March 18, 2015

How To Be Cool: The 5 Quintessential Qualities Of Coolness (and why they’ll put you at risk of being dangerously wealthy)

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The reason it is worth using ink to address the seemingly trivial topic of coolness is that being cool does carry certain advantages. The type of effort and engagement the young cool teacher can inspire is nothing short of amazing. – MATTHEW JOHNSON, teacher/author

Let your soul stand cool and composed before a million universes. – WALT WHITMAN

I’d rather be dead than cool. KURT COBAIN, 1967-1994

Today I want to share with you one of the top-secret weapons in my personal War On Poverty arsenal. If I was James Bond this would be his martini “shaken, not stirred.” Maybe not the first thing you’d think of when asked, “Why was Bond such a bad ass?” but nevertheless absolutely essential to his overall effectiveness as a professional lady killer.

The top-secret weapon is this:


I am literally the coolest person anyone I know has ever met.

As if to prove my point, do you know how hard it is to be able to say what I just said and still be cool?? Saying, “I’m cool,” is one of the douchiest things you could possibly say and is grounds for immediate expulsion from the Cool Club. But I said it, and I’m still in.

This is a mystery we need to explore for your sake.

Let’s lay the groundwork:

People do business with those they know, like and trust, right? (This is common knowledge that hopefully you know. If you don’t I may need to move you over to my remedial blog at

Well there are three types of people:

– Those that most everyone is indifferent about  <— this is the worst possible scenario, and it encompasses the majority
– Those that are liked by some
– Those that are liked by nearly ALL

Now picture that one person in your life that almost everyone likes. I mean maybe some people hate him or her, but absolutely no one is indifferent. (The one’s who hate are envious or don’t matter.)

Guess what that person is.


Now this person may not be wealthy because possibly not enough people know him or trust him. Or maybe he simply has no business sense. I mean the whole “know, like and trust” thing is just one component of business success. But it logically follows that, as far as that component goes, the cooler you are the more money you’ll make.

Being genuinely cool greases the wheels for you in the business world. Is it a necessity? Of course not. I know a ton of rich douchebags. But they have to work a lot harder than I do, and everyone hates them.

And no, “douchebag” is not a bad word in case you’re getting offended. I researched it because I try not to curse. Shakespeare coined it hundreds of years ago in his Sonnet 23 so it’s officially classic poetry:

As an unperfect actor on the stage,
Who with his fear is put besides his part,
Or some douche-bagge replete with too much rage,
Whose strength’s abundance weakens his own heart

I’m reciting that from memory, but definitely don’t double check me on it.

But besides Shakespeare’s douche endorsement …

Guess what I typed into Google to find this picture.

I rest my case.

So, what do I mean by being cool? Isn’t being cool superficial? By some definitions, yes. The guys from the Jersey Shore back-up cast in that picture all think they are very very cool, and, unfortunately, a small but hopefully shrinking segment of America agrees with them.

But my idea of cool is just being the very best and most authentic human being you can possibly be. In my world being cool is normal; being uncool is an abnormality. It’s not that there’s something special about the cool person, it’s that there’s something wrong with everyone else. Call it semantics. Potato tomato. Whatever.

Anyway, experience has shown me there’s about a 97% chance you personally are not cool. NEVER FEAR! I will not allow you to remain in your dorky and impoverished condition. Do exactly as I say, and you will be transformed from Urkel to Usher before you can say, “Who is Urkel and Usher?” which will only serve to prove my point.

To be cool you have to be confident, socially intelligent, fashionable, authentic and funny.

Let’s begin.


“Why should I care what other people think of me? I am who I am. And who I wanna be.” ― AVRIL LAVIGNE, rockstar

First let’s take a look at’s list of synonyms for confidence:


Well whadya know … cool. So we see that being confident and being cool are, if not the same thing, very closely related.

Confidence is so rare in this world that the majority marvels at the minority who have it. They marvel to the degree of admiration. And when you have people admiring you, you have people liking you – the whole point of being cool.

A lack of social confidence (and all business is essentially social) boils down to one fundamental misbelief:

You think other people are better than you, and therefore you necessarily care what they think.

