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#92 - Equestrian

#92 – Equestrian

Equestrian
Price: Saddle sores/horsemeat scandals

If you are serious about being wealthy, one of life’s great pleasures is developing a sense of class that is far beyond that of the common man. This means enjoying activities like polo, croquet and collecting ascots. While nearly everyone has donned a cowboy hat and straddled a petting zoo pony or mounted a dude ranch work horse better named Gluestick than Silver, the truly wealthy do not consider these representative of a true equine aficionado. In fact, the rich consider anyone that wears blue jeans and a straw hat more likely to be proficient with a pitchfork and a wheelbarrow than a saddle and a bridle. Instead, one simply must own a proper collection of riding boots, flared riding pants and a helmet reminiscent of Marvin the Martian, if Marvin owned a Bentley.

While a trusted steed may elicit images of John Wayne, the Lone Ranger or Clint Eastwood, rich people know that only and elite few can exhibit the grace and elegance of an equestrian rider. The majesty of rider taming a well-papered beast and becoming one as they gracefully vault over obstacles in a race against time is akin to watching a an Italian mechanic tune a classic Ferrari…while it is moving. Equestrian may at first blush appear a frivolous pastime but one must move beyond the literal interpretation and realize it is in fact a metaphor for success as many wealthy patrons believe they have pulled themselves up by the bootstraps overcoming humble beginnings as trust fund children who did not see a penny until they turned 21 or until they narrowly graduated from an Ivy League college at a campus littered with buildings named after their forefathers.

As always, the challenge is not how to mock the frivolities of the wealthy but to embrace them as a means to gallop into the inner circle. Naturally, as with other stuff rich people love, there is a vocabulary to learn. Understanding that the obstacles are called verticals or fences and that the horse and rider are called jumpers is table stakes, so the ability to discuss the finer points of the sport becomes critical. I recommend intimating a knowledge of dressage or perhaps the cultural importance of the fox hunt as light-hearted means to inspire your host to wax poetic on their thoughts about warmblood and thoroughbred breeding or their leaning towards Badminton versus Burghley as the pinnacle of success. Some may suggest that sincerity and genuine interest are keys to winning friends and gaining influence. Others believe that rich people are much more inclined to appreciate a sycophant that feigns interest rather than engaging in meaningful dialogue. Perhaps it is why horses make such great team mates.

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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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#89 - Cufflinks

#89 - Cufflinks

Cufflinks
Price: Accepting the French

In the immortal words of Little Orphan Annie, “you are never fully dressed without a smile”. This whimsical idea may apply to the vast majority of pencil pushing middle managers trying to keep their head above water in spite of a partner that believes shopping at the newly opened Crate & Barrel is akin to the second coming of Jesus. This little cliché certainly does not apply to the proverbial upper crust. While custom tailored shirts are a staple of any well-to-do wardrobe, they hardly provide the opportunity to flex one’s personality and showcase their avant-garde sense of fashion. Enter the French cuff and Louis XIV’s fashion forward gift to the world, gilded studs called cufflinks.

To the everyday man and woman who feel that Starbucks charging $1.50 for a cup of Joe is unconstitutional the idea of spending hundreds, if not thousands of dollars, on two chunks of semi-precious metal in place of a twelve cent button must seem certifiably ridiculous. It is this difference in the classes that keeps Pabst and Camaros popular in trailer parks and cufflinks in vogue on the Upper East Side of New York. Naturally, throwing on any old piece of kitschy jewelry won’t cut it at the club. While your groomsmen, who believe white socks and tuxedos go together like fried peanut butter and banana sandwiches, will commend you on your compass with built-in thermometer or roulette table cufflinks, you have a better chance of catching Dora the Explorer in Playboy than seeing Gordon Gekko adopting your mischievous sense of fashion or glimpsing Bruce Wayne sporting batman logo cufflinks. Instead, rich people opt for subtle designs that reflect their personal interests. This may be collecting impressionist art, classic cars or a layman’s interest in Adam Smith’s Wealth of Nations and its influence on the credit default swap crisis of 2008.

