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Photo via RootStartup
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Bring together a bunch of highly-successful entrepreneurs in one room and you’ll notice a few common qualities. These people work their tails off, have an immense passion for what they do and exhibit excellent leadership skills.

But beyond that, is there a certain toolset every entrepreneur must have to succeed in this ultra-competitive startup world? Two Seattle entrepreneurs just penned a pair of insightful blog posts that touch on this.

Chris DeVore, a general partner at Founders Co-op, first wrote a piece yesterday titled “Ambition,” which discussed the different qualities between an angel and venture capital business. It’s something DeVore has found himself explaining more often to people he meets.

Chris DeVore keynoted the 2012 GeekWire Awards.

“The difference between an ‘angel’ business and a ‘venture’ business has nothing to do with the size of the first check (or even the kind of people who write those checks), and everything to do with the ambition of the founders seeking capital,” DeVore writes.

DeVore continues his post and then describes the specific kind of entreprenuer he wants to join foces with: “the relentless, hungry, flawed, brilliant, monomaniacal freaks who actually believe they can do it better, smarter and bigger than anyone else in the game.”

That one sentence caused Moz CEO Rand Fishkin to respond with his own post. Fishkin does not think DeVore’s statement is wrong, but he’s had a difference experience as a successful entrepreneur.

Rand Fishkin. (Erynn Rose photo)
Rand Fishkin. (Erynn Rose photo)

“It’s just that none of those adjectives describe me at all,” he writes. “Except one. Flawed. That one fits. The rest… just don’t.”

Fishkin details why “relentless,” “hungry,” “brilliant,” and “monomaniacal” are adjectives that just don’t resonate with him. Then he really opens up toward the end of the piece, writing about a belief within himself not that he can be better than anyone — rather the belief that he “sucks.”

It’s a thought that is in his head “pretty much every day”:

When I look at myself in the mirror, and when I think about who I am and what I’ve done professionally, all I can think is “look at that underachiever.” It’s my deepest belief about myself. I know I can do better than I have done. I know those nights when I went to bed at 1am I could have stayed up until 2 and gotten that really good post finished. I know that the presentation I built for that conference should have been better. I know that email I wrote to the team could have been better. I know that the tool we launched to help marketers with XYZ should have had better usability, more features, a cleaner interface, better export functions, and we should have shipped it earlier too. I know we could have converted more customers, could have helped more people get more value from our software, could have made better investments in infrastructure earlier, could have, could have, could have, should have, should have, why didn’t we?!! what’s wrong with me?!! you’re better than this, rand. you owe. you don’t get to cash out because you still have debits in the account. get back to work.

I don’t think that my psychological condition of self doubt and my self-knowledge of underachievement can be defined as “ambition.” It fits better under “obligation.” I feel an overwhelming obligation to someday, somehow live up to my own standards.

Fishkin ends the piece thanking investors who backed an entrepreneur that is “scared, angry, possessed of mediocre intellect, polymaniacal – an accidental founder whose only driving belief is that he’s capable of doing better and needs to live up to that capacity.”

DeVore responded to Fishkin’s piece with this comment:

Great post, Rand — thanks for reading mine and writing this. On your last point, I think competitiveness and insecurity are twins: the hunger to win is a symptom of the need to prove yourself worthy (because you secretly suspect you aren’t as good as others). You may not see yourself in my description, but the psychological core of the two types may not be so far apart.

Give the two pieces a read — what are you driven by? Ambition? Obligation? Both?

Editor’s note: Moz is a GeekWire annual sponsor.

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