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Tim, you’ve just released your book “The 4-Hour Workweek“. In a nutshell, what’s it all about?

It’s about how to outsource and automate your life. How to use lifehacks, technology, and more to create a luxury lifestyle of time abundance and complete mobility.

I hear you outsourced your online dating. Such a crazy concept, even for my readers. Could you explain the general idea?

A friend challenged me, over some wine, to the limits of outsourcing your life. He said I couldn’t outsource my dating, as one example, and I bet him that I could. Online dating is largely a numbers game, so I hired virtual teams of people all over the world — India, Phillippines, Jamaica, Canada, and others — to compete against each other and set dates for me on an online calendar. Each of them were assigned one of my accounts on either online dating sites like Match.com, or on social networking sites like Friendster, and there would be a $150 bonus to whichever team set the most good dates.

Did you just “cold turkey” the outsourcing, or did you work out a system first?

I worked out a one-page “rules and regulations” sheet with all of the goals and guidelines, being sure to include links to girls I found attractive, must-haves and must-not-haves, etc. I moved all of my online to the teams at once. The experiment was 4 weeks long, and I got more than 20 dates. It was unreal.

What is the best word of advice for guys looking to meet women online?

Rotate your profile photo, use direct subject lines for email, and focus on volume. I used clever, time-consuming subject lines that got nowhere, then one Filipino pulled in ridiculously good results with “looking for a date” as the subject.

How did outsourcing work for getting the types of women that you’re attracted to?

It worked extremely well. Perhaps a 70% hit rate, which is just as good, if not better, than what I was averaging on my own.

What sites did you use and which ones had the best results for you?

Match.com has the most profiles but also the most competition. It’s good for short emails with direct subject lines. The social networking sites consumed more time but got more dates.

Did any problems arise while outsourcing your dating?

Only once. One of the outsourcers neglected to put a date in the calendar, and I happened to be in the spot where the girl and I were supposed to meet at the right time. She walked right up to me — I was writing on my laptop — and started chatting like an old friend. I had absolutely no idea what was going on. I felt really badly about it, but the entire 4-week process was — after all — a social experiment. If I hadn’t had any problems, I would have felt like I hadn’t tried hard enough.

Thanks Tim!

My pleasure. I should add that every girl I had a second date with was told about the outsourcing. This was part of my litmus test. I needed a girl with the same odd sense-of-humor that I have, and if she couldn’t find the outsourcing at least a bit funny, we wouldn’t last anyway. The result? Most of the girls called me a jerk with a smile but found it pretty damn funny. Those are the keepers who will keep me sane when I take myself and the world too seriously.

The Four Hour Workweek

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