If you don’t feel a burning desire to retire your dress shirts and adopt French cuffs throughout your wardrobe, fear not! There are two things to remember when befriending the wealthy; as any first year associate on Wall Street quickly learns rich people don’t like when common folk wear cufflinks and complimenting a rich person’s sense of fashion is substantially less expense than dressing like them. While wearing cufflinks will not ingratiate you, asking leading questions will. The trick to making friends with the rich is to walk the fine line between ass kissing and cerebral flattery. For example, telling a wealthy man or woman that their cufflinks are really impressive is blatant brown nosing. Asking if their sense of fashion enhances their success or if their success enhances their stylish appearance is the fast track to gaining the respect of the rich. So next time you button-up before work, think about those inconspicuous pieces of cuff candy and consider how they could enhance your own life.

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#88 - Producing Movies

#88 - Producing Movies

Producing Movies
Price: Casting Couch and A Wallet 

Most people are familiar with the phrase, “those who can, do; those who can’t, teach”. I’m not saying I agree with this adage but I am confident that my woodworking teacher’s seven fingers didn’t improve his street cred. While working for NASA is an unlikely endgame for a high school physics teacher, rich people see no reason to thwart their ambition over something trivial like talent, skill and experience. It is this eccentric quirk that makes the world of Hollywood turn and ensures that even the very worst scripts can still make it to the silver screen thanks to a terrifically uninformed bankroll. Meet the Executive Producer.  

The Executive Producer plays a critical role in every film; provide financial backing and stay out of the way of people who claim to know what they are doing. It is easy to assume that these captains of industry, having made their fortunes in gold mines, oil wells, shipping or real estate, are interested in further padding their Swiss bank accounts with the next Avatar, Toy Story 3 or Inception. Au contraire reader, becoming an Executive Producer is the proverbial golden ticket that rich people need to pull back the curtain and gain access to Hollywood’s red carpet; think Christina Hendricks, Isla Fisher and Jayma Mays. In Los Angeles’ film circles there is only one rule; the bigger the bankroll, the bigger the celebrity. It is this simple rule that attracts the modern day robber barons to sink their millions into terrible scripts written by “starving artists” and directed by “tortured souls”. In exchange, they all but guarantee themselves discussions on method acting with George Clooney, cinematography lessons from Scorsese and a performance by Justin Bieber at their daughter’s Bat Mitzvah. In many cases profitability is an afterthought and a pleasant surprise.  

While spending millions to be on-set at Hollywood’s next box office bust may seem excessive to the average autograph hound, rich people have an innate knack for justifying almost any financial failure; the tax-loss carry forward. This little taxation trickster is the fix-all for blowing their wad on a film that will quickly pass from theater to distant memory without a hint of embarrassment on the part of the producer. Losing an eight figure investment not only appears acceptable within their social circle, it actually makes rich people seem quite savvy! This “win-win” situation means rubbing shoulders with Brangelina, a significant tax write-off and the opportunity to talk like a Hollywood insider. Oh, and for the trust fund hipsters, a well stocked casting couch is a significant perk because while you can’t buy happiness, money lets you choose your misery. 

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#87 - Doormen

#87 - Doormen

Doormen
Price: Confused By Push Signs

If you are like me you grew up in a city where people learned how to do things for themselves. In places like Winnipeg it means knowing how to dress for sub-zero temperatures throughout the year. Native Australians can protect themselves from kangaroos, great white sharks and hide their offspring from wily dingoes. Meanwhile, growing up in Mumbai teaches people to effectively operate a call center or program in C+ without the need to outsource this skill to other countries. The rich, unlike those without money, don’t take kindly to having to perform tasks themselves. Menial annoyances like blow drying their hair, cleaning their home, landscaping their estates, looking after their own offspring or sculpting their good looks can all be delegated to under-appreciated professionals…opening doors is no different.

