Money can buy you love, if you have a contract with this Harvard MBA

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In their wedding photo, Elena Wechsler and John Simpson are the picture of matrimonial bliss. The image captures the modern-day Romeo and Juliet in medias res: Wechsler appears to have run, perhaps in slow motion, to her husband, who has gathered her into his tuxedoed arms, lifted her above an impossibly green field of grass, and proceeded to kiss her so thoroughly that Wechsler's bare left foot has kicked up behind her in response. The resulting visual falls somewhere between adorable and beautiful, cliché and earnest. In short, it is perfect.

Printed in the New York Times Vows section, the photo has a story behind it — and the real author of this love story is not a Times reporter, but a Harvard MBA who cashed in on her marketing expertise to create a romantic empire.


Rachel Greenwald's greatest success story might be her own. As she takes a window seat at Cucina Colore, a contemporary Italian restaurant in Cherry Creek, the woman who coached Wechsler in finding a mate is all concentrated grace. Her face framed by delicately curled hair and thin oval glasses, she smiles (elegantly), shakes hands (firmly) and then smoothes her shirt (carefully) as she sits.

"You will make a lot of dating mistakes, and you have to get those moving," Greenwald says before she even finishes looking at the menu. She is a firm realist, if an exceptionally polite one; she is not a feminist. "You're going to have lots of failed relationships. Have you thought about how many kids you want?"

Greenwald is originally from Denver, and she attended Graland Country Day and Kent Denver before moving on to Wellesley, Harvard and big marketing gigs on the East Coast for companies such as Evian and Carolee Jewelry. If this were a first date, she would not have to worry about snagging a second one.

Her clients, however, still do. Over the past twelve years, Greenwald has crafted a second career as one of the country's most well-respected and frequently requested matchmakers — a career that started as a calculated afterthought. When Greenwald was in her late twenties and living in Boston, still single, she knew that she wanted multiple children and began to feel constrained by time. But the first step was finding a husband, so she set out to find one, using everything she'd learned while getting her bachelor's in psychology and a Harvard MBA. Among other things, she threw a party — an event carefully constructed to draw men who had the potential to become a future husband, or could introduce her to a man who had that potential. Working on her invitation list, she was looking through a directory for an acquaintance with a big social circle and decided to invite a more distant acquaintance listed underneath him, a man she had spoken to on the phone a year earlier. He made the cut despite Greenwald's thinking that his directory photo was unattractive. In real life, though, he was anything but. Brad Greenwald asked her out the Saturday after the party. Three years later, they were married.

In 1999, with two children and two successful careers, the couple moved back to Denver. The next year, as they contemplated having a third child, then-34-year-old Rachel realized that she was unlikely to find a marketing position that would be flexible enough to let her focus on her home life. So she decided to find a job that fit better with the rest of her life. But what job? Months of brainstorming ended with a brazen concept: Greenwald, without ever composing anything outside of a term paper or a party invitation list, would become a writer. Writers have completely free schedules, right? Having determined this, she turned to the Internet to research her new career. She searched for "How to become a book author" on Amazon.com and unloaded a couple hundred dollars on the highest-ranked results.

But to be an author, you must have something to write about — and Greenwald's plan didn't yet extend that far. In order to identify her passion, Greenwald used her practical experience to record in a journal a week's worth of activities in hopes of finding meaning in one of them. While compiling her list, Greenwald ranked every activity on a scale of one to five, depending on how much she enjoyed it.

"How many things do you think you would rate a five by the end of your week?" she asks, and then shakes her head. "Somehow, I only had two: drinking my morning tea and talking to a single friend on the phone who had called to complain about her love life. I was so excited, pacing my kitchen while telling her all the things she had done wrong and how to fix them." One year later, her friend was married — and she credited Greenwald's advice with making the match possible.

Today, close to 800 married couples can thank Greenwald for not making her next career tea-drinking. Instead, she decided to apply everything she knew — both from her formal education and from her own romantic life — to writing a book about finding a husband. She began working with friends and acquaintances, all of whom could serve as examples in the pages of that book. The way she found her husband — it's not really appropriate to say she "met" him — is outlined in "The Program" in that book, specifically step No. 12: hosting a party. By the time Find a Husband After 35: (Using What I Learned at Harvard Business School) was published in 2003, Greenwald had that third child, as well as the beginnings of a new career that would go far beyond just "writer."

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.

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."


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.

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."

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."


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."

The first step to creating a business out of love is marketing it. Immediately after she finished boot camp, Richards bought a domain name, created a website and worked with a company that specializes in search-engine optimization to make coloradomatchmaking.com one of the highest-ranking sites of its kind in the area. From there, she chose a clientele niche: For matchmaking, Richards helps wealthy men in their forties through sixties find women who are twenty years younger and a ten out of ten. "Tens don't really exist," Greenwald says. "But nines do."

