Never Be Like Them

October 7, 2012 — 25 Comments

About two years ago, I went to an advertising conference in New York City. I was the youngest person in the room by far. The only one who wasn’t in a suit, wasn’t talking about vacation houses, about cars, wasn’t hoping to hook up with some other gross lonely person while away from home. I remember thinking very vividly at the time: this is the track I am on. Right now I am young but soon, soon I will be one of these assholes.

I can’t express how much this shook me. I felt a kind of creeping dread that I would be absorbed into this crowd. That the things that were important to them would be important to me. That I would become just as parasitic as them; selling the same shit they sold, convinced—because I would have to be—that it wasn’t shit. It was not long after this that I dropped out.

Last week, I happened to be in town during the same conference. So I went again. How different it felt. The claustrophobia was no longer there, the anger and resentment too. All I felt was relief. Why relief? I am nothing like these people. I am firmly off this track. The preceding two years were very good to me: bestselling book, national media platform, new clients.

But the irony did not escape me. Last time, I was despondent. I felt like that I’d never be able climb high enough on this pile to breathe my own air, not in that suffocating rat race—that because I could never play by their rules, I’d forever be some bit player. So I resigned. I took my sharp right turn. And the result? Well, that’s the irony.

Today, I am very busy and no longer as obsessed with the industry as I once was, but last week there wasn’t a single presentation at this conference that wasn’t in some way chasing work that I had done. Facebook showed a screenshot of one of my articles and tried to dispute it on stage. Other companies were “announcing” the opening of platforms I’d been using for more than a year. I’m not saying that people were whispering my name or anything, but my finger prints, well I could see them everywhere. I was the only one in the room with a book, the only one doing the thing I’ve done.

That is not to say it was an easy year, leaving this world was incredibly difficult. And scary. And uncertain. It took denial and discipline. And to quote Henry Flagler, “it was hard on me but I would rather be my own tyrant than have someone else tyrannize me.”

So it goes, now on to the next worry. I’ll never be one of those assholes, sure, but now it’s time to make sure I don’t become some other type.

Some Recent Writing

September 25, 2012 — 6 Comments

Here are some recent articles from me:

New York Observer (where I am now a contributing editor)
Apple’s Free Ride: Why Journalists Treat Product Launches Like News
Broken on Purpose: Why Getting It Wrong Pays More Than Getting It Right
Forget Lehrer and Zakaria—Most Online Journalism Is Rotten to the Core

Fast Company
Why Books Are The Ultimate New Business Card

And some info on my next book, which will be on the intersection of stoicism, opportunity and strategy.

A Hustler’s Art

September 12, 2012 — 20 Comments

I have three pieces of art in my house. One is a beautiful wax portrait of my hero William T. Sherman, one’s a painting done by an elephant and the other—my favorite—is a framed, signed original Joey Roth Hustler poster.

I’ve come to know Joey Roth since I discovered the piece. But even if I hadn’t, it would still be one of the most striking pieces of art I’d ever seen. It’s the only piece of art I’ve ever given as a gift (to Robert Greene, Neil Strauss and others). It’s one of the few things I’ve ever thought of getting as a tattoo.

Why? Because I think it properly defines the differences between a charlatan (all talk), a martyr (only action), and a hustler (action and talk in a feedback loop, fueling each other). The message was exactly what I needed at 22 or however old I was when I got it. I was a hustler then, and it’s taken me to where I am today. Now, I feel like I’ve internalized the message. I was ready for what comes next.

And now there is a second piece in the series. Where the first was about just one side of the equation. This one is about the whole thing. Inspiration, discipline, risk, humility. The virtues, the epithets of people who get shit done. Together, they form bullet, the bullet that if assembled properly, if struck correctly fires at four thousand ft a second.

To me, the second poster unpacks the hustler column from the first poster—perhaps, a more accurate version of it too. There’s no better metaphor for a hustler than a bullet. Lethal, vicious, a machine. All these things, yes. But as a hustler gets better, they realize there is more to the game. They decide they don’t want to be a casualty of it. They can start to transcend the rules they understood and manipulated.

As Roth writes, they learn to “design your project to cut through apathy and reach those who will appreciate it, but realize that once it’s in the world, its success and failure are no longer yours. Temperature, dew point, and Earth’s rotation affect a bullet’s flight as much as the shooter’s intention.”

A young hustler is supremely confident. A wise hustler is confident, but detached. They know that nine of ten projects will fail—rounds will miss their target—and they’re ok with that, they can see the bigger picture. They’ve moved from the short play to the long play.

I find myself wrestling with that transition now. So this poster will go on my wall alongside the others.