And this crippling lie you are believing leaves you FROZEN. Paralyzed. Incapable of taking bold, meaningful, effective action that would naturally bring you all your heart’s desires. You may know what to do, and you may even want to do it, but for some reason you can’t find it in you to actually DO it.

Until now you have not known why.

Now you know.

Let me help you with this …


You are going to get that out of your head right this instant.

Do you think I’m better than you? Actually I’m a bad example. : ) Just kidding. Dude I worked at a BBQ restaurant while my friends were in college. I was a drug addict. The majority of my life has been an almost seamless string of moral and financial disaster. I’m a regular guy except for one thingI don’t care what anyone thinks about what I do or don’t do.

I may go to certain lengths to make sure I’m perceived in a certain way by people who matter. But in general, I do not give a flying flip about what anyone on earth thinks about my life. It’s MY life.

Not caring what other people think is at the very core of cool.

Personally, I do whatever I want in both business and life (within moral boundaries of course). And I almost always think what I end up doing is the best in the world.

Why do I think that?

Because it’s uniquely me. And I’m not scared to show you me because I’m freakin awesome. So are you, you just may not know it yet.

One of my mentors says something pretty smart. He says, “The more unique something feels to you the more universal it probably is.”

Do you feel like everyone has it all together and you don’t? So do they. I feel like that at least once a day, but I just have to remind myself it’s total bullcrap. That’s not a curse word either. It’s French, and there are no curse words in France. Everything is a curse word there so they all cancel each other out.

***WARNING*** I used to be confident to the point of recklessness. I didn’t just think I was as good as everyone else; I thought I was better. That is not confidence; that’s pride. And it’s a one-ingredient recipe for disaster.


So how do you gain confidence if you feel like worm poop?

1. Believe that what you’re wanting out of life is possible. Start wanting it 100 times more than you currently do. You can actually have it if you simply learn how the world works and go work the world. It’s not rocket science. But it is science.

2. Realize the truth: No one, and I mean no one – not the pope, not the president, and maybe not but possibly Richard Branson – is better than you. They simply know something you don’t know, believe something better than you’re believing, and are doing something you’re not doing. Those are all things you can change very easily.

3. Whatever areas you’re not feeling confident in, whether general personal development or business or health, read as many books as possible in that area, go to as many seminars as possible, and find a QUALIFIED mentor to breathe confidence into you. Fire all unconfident friends. You officially have nothing in common with them.

4. Put personal and spiritual growth near the center of your life. The more you grow as a human being the less reason you’ll have for feeling inferior.

A word of caution:

There are a lot of confident idiots in the world. Confidence is only cool when seasoned with

Social Intelligence

Diplomacy is the art of letting someone else have your way. – DAVID FROST

Social intelligence is basically your ability to read people and skillfully anticipate the likely impact your words and actions will have on them. The product of social intelligence is diplomacy. And coolness.

Picture being the Secretary of State in a meeting about whether we should bomb another 3rd world country into oblivion. This is exactly what will be going through their mind:

“If we bomb this country, X will happen. If X happens, Putin is going to get angry. If Putin gets angry there’s a 50% chance he’ll jump on a horse, take off his shirt, and go do something manly on camera.

putin1 putin2 putin3 putin4

Then he’ll most likely do Y, which would cause China to do Z, which would cause the United Nations to do absolutely nothing because no one knows why there is a United Nations – we’re not united. We probably shouldn’t bomb this country. …

… ah what the heck. Let’s do it!”

This is exactly how you should think prior to speaking or sending that email.

Social intelligence is a basic two-step dance.

Step 1: Put yourself inside the other person’s skin (your customer, your boss, your employee, your joint venture partner, your spouse – anyone you care about).

What type of personality does this person have? What’s going on in their life right now? How are they feeling? How have they acted in the past? What’s your history with them? How do you think they perceive you? Do you think they like or respect you? Have you done anything of value for them recently? Do they owe you any favors? Do you owe them any favors?

Where is the relational account balance at right now?

Step 2: Mentally play the movie forward.

“If I ask for help from this person, he’s likely to either say ‘no’ or expect me to do X sometime soon. But if I do X then I won’t be able to do Y for this other guy I promised to do something similar for. Maybe if I randomly do something of value for him now and postpone my request for a month, I’ll have a much better chance of success.”

As opposed to just mindlessly calling this person and asking for whatever you need with no care at all as to how you’ll be perceived.

