Why Successful Entrepreneurs Are Often Jerks (but You Don’t Have to Be)

10 min read

Let’s just get this out there:

There are a lot of highly successful people out there that many of us would probably classify as arrogant, unkind or, simply, as jerks.

Ever stop to wonder why? Because the pairing of success and arrogance isn’t a coincidence.

As it turns out, the traits of jerks can actually make for highly effective leaders and equally successful businesses.

Jerks become successful because they run their business the way they want to, with no regard for those beneath them. They know what they want, they know how to get it, and they aren’t going to let anyone stand in their way; especially their team.

Though unpleasant for those around them, this relentless drive and unyielding commitment to efficiency can lead to pretty impressive results. Or, as Alyson Shontell put it in the article linked above, “Inside Silicon Valley, arrogance runs rampant and investors seem to reward ruthless behavior with piles of cash.”

I wanted to know if it were possible to achieve similar results without the arrogance and ego of a jerk, so I sat down with Daniel Dargham, a man I respect not only for his ruthless efficiency but also for the way he cares for (and is loved by) his team.

The Counter-Intuitive Secret to Getting Ahead (Without Burning Bridges)

Daniel is president and CEO at Lohika, a high-end software development firm that, in their own words, “works extensively with VC-backed companies on projects ranging from high performance cloud solutions to highly scalable social platforms.” Some of their more prominent customers include Skype, Twilio, and Buzzfeed.

Prior to his success at Lohika, Daniel held full P&L responsibility at KLA-Tencor, where he achieved 250% revenue growth in just three years.

Through interviewing Daniel, it became clear to me that he’d found a way to reach the same levels of productivity and efficiency as his less-liked counterparts by establishing a series of strict, surprising, and even counter-intuitive rules. For example:

Showing up late? Don’t bother showing up at all.

If a meeting is scheduled for 1:00 PM, the doors are locked at 1:01 PM. Show up late and you aren’t getting in.

The same goes for virtual meetings. If someone signs into a Zoom meeting late, they’re booted out; no questions asked.

Once the meeting has ended, it’s on them to figure out what they missed.

Talk business, not emotions.

When things go wrong, it’s tempting to start pointing fingers. But come to Daniel with accusations about someone else and he won’t hear a word.

When problems arise, Daniel doesn’t want to hear about the person, he wants to hear about the problem. More importantly, he wants to hear about the solution.

Instead of, “Aaron screwed up and now I have to clean up the mess,” Daniel expects, “This is what happened. This is what should have happened. This was the responsibility of this role. This is how we fix it. This is how we prevent it in the future.”

Anything more and you can expect Daniel to tell you to take a “military night” and come back once you’ve calmed down.

No presentation? No meeting.

Daniel believes meetings are a place for discussions and planning, not status updates or new information.

If a meeting you schedule has accompanying data or presentations, it must be supplied to all attendees at least 24 hours in advance. If it isn’t, the meeting is canceled and it’s on you to reschedule.

Those three rules (along with several others) are enforced without leniency or exception.

Seem strict? It is. But that strictness seems to be what makes the Lohika team so effective, efficient, and successful.

You might think this effectiveness comes at the cost of company culture or employee fulfillment, but the Glassdoor ratings speak for themselves:

Simply put, people love working for Daniel. Even more interesting is the fact that they seem to love working for him because of his rules, not despite them.

Why Effective Leaders Have Rules

What sets Daniel apart from jerks, is that his rules aren’t created out of arrogance or ego; they’re created because he knows the success of his business is directly related to the effectiveness and efficiency of his team.

As far as Daniel’s concerned, you can’t separate success from efficiency, nor can you separate efficiency from rules. Think about it:

That late arrival rule?

Showing up late to meetings is inefficient at best and outright rude at worst. In the best case, your team starts without you and must waste time filling you in once you arrive. Worst case, they wait to start altogether.

Either way, you’re dramatically hampering the effectiveness of that meeting, which directly contributes to why people think they’re are a waste of time in the first place.

The emotion-free conflict rule?

Conflicts arise when one person’s ego-driven impulses trigger another’s, creating a cycle of emotional escalation. And as tensions rise, productivity falls.

By removing emotions from conflict resolution, you ease tempers to focus on what really matters: The “resolution” half of “conflict resolution.”

And the presentations rule?

Per Daniel, meetings should never contain new information. By sending out the data and presentations in advance, you give your attendees a chance to review the content and come up with questions and concerns beforehand.

When everyone shows up with pre-thought out questions, you’re going to have a much more insightful, valuable, and results-focused meeting.

