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Glenn Kelman

Are entrepreneurs better off being a little crazy — guided by their emotions?

Or should they stick to good-old fashioned number-crunching, letting rationality rule the roost?

That’s the topic that Redfin CEO Glenn Kelman raises today in a fascinating blog post titled “Never tell me the odds.”

The entire post is worth reading for any startup founder, but I was especially struck by this segment in which Kelman discusses the importance of following your gut and the importance of making decisions based on emotional factors.

“What’s really hard about this job is knowing when to be crazy and when to be calculating, because you can’t just be one or the other. It’s certainly easier to be calculating. It takes confidence to ignore numbers, to set aside focus groups and advisers, and do what you believe in, because then the only person you’ll have to blame for your craziness is yourself. But if I met my old self, the one just starting out in a consumer Internet business, the first advice I’d give him would be: have the courage of your convictions.”

This gets to the heart of a fascinating debate.

Entrepreneurs, at least some of the more successful ones I’ve met, over the years are outcasts. They don’t always fit in, and they definitely see the world in a different way. I am reminded of an interview I did with venture capitalist and aQuantive co-founder Nick Hanauer a few years ago in which he told me that “the conventional view is always wrong,” and then went on to list how some of his most successful investments were deals where other people thought he was just crazy.

That’s certainly what it takes, in some instances. But there are counter examples too where hard-charging execution and persistence lead to success.

It seems like the best is a combination, a person who shows that emotion and is willing to float some crazy notions, while also being rooted in the numbers. Seattle venture capitalist Bill Bryant addressed that very topic at a talk last month, saying the entrepreneurs he likes the best “are visionary for sure, but grounded at the same time.” 

What do you think?

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