The greatest entrepreneurs follow their gut and as a result are perceived as difficult at best and abrasive at worst.

Most people who know me say I’m too diplomatic, but last week my advisor told me that someone asked him if I was “difficult”.  His answer was “if Ash was difficult, I wouldn’t work with him.” I was going to write something on the matter, but felt that doing so would make me come across as, you know, difficult.

But after a recent brief discussion this week with a fellow executive ended in disagreement, I thought to myself: “well that guy’s definitely going to think I’m difficult”, even though only a fool would have accepted his offer.

It reminded me of that Chris Rock line“What’s sexual harassment? When an ugly guy wants to get some?” Well, what’s being difficult? When someone doesn’t give you what you want?

A Different Kind of 1%

Even if 99% of people think you’re reasonable, there will always be the 1% that thinks you’re difficult.  Personally, in my situation, it boils down to being a self-funded, bootstrapped founder who’s the company “CXO”, wearing many hats and not having the luxury of having a fellow C-level executive come in afterwards to play the bad cop. Ultimately, I have to deliver on my word, so occasionally this means I won’t say or do what someone may wish.  This avoids larger problems down the road.

Equity Means Ownership to Others; Control to Entrepreneurs

There’s a fine line between being assertive and an ass.  We’ve already touched on how you can get others to do what you want.  This article isn’t about management of employees, it’s about negotiations with outsiders and others thinking you’re difficult when

i)                    you don’t offer them what they want and/or
ii)                   you don’t accept what they offer.

That might make you come across as difficult to them, but that really says more about them than you.

My philosophy on negotiations echoes Time Warner’s Dick Parsons: “When you negotiate, leave a little something on the table”, otherwise no one would want to deal with you in the future  In fact, I try to avoid saying “I’m being reasonable”, because everyone thinks they’re reasonable: it’s more important how others perceive you in your wheeling and dealings.

There’s way too much envy and jealousy in the world and our industry, so part of what makes critics think that entrepreneurs are difficult stems from that, though no one will admit it. No one is “driven by money” until they realize that someone is about to make money or has made money, at which point everyone inherits a sense of entitlement.

Control vs. Stability: Missionary vs. Mercenary Mindsets

While founders seek missionaries (in a secular sense) to join their cause, they tend to draw mercenaries. Despite the high failure rate of startups, the perception of overnight success and quick riches is high to those driven by money.

As such, to the founder, equity means control and the ability to prioritize the stakeholders’ needs and wants according to his moral compass.  To the recruits, ownership rarely means control (since they have minority stakes) but rather, possible wealth.

The following nuance is key in both understanding and reacting to claims you’re being difficult: managers and employees usually get equity as a bonus and incentive for joining a fledging startup; whereas investors are getting equity in exchange for an investment.

Not All Stakeholders Are Created Equally

However, oftentimes you’re accused of being difficult by would-be investors and future employees. Their feedback may be really valuable and to some extent correct, but it’s impossible to please everyone, especially if the majority don’t view you as difficult to begin with.

While it’s important for your clients and employees not to think you’re difficult; it’s actually not the end of the world for your investors, board, competitors and even your suppliers to think that you’re at least a little bit difficult.  If dealing with you is akin to taking candy from a baby, you’re doing something wrong and will end up like the founder who had 0.5 percent of his company after five years.

In fact, to please some stakeholders, you need to resist others; that might make you seem difficult to narrow-minded stakeholders that don’t like your position on a matter, but it absolutely makes you a better leader over time.

To some, Mark Zuckerberg wasn’t being reasonable when he turned down offers from Yahoo, Google or Viacom early on, but in hindsight, everyone that doubted him then supports him now.

So it’s not the end of the world if would-be advisors and investors think you’re tough, because there’s actually a very weak chance they’re really interested anyway (especially since sometimes would-be investors want you to upset your existing investors).  You’re building the company so the best investors and advisors are the ones who understand and support you.

I’m not saying to go to ignore feedback or become abrasive, but to quote football coach Steve Spurrier: “If people like you too much, it’s probably because they’re beating you.”

The Irony of Honesty

Many entrepreneurs eventually drown self-doubt out through naïveté, idealism and determination, which spills over into how we communicate our vision and rationalize criticism.  Ultimately, people appreciate candor until you’re forthright with them, at which point you’re impolite.

As impossible as it seems, if you can leave your emotion aside when people give you feedback and choose your spots when it comes to dishing out the criticism, then you’ll become a very effective leader.

The Hypocrisy of Time

Entrepreneurs are always told that “time is the most precious asset”. Perhaps. But when we cut to the chase and pass on an idea or offer, we’re sometimes told we’re difficult, even though the greatest skill an entrepreneur has is listening to his gut.

The Double Standard of Being Difficult

As an entrepreneur, it seems that everyone goes out of their way to be difficult with you.  Now it’s the entrepreneur’s turn to get over it, no one forced you to lead this life.

In the end, a little bit of understanding of the other person’s situation and background would help everyone be, well, less difficult.

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