How HowAboutWe Keeps Happily-Matched Users Coming Back For More

Online dating has ballooned to a $4 billion business. Now the industry faces new players (Spotify) and challenges (how do you keep happy couples engaged in a dating site once they’re, well, engaged?). HowAboutWe's Aaron Schildkrout shares his ideas for engineering better relationships.

Photo by Gus Powell

Aaron Schildkrout

CEO / HowAboutWe / Brooklyn, New York

Problem: From a profit-perspective, the online-dating business is like psychiatry: When you succeed, you lose. Why? A happy customer is a lost user.

Solution: HowAboutWe, a site that connects people based on user-suggested activities, is launching a service that sells curated dating experiences. The objective: Keep the love flowing between couples.

"Traditionally, online dating has only helped couples at the beginning of their relationship, by introducing them. That's a limited market. We want to figure out how to remain relevant for couples over the 5, 10, or 50 years of their lives together. Through a periodic digital catalog, we'll sell a variety of prepackaged, offline experiences for two. You'll get the restaurant, the show--even perhaps the babysitter and the transportation--all in one. This is not date advice. And it's not daily deals. We're not interested in providing access to the worst, most distressed inventory at the cheapest price. Our goal is to build long-term relationships with our business partners and couples by crafting innovative date experiences, with an editorial approach that highlights the date-worthiness of any experience we choose to include."

Courtesy of Rolling Orange Bikes (Bicycle)

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