In order for Greenwald to tutor you as a matchmaker, however, you must pay, in full and up front, the "very pricey" fee for the intensive two-day workshop. If you need to cancel after paying, too bad: Your money will be diverted to Greenwald's pro bono karma fund, which she uses occasionally to help clients who cannot afford her daily rate.
The first day of Greenwald's training centers on public relations and pricing, while the second focuses on event management, tactics and communication skills. Both days last nine hours, during which none of the five students (maximum) leaves the room; lunch is delivered. But if a student lasts through training, she (and they are almost invariably female) will get customized career advice from Greenwald. "It's an incredibly flexible profession," she notes. "There's no degree requirement and no start-up costs as long as you own a laptop, and the hours and geography are whatever you want them to be. One boot-camp client wanted to work exactly from 9 a.m. to 3 p.m. in Chicago, so I developed a business plan for her in Europe to work in those hours."
Marea Evans
Rachel Greenwald's list of happily-ever-afters includes her own: She found her husband through her own marketing strategies.
Jim J. Narcy
One of Jaime Richards's earliest successes was finding a mate for her own mother.
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Greenwald teaches her students to specialize in order to create their own matchmaking niches separate from those of the competition. Her last boot camp included a woman from Australia, a sixty-year-old retiree looking to tap into Boston's seniors market, and a Mormon widow. "When I wanted to break into the LDS community that I belong to, Rachel thought that was a great idea," says Chris Wilhoite. "It's a world where matchmaking isn't utilized as a profession."
Although the intensive training session focuses on building business skills, perhaps its most practical tool is Greenwald's own seal of approval. After class, she'll donate her rejected business requests to the matchmakers that she has nurtured. (Matchmakers can also purchase clients from each other if they think some are better suited for another customer.)
"Rachel's success is a huge thing," says Heidi Wicks. "She has an excess of clients she can't take in, and she passes them on to us based on our specialties."
Greenwald confirms this with a smile. "This is not a non-profit organization," she says. "It's a business."
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The enormous diamond on Jaime Richards's immaculately manicured left hand is as distracting as it is comforting, but "it's nothing compared to the man who gave it to me," she says.
Although many of Greenwald's matchmaking graduates are single when they start their careers, a wedding ring can be reassuring when it's on the hand of the person you just paid thousands of dollars to help get you down the aisle. Reassuring enough that you're willing to listen to her blunt advice. "I hope I don't offend you, but I have to tell you," Richards says. "You should really never wear those tights with those shoes ever again. A man will look at you and get worried."
Of all Greenwald's local students, Richards is the closest in both style and ambition to her mentor, though the two differ on a handful of issues. "Rachel doesn't love that I don't go national, but I don't want to travel," Richards says. (One of Greenwald's wealthier clients, a billionaire from Texas, once flew her to him on a private jet. For such occasions, Greenwald exercises a buyout option, through which clients can pay more to purchase 100 percent of her time for an agreed-upon span.) "We were kind of at odds about that."
Richards discovered Greenwald's books after her seven-year-old daughter motivated her to become more aggressive about dating. "I was a single mom, and I had dated and been married enough to know I wasn't going to screw it up this time," Richards says. "I made a decision that I was going to research everything I possibly could about online dating, which was my only option at home with a kiddo."
She started experimenting with her mother, setting up an online dating profile for her and frequently logging into that account to reword aspects of that profile after her mother had changed them. It worked; her mother is now married. And Richards met her own husband, who runs a home-electronics business, through the same website. It was after that that Richards, who was working as a real-estate loan agent at the time, realized she could make a career out of matchmaking and took Greenwald's course last January.
Today Richards is a confident matchmaker and dating coach: If your hopes are not high enough, she will readjust them. If your expectations are too picky, she will correct them. If you are not assertive enough, she will flirt with people for you. Last year, Match.com temporarily blocked her home IP address after she winked at too many people for a client.
Her business comes with rules, and it comes with results. According to Greenwald, the single most common end to matchmaking careers is a lack of self-confidence. "People are typically terrified to charge what Rachel tells them to charge," Richards says. "But I'm completely okay with people walking away when I tell them the cost. I'm probably the second-most-expensive matchmaker in Denver after Rachel."