John Keegan in Entrepreneur Magazine

How three entrepreneurs got their start in the growing niche business of love.

by Jason Fell

If you’ve ever seen the 2005 movieHitch, then you probably get the idea. Actor Will Smith plays Alex “Hitch” Hitchens, who coaches clients on the art of dating. In the movie, Hitch says: “No matter what, no matter when, no matter who — any man has a chance to sweep any woman off her feet. He just needs the right broom.”

The dating coach market is a mix of multimillion dollar dating businesses and one- or two-person operations that market themselves primarily through word-of-mouth and their websites, says Angel Donovan, a former analyst who co-founded DatingSkillsReview.com. Among the types of businesses in this market are professional wingmen, dating coaches, relationship advisors, as well as professional pickup artists. While dating coach businesses often focus on helping clients find healthy relationships, pickup artists traditionally have had a more aggressive philosophy aimed at getting clients to “hook up.”

Dating coach services can include one-on-one coaching, virtual coaching, seminars, books and other products, says Donovan. Prices can range from $100 an hour for coaching services to more than $10,000 for group learning “boot camps” and other long-term programs.

Donovan says he has collected information on more than 500 businesses worldwide that offer dating coach services — with almost 350 of those operating in the U.S. And the number of these businesses has surged since 2005, following Neil Strauss’ New York Times bestselling book The Game.

New York City dating specialist John Keegan got his start following a difficult break-up. Newly-single, Keegan made a plan to initiate a conversation with five different women every day for three weeks and ask each for their phone number. The experience led him to launch The Awakened Lifestyle, a dating- and social-consulting service, in 2007.

The Awakened Life founder John Keegan.

The Awakened Life founder John Keegan
Photo courtesy of Brandon Stanton.

“The biggest thing I do is help men really like themselves and have fun being themselves while doing what they were born to do — connect,” says Keegan.

Keegan prefers working with clients in everyday locations, including cafes, bookstores and art galleries, to help clients make connections while in their day-to-day routines. “We can meet interesting people anywhere — on a park bench or even the middle of a crosswalk, or a subway car or in line at the bank,” he says.

Keegan says the majority of his New York City-based customers opt for his six-week program, which includes two-hour meetings two times a week. His fee for the program is $8,000 per client.


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