The book's reviews were glowing. "Want a spouse? Read this book!" proclaimed Fortune. The Observer raved that "Greenwald is the hottest thing to hit the dating scene since Sex and the City." The New York Post praised her pragmatism. Requests for help overwhelmed her inbox. Soon Greenwald expanded her business beyond merely writing about love to actually working as a matchmaker for male clients and as a dating coach for women.
Greenwald continues to write about love, though more briefly and regularly, for the Huffington Post, on dating websites such as Match.com, and for other sites including YourTango and GenConnect. She followed up on Find a Husband After 35 (now out in a new paperback version) with 2010's Have Him at Hello; together those books have pushed her career as a matchmaker for millionaires and earned Greenwald a spot on the NBC dating reality show The Match-Off. She has been featured on The Today Show, CNN, ABC Nightline and The Early Show, and in the pages of the New York Times, People, Fortune, the New Yorker, Cosmopolitan and Glamour.
Jim J. Narcy
Heidi Wicks worked in retail for years before attempting matchmaking.
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Greenwald cannot begin to fill the country's matchmaking needs on her own. So four years ago, she developed a series of workshops to train others who want to enter the multibillion-dollar industry. At exclusive and demanding boot camps, she now spends two days a year instructing these acolytes in the secrets of successful matchmaking. And in 2010 and 2011, Greenwald delivered the keynote address at Matchmaking Pro's national conference, which is devoted to supporting a career that was not even a viable financial option when she took it on.
"At that point, when I started, there were probably only about ten full-time national matchmakers in the United States, so it was really off the radar," she says. "Online dating was just beginning, but matchmaking has become incredibly popular as a living since then."
The only reason she turned down a repeat performance at this year's national conference is because her eldest son's SAT is scheduled for that day, and she didn't pick this career so that she could ignore her family.
In college, Greenwald had more first dates than any of her peers. Today, she says, she is offered more business than most of her Colorado matchmaking peers, though she rejects roughly 80 percent of those inquiries. Greenwald's matchmaking and date-coaching strategies continue to center on the same ones she used in the business world: branding, packaging and niche marketing. "Rachel is an amazing businesswoman," says Jaime Richards, one of Greenwald's most recent disciples. "She doesn't even bother with anything that isn't profitable."
The media has dubbed Greenwald "The WifeMaker." But she has another word for her career: "magic."
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The opening scene of Hello, Dolly! finds the title character walking across what appears to be the entirety of Yonkers, New York. Her goal is to build a client base, which the matchmaker then spends the rest of the movie systematically turning into couples. Dolly Levi is sassy, bossy and almost omniscient in her quest. She is also Barbra Streisand, so this scene, though classic, has absolutely nothing to do with Greenwald's business. Even Millionaire Matchmaker's Patti Stanger has yet to be commemorated in song, despite spending five seasons dispensing highly quotable advice to people with high net worths.
But Dolly, the meddling older lady, continues to be one of the two most prevalent matchmaker stereotypes; the other is the frigid bitch. Stanger fits somewhere in the middle of this spectrum, but Greenwald avoids it entirely: To her, matchmaking is a serious business. "It's a career everyone thinks they can do, especially women who think they have been doing this all their lives with their girlfriends," Greenwald says. "People think they're just going to go around and fix happy people up all the time and it's all joy and flowers, but that's not true."
Strategic matchmaking is an expensive process, and even in these tough times, people do not hesitate to pay thousands of dollars for the right modern-day yenta. Time reported a steep rise in business for high-end matchmakers last year. (It also reported that in 2009, the matchmaking industry was one of the Council of Better Business Bureaus' top industries for complaints by consumers.) "When you're faced emotionally with loss all around you — loss of finances — all you want is love," Greenwald explains. "People are not going to Starbucks to spend $4, but they're spending $10,000 on a matchmaker. It's like everything in the world is crashing around you and you just want to be in love."
Although she admits she is "incredibly expensive" — her date coaching can cost as much as $2,000 to $5,000 a day — Greenwald declines to reveal the cost of her annual boot camps (the next one is scheduled for April in Denver). "Price is usually its own screen," she says. "People who are really serious about starting their own business self-select. Two-thirds of the people, I never hear back from again. If people have to ask how much it costs, frankly, it's not for them."
There are other options, of course, and the tools of the trade vary in direct proportion to the seriousness of their buyer. Matchmaking Pro, for example, sells a boxed notebook starter kit for cheaper beginners.