As I See It: Paying To Play

It was Fitzgerald who is credited with making what is surely one of the more self-evident observations in history. Namely that “the rich are different from you and me.” To which Hemmingway supposedly replied, “yeah, they have more money.” It didn’t actually happen that way, but small matter. The exchange–more literary than conversational–stuck in the popular imagination.

Different though they may be, the rich have the same essential needs as their less affluent brethren. Like the rest of us they crave connection, but that craving is informed by a fear of being taken advantage of. That, in brief, is the dating dilemma facing the affluent men of Silicon Valley. (OK, the fact that they work crazy long hours and have poor interpersonal skills may have something to do with it, too.)

Being uber-wealthy, they struggle with a contradiction. When they do socialize, they carry the suspicion that they are chiefly attractive because of their wealth. But conversely, their experience suggests that money can solve most problems, including loneliness. Holding contradictory beliefs, it seems, is not solely the purview of the impoverished. Regardless, there is both solace and trepidation in the knowledge that in relationships, like in investing, money provides an overwhelming advantage. Solace in the fact that you don’t ever have to be alone if you don’t want to be; and trepidation from never fully trusting the motivation of potential partners.

It’s a quandary. Happily, like many problems facing the rich, there is a purchasable solution. Those who’ve made their fortunes in Silicon Valley can get professional help to find that special person certain to see beyond their latest I.P.O. to glimpse the spray-tanned, timorous millionaire within.

For a price, of course.

Two women, with a brilliant understanding of the fears and needs of the nerderati, are providing dating services to the rich and lonely. The first is Amy Andersen who, according to a recent Vanity Fair article, promotes herself as the “Love Concierge,” which sounds infinitely more promising than a love bellhop. (In the interest of full disclosure, I actually met a love bellhop in a hotel in Bangkok once, but the love he was promoting was of a more fleeting variety.)

In any event, Andersen appears to do some of her best work on behalf of certain gentlemen who frequent a swanky bar called the Rosewood. There, on Thursday nights, venture capitalists gather like salmon, presumably intent on spawning before they die. Andersen saw the potential and promoted the gatherings and soon, eligible women–many of them older, it turns out–came to do a little fishing. Attired in close-fitting dresses and dangerously impractical footwear, they trolled the event to the delight of socially awkward men seeking attention. Soon these Thursday night gatherings became known as Cougar Night, a somewhat unflattering designation albeit titillating enough to be included in the name of the Vanity Fair article: Cougar Night in Silicon Valley.

Ordinarily, when men and women gather, nature would simply take its course, but these are the rich after all, and both sexes struggled with their own insecurities. The venture capitalists (nearly 90 percent of whom are male) were suspicious that “capital” was the operative word that defined their attractiveness. As for the women, many of them either still work, or have worked in Silicon Valley. To survive and thrive in a male-dominated industry they had to be strong, competent, capable, and competitive. But as a result, some had difficulty projecting a softer side. The notion of strong women intimidating anxious men may seem like a worn cliché, but even places that produce leading-edge technology don’t necessarily produce leading-edge consciousness. In the words of Andersen’s colleague, life coach Nina Ericson, “the guys might want to hire them, not take them home.”

Having married a strong woman, I am instructed to say that strong women are fabulous. But if that’s not sufficient to assuage your fears, don’t worry help is but a small fortune away. For an initial $500, each client (and there are about 1,000 of them) goes through a rigorous intake procedure. If they qualify, the real work begins. There are four levels of service that include coaching and varying numbers of introductions to prospective partners. The price starts at–drum-roll please–$20,000 and goes up, up, and up. For people who actually have to save their money to go out on a date, this may seem excessive. But that kind of poverty mentality will never get you a spouse in Silicon Valley. Not surprisingly, the service is exclusive and discrete. It’s “not available to the masses,” according to Andersen.

Well, certainly not at those prices.

Given the fees involved, it’s safe to say Andersen and Ericson must be skilled at what they do and able to deliver what they promise. Yet there is something sadly ironic about otherwise intelligent people, concerned that their wealth trumps their likeability, spending tens of thousands of dollars to become likeable.

There is also irony in people yearning for a “real” relationship, but paying to learn how to dress differently than they ordinarily dress, frequent restaurants they might not otherwise frequent, learning something called “date preparation techniques” and how to bleach their teeth, darken their unhealthy pallor, and generally become someone they’re not. Starting a relationship by being inauthentic bodes poorly for the long term.

Social media has turned dating into an industry. Perhaps the greatest irony is that the more connected we are online, the more isolated we become. There are dozens of dating services, online and off, each dangling the elusive carrot of compatibility. (Not an unusual challenge for Silicon Valley.) The very essence that makes Silicon Valley possible–the brain-bound qualities of the people who sustain it–makes relating to others harder than relating to machines. Thus, the business opportunity to help adults master a process the rest of us learned as teenagers.

Silicon Valley’s approach to dating is reflective of many of its products: it’s become needlessly complicated. The reality is, no matter how much you spend to meet “the right person,” someone who will care for you beyond your wealth, no one can discern another person’s intentions. We do things for our own reasons, some conscious and some not. Maybe all that is required for successful dating are willing participants.

Meet Emily Holt. She is a fashion writer with bi-coastal dating experience. A transplant from Manhattan, she wearied of dating the suits on Wall Street, and decided to try her luck with the hoodies of Silicon Valley. She wrote about her experience in Vogue. After all, she notes that the ratio of single guys to women is extremely favorable in Silicon Valley. And, listen up all you guys hanging out at the Rosewood, she thinks she “can do nerd.”

Not much on which to base a venture capital investment, but it’s a start.