From there, she synced her brand with Twitter, where she is @denverhitchette, and Facebook, where her company is called Happily Ever Afters. All of her prices are based on Greenwald's fees, and she works month to month with no contracts because Greenwald structured her own business that way. Richards oversees no more than five matchmaking clients at a time, a recommendation that meshes with Greenwald's push for low-volume, high-dollar business. But in the year that she has spent adapting her training, Richards has developed her own rules, too. She often pre-dates women herself to weed out unfit candidates, and her matchmaking services extend to shopping for her male clients and even helping them clean up their electronic footprints. "I don't guarantee a number of dates, and I don't show men photos of the women they're dating, because I want them to trust me," Richards says. "I don't give them contact or name info until right before the date, because I don't want them Googling each other. I have done this enough to know what is best for them, and all they have to do is let me go."


The United States currently houses more single people than any country outside of China and India. Roughly 40 million Americans use online dating sites, and that industry is expected to reach an annual worth of $1.3 billion in 2013. Although many assumed it would be a death knell for yentas, the rise of online dating actually boosted matchmaking in two distinct ways. First, it made it okay to outsource your love life. In the sense that you can write exactly — exactly — what you're into on your dating profile, love is no longer a private experience, and neither is your quest for it. "Today, if you're not online, you're not single," Greenwald says.

Second, people become frustrated with online dating — and that's when a matchmaker's services prove invaluable. That massive process of weeding through potential mates is exhausting, and some of the people winking at you turn out to be married or creepy. It's a tough job to tackle alone, and it's an embarrassing one to mismanage.

"I once had an Orthodox Jewish girl I was working with in New York, and she had been dating someone for four or five dates and let him sleep over," Greenwald says. "Well, the next morning he has to go to temple, but it's Shabbat and it's too far away for him to go without using technology, and he didn't have his tallis, his prayer shawl. She runs to the bathroom and is texting me because she doesn't know whether it's him freaking out about sleeping together or about his tallis."

When Greenwald peeks at her cell phone, the move is subtle, as though she's just reaching for a fork and accidentally encounters her BlackBerry. In case of dating emergencies like the tallis incident, she and her disciples keep their cell phones turned on and are always available to tackle romantic problems as they develop.

A typical date-coaching session with a female client covers a strict regimen of training, refinement and blunt honesty. Before even starting out with a new date-coaching customer, though, Greenwald asks the woman to request a minimum of six letters from friends, family members and ex-boyfriends, explaining why this client has not yet found love. After that, a client will fly in to Denver (most of them are from New York), where Greenwald will book her into a comfortable hotel and then wake her up at eight the next morning to have her makeup and hair done in Cherry Creek.

From there, the client will visit Marea Evans, Greenwald's go-to photographer, to have flattering photos taken for her dating profile. All clients are required to purchase a brand-new push-up bra before being photographed, and Greenwald approves their wardrobe options before the photos are taken. The rest of the day consists of one-on-one date counseling with a short lunch break, during which Greenwald actually stages a pretend date.

All of this work takes time and expertise, and Greenwald encourages the matchmakers she trains to charge heavily for them. Some clients do not even trust matchmakers who do not approach the expensive end of the scale, she points out. The issue of price is frequently debated at her boot camp, though most followers elect to follow Greenwald's scale, or at least an approximation of it. But Boulder dating coach Heidi Wicks has elected to ignore it.

"My feeling is that everybody deserves love, not just the wealthy," Wicks says. "There are a lot of business models that only cater to the wealthy, and that just rubs me the wrong way. I want to be available to people with less money, but I still want to make money."

To that end, Wicks has adapted the boot-camp training she received from Greenwald in 2009 to focus on the general public. Late last year, for example, she received a request from a high-school junior. But even after downgrading her price, Wicks's fees are still similar to those of a psychiatrist: Initial consultations cost $200, and coaching runs $75 an hour from there. Still, her role as Boulder's only full-time dating coach affords flexibility while she develops her brand.

After working in retail, the 42-year-old Wicks attended the National Matchmaker's Conference in 2009, where she met Greenwald and decided to sign up for her boot camp, then try out a new career. "I had seen so many bad dating profiles and been on so many bad dates myself, and I had helped friends with their profiles," explains Wicks. She met her own future husband on Match.com.

Once Wicks commited to matchmaking, the first step — even before looking for clients — was to print business cards, then create a logo for the website that would attract daters to her service. As Greenwald teaches her students, marketing is important: If you build it, they will come. The next step is to ensure self-confidence. If a matchmaker doesn't believe in her business, none of her clients will. "I'm kind of a shy person, so it's hard to put myself out there," Wicks says, comparing herself to Greenwald. "I still feel like I'm behind. I'm no marketing maven, but the only person holding me back is me."


If you cannot afford a $9 salad, you cannot afford me," says Chris Wilhoite, waving her right hand in disdain as her left hand balances a teacup. And then she issues a truly weighty sigh. Just because they help other people perfect their love lives doesn't mean that matchmakers' own love lives are perfect. Earlier this year, Wilhoite went to Applebee's on an ill-fated date (among other things, the man wore an entirely black-and-white outfit and attempted to convince her the look was big in Italy), and she has yet to completely recover.

