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.
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 ultimately self-defeating to themselves and their companies?
Do they have a cofounder who can balance them out? Pair a Difficult CEO with a COO/CTO/CPO who knows how to manage alongside and whole just might be greater than the sum of its parts. Make sure to talk with this person as well. They can give their own unique insights into why they fit together, or share their own mounting exasperation.
For an investor, partnering with Difficult Founders also comes down to how you both think about relationship building. Are they Difficult but know what they’d be signing up for with you? Do you feel like it would take effort, but you could build a relationship? Do you trust them?
So net net, Difficult is definitely not disqualifying for us, but they do cause a second set of questions to understand whether the person can be a great leader/CEO and whether we’re going to be the best investor for them.