We are all familiar with the difficulties that opening doors can pose. There is the tiresome task of finding one’s keys and the mentally exhausting struggle of push vs. pull. This may be simple to you but you likely are not rich and cannot understand the challenge that ingress conventions cause. As such they look to others to solve the wealthy equivalent of Schrödinger’s cat. Interestingly, while most everyone that works for the rich is at the beck and call of those with ample Ben Franklins in their Prada wallet, the doorman is a special breed of help. Equal parts security, concierge, confident, sycophant, gossip snitch and stanch union member the doorman can make a tenant feel welcome or thoroughly ignored. While the rest of the world world bows to the fancies of the wealthy, even agreeing with a milkaholic’s whimsical dream of launching a clothing line, an NYC doorman is protected by the Local 32BJ and needs not bow to the fickleness of the upper crust. In fact, if the right of the doorman to deliver sardonic humor and unsolicited advice to their pedigreed counterparts is compromised swift strike action is threatened which throws the city into turmoil. The result of this unlikely relationship is that the doorman is privy to Upper East Side indiscretions, SoHo secrets and Tribeca trysts.

Naturally, if you would like to wriggle your way into the lives of the fabulously wealthy a doorman may represent Prometheus waiting to share the secrets of the Gods. While discretion is the better part of valor, if gossip columnists can break these vaults of secrecy surely you can find a way to eke out a sound bite or two and gain familiarity with their wealthy patrons’ likes and dislikes. Perhaps the couple in 15B enjoys the thrill of meeting new people over Manhattans and dinner at a Gramercy Tavern barstool on Tuesdays while 12D loves sailing in the Maldives and 14C has a weakness for custom oxfords from John Lobb on Madison. If you can’t turn these nuggets into sparkling conversation over grilled sturgeon there is no hope for you to impress the well-heeled. Succeed and there may be enough wind in your sails to solicit an invitation to enjoy lunch in a stunning co-op overlooking Central Park in spring. Land ho you scallywag.

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#84 - Designer Cupcakes

#84 - Designer Cupcakes

Designer Cupcakes
Price: $36 a dozen

Prevailing wisdom dictates that little girls are made of sugar and spice and everything nice. Spend some time in a trendy shopping district and you will soon find that this is largely due to designer cupcakes, emphasis on the sugar and light on the nice. Thankfully, for the financially endowed, they need venture no further than around the corner in their hybrid SUV to satisfy a craving that used to take their private chef as much as an hour to whip up. Designer cupcake shops are becoming so popular, they are threatening to supplant Starbucks as the storefront voted most likely to replace a former tenant, although Vietnamese nail salons run a close third.

While common people may purchase these single serving delights at the supermarket, this could never satisfy the sophisticated sweet tooth of a high net worth individual. For starters, store bought icing isn’t rich enough; cupcake shops appear to have cracked the age old problem of condensing a full pound of butter into a half pound of icing. Second, buying a dozen chocolate cupcakes is blasé; the baked pleasures of the wealthy deserve creative names like “Tickled Pink”, “Lady Baltimore” or “Dirty Blonde”, the latter may also describe one’s third wife. Finally, the creativity doesn’t end with naming cupcakes, rich people love to fawn over the playful shop names where they purchased these heavenly indulgences; think Babycakes, Buttercup and Flour Girls for starters; I adore the t-shirts from Babycakes in NYC.

While many quirks of the wealthy are out of reach of the common man, a love of rich desserts is a human condition that knows no economic boundaries. With this in mind, impressing the wealthy is simple when done by the dozen. Discussing your favorite cupcake shop will certainly do in a pinch but it is the gift of cupcakes that will truly impress. The elegance and tastefulness of ribbon wrapped sugary goodness will have your hosts beaming at your thoughtfulness and once it comes to naming these savory delights, they will figuratively if not literally be eating out of your hand. An excellent conversation starter, your affection for cupcakes will win hearts, minds and stapled stomachs. Be sure to save the “Sexy Red Velvet” for the beautiful heiress you’ve been watching and she may turn out to be your sweet temptation!

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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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