David here.

Last week, we spoke about the importance of emotional intelligence and humbleness in a founder. A founder with the ability to adapt and be flexible will often find great success – and respect – as leader.

But today, I want to point out that sometimes, the most successful entrepreneurs are those that don’t adhere to conventions at all.

In fact, they do quite the opposite.

Some of the world’s most brilliant minds and most successful entrepreneurs all had or have a similar operating style: no mercy on their employees, a giant vision, great charisma, and overall unique personalities:

  • Steve Jobs (Apple) was known to be a “brilliant jerk” who was nasty and tough.
  • Elon Musk (Tesla) is known to have spent weeks on end sleeping in his factories, pulling all-nighters, and firing people on the spot.
  • Adam Neumann (WeWork) expressed interest in becoming the “President of the World.”
  • Travis Kalanick (Uber) was kicked out of Uber due to his operating style.
  • And just recently, Bill Gates (Microsoft) compared himself to Michael Jordan – as depicted in The Last Dance – in that he was extremely tough on his employees and was often thought of as a jerk.
As an investor, I always adapt to the personalities of each founder I work with.

And most importantly, I adapt very heavily when I feel like I’m working with a giant visionary and strong personality… one that some may call a “brilliant jerk.”

But what exactly is a “brilliant jerk”? And how can you adapt to working with them?

Let’s dive in.

What is a Brilliant Jerk?

In his classic book, The Brilliant Jerk Conundrum: Thriving with and Governing a Dominant Visionary, distinguished professor Mark Epstein discusses exactly this.

The book gives advice that I’ve found super useful as an investor:

Some entrepreneurs are such visionaries that they’re often unpredictable, brilliant, and oftentimes downright difficult to work with.

These leaders can be successful and lead successful companies, if the company is structured correctly and if the leader has the right people working around him.

But here’s the thing… “Brilliant Jerk” leaders are also extremely controlling. How do they gain so much control?

  1. They take control of the board. Many leaders will assume the position of chairman and CEO, thereby calling the shots.
  2. They have cult personalities. These leaders are charismatic and confident… but they can turn into bullies when they aren’t being respected.
  3. They’re opaque. These leaders can limit the flow of information to retain total control and create a lack of personality.
That sounds a little daunting, right? But not to worry…

How Do I Work with a Brilliant Jerk?

As Epstein points out, and as I can attest to, it’s important to know that if you’re investing in a brilliant jerk, it doesn’t mean there will be a problem.

It just means that you need to come in with the expectation that they need to be handled differently. You must deal with them differently, because they are inherently different.

For example, a brilliant jerk may be very particular on how to handle certain parts of the business, despite those views being subjective and not based on data.

In this case, it is wise to defer to the brilliant jerk and let him or her get their way.

What Leadership Style Do I Prefer?

As an investor, I prefer to work with founders who fall somewhere in the middle.

These founders are both visionaries and good managers. They’re brilliant, but they can work well with others.

Because ultimately, when you invest in a poor manager, it’s bad news for you.

That’s why I always seek out the founders who get my attention right from the beginning… but who have personalities I’m willing to work with for years to come.

I believe those are the types of founders you should look for, too. And I’ve sourced six different founders who can show you how to you get started.

These founders are among the best of the best. I’ve already put my money into every single one of their companies… and for some, this is my second or third time working alongside them.

Today, I’m sharing all the details on the independent research team’s deal analysis and showing you how to take advantage of each deal recommendation right now.

Just click here to enter the dealroom analysis meeting.

I’ll be back on Saturday to talk about why entrepreneurs need to be open to feedback to build a successful company.

Very best,

David Weisburd