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The Altucher Confidential: Brilliant, Hilarious - and Always a Great Read

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h1 Every sentence must be an experience and evoke an emotion. Every sentence must be a cliffhanger.

James Altucher, The Altucher Confidential

James Altucher is only in his forties, but it seems he's already lived a few lives. He's a trader, investor, writer, and entrepreneur – and has written more than a few books. He's started, sold and had a hand in many companies that have failed. And he shares it all in his stream-of-consciousness rants on Altucher Confidential which cover everything from finance to bad investments to health and self-improvement. The posts are half-brilliant, half-hilarious and always a great read. Typical Altucher headlines: How I Screwed Yasser Arafat out of $2mm (and lost $100mm in the process), 10 Unusual Things I Didn't Know About Steve Jobs, and Ugly Men Don't Get Clicked On (some of his posts also appear on TechCrunch).

A recent inductee into the Say 100 business channel, we caught up with James to find out why he thinks the world is out of balance, his secret is for great headlines, and how he knows he's got a winner when investing.

Your site tagline is Ideas for a World Out of Balance. What's out of balance? And is it fixable? People are stuck in "ambition" where ambition is usually defined by some external goal. The world will get balanced as people move from ambition to meaning, i.e. start to focus on internal themes first.

You spill a lot of great advice for entrepreneurs and businesses on your site. Why do you feel a responsibility to share advice instead of just making money? The easiest way anyone in the world can make money is by constantly trying to enhance the lives of the people around them the best way they can. This is my way.

You have an amazing knack for great headlines. Do you start with a headline and then craft a story? Or the other way around? What makes a great Altucher headline? Every sentence must be an experience and evoke an emotion. Every sentence must be a cliffhanger. Every sentence must deliver value. Headlines,first sentences, final sentences, and everything in between. A great headline breaks all the rules but delivers value and gets you to click. A great headline is one that has never been written before.

What are you all-time most popular posts? And what do you think that says about what people crave? "I Want to Die," How to Deal with Crappy People and How to be the Luckiest Person Alive. I think people are scared. The world is a scary place. Bad things happen. People are lonely and anxious and angry and filled with regret. These posts help them come out of that so they can live lives of fulfillment.

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You've invested in a lot of companies as an angel including companies like and Buddy Media. How do you feel like you've got a winner - and when do you decide to pass?

I use a checklist:

A) CEO who has done it before

B) A good co-investor (so I dont have to do all the due diligence work)

C) A good demographic trend so the wind is behind us

D) A good valuation compared to any comps

E) Revenues and even profits (at the very least: light at the end of the tunnel that I can clearly see)

F) An understandable exit. (i.e. how will they get sold in less than 5 years.)

You've said your investments in business are always based on demographics: How are you feeling about Facebook and Boomers these days? Facebook is in inning two or three of its huge demographic trend. Inning one was getting all the users. Inning two was beginning monetization. Inning three is rolling out more revenue products, which they do every week and people scoop them up.

What's your media diet like? Where do you go for business advice? I don't look at any media ever. When I feel the urge to look at a news site I say, "Do I look at a news site or do I read a really good book" and I always choose the book.

You're in your 40s but you seem like you've already lived a few lives. What do you want your legacy to be? In 100 years, none of us will have our names on any buildings. I won't have any legacy. Dreaming for a legacy will be wasted thoughts. I could be sleeping or something instead of planning my legacy.

How would you finish this sentence: When in doubt… That sentence already has a good ending. I wouldn't change a thing.

Follow James on Twitter @jaltucher - you won't be sorry.

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