Break Out of Prison

We were about to convince a bunch of Arab sheikhs that their investment in our VC fund was still worth something and maybe they should invest more. It was 2001. About a few months before our biggest investor shut us down. Until then there was still a vague hope that we were good at what we did but we knew we weren’t.

We were boarding the plane to Miami. Why Miami? After all the meetings, all the investors liked to go to the strip clubs while they were in America. Our biggest investor, a private equity fund that will remain nameless, had a line item in their budget for strip club entertainment for events like this. Miami was supposedly the place to go and we were staying in the best hotel there. The guys from the private equity firm, after the meetings of the day where we spewed vomit and charts, would take out the foreign investors to the strip clubs all night.

(I googled “best strip club miami”)

Mark turned to me. “How did this happen? I’ve lost so much money in the past year.”

I said, “we’re mortal now.”

“Yeah,” he said, “that’s it. We used to be immortal! Now we’re not!”

He laughed. I laughed. I felt good for a brief second and that was about it. I liked Mark. Now he’s a banker at Bank of America and the last time I saw him he smashed the screen on my Defender arcade game, said, “have a nice life” to me and walked out. Then the VC fund was over. Then I was kicked off the board of the company I started. Then the two buildings five blocks from where I lived blew up. Then I went broke. Lot’s of bad things happened to a lot of people.

I feel like since I was born I’ve gone back and forth between fear of living and fear of dying, often at the same time. I want to be immortal. But being mortal is usually filled with fear. So I built an artificial net that I thought would catch me:

Money: if and when I have it I can do anything. It’s a rush. I can cure all ills. I’m SAFE! I can fly helicopters. I can leave $100 tips with cabdrivers. People think I’m smart. I think I’m smart. When I don’t have it I’m worse than dead.

Wife: “til death do us part”. We get immortality in the certainty that the relationship will last “forever”. But then I get afraid. EVERYTHING has to last forever. The romance, the sex, the respect, the interest. What if it doesn’t? What if any one of those falls apart? Help!

Corporate safety: A corporate job has the illusion that it will last forever. Until it doesn’t. Until a tiny bit more greed squeezes the last mindless juice out of us before kicking us to the street.

Religion. Every religion has their way of saying, “calm down, calm down. Here’s what happens when you die.” But why is a Jewish person on this tiny planet any more or less right than a Buddhist on the other side, or a Catholic in the middle, or a Muslim next door? I hedged my bets by trying to believe in everything. Jesus = Krishna = David = Buddha = Lao Tzu. Who knows? Anyone who tells you they have the answer is the last person you want the answer from.

Family. Well at least I have my family. Blood lasts forever! Right? But as I get older, the bonds with my old family seem to get thinner and thinner. And the bonds with my new family (my kids) will eventually get thin. I can’t control them anymore. They grow up and become adults. And the best I can do is tweak here and there and hopefully they listen but they will live their own lives.

Place. I’m an American! From New York! The capital of the world. And I have to protect my way of life. Because democratic capitalism will spur growth forever. So it’s ok to bomb everyone who threatens my way of life, right? And I have to make a lot of money also to prove this is the right place to be in.

Social connections. Not only friends. But something inside of me feels there’s more value in my life when I get more twitter followers, facebook likes, klout score. Lost money today? No problem. I got 500 more twitter followers.

What else? We all build this net that can catch us as we fall into the abyss we sooner or later start to fall into. What’s is your net made out of?  If not money, then religion. If not religion, then place. Or family. Or friends. Or a poker bankroll or chess rating or klout score.

But the net is frayed. The net becomes a prison. All the things you are afraid to lose. And the fight to keep the net from breaking is often painful. And then we see it was only a dream.

A good friend of mine wrote me today. I felt bad because I haven’t been able to respond to his last few emails. He threw me out of graduate school 20 years ago when he was a dean. Now he’s a friend.

“My sister died,” he wrote. “Can you talk?” So I called him and we spoke for awhile. It was a shock to him. He only knew she was sick ten days earlier. I felt real bad for him and real bad I haven’t been in such good touch.

The last time he visited NYC we were walking up Wall Street and I showed him the engagement ring I had gotten for Claudia but hadn’t yet given her. He slapped me on the back and congratulated me. We both smiled. That was one of the last times I spoke to him.

We’re not immortal. We don’t have a tribe that will protect us. A philosophy that will comfort us. A corporate job that is always safe. Money that we don’t have to worry about. A wife that will enjoy sex with us forever. A million twitter followers every day.