How to Repay Your Enemies

September 4, 2012 — 18 Comments

How do you repay the people who fucked you over?

It is a little harder to get into one post just because there are so many ways that people can wrong you. There is the overt action: the attack, the theft, the lie, the deliberate slight. And then there is the let down, the negligence, laziness, and occasionally, there’s someone with contagious bad luck. Most of the time, we ignore it. As we should. But sometimes, we can’t.

Imagine you are Sam Zemurray. You try to give friendly advice to the company you love, try to contribute through the proper channels, but they slam the door in your face. They are running your baby into the ground. You know what must be done.  So you go to the board meeting in New York City, you sit there quietly. Then you raise your hand and speak. They laugh in your face, mock your difficult accent. You storm out, maybe they think they’ve won.

When you return, it’s armed with the stock proxies for a majority share in the company. “You gentlemen have been fucking up this this business long enough. I’m going to straighten it out.” And now it’s time to drop the hammer: “You’re fired. Can you understand that, Mr. Chairman?” as you fling the bag of proxies across the table.

Sometimes an aggressive strike, or even revenge, is not emotion—but strategy (like a co-worker who is steadily encroaching on your projects despite discussions, or perhaps you need to generate a little controversy to get press). Robert Greene calls this “knowing when to be bad.”

One element of mastery is the ability to no longer need to react emotionally. To know what you need to do and not be distracted by immediacy. Repaying your enemies properly—and effectively—maintains that rule.

Only the top predators can afford to toy with their prey. As Ambrose Bierce once said, real skill is to “stab, beg pardon and turn the weapon in the wound.” Only the best can manage effective action as an artistic statement. But those who can, have all the fun.

A sad part of it all is this: people do you wrong out of incompetence a lot more of than they do out of malice. If they were consciously trying to harm you, believe it or not, they’d probably have done less damage. I’m not saying that because it take the sting out of it. Rather, that you can’t get back at someone who already lost—who can’t get things right even when they try. These people, you must ignore.

But as for the rest of our lives, there is one unescapable political fact: People will fuck with your stuff. They will treat you bad. Mess things up. Try to disrespect you or keep you out. What happens? You get pissed and you feel like murdering them. You sit there and stew and rage and rant. You’re only tipping the scales further out of your favor.

As I tried to explain to myself a few years ago in exactly one of these moments, this is no reason to grind your teeth. Smile, they just gave you an opportunity. Not an excuse, but a justification.

Enjoy it. Learn from it. Remember, as Plutarch one titled an essay, How To Profit By One’s Enemies. In a world, where so much will go wrong and sadly, so many people will wrong you, you better know how to turn it something positive or at the very least, into a cathartic game. Or you will be one angry person.

How to Repay Your Mentors

August 20, 2012 — 12 Comments

How do you for people who have done so much for you? How do you thank them?

Well, first let’s get something out of the way. Very rarely does anyone else help anyone else out for genuinely altruistic reasons. Unless your mentors were blood relatives, they took an interest in you in large part because there was an interest in it for them. Having a whiz kid or a protege around is good for business, that’s why they’re doing it.

So deliver. Have your shit together. Want it more than they want it for you. Don’t be crazy. Spot new opportunities, never care about credit. All the “Advice to a Young Man” stuff.

But after that, when it comes to all the intangibles–everything they gave you that extends way past any reasonable definition of “work obligation”–there is only one thing you can do: earn it. They invested time in you, they gave you a bit of their truly non-renewable resource. You can’t pay them back. You can only make it have been worth it. Validate the investment and make it clear that you appreciate it. Be a good person; do what you love.

Without being cheesy, I also have to discuss the final step: paying it forward. The people who gave you your first job, showed you their secrets, picked up the check when you couldn’t afford to? They don’t want that stuff back. They want you to see you learn from their example. I’m not saying it’s good karma, but think about it like this: the stuff they gave you, that wasn’t a gift. It was given to you in trust. You don’t exclusively own that knowledge, you aren’t entitled to profit from the advice, you didn’t get some free ride. No, you just got access to it for a while, access that was contingent on you referring other deserving people to it down the line. Got it?

As we get older and more successful, we find ourselves in the position to help people. We were once in their shoes, and we know how we got from there to here. We find meaning in that journey and want other to experience it. At the same time, success makes us soft. It alienates us, makes us a little less hungry. But our experience makes us smarter–we know that our skill combined with someone else’s inefficient but fresh energy would be potent. More potent than either attribute in isolation. Which is why both parties seek each other out and benefit from it.

Just remember that that’s what mentorship is. And that whatever role you play in that equation at whatever time, you better fulfill it completely. It’s what you owe.