What, Exactly, do Entrepreneurs Look for in a Date?

There are a lot of people out there who would consider Valentine’s Day a Hallmark Holiday, and I’m one of them. But there’s no getting away from the fact that February is a month dominated by love and romance.

It can be difficult to get out into the dating scene tough, especially if you’re an entrepreneur; the very nature of entrepreneurship means that setting aside time for dating is often difficult. However, there’s an online matchmaking service out there, Tawkify, which wants to address this pain point for entrepreneurs and anybody else looking for the perfect date.

It’s crucial to realize that it’s not an online dating service, this is matchmaking. For $500 a month, Kenneth Shaw, CEO, and his team at Tawkify will send you on dates: all you have to do is show up and have a good time; no browsing, connecting, or managing needed.

The process is very simple too. Answer 10 questions about yourself and you’ll get assigned to a personal matchmaker who you can meet face to face or via video chat.

Your matchmaker will head out into the world and find matches for you. They’ll scour events, landscapes, and cities to find you the right date, and the company matchmakers have learned some serious wisdom and insight when it comes to looking for the perfect date.

“It’s important you don’t forget that your partner can be just as important as your company, so you should take your relationship as seriously as you take your job,” says Tawkify Matchmaker Cynthia Rouf.

Matchmaking is a practice that’s been around for ages, but most agencies charge upwards of $10,000, sometimes even $20,000. Now, if I’m paying $20k and all you’re going to do is connect me with somebody via email, it’s not worth it.

Tawkify, on the other hand, seeks to be entirely different from the paradigm of matchmaking that’s been set up. At the very minimum, each month you’re guaranteed two to three first dates. According to Shaw, it’s not a question of if you’ll get a date but whether or not you’ll go on a second date.

“People treat online dating like work. It feels like you’re shopping for a car,” says Shaw.

To put it in entrepreneurial terms, using Tawkify is like outsourcing your coding and development work. And since the matchmakers have screened your date before you meet them, your first date is almost like your second date because you know the person will fit.

Operating out of San Francisco and New York, Tawkify has been collecting dating data for some time now, and they’ll refine their methods as they continue to expand. As it turns out the Bay Area clients tend to be 30 percent entrepreneur, and 50 percent of the overall Bay Area clientele work with startup companies.

But what, exactly, do entrepreneurs look for in a date? Rouf and one of her contemporaries in San Francisco, Evyenia Trembois, see a generational patter to entrepreneurial dating.

Older entrepreneurs are looking for the trophy wife while younger entrepreneurs are interested in smart, intelligent, and passionate partners. What unifies these entrepreneurs, however, is that their expectations are usually unrealistic.

“They often come in with check lists, and it feels like they’re interviewing for a business partner instead of someone who is romantically compatible with them,” says Trembois. “Carrying the mentality of your work life into your relationship life isn’t conducive to forming a genuine connection.”

Rouf and Trembois also noticed that the entrepreneurial mentality to chase ‘the next big thing’ leads people to miss out on the ‘here and now’ romance and love.In fact, a lot of Trembois’ clients think that they can put off their relationships until they’ve achieved something big. According to her though, life doesn’t work that way; it’s about the people we have in our lives, and maintaining a work-life balance is crucial.

“Don’t look at everything as a prize or trophy. There’s something beautiful in finding someone who you just really connect with,” says Trembois.

Maybe you’ve been dating the wrong people, or maybe you just stink at approaching people in public settings. Any way you spin it, perhaps it’s time to change up the paradigm of dating in your life if you’re single and looking to mingle. Let this Valentine’s Day be the one when you reassess, rebuild, and iterate a new you for the dating scene.



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Written by:
Will is a Senior Writer with Tech.Co, based out of America's Finest City: San Diego. He covers all territory West of the Mississippi river, digging deep for awesome local entrepreneurs, companies, and ideas. He's the resident Android junkie and will be happy to tell you why you should switch to the OS. When he's off the clock, Will focuses his literary talent on the art of creative writing...or you might find him surfing in Ocean Beach. Follow Will on Twitter @WJS1988
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