The net’s going to break and only then we find out the real Truth.

And then we either fall into the horror. Or we realize we have wings. We never needed the net.  And then we fly forever.



  • Anonymous

    ” Anyone who tells you they have the answer is the last person you want the answer from.” I’d say that goes well beyond spiritual matters. Stocks, investing, relationship advice, whatever.

    “Beware the advice of succesful people, they do not seek company.”

    Good post. Like to believe I have wings, but they seem to not work very well……….

  • Mark

    That was beautiful!

  • Humans are strange beings.  We are compelled to busy ourselves with the weaving of ever more ornate nets, yet we continue to be alarmed each time we rediscover the fact that we’ve made them ourselves. 

  • JackBlack

    Great post — your blog has been a great inspiration to me over the last few months…

  • cowboylogic

    Be gittin it on your mind. Life is a timed event.

  • I have zero net.  And I am trying to figure out how to deal with this.  Maybe I am lucky because I realize this, or maybe I am one of those people that others are happy not to be?  I don’t know and I barely care. 

    Thanks for your insight.

  • Tamás Bakos

    Your net is your ability to persistently create and share value. For your clients, for your connections, and for your family: in a broader sense, for the entire world. Great post, James!

  • Jason Casey

    Great post. Thank you.

    It reminded me of this:

    “Nature loves courage. You make the commitment and nature will respond to that commitment by removing impossible obstacles. Dream the impossible dream and the world will not grind you under, it will lift you up. This is the trick. This is what all these teachers and philosophers who really counted, who really touched the alchemical gold, this is what they understood. This is the shamanic dance in the waterfall. This is how magic is done. By hurling yourself into the abyss and discovering its a feather bed.” 
    ― Terence McKenna

  • Once we lose desire and strength we turn to dust.  That goes for everyone whether you have money and security, or you’re poor and destitute…some people being both in one lifetime.  What’s left is the ripples we created in our lives that touched everyone we’ve ever come in contact with.  We need free spirits while we’re alive so that we’re not controlled by imaginary safety nets.  Worrying just takes away from the present moment.  It doesn’t add anything to your future.

  • Anonymous

    Whenever i am remembering do my pranayam and living in the moment i feel just like the beautiful butterfly in the picture…..
    Thanks James !

  • Ridding ourselves of attachments is a very powerful mind. Great post James. 

  • Krisk

    Don’t. Stop. Writing!!!!

  • You realize your sick, right? After Matt Trainer suggested I start reading your dribble i thought cool. Great stuff. I was so wrong!

    F#cking incredible stuff…I’m thinking you might not be able to spit this “science” out fast enough and that a screenplay deal hasn’t sounded good enough yet.

    You scare the herd…I and I fucking love it!

    Keep it up…there is honor in failure…when we learn and teach:)

    Emile Jarreau

  • Turtle


    Thank you for listening… for understanding … and for the clarity.

    You brought a smile to my face, 2 days in a row.

    I’m flying ……..

  • Sebastien Latapie

    I never understood the association of business and strip clubs. What is the appeal that I’m missing here? Living in Montreal you are exposed to strip clubs on a daily basis, but I’ve always found them quite vile. 

    Great post as usual!

    • I think the main appeal is that those clubs are not readily available in other countries. I know we had lots of male clients (mostly from the Middle East) that when visiting us in Miami and after doing business with us would ask information about strip clubs.

  • Impermanence is the truth. All we ever have is this precious moment. Love is the only way.

    Here is a quote from your favorite.

    “Remembering that I’ll be dead soon is the most important tool I’ve ever
    encountered to help me make the big choices in life. Because almost
    everything all external expectations, all pride, all fear of
    embarrassment or failure – these things just fall away in the face of
    death, leaving only what is truly important. Remembering that you are
    going to die is the best way I know to avoid the trap of thinking you
    have something to lose. You are already naked. There is no reason not to
    follow your heart.” – Steve Jobs

  • Every day you find a new interesting topic and for that I AM GRATEFUL.  

    We learn so much from reading and that reading then, hopefully, helps us think and either leads us to read more but then ultimately produce something in writing.  

    I find the comments on your blog to be a lot like the material – worth reading.  Rarely, do I come across an unthoughtful response to something that you wrote.  Between simply saying “thanks” for you said something that they wish they could have the world see or someone else sharing an insight that they found just by reading this blog.   