The very best way to increase your social intelligence is to start carefully observing people. Pay attention. Try thinking about something other than yourself. Get out of your own head and look around. Take mental notes.

I just like observing people – it’s something I’ve done ever since I was a kid, and I got really good at it. That’s a big part of why I became a comedian. My audience is filled with every kind of person you can imagine, and I love that. – ELLEN DEGENERES

Watch, listen and learn.

Sounds basic right?

Well why is it that virtually no one does it?

I was having dinner with a friend once, and he said, “Man, you are a really good listener. Nobody listens to me the way you do. You’re, like, actually paying attention.”

At the time I thought it was weird because I didn’t really see how you could have a conversation without paying attention, but now I see it clearly. Everyone hears; very few are listening (or caring). Everyone sees; very few observe and comprehend.

I was watching this show on TruTV called The Carbonero Effect recently (HIGHLY recommend). Each scene is an undercover magician in different situations with real people presenting his magic as though it weren’t magic. Absolutely brilliant.

For instance, one scene was him working at a pet store behind the register. When people came up to the counter he would offer them a fish-shaped sticker that turned into a real fish when placed in water, which he demonstrated to their amazement.

The funny thing about the show is no one ever says, “How did you do that?” They all just ask how it works and proceed to buy ten sticker-fish for a dollar fully expecting them to turn into real fish when they get home.

Don’t believe it? I wouldn’t either. “Videos speak louder than words” as they say …

That in itself is interesting and worth noting. Especially when you’re doubting your ability to sell someone something.

But what’s more interesting is this one episode where, right before the scene, he looked in the camera and said, “OK, this one is going to be for kids. Man I’m nervous. Kids are the hardest to fool. They’re actually watching and paying attention.

The world is in a trance. It is the person who wakes up and goes about the business of waking others up who truly succeeds. And is cool.

But it’s not enough to just wake up. You have to wake up and put some clothes on. And those clothes need to

Be Reasonably Fashionable

 Whatever rappers wear is cool to people. – FRENCH MONTANA

I hate the fashion industry with a passion.

When the E! TV host asks the stars, “Who are you wearing tonight?” on the red carpet, it makes me want to strangle my wife’s dog.


“They can’t hear you,” my wife quietly loves to remind me.

That being said, I am very fashion conscious. And I do just enough to be cool.

Why? Why not just wear whatever I want and stick to my guns about not caring what other people think?

Well first of all, I do wear whatever I want. And what I want just always turns out to be pretty cool somehow. There’s plenty of things that are in style you wouldn’t catch me dead wearing. Peg leg pants for guys are in for some reason I don’t think I’ll ever even partially understand. I’d rather base jump off a Madison Avenue skyscraper and use those peg legged pants for my parachute than actually wear them.

But the main reason I don’t just wear “whatever” is it would make me have to do extra work to connect with people. It’s hard enough to connect with people as it is. You don’t want to add a black belt with brown shoes on top of it, trust me. That’s a tough bridge to gap.

And in case you really want to get all holier-than-thou on me about his, let me just point out that Jesus himself rocked a seriously rad tunic in his day. He didn’t go out changing the world in just any old tunic. It was seamless – very rare and expensive. True story.

I’m a Muslim, but I think Jesus would have a drink with me. He would be cool. He would talk to me. – MIKE TYSON

But no matter what designer tunic Jesus wore, I’m not even limiting this concept to just clothes. I mean fashion in general – pop culture.

Now mind you, I hate pop culture with a passion rivaling that of fashion. But I know what time it is. I know the latest lingo, music, movies, trends, etc. I’ll stay up to date with it until I die, and I’ll use it selectively when the situation warrants it.

Why will I do this?

I’ll do this for the same reason I stay fashion conscious: to connect with as many people and have as big an impact in this world as is humanly possible.

Are there wealthy successful people who are fashion/trend oblivious? Sure. But they’d be wealthier, more successful and have a bigger impact if they weren’t. Picture Obama if he wasn’t fashion/trend conscious – if he wasn’t cool. He probably wouldn’t even be president. And that’s not a put down. Kudos to him for playing his cards right.

