When I first got hired to work as a matchmaker for an elite dating service in New York, I assumed I'd have to transform myself into a version of Patti Stanger. Thinking about her blunt confidence, decisive nature, and occasionally brash tone made me nervous. After a year of dabbling in matchmaking as a hobby — I set up my college classmates and wrote about their blind dates for a column on my school's student-run blog — I was about to put my skills as a matchmaker to the test in a professional setting. I was terrified. On my first day of training, I was just 21 years old; my most formative romantic experience to date was getting dumped at a grocery store. Did I really have what it took to make it as a matchmaker?
During a series of training sessions, my fears were mostly put to rest. I learned that matchmaking is more of an art than a science, and that every matchmaker approaches it differently. I learned that my boss's academic background was in communications and her professional background was in the hospitality industry; she was intuitive, excellent at reading people, and had an ultra-soothing presence. Her style of matchmaking was based on understanding people's energy. Another matchmaker focused on offering coaching services to his clients, to make them feel as confident as possible on their dates. Another was naturally very social and liked to find fascinating matches for her clients while out with friends. The message was clear: as long as I followed a few basic principles of what makes a strong match, I could put my own spin on the job. I just had to figure out what worked for me.
I began the job with a small handful of clients, with the goal of taking on more as my skills progressed. Here's how it worked at my company: Clients paid $600 a month for two first dates with different matches. Matchmakers were always on-call to offer pre-date pep talks, outfit advice, and post-date analysis. Every time I was assigned a new client, I'd meet with them one-on-one to learn about their relationship history, what kind of relationship they're looking for now, what their lifestyle looks like, who they're attracted to, and so on. From there, it was up to me to find potential matches, screen them all to determine which one are a good fit, choose the winners, and arrange the dates. I found matches in our company's massive database of eligible singles, plus I used up to eight different dating apps and sites at a time, scoured my personal network, attended singles events, chatted up attractive people on the subway, and more.
I won't lie, matchmaking intimidated me. I'm an introvert, not a people person. I had zero experience tracking down the kind of successful, sophisticated, attractive, and charming people my clients expected me to deliver. I was afraid people would lose faith in my abilities once they realized how young I was.
But I had one asset on my side. Prior to matchmaking, I had studied journalism, worked as a reporter for my school's blog, and interned at a variety of magazines. I was a solid interviewer. And really, isn't the process of getting to know my clients and their potential matches deeply just a series of interviews? The skills I used as a reporter — researching my subject, acting approachable, asking smart questions, and listening well — translated directly into my work as a matchmaker. It's like what I learned in journalism school: You might not know everything there is to know about a topic when you begin reporting a story, but if you ask the right people the right questions, you'll get there.
It was exhilarating to feel myself learning new things every day, whether that was a list of which hotel bars in Manhattan took reservations and which didn't, or a profound lesson on love.
I loved matchmaking. It was my window into a new world. Sure, I might have been a 21-year-old who considered an eight-dollar bottle of wine to be a splurge, but my clients were glamorous, well-traveled 30- and 40-somethings with enviable careers. And I loved the adrenaline rush that came from toggling between dating apps, sprinting across the city to interview a match, and the sweet satisfaction of setting up a perfect first date. It was exhilarating to feel myself learning new things every day, whether that was a list of which hotel bars in Manhattan took reservations and which didn't, or a profound lesson on love.
I also learned the importance of finding a career that suits your personality. As much as I adored my job, I crawled into bed every night feeling drained. Keeping up an aggressive social façade while carrying on dozens of intimate, deeply difficult conversations a day was not my cup of tea. I found myself missing the relative calm of my old life, typing alone behind a computer. Even when I wasn't working, I didn't feel like myself. I didn't have the emotional energy to get through a date (for myself) after spending all day arranging dates for my clients.
Playing With Matches, By Hannah Orenstein
Ultimately, I scaled down my role at the company so I could return to college in the fall, and I left the position that winter so I could intern at a digital publication during my last semester of school. Once I graduated, I pursued work in media, as I had always planned — first, as a writer at Seventeen.com, next (drawing on my matchmaking experience), as the dating editor at Elite Daily. My first novel, Playing with Matches, came out earlier this year. It's about a young matchmaker who's in way over her head, drawing from my real-life experiences as exactly that. In the years since- I've set up a few couples on a purely recreational basis, but I have no interest in returning to my former career full-time.
I'm glad that I gave matchmaking a chance. It was a once-in-a-lifetime career opportunity and I'm so grateful that I tried something new. The experience truly changed my life. Even if I didn't stay in matchmaking for long, it taught me a valuable lesson: an amazing job isn't so amazing if it's not suited to your personality.
My best match yet? Picking a career — writing and editing — that makes me feel like the best version of myself.
When their frustration with current fabric care options had fashionistas Gwen Whiting and Lindsey Boyd worn out, the two entrepreneurs made it their mission to start a new niche and launch their very own at-home, eco-friendly laundry detergent line.