    The whole process inspires me.  It continues to stir thought and drive me to produce.  I’m continually trying to find time to write more and be free.  Regarding advice, I think it’s a scam for anyone to say “hey, I did this and it worked – so you go do it”.  That’s rotten and I wish more people realized that.  But sharing experiences and trying to translate those experiences which have shaped OUR OWN lives is the best implicit advice anyone can give.  


  • Roy

    would love to know which country those sheikhs were from? =)

  • I wanted to write this freely when I started my blog but I gave up after a few (mostly erased) attempts at it.  I was not able to tolerate strangers leaving messages of hate for me.  So now I just document my net-building in the most mundane detail, and groups of people doing the same enjoy reading about my activities (strangely enough.  I find it crashingly boring reading material.  I think the voyeuristic aspect is what makes it more interesting from the outside looking in.)   I grew up with a net and sensed it was there but I didn’t understand the nature of it. I learned about it only within the last few years, and learned at the same time that my instinct had been correct – it was quite an impressive net, indeed, exceptional, even, but there was only some of it left.  I was and still am angry that the generation above me didn’t take good care of it and I became forgotten and alienated from what was left of the net (I’m talking about human capital now as well as regular capital.)  Then I clumsily ruined it (the regular capital) in a very short order of time..  I am trying to repair what is left of the net and reconstruct what I destroyed out of ignorance and well-meaning but grand-scale mistakes.  It may be an illusion but it’s the best net I’ve got.

    By the way, the woman in the net resembles a fetus in an amniotic sac.  She has not been born yet.  Choosing not to venture outside the sac (the net) at least some of the time can hold a person back that way!

    Thanks for writing in the manner I am afraid to; I enjoy reading what others write in a style and tone I can’t muster to courage to use.

    • Jim

      You could try it again with comments turned off.  I’ve seen many bloggers turning their comments off for just the reasons you mentioned.  Just a thought.

      •  Thanks for the idea, Jim.  I did consider that and may do it someday.  I think for now I’ll leave room for interaction and I’ll ease into being myself as I get more confident that I can fend off and deal with “meanies.”  I don’t have a problem like this in real life, which is odd.  That’s the nature of the internet, though – typically anonymous people like to drop nastygrams to gain some sort of sadistic pleasure.

  • Anonymous

    Good one!

    Cliche alert!-
    “Live as if you were to die tomorrow. Learn as if you were to live forever.”

  • Emmanuel Iko Ojotu

    It sparked in me,and left me loaded with inspiration.Another great one,Jim.

  • John

    I googled “best strip club in miami” and I got a picture of James. Wow, talk about failure.

    • mmm I Goggled the same thing before reading your comment but his pic did not show up.

  • chris

    I live in an amazing part of the world. People pay thousands of dollars to holiday where I live. I’m surrounded by beaches. Sun. Surf. Fun. And beautiful people.

    I hate it so fucking much.

    To relax and escape this perfect world, I regularly drive my family 80 miles inland to swim in a pissy little creek. My wife and kids love it. So do I. It reminds me of my childhood. A place where anxiety dissolves. 

    It costs nothing to go to the creek. But I would pay millions of dollars to be able wake up each day with the emotional freedom that creek gifts me.

    The creek isn’t perfect. Which is perfect.

    • Roy

      Hey Chris

      where do you live? just curious….

      • chris

        Roy, I live on the Sunshine Coast in Queensland, Australia (see here:

        It’s very beautiful on so many levels, but I grew up in a very remote part of Australia so any gathering of more than two people makes me anxious! :)

        James’s New York would represent my idea of hell. 

        Plus James lives there … which would just make the joint truly unbearable. (I’m joking, Altucher!)

        • Contextswitch

          Lucky you.. Hoist a VB over a plate of monteray bugs for me!

          • Chris


            You make it sound like us Aussies just drink alcohol and prop up BBQs full of seafood … well, you’d be wrong. I’ll have you know that more often then not we cook sausages and steak!!

            Life’s pretty weird when someone like me can bitch and moan about drowning in affluence whist James would have just been swimming in a tide of poverty in India.

            First world problems, hey? 

            What a tough gig.


          • Mike

            I hear you Chris – I live in Bondi, same sentiments. Could be worse though, at least we don’t live on the Gold Coast.  

          • Chris

            Mike, I actually saw two foreigners the other day. 

