Before founding Tawkify, a company that brings the personalization of matchmaking to the masses, Kenneth Shaw was working as Principal Imagineer at One Kings Lane. Under pressure from well-meaning colleagues to find a girlfriend, he considered jumping into online dating. Looking into his options, though, he felt resistant. Seeing so many classmates, colleagues, and managers on these sites brought up questions of privacy. What’s more, the difference between who these people were and who they claimed to be in their profiles was surprising. For example, while everyone wrote that they loved long walks on the beach, Kenneth, who knows Bay Area beaches are freezing most of the time, was skeptical. Online dating also seemed to be a numbers game with very few winners and lots of burnout, a painful prospect on top of all the normal stressors of life. His guy friends would send out five hundred messages and get only ten responses, with one turning into a coffee or phone call, while his female acquaintances dealt with even worse. After filtering through thousands of bizarre messages and unsolicited photos, going on an actual date safely required multiple precautions. With disposable income but not a lot of time, he then considered more traditional matchmaking but was similarly unimpressed. Charging at least fifty-thousand dollars upfront, the matchmakers would give him a ballpark number of dates he could expect in a year but refused to be liable if they delivered less. What’s more, these “targeted dates” were just email introductions. “For this price, they should at least call me an Uber,” thought Kenneth.
Since his time studying Economics at Stanford, Kenneth had enjoyed solving his own pain points and scaling these solutions to multiply the impact on people. As a junior, he started a collaborative gift-giving company called Homeslyce so friends could pitch in on gifts more easily. After graduation, while working as a product planner for Microsoft, he built a Facebook app called My Purity Test, a spin on the Stanford Purity Test tradition, on the side. Told he couldn’t make it succeed without spending a lot of money, he was up for the challenge. The app gained ten users the first day, five-hundred thousand users within the first three weeks, and had reached six million users within three months. In 2007, Tim O’Reilly ranked My Purity Test one of the top thirty facebook apps of the year.
By the time Kenneth was evaluating options in the relationship industry, he and E. Jean Carroll had known each other for three years. E. Jean, the longest-running advice columnist in history, had reached out to him in the wake of My Purity Test’s meteoric success and had already imparted many of her insights about relationships. Realizing the gap that existed between dating websites and matchmaking services, they and co-founders Patrick Shih and Susan Huang set out to create a better option. For Kenneth, who found the uncertainty of relationships frustrating, it was important to create a company that used data to assist essential human insight while leveraging technology and operations to relieve the obstacles in relationships. While building the company, the team credits mentors at StartX for helping them recognize their strategy for what it was. Long before “uber for X” appeared in startup pitch after pitch, Tawkify was opening up a completely new market. If online dating was the taxi and matchmaking services were the equivalent of the town car, Tawkify offered the best of both at a more affordable price.
Six years later, Kenneth’s vision is a well-tuned reality. With a ‘Romance Rolodex’ of over one million, Tawkify is delivering results in an industry that is still the wild west. For some sites, success is a mutual swipe. For others, it’s a couple of messages back and forth. Kenneth is inspired by the idea of setting the standard of meaningful relationship outcomes and being able to measure success further and further downstream to remove relationship uncertainty.
The pandemic has highlighted how much clients look to their matchmakers to remove dating uncertainty when other aspects of their lives are in chaos. In addition, continuing to operate during the shift from in-person to virtual dates has provided a lot of qualitative and quantitative data that simply wouldn’t exist otherwise. For example, the team has noticed a clear change in what people are looking for; a huge shift from the external to the internal. While pre-COVID date feedback used to focus on how their date interacted with others, for example, how they treated the waiter, it has now turned toward more self-exploration and building a real connection. To support this, the importance of height, formerly ranked very highly, has also gone down, likely due to people talking on video. While the shift may be positive for some clients, others have found it challenging. A lot of feedback around conversations being awkward from those for whom this was previously not an issue indicates that people who dated well before COVID may have more difficulty dating virtually. It seems that some male clients are fine meeting people in person where there are distractions and activities, but can feel put on the spot when having a forty-five minute to an hour conversation. Dating behaviors have also changed, with new trends reminiscent of a different time. People who meet virtually will text or call right away back and forth and then the next steps are typically two dates in the park, before going to each other's places.
When it comes to the future of dating, Kenneth compares it to the future of work. Post-pandemic, a lot of people will want to go back to meeting in person, but others may feel the most at ease with virtual first dates. Before, Tawkify matchmakers would use data to make the call between date venues; choosing a wine bar for some and a comic book store for others. Similarly, if video is the best environment for a client to build a connection forward, then it should be utilized. After all, isn’t that the best definition of an optimized solution?
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