How I Became a Successful Matchmaker

Renowned matchmaker Rachel Greenwald shares how she turned her passion into a career...

By Rachel Greenwald | genConnect

"How did you get such a fun job?" I'm frequently asked. Well, I'm 48 years old now, but not too long ago I graduated from Harvard Business School (okay, it was 19 years ago, but it feels like yesterday). I was on the business fast-track selling designer water to supermodels at Fashion Week in New York City.

Want to embark on a career in matchmaking? Click here to find out how...

But, when I got married and was expecting my first baby, I realized the corporate mommy-track was not for me. What's a smart, successful, driven MBA to do when (3) babies arrive? I had absolutely no clue, but I knew one thing: I could no longer go into an office and pretend that $5 bottles of water were the most important thing in my day. Like many women in my generation, I wanted to find something I could be passionate about, but do it from home around a flexible schedule. 

So I decided to create something I called an "Adrenaline Journal". I wrote down everything I did each day, from the mundane (brush teeth, grocery shopping) to the meaningful (read book to my baby, go to my favorite art museum with my mom), and I'd rank each action on a scale of 1 to 5 stars with how much adrenaline I felt surge in my body while doing it. One star meant "boring/blah" and 5 stars meant "I'm super-passionate about this, what an adrenaline rush!"

It was a fascinating experience to help me understand what revs my engine, and at the end of the week, surprisingly there were only 3 actions that rated 5 stars: drinking my English Breakfast tea in the morning, kissing my husband, and talking to a 41-year-old single friend of mine who was struggling to find Mr. Right. The first two actions didn't seem like potential candidates for a new career, but the third one was the charm. I loved the excitement I felt that week as I told my single friend how to meet men. I was on the phone with her pacing the floor as we spoke, gesturing my arms wildly as I told her "don't do that!" and "do more of this!" I realized my dating tips were the same strategies I had used every day in the business world, centering around branding, packaging, and niche marketing.

Fast forward to my friend's wedding a year later (my first success story), and my matchmaking business was born! As of September 2012, I am now responsible for 801 marriages, my dating advice books now include a New York Times bestseller and are translated into 19 languages.

So, I think I'm the first Harvard MBA to enter the "love business", but here's what I know for sure: I am IN LOVE with what I do, my schedule is 100% flexible and I can safely say that the dating business was a very unexpected career choice for a happily married woman of 20 years. 

How about you, maybe you'd make a good Cupid, too? Join me on Oct. 25-26, 2012 and find out (I'm teaching a Training Bootcamp in Denver for people who want to explore a career as a matchmaker and dating coach).

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Matchmaker, Matchmaker

As it turns out, I am living in a daytime soap opera. Specifically, one where Jane would invite Jenna and Candy to a party that didn’t exist yet, and then when Candy couldn’t make it but Jenna could, actually throw a party. I didn’t believe it at first, but the evidence was undeniable.

First clue: Upon arriving, my first thought was, “Who are all of these people?” I’ve met most of Jane’s other friends, and most of the guests were strangers. Ben’s first thought, or at least the first one he said out loud: “There sure are a lot of ladies here.” And there were. And they were all hot.

Second clue: A suspicious Jenna, having done a round of her usual event planner mingling, had described the party as having a “disproportionate amount of ladies who like ladies in attendance.” Still, even Jenna thought the idea that Jane would have gone to all this trouble just to play matchmaker was completely insane.

Third clue: Until we compared notes on our invitations. Jenna’s had been via phone call Tuesday night, and mine had been via bcc-list email on Wednesday morning. Jane had asked Jenna if she and Candy could come, and when Jenna had said Candy would be out of town, Jane said, “Bummer! But you’ll still come, right?”

Some people would have been offended by a friend’s attempts to fix them up while they were in a relationship, but not Jenna. Instead, she shrugged and said, “Oh well, I might as well circulate,” and then made her way over to a short blond with red lipstick and complicated sandals.

Ben was deep in conversation with David, Jane’s husband, so I was left alone. I looked for Jane, and found her mixing drinks in the kitchen.

“I hope that if Ben and I ever break up, you’ll plan a hot guy mixer for me,” I told her. “Where did you find all of these ladies?”

Jane looked crestfallen. “Does Jenna know?” I nodded. “A few are college friends,” she explained. “Plus a couple of women from my yoga class and crafting group. And their friends. Who is Jenna talking to?”

“Blond. Kind of looks like Gwen Stefani. Rachel?”

“Rachel!” Jane said. “From yoga. I knew Jenna would like her!”

Jenna was still deep in conversation with Rachel when Ben and I left, all body language signs pointing to hooking up later that night. Here’s the thing about Jenna. She never really gets “settled” in relationships the way other people do. And more often than not, she starts a new relationship before ending the old one. Despite the fact that she’s a loyal friend and all around wonderful person, she cheats on her girlfriends–and in the past, her boyfriends–a lot.

I’m actually going to meet her right now. I’m sure she’ll tell me all about it while we get our pubes ripped out with hot wax. Good times!

Posted at 2:02 PM

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