            Almost destroyed my argument about the Sunny Coast being an inbred mono-culture!

          • Abc

            Chris: I dont know if Australia is a “First World” or not but I surely think Australia has a culture problem of not respecting non-white individuals. The blatant killing of innocent international students from the Indian sub-continent and the reaction of police officers makes the poverty in India much more desirable than the guilt of being a racist in the 21st century!

  • davesh

    James – Thanks for this great post. Today was crazy for me. I just turned down a raise/promotion at work because I knew it wouldn’t allow me the time I need to build a business I’ve started that I really believe in. I have a wife and a 5-month old baby so I’m freaked out that I’ve sabotaged myself but I refuse to stay in a corporate prison forever (I work in banking as well so even worse). Thanks for writing. Keep inspiring!

  • PC

    James, great post and sure most of our safety nets are bullshit. But what about our choices? Maintaining our focus in the present may be our only real net to catch us. I worry about the future, brude over past, deal with feelings of vengence, shame, anger, gilt, and unworthiness. I spend time being petty and frustrated. This all effects the time I spend in the present and errodes my ability to act in my best interest. Which I often don’t! Thanks for the post.

  • Anonymous

    Whenever I get a bit too caught up in my own net I remind myself that I am one of more than ONE HUNDRED BILLION human beings who have lived on earth.

    And when I look at fellow humans like, say, Rupert Murdoch, I wonder what keeps driving them? Do they really think that what they do matters, and that anyone will even remember them a few short years after they are gone?

    • BBH

      What’s driving them? Their minds! Read ‘The Power Of Now’ (by E. Tolle) and you’ll know what I mean by that. 

      I really doubt that R. Murdoch is happy. Yeah, he probably has a lot of nice cars, houses and yachts, but I don’t think he’s a happy person. I doubt he is looking forward to these times when media is bashing him day in and day out. Deep inside he is likely a miserable person. Simply because he doesn’t know what life is. 
      Take Jesse Livermore. He was beyond successful back in the days, but yet he was suffering from a serious depression pretty much his entire life. 

      • Anonymous

        Yeah, agreed, I recently read a biography of poor Jesse.

        But I think happiness is a separate issue, there are actually some pretty happy, driven people in the world: Warren Buffet and Bill Gates come to mind (although of course one never knows what’s really going on in another person’s mind).

        It’s the drive to “be remembered” that always mystifies me. I have one
        friend who is determined to fund and leave a building in his name at his
        college alma mater. The same friend has a clause in his will requiring that his
        descendants hold an annual dinner in his honor. Bizarre.

        Rereading Oxymandias is another trick I use whenever I get too caught up in my own petty concerns:

        I met a traveller from an antique land

        Who said: Two vast and trunkless legs of stone

        Stand in the desert. Near them, on the sand,

        Half sunk, a shattered visage lies, whose frown,

        And wrinkled lip, and sneer of cold command,

        Tell that its sculptor well those passions read

        Which yet survive, stamped on these lifeless things,

        The hand that mocked them and the heart that fed:

        And on the pedestal these words appear:

        “My name is Ozymandias, king of kings:

        Look on my works, ye Mighty, and despair!”

        Nothing beside remains. Round the decay

        Of that colossal wreck, boundless and bare

        The lone and level sands stretch far away.

        • Anonymous

          Great poem. I use it for the same purposes.

  • MikeBN

    The only ”religion” which seems to make sense is Buddhism. Especially because of what Buddha said by believing. It went something like ”don’t believe what anybody says (including myself) – try it out yourself.” And by meditating, you can actually find out yourself that everything Buddha taught actually checks out. Unfortunately, that’s not the case in Christianity, Islam, etc. They simply want you to believe something. They want you to believe that there is some guy sitting on a cloud judging us (while simultaneously allowing all sorts of horrors to take place around the world). 

    I do think in essence all religions try to give out the same message. After all, there are numerous sources claiming that Jesus spend a great deal of his youth in India studying Buddhism. Unfortunately, Christianity, Islam & Co. suffer from a problem called ”humans.” Since they do not advocate meditation, they do not find enlightened. So they’ve built a human society around the religion. In other words, they’ve taken Buddhist teachings and modified them according to their own needs and desires (for power, control, etc). Why else would you explain why marriage is now a serious part of Christianity, when until about 1200 AD the Church literally contemned marriage. Until 1200 AD the Christian Church said that we should only love the lord.  