Episodes like this one, though, provide the fodder that Wilhoite uses to relate to her clients, and this is extraordinarily important for her. Wilhoite's business, while still young, caters specifically to Mormon clients, and her 23 years in the LDS community have given her a head start on exclusive rights to the love lives of Denver's Mormon population.

"I see this niche as untapped," she says. "Marriage is viewed differently for an LDS family because they say 'till death do us part,' but we say 'for time and all eternity.'" That's a big difference, she notes, and a fear of divorce leads many Mormon singles to place extra — and conservative — pressure on the concept of marriage. "Their modesty standard includes longer skirts, capped sleeves instead of sleeveless," she explains. "You wouldn't meet someone in a club, because we don't drink. When you're sitting by yourself on a church bench, it's lonely. It's just enough of a difference to matter, and I know their background and doctrine."

Wilhoite, who converted to the religion at 22, marks a trend in modern matchmaking that is quickly moving daters toward more niche-oriented ventures. Online, vegetarians can find love at veggieconnection.com, while seniors have a huge variety of age-specific options. LDS daters can be matched on LDS Singles and LDS Planet, while Jewish daters have J-Date. And if you're an Anglophile, look no further than DateBritishGuys.com. "No matchmaker should be tapping into the same market as any other," Greenwald says. "If you do, you're doing it wrong."

Right now, Wilhoite describes herself and her slowly moving business as a "tortoise" — but if Greenwald is the hare, then there are lots of turtles. "That's the wonderful thing about this business," Wilhoite says. "There's nobody saying 'Do this right now.'"

When Wilhoite takes a seat in her living room, she automatically chooses the exact center of a wildly flowery couch, which places her head immediately below her head inside a framed portrait of Wilhoite and her late husband, Nolan, hugging as their four children posed around them in matching outfits. For Wilhoite, who was married for thirteen years before Nolan passed away from pancreatic cancer, absence has made the heartbreak grow fonder.

"I had a great marriage, and I want to spend my living watching people fall in love," she says. "I still think the sun rises and sets by my guy. Rachel asked me if I still have pictures of him in my house, and she wants me to take them down, but from an LDS perspective, that's not something we'd do."

Although her specialty comes with its advantages, it also brings a generous share of awkwardness. Despite attending church in the area, Wilhoite is uncomfortable directly recruiting church members for the business she started after attending Greenwald's boot camp a year ago. Instead, she has organized a "fireside," a church discussion group, to teach constituents about creating an online dating profile in hopes that they might also approach her for more coaching.

During the four years she has spent training other matchmakers, Greenwald's students have come from a wide spectrum of specialties and backgrounds — but the most common constituency, she says, is mothers like her who are searching for a career that can be completed from inside the house without any strict routine.

Wilhoite was walking by a bookstore when she spotted Greenwald's first book, Find a Husband After 35, in the window. She read it over, then went on to purchase her second, Have Him at Hello, and then e-mailed the veteran matchmaker for advice. She wound up enrolling in Greenwald's boot camp after asking her for date-coaching help and being rejected.

She'll still occasionally ask Greenwald for advice. To date, Wilhoite's greatest difficulty has been developing a brand inside the Mormon community without accidentally offending it. "I look at my website, and I ask myself, 'Does that really represent this population?'" she says. "'Does that capture my message?' I get nervous and think, 'Can I do this?' Rachel's so good at it."


Whether through intention or some sort of occupational hazard, a first meeting with Greenwald feels a lot like a first date. By the time she's ready to leave Cucina Colore, Greenwald has even split dessert, a bread pudding she charmingly recommends to clients she sends to this restaurant. After she takes the last bite, her spoon is clean and she politely places it on the very edge of her plate, which she then moves to the corner of the table for the waitress to collect. She does not reach for the check. She has probably never had food in her teeth in her entire life.

As she stands, smoothing down her skirt and gathering her bag, her last words are on the industry. "The hardest part is the emotional roller coaster," Greenwald says, brushing a strand of hair from her glasses. "When your client gets married, when they invite you to the wedding, when they send you a letter from their honeymoon, those things are too few and far between all those moments of sadness, loneliness, rejection, denial and fear."

The exceptions are clients like Elena Wechsler. Had the 38-year-old Harvard radiology instructor's parents not called Greenwald for help in 2005, that photo in the New York Times might not exist. With Greenwald's help, Wechsler prioritized dating, went shopping and created an online profile, which is how she eventually found Simpson. The couple recently welcomed their second child.

The best part of the job, then, is the freedom to create happiness — what Greenwald refers to as "the magic." It's still possible to create a marketing empire based solely on filling mankind's greatest emotional need. "We still think of matchmaking as the little old yenta on the corner, and there's less expectation that we'll be certified in some way," she says. "It interferes with that leap of faith and the belief that it's still magic. Because it is. It's magic."

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