despite the underlying rationale; young Alistair chose tartan over haggis following a lost wager to a member of the MacLean family. 

Nonetheless, tartan prints are an excellent means to kick start a wealthy friendship. While purists would recommend honing your ability to identify the more than 13,000 tartan patterns, this is time consuming and frivolous. It is highly unlikely that your plaid sporting friend’s knowledge of Scotland extends beyond Braveheart, whisky and the Loch Ness Monster and could not identify the tartan they are wearing even if you could. In fact, it would make them uncomfortable if you asked them anything about the history of their woven cloth given their ignorance of the topic. Instead, draw on the strength and power that a tartan represents. Asking if wearing such a print reminds them of their own success and prowess in life could be magnificent. You will be tiptoeing through the DMZ that separates blatant brown nosing and world class flattery but when it works it really works! Fine tune this skill and you’ll be sipping single malt with the upper crust, otherwise you will face the social guillotine without the historical significance attributed to Mary Queen of Scots. Tha mo bhàta-foluaimein loma-làn easgannan! 

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#73 - Cooking Classes

#73 - Cooking Classes

Cooking Classes
Price: Trip to the Lipo Clinic

Despite the trappings of fabulous wealth, life can become predictable and eventually dull for the rich. Fortunately there is a world of exhilarating hobbies available to the wealthy that aim to inspire before the doldrums of life consume them. For most people, hobbies like skydiving, bungee jumping, scuba and rock climbing add the joie de vivre missing from their mundane existence. Not to be outdone by middle class thrill-seekers, the wealthy also like to step it up when choosing hobbies by throwing caution to the wind and selecting activities that they never thought they would do. These include driving themselves, working eight hours a day and cooking. While your evening likely includes preparing dinner, the wealthy consider this an unfathomable task that the chef, butler or, as a worst case scenario, the nanny will take care of. As such, signing up for private cooking lessons can be a thrilling way to spend a summer and an excellent excuse to visit France, Italy or perhaps Switzerland if checking on the private bank account is required.

While cooking classes are not an impenetrable bastion of the wealthy, rich people tend to have a different set of expectations for these courses. For the rich, being surrounded by world renowned chefs, fresh ingredients from around the globe, the finest kitchen implements and closely guarded cooking secrets is occasion to uncork another bottle of red while the pros create their masterpieces. Spending a month drinking in the Tuscan sun while observing a veteran of the dutch oven fold egg whites, fabricate port reductions and spawn the perfect soufflé lends the credibility required to authoritatively critique a Michelin four star restaurant and is therefore an invaluable experience. Cooking classes are a little like the Dummy’s Guide to becoming a New York Times food critic without the need for a sophisticated palate, experience or a cynical writing style. Nonetheless, such an experience will promote Bunny McCooking-Class to head of choosing restaurants and ordering lunch for her country club ladies group. Like port with chocolate, this newly developed expertise is best served with tales of Fabrizio the pool boy and his prowess in sunscreen massage.

But how does this help you? The best way to leverage this champagne fountain of knowledge is to grease the baking sheet of inquiry. You must walk the fine line between asking questions about the cooking school without broaching the subject of cooking technique; a surefire approach is to ask about the region in which the class was held. This enables them to speak about the setting without being put on the spot about class content. Bonus points if you can steer the conversation to the Le Creuset and Emile Henry cookware they outfitted the estate kitchen with afterwards. After all, their staff deserves the best when cooking for a discriminating palate like their own!

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#68 - Mounting Animals

#68 - Mounting Animals

Mounting Animals
Price: Losing Vegan Friends

Rich people love to mount animals. Please dislodge your mind from the gutter, if you gasped know that taxidermy is alive and well. Hunting has always been a favorite pastime of the wealthy and as long as there are automatic weapons, ammunition and animals obliviously wandering their natural habitat, they will be shot, stuffed and hung on a wall of similarly ferocious beasts. Back when Captain Caveman, the Flintstones and a young Larry King first roamed the earth, hunting was a necessary and effective means to feed the tribe. Centuries later it evolved into feeding one’s ego. For the rich, a room full of hunting trophies is a sign that a man’s man is among you. In such a setting, the scent of rich leather, mahogany and testosterone is intended to impress the toughest of men and seduce the most virtuous of young vixens.

At the turn of the nineteenth century, these public displays of masculinity may have been enough to bring a young woman to her knees but today woman are more likely to hold a membership in Greenpeace than be green with envy over these feats of manhood. Nonetheless, lions and tigers and bears (oh my) continue to adorn the walnut paneled walls of estates the world over. The simple explanation, the rich are oblivious to shifting social norms and as such believe that donning a pith helmet to tag and bag a rhinoceros is all in a good day’s fun. Furthermore, their hunting junkets are a form of financial aid intended to prop up the local gin and tonic trade and keep the natives from getting restless.

Your distaste for this archaic tradition could still help you to score big. Social gatherings can prove the perfect arena to outwit your host, the cagey hunter. Examine your surroundings and determine if there is division in the crowd. If you are lucky, a beautiful heiress is in your midst looking for a distraction from the cookie cutter guests. The trophy room can act as the ideal conversation starter to distinguish you from the “yes men” attentively listening to epic tales about Serengeti safaris. Mentioning that a skilled taxidermist can make a squirrel look threatening to the young gazelle could prove the difference between an evening among old men with pipes and a romantic tour of her well-manicured garden. That said, do not let your guard down in this setting, you never know when a cougar is in your midst…pad, pad, pounce and it is lights out!

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