Former high-school teachers Brian Schechter and Aaron Schildkrout successfully changed the digital dating game by founding the site HowAboutWe -- attracting 1.5 million users and ostensibly paving the way for a new wave of dating start-ups like Coffee Meets Bagel and Sparkology. Since then, co-CEOs Schechter and Schildkrout have attempted to grow their first business by expanding the brand with HowAboutWe for Couples and most recently The Date Report -- securing another $4.2 million of new venture capital in the process.

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