History in the dating industry...

It all started out somewhat serendipitously- as you would hope any story about dating would. The story begins where another one ends. I had a shattered picture of what my life would be like and no idea what to do. I was going to law school. I was going to be an attorney and I would wear tailored pantsuits and be able to reference case law from memory. I had it all planned out and was on my way.  But it was 2010, and the economy had crumbled. Lawyers were out of work and all of a sudden my shiny path seemed more like a trap. Fears of student loan debt, unemployment, and hours spent drawing up contracts in a windowless office like a millennial Bob Cratchit were looming.

Around that time, a college classmate was working in Beverly Hills for a matchmaking agency. I heard from her there was an opportunity in Boston. Matchmaking seemed glamorous (the opposite of law) and so I applied. I was emphatic during interviews, that my experience dealing with constituents and lobbyists in government would make me well suited to deal with their clients. To my surprise and relief- they hired me.

A week later I was in their Beverly hills office, meeting the people that make up a matchmaking company: the sales people, the matchmakers and the client services. Here is how it worked: salespeople are trained to make highly emotional sales. This means using psychological techniques to get people to open their hearts and tell tales of heartbreak and loss, love and desire. They are then asked to explain in great detail the ideal person they would want to date. By the end of the meeting they are filled with hope that this ideal person exists, and are both vulnerable and relieved because another human finally agreed with them on something they had secretly known all along: every failed romance in their lives up until that point, was not their fault. The only fault they had- was they were not skilled at choosing partners. Luckily for them, they were a mere $10k membership away from those problems being a thing of the past.

After the monetary transaction, these clients were transferred to the matchmakers. Matchmakers serviced these clients by sending them emails once every two weeks with a potential match. They also were responsible for sourcing people outside of the client database to match with paying clients. This was problematic not because when a person spends $10k and has described in excruciating detail the type of person they are looking for- they come to expect unicorns. It was problematic because matchmakers cannot source, much less create unicorns.

After the matchmakers failed in the client's eyes (99% of the time) the client services would come in. These are the people who essentially put out fires, prevented lawsuits, litigated in lawsuits, and spent 80% of the workday on the phone with someone crying, threatening to sue them, or both. They would also get pressure from accounting because chargebacks and refunds would effect the books. This pressure was then transferred to sales who were instructed to use higher pressure sales techniques. Sales then pressured matchmakers to use more creative sourcing techniques.
As you may imagine: working every day trying to match people and source people was emotionally draining. I decided at age 24 I was going to be a salesperson. I was the youngest person by far at that company and my request was initially not taken seriously. I was persistent, and eventually I was trained by one of the most brilliant minds in sales I had ever met. I became quite good at sales. I learned to listen to people’s word choices, their stories, their body language, their patterns. I started to understand what self destruction meant, what divorces do to people, how grief and pain and loss shape the way we see ourselves and each other. I became fascinated by these people. I was in a unique position to ask any and every question to them no matter how personal and to dig deep into the motivations and desires behind behaviors. I started learning who was successful in dating and why. Who was unsuccessful and why. I was a quick study at human behavior, and I cannot overstate how much that experience gave me in terms of my emotional intelligence.

It may come as a surprise to you reading this, but the business model wasn’t a recipe for success and the legal liability was making it a sinking ship. I decided to use my skills for good. I started a company called Dateover which was intended to be a makeover for people’s dating lives. I worked with clients on dating coaching, image consulting and helped them re-work their online dating profiles. I was as subcontractor for national dating companies doing events and I consulted with other companies trying to break into the space. It gave me an understanding of the dating industry as a whole and all the myriad of ways people find love. I came to understand a few things: 1-  that relationships and connections (not just romantic ones) are the most important things in a human being’s existence. 2-That lack of connection leads to isolation and suffering, and 3- people will throw endless money, time and resources into any hope of ending this suffering. Dating is a big business, and I was not the only person fascinated by it. During this time I got featured in local press, went on part of a speaking tour on dating, and got asked by many people to help them with dating issues they were having...often in inappropriate social settings.

Around this time I connected with a friend in the media lab at MIT. He introduced me to some other people there, and I was struck and mesmerized by how cool the projects they were working on. These people were changing the world! I was only working on one person at a time. We began brainstorming and designing a product that would verify attributes about users to streamline a process that would create a mid market between cost prohibitive matchmaking and unchecked free online dating. The project never got off the ground, but the startup bug had bitten me- hard. I knew I had a unique perspective into the world of dating and I could use that to my advantage. I just had no idea what or how that would work. While I was trying to figure this out I got my realtor’s license and bought the domain “LoveAndRealEstate.com”. This idea caught the attention of producers in LA who wanted to do a reality TV show about the intersection between dating preferences and real estate preferences. We filmed a teaser but the show did not get picked up.

One summer day, I was sitting outside in the garden of my Back Bay apartment and the idea for Paper Airplane hit me. About a month prior to this I was working with a dating coaching client on the concept of “putting out the vibe”. What I was trying to convey was that a person’s energy introduces them and by making yourself appear open and confident- you will attract people. My client asked me how far away from someone he had to be in order for him to “put the vibe out” and I had answered “paper airplane distance”. I probably chuckled in my head because it was a funny analogy and continued the session.

For some reason on that summer day - I realized that my client wasn’t the only person who needed help putting the vibe out. And he wasn’t the only person who had no idea where to go to meet women. Everyone had these problems. A paper airplane is how grade school kids solve this problem- why couldn’t adults with our smartphones do that too? I mocked up the designs and Paper Airplane was born.