With a mission of turning an everyday domestic chore into a luxurious experience, these entrepreneurs not only conjured up an idea for an unconventional product line, but they successfully built their business while turning down the offer of every venture capitalist to knock on their door.
Gwen Whiting and Lindsey Boyd co-founded The Laundress in 2004 after dealing with their own personal frustrations with limited clothing care options. Whiting, having worked at Ralph Lauren in design and Boyd having worked at Chanel in corporate sales, soon accumulated a stylish wardrobe of designer pieces as perks of their jobs in the fashion industry. However, the duo quickly realized that the maintenance required for upkeeping these items were far from adequate. Laundry products on the market at the time did not cater to delicate textures and fabrics such as tweed blazers, cable-knit cashmere and silk blouses. Taking their clothing to the dry cleaners also proved hopeless as their clothing would often come back with stains or even be ruined despite the overload of chemicals used to clean them. With nowhere left to turn, Whiting and Boyd were determined to create their own laundry solutions designed for specific fabrics.
Not only did the entrepreneurs develop the business expertise needed to finally begin their own company, but they also shared the same educational background that equipped them to pursue their unconventional business venture. Whiting and Boyd met in college as students at Cornell University majoring in Fiber Science, Textile, and Apparel Management and Design. The pair was introduced by a mutual friend and instantly knew they would become business partners. "It was inevitable that we were going to have a business together. We are both extremely entrepreneurial by nature, and it was one of the connections that we instantly shared" said Whiting. After focusing on pursuing their own individual careers for a while, Whiting and Boyd quickly discovered a void in the fabric care marketplace when their clients would continuously inquire about the upkeep of their designer pieces.
The entrepreneurial duo was committed to researching and developing their own eco-friendly laundry products and soon launched their own at-home solutions for specific fabrics like silk, wool and denim, which ultimately eliminated the need for dry cleaning for those particular items. Despite their products filling a necessary void in the market, it quickly became challenging for the founders to persuade people to shift their focus away from traditional laundry care options in order to try their products. However, Whiting and Boyd believed in their mission for the Laundress and bootstrapped from the very beginning, refusing all venture capital funding with the goal of growing organically. In order to be successful, they had to get creative in fundraising. "In the very early days, we funded business development by hosting a 'for profit' party at a New York City restaurant and inviting friends, family, co-workers, etc. to support our new venture. That was pre-Kickstarter and an inventive way to make everyone feel a big part of our decision to be entrepreneurs," said Whiting.
While turning down VC funding as new entrepreneurs seems unimaginable, it is as equally unfathomable to consider how these women gained national traction without social media, all the while hustling to fund their business. For Whiting and Boyd, who started their business before social media existed, it was imperative that they promote their brand by leveraging the resources they had available to them. The CEO's were one of the first to sell consumer goods, let alone detergent, online with the goal of reaching a national audience. Despite having limited retail distribution, they leveraged the power of their website and became featured in publications on both a national and international scale. "Before social media platforms existed, we nurtured our own Laundress community with engaging content on our website, step-by-step tutorials on our blog, and one-on-one communication through our Ask The Laundress email," Whiting explained. With technology evolving and the birth of social media platforms, the founders expanded the conversation about their products from website, blog and email to platforms like Facebook and Instagram.
As female entrepreneurs, Whiting and Boyd faced additional hardships as misconceptions about their mission ultimately proved to disappoint more than it encouraged them. As women selling luxury detergent, there existed a preconceived notion that funding would be more easily attainable based upon their gender.
"Everyone thought it was easy to access capital as female entrepreneurs, but it was actually very challenging. We had this unique and disruptive idea within a very traditional space and it was hard to get people on board at first. It's been a continuous journey to educate people in fabric care and home cleaning," said Boyd.
Reflecting on their journey as entrepreneurs, the founders express no regrets about refusing to accept venture capital throughout the process. "Over the years, we could never quantify the cost benefit of VC funding so we continued to grow organically and remain independent by funding ourselves with credit cards and loans," explained Boyd. While their decision proved fruitful, the duo expressed their consideration towards other entrepreneurs who may not be able to fully fund their business as they grow. Because funding is a situational experience, entrepreneurs must ultimately do what is best for their business as no one path is optimal for every entrepreneur or every business.
With an increasing amount of women entering entrepreneurship with their own unique set of products or services, the CEO's offer up one piece of advice on how female entrepreneurs can be successful in their endeavors.
Whiting: "Our advice to anyone looking to build their brands: Have a strong business plan and vision. If you are not disciplined to write a business plan first then you are not disciplined to start a business. Get your ideas down so you ask yourself the right questions; it helps you get organized and plan next steps."
Boyd: "Create quality products without sacrificing the ingredients—no cutting corners. What you create should be the most important piece. Stay passionate, and trust your instincts and follow your gut—something woman are awesome at!"