Want people to like you? Want to be cool? Get your fashion straight. Don’t conform, but don’t do this either:

Proof that there ARE rules to fashion

One caveat: Don’t try to be something you’re not. If deep down you are truly just a little nerd, and there’s no escaping it, be a nerd. But be a nerd who still knows what time it is. Be a cool nerd. All that’s saying is be socially and culturally aware. But don’t put on a show. Because to be truly cool you have to

Be Authentic

Being cool is being your own self, not doing what someone else is telling you to do. – VANESSA HUDGENS

People know a faker and a manipulator (same thing) when they see one. And almost everyone is a faker. That’s why the unique individual who dares to be who they really are with little regard for public opinion is generally referred to as cool.

It takes a lot of confidence to take your mask off in a world full of … mask-wearers. I couldn’t really think of anything clever to write there, sorry.

When I first went into business for myself buying and selling houses I determined from the outset to do and say whatever the heck I wanted. I didn’t leave the confines of the rat race to be once again confined to some unspoken guide of acceptable business practices. I left for freedom.

So instead of “Here is this house for sale. If you’re interested please advise at your earliest convenience,” I’d describe the property and then say, “If someone doesn’t buy this stupidly cheap house in the next 45 minutes … the duck gets it.” Followed by this picture:


Was this just marketing hype? No. It was me being authentically me. Totally free and having fun. It just so happens that “free authentic me” happens to make for some good marketing.

Whereas most people would dress up for videos, I would wear shorts, a t-shirt that said “F The Economy” and my hat on backwards. But again, I wasn’t putting on a show. I’d been wearing t-shirts with the F word on it and my hat backwards since I was 18 years old. I don’t wear those t-shirts anymore, but I did then for some angry reason.

So you want to be authentically you, but as we’re seeing in this post, it’s helpful if the authentic you is pretty cool.

I’ll close this article with both the number one way to diffuse the offense you’ve caused by your F word t-shirt AND the number one way to be cool. They are one and the same.

You absolutely must …

Be Funny

“If you want to tell people the truth, make them laugh, otherwise they’ll kill you.” – OSCAR WILDE

Humor cuts through all guards. It diffuses all social bombs. It holds attention, increases attraction, creates bonds, raises trust levels, increases sales conversions and MAKES YOU COOL.

The only humor that doesn’t make you cool is slapstick comedy and self-deflective humor (born of insecurity).

Why does being funny make you cool?

Because being cool is essentially about being a master of your social and material environment.

Want the perfect illustration? Let’s watch the coolest person that ever lived in action: The Fonz himself …

               Happy Days went on air the year I was born. Coincidence?

What did you think after watching that video?

Did you think, “That’s just TV. None of that would work or is even possible in real life.”

Or did you think, “That’s freaking awesome. I could totally do that.”

I thought the latter. And I thought it knowing it’s more than possible.

What does this have to do with humor? I forget. Let me scroll up and see where I was going with this …

Ok yeah, being cool is about being a master of your social and material environment … got it.

To be masterful in your social and material interactions you must have a profound grasp of truth. You have to know how and why stuff works – how and why people say and do the things they do. You need to know how the world operates at a deep fundamental level.

The two things I understand best are stand-up comedy and martial arts. And those things require an ultimate grasp of the truth. You have to be objective about your skills and abilities to compete in both. – JOE ROGAN

Humor at its core is nothing more than helping people see the truth about both themselves and life in a clever and surprising way. It takes such high levels of intelligence to be genuinely funny, that people immediately trust you more at a subconscious level.

And if you actually make them laugh and bless them with the gift of a refreshing endorphin release??? They officially owe you according to the law of reciprocation.

Do you want to quadruple your income almost instantly? Do you want more people to like you? Do want to be cool?

Study comedy.

Humor is absorbed, not taught. Watch all of Kevin Hart and Dane Cook’s stand up routines and allow your mirror neurons to transform you. Watch all Vince Vaughn’s movies. Keep reading my blog posts.

Alright that’s a wrap for now my friend.

Be confident, socially intelligent, fashionable, authentic and funny … and you will find yourself dominating whatever industry you decide to get in to.

You will be COOL.

P.S. If you laughed one time and/or learned three new things you owe me a share and a comment. I’m not just making this up. It’s a new law buried deep deep in the FCC’s new Net Neuterality bill (yes, I spelled it that way on purpose).


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