Some of the Best Founders Are “Difficult” People

What To Look For When Reference Checking Polarizing Entrepreneurs

Hunter Walk

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There are certain words I don’t want to hear when doing backchannel references on a startup CEO. Sketchy would be one. Unmotivated another. Or those special little bombs of a phrase like “enjoys playing founder more than being one” and “tells a good story but no follow-through.” These come up — once is a warning, twice is a goodbye — and I’m not making the investment. But there’s another characteristic that on the surface could seem disqualifying but actually deserves analysis, and that’s “Difficult.” Are we talking abrasive, egotistical, read the Steve Jobs bio and thinks yelling was the key? Or the opinionated, driven, strong-willed, fast twitch muscle type? Because while the former might have big time Life Is Too Short energy, the latter perks my considerably sized ears. But you need to go deeper and unpack the ‘Difficult’ a bit.

Don’t Be This Type of Difficult [screaming baby in a business suit, digital art — DALL-E]

Difficult can mean polarizing, not necessarily an absolute negative. If you combine this with self-awareness, you get a powerful combination for an early stage CEO. The things they are particular about — the stuff that makes them Difficult — they actually need to be good at, not just forceful. Is it a gruff exterior but with just a desire for excellence and impact, versus the difficulty being…

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Hunter Walk

You’ll find me @homebrew , Seed Stage Venture Fund w @satyap . Previously made products at YouTube, Google & SecondLife. Married to @cbarlerin .