Meeting Jason Calacanis

I met Jason Calacanis at the blogger breakfast this morning. Duncan Riley was there, although I didn’t meet him. Somebody said he (Duncan) was a big wig, so I was checking him out online after the meeting. I came across Duncan talking about Jason. Jason originally posted, 37 signals responded (my favourite post of the lot), and finally Jason somewhat retracted.

Personally, the key quote comes from Jason’s follow up post:

My work *is* my life.

That’s in line with my impression of Jason from this morning’s breakfast. He struck me as the typically edgy, always on the go, workaholic, American entrepreneur. He has that craving that so many entrepreneurs have. I think it’s what drives them to achieve greatness. By contrast, I think it’s also what keeps them from being happy.

I met Jason’s wife at the event. If I’d read all this stuff beforehand I’d have been interested to get her opinion.

Personally, Jason epitomises the type of entrepreneur I don’t want to be. I respect his success and his drive, but it’s definitely not how I want to live. I’m much more in line with 37 signals thinking. In any venture, I’d want people to work as little as possible, while still getting the job done. I value my free time more than the money that any business success might bring. I’ll give the workaholics a wide berth.

3 thoughts on “Meeting Jason Calacanis”

  1. Great meeting you… I don’t suggest the entrepreneurial life for everyone. however, I’ve never been so happy in my life, and I’ve never worked so hard. So, I’m not sure what to make of that. 🙂

  2. @Jason: Thanks for sharing.

    I think Matthieu Ricard gives an excellent definition of happiness in his TED talk. My take away was that happiness is a deep, inner state of contentment, serenity. That’s along the lines of how I define happiness.

    I believe one can find a form of happiness in being very busy. It’s almost like meditation. The mind is fully occupied, so it can feel content. But, I also believe, that in the little gaps of quiet, when one is not busy, one quickly loses that happiness. I think the happiness is linked to the activity. So long as one is busy, one can remain happy.

    My personal aim is to work towards the underlying state of happiness which pervades every other state.

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