The Importance of Rules

Without context, Daniel’s rules might seem unfair, arrogant, or even over-controlling. But what sets them apart is how they’re communicated and established.

The truth is, every CEO or manager has rules. But when you work for a jerk, you usually don’t know the rules until you break them.

Even then, there’s no guarantee the rules won’t change in the future; so you’re left constantly walking on eggshells. And, as research has shown, the constant state of stress this creates is unhealthy not only for an individual, but for the team and company as a whole.

In Daniel’s team, the rules are discussed, agreed upon, and established in advance; they’re the price of admittance to being a part of the team. At the end of the day, each member not only knows what the rules are, they also understand why they’re important.

But Daniel doesn’t just tell the team why the rules are important; he shows them. Each rule must consistently produce measurable positive results. If it doesn’t, it’s cut.

As a result, these high-performance rules end up defining the culture of the team. They create a sense of structured, routine stability for his employees; something solid and unchanging to rely on in the volatile, unpredictable world of startups.

Establishing new rules

So here’s the question: How can you emulate Daniel’s results? How can you become a results-generating, rule-driven CEO without becoming the boss everyone badmouths over lunch?

By turning the rule-setting process into a transparent team effort.

Like Daniel, you need to make sure your employees not only know the rules; they must also understand, respect, and, most importantly, believe in them.

The best way to do this is with a team-wide meeting. Here’s a 5-step process to run your first rule-introduction session.

Step one: Introduce the rule

For example: All meetings will start on time. Anyone late to the meeting will not be admitted.

Step two: Explain why the rule is important

For example: Without this rule, we either waste our time waiting for someone to show up or waste our time catching them up. This isn’t fair to those who were on time and isn’t an effective use of time.

This rule will create a culture where everyone is punctual, meetings start on time, and everyone stays on the same page. As a result, we’ll have a more cohesive and communicative team.

Step three: Explain the consequences of breaking the rule

For example: If you show up late to an in-person meeting, the door will be locked. If you sign in late to a virtual meeting, you will be disconnected. It will be your responsibility to find out what you missed once the meeting has finished.

Step four: Explain how to handle a broken rule

For example: If you’re going to be late, let the team know in advance. This way we know what to expect and, if necessary, can reschedule the meeting for another time.

Step five: Allow time for questions and feedback

It’s important that each team member understands and embraces the rule, or is at least willing to give it a try long enough to measure the results. Take the time to answer any questions and alleviate any concerns they may have.

And most importantly, be open to their feedback; they may have thought of something you didn’t, requiring revision or even elimination of the rule.

Enforcing new rules

Setting rules is easy. Enforcing them? That’s a different story. But, as Daniel points out, there’s no point in having rules if you are aren’t going to follow them.

As a leader, one of your most important jobs is staying committed to the rules you set. Because every time you make an exception to a rule, you weaken it; you say it doesn’t matter. And if you, as a leader, say the rules don’t matter, your team will follow suit.

Enforcing rules starts with believing in them, and that belief is vital to their long-term success. But don’t worry if you’re not 100% convinced yet.

As the cognitive dissonance theory outlines, it’s possible to alter your beliefs through your actions. Enforce the rules long enough to generate positive results and you’ll make believers out of both yourself and your team.

Why good leaders struggle to enforce rules

Many managers and CEOs fall short here because they’re afraid of upsetting their team.

What they fail to realize is that practically everyone wants to be more successful, effective, and efficient; and if they provide an avenue for their team to do so, they’ll gain their respect and appreciation as a result.

Besides, rules don’t have to last forever. If one stops producing positive results, analyze why. If it’s become obsolete, drop it.

Quick note: Immediately following the introduction of new rules, your team is probably going to mess up. That’s expected, but it isn’t reason for leniency.

Just make sure you clearly communicate step four in the rule-setting process: Explaining what should be done if a rule is broken. And, of course, follow through on any consequences.

In most cases, it won’t take more than a week or two of enforcing a new rule before it becomes habit for your team.

Your Rules Create Your Reality

Moral of the story? You can have rules without being an arrogant jerk.

As Daniel has shown, you can replicate their results without replicating their reputation. More importantly, you can replicate their results while earning the respect and loyalty of your team.

Besides, most those people you think are jerks probably aren’t, anyway.

In the end, it’s as simple as this: Good leaders have good rules, and good rules produce good results [Tweet this!].

Your turn: What are the most effective rules you’ve seen? What about the most ineffective? Get in on the discussion in the comments below.

Happy rule-setting!

Want more on becoming a better leader? Check out Silicon Valley Success: 3 Traits of the Most Effective Founders, CEOs, and Entrepreneurs.

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