November 2, 2012 — 42 Comments

You are soft. If you were born in my generation or thereabouts, you are almost certainly soft. You live a nerf life in a nerf world, filled with nerf delusions.

Check the boxes. Put in your 8 hours a day. Get what you you earned. Get anything.


That’s not how it works. But you don’t get to complain that the game is rigged. Why? Because it’s basically fairer than it ever has been. It’s unlikely you’ll suddenly die. You don’t have to go to war. You can travel from place to place and never, ever worry about pirates.

Yet we’re soft. We quit early. Settle. Complain. Think we deserve a break. Make lazy, self-serving assumptions. Try to get the most for the least work.

Stoicism is hard. Cato was hard. They were obstinate, in a good way.

Consider what hustlers call their work: “grinding.” Not “the grind,” diminutively like us, but grindin‘. The hustle. Working all day and all night, looking for an angle, taking their share. They have to, there is no other way.

You have to cultivate that hardness. And you better start soon, because we’re all in the same ghetto now. How? Savagery is one way. You have to learn to love the struggle. To know how to grit your teeth, and promise yourself that you will never, ever let something like that happen to you again.

Everything is a test. It’s a test to see how hard you are. Will you keep going? Can you get to your knees? Can you get you to your feet? Can you try again? Can you bear it? There’s no end in sight, how long can you last?

Stop failing this test. Stop being soft.


October 16, 2012 — 19 Comments

How could one of Rome’s—and history’s—most respected “philosophers” have gotten away with never really writing anything? Because stoic philosophy is about action, not words. Men were considered philosophers based on how they lived life, not on how they studied, wrote or spoke about it.

Cato was such a man. He was a soldier, a politician, a thinker and most important an example. His unassailable place in Roman culture is best seen in the old proverbial expression used to make excuses: “We’re not all Catos.”

He lived on principle—often stubbornly and ineffectual so. But it wasn’t just for show. Cato also died on principle—gruesomely, and heroically so.

For whatever reason, as a historical figure, he has been so intimidating that basically no one has written about him since Plutarch. The legends, it seems, were more appealing than a human biography. I’ve tried to write about Cato before. And I’ve referred to him in other posts and places. But in terms of books, the offerings are scant.

Two friends of man have taken a stab at it though. I’ve been lucky enough to see the book develop, and as a result of the early drafts, been thinking about Cato for close to 18 months now. Like the authors, I struggled with strong feelings about Cato—both respect and disgust in fact. It’s hard to wrap your head around a man who was so brave, yet often so petty. He was a constant violator of the final law of power: assume formlessness.

Cato could not compromise, ever, even when it was best for the cause he claimed to hold dear. He’s a tragic figure in that sense, more Greek tragedy than Roman pragmatism. But an inspiring, bold and self-sufficient moral example nonetheless.

I’ve recommended a lot of biographies on this blog, from Everitt’s books on Augustus, Hadrian and Cicero to Liddell’s Sherman. I love biographies. I think they are the best way to start a deep study of a subject. Start with people, move on to events and then you can understand the ideas behind them.

Rome’s Last Citizen: The Life and Legacy of Cato, Mortal Enemy of Caesar is a book like that. It’s subject is worth studying, particularly today. There’s a lot to learn from a politician who couldn’t be corrupted. A philosopher who refused to write. A millionaire who lived among his soldiers and people. He is Marcus Pocrcius Cato, a man of a different epoch—some two thousand years passed—but a man, who we, without a question, are better off knowing. Cato, as Paul Johnson said of Socrates, is a man for our times.

Never Be Like Them

October 7, 2012 — 28 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 — 21 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.

UPDATE: I can’t believe this happened but Joey actually collaborated with me to create a poster based on The Obstacle Is The Way. There’s only 1,000 of them and his stuff usually sells out. Hope you like it.