    Or let’s take the Jewish tradition of keeping certain meals separate. I’m not Jewish, and I do not know about THAT much, but what’s the deal with separate kitchens at some point? I hardly believe it matters at all once we’re dead. It’s just a nonsense made out by people. 

    So I remain very specifically to whatever all other religions say besides Buddhism. 

    • I think  Advaita teachers also  say something similar: try it out for yourself. 

    • Anonymous

       What did Buddha say to the hotdog vendor?
          Make me one with everything!

      • wm elder

        And he handed the vendor a $10 bill. After getting his hot dog he said “where’s my change?” The vendor said “change comes from within”

  • Ignac

    My guess is, we get wings the moment we die.  

  • Nice and raw, James. I like your last few lines–do you believe them? Or only in rare moments of calm? 

    • Hope, I do always believe them. Can I always practice flying? It’s hard.

  • ChristianB

    Beautiful. Break free from the list thing, man, you’re a great writer.

  • Kglevine

    Nice and also good to accept that in time we don’t always fly, but until the fall takes us to our grave usually we can crawl back to our feet and be grateful we survived.  Stay strong. 

  • Anonymous

    “We’re all just passing through” was simplistic phrase my uncle would say while I was growing up. It made me feel like life is fleeting even at that immortal age. Then I remembered a quote on a billboard while driving through beautiful Newark NJ that I didn’t understand “rushing to your death?” It was put there by an artist from Hoboken and the real message is “when you truly embrace death, you can embrace life” which I kinda get. There’s a lot work embracing life and being happy, so lighten up and drink RED BULL!

  • Anonymous

    My net is my creativity. Creativity is spirit manifested, and the spirit itself is indestructible, even though the products of it may wither and die. 

  • FGS

    Strip clubs in Miami after dinner at the expensive steak place by Government Cut? Sounds like a hedge fund gathering I attended! Wow! Those pirates knew too well how to spend investors’ money lavishing promoters with alcohol, food, and sex!

  • Onebornfree

    “Then the two buildings five blocks from where I lived blew up.” James, if you re talking about 9/11, it was 9 buildings, that “blew up” not 2.  My apologies if my guess about what you were referring to was wrong. Regards, onebornfree

  • Jovanu

    Flying seems so rare.  Usually as strenuous exertion just to slow the fall. 
    James I appreciate your focus on generating ideas.  And giving of ourselves.

  • Kool post, at first I thought you were really talking about prison. But now I see you meant it in a different way.

    Check out this when you can and give me your comments:

  • Andrew_Ferri

    I’m from NY too!  And america…

  • Pratyush Agarwal

    One week from now, I’m freeing myself from the net, and it is very scary!

  • Sales
  • Foobar

    You are an awesome person man… when I read your stuff I see a lot of myself in terms of the internal struggle and I like that you have worked to over come it. 

  • Jamie Yuikes


  • Anonymous

    This posting reminds me of a song penned by the great songwriter Guy Clark, entitled “Cape.”

    Eight years old with a flour sack cape Tied all around his neck He climbed up on the garage Figurin’ what the heck He screwed his courage up so tight The whole thing come unwound He got a runnin’ start and bless his heart He headed for the ground Chorus He’s one of those who knows that life Is just a leap of faith Spread your arms and hold you breath Always trust your cape All grown up with a flour sack cape Tied all around his dream He’s full of piss and vinegar He’s bustin’ at the seams He licked his finger and checked the wind It’s gonna be do or die He wasn’t scared of nothin’, Boys He was pretty sure he could fly Chorus Old and grey with a flour sack cape Tied all around his head He’s still jumpin’ off the garage And will be till he’s dead All these years the people said He’s actin’ like a kid He did not know he could not fly So he did 

  • I am aware that our life is just a blip of a moment and it demande from us to adjust/change all the time.  Where do we get new energy for it? 

  • Justin

    Man, the closing paragraphs of this post are epic, James… This one is going in the “permanent” file.

  •  Very informative and well written post! Quite interesting and nice topic chosen for the post

  • Amira

    I also have a hard time accepting the permanence of the impermanence and the certainty of the uncertainty. I’m currently reading a book by Ma Jaya called “The 11 Karmic Spaces” and I think you’d like it if you haven’t read it already.
    She says: ‎”All that exists is inside you. All that you seek is available. There is a life, a death, and a resurrection in every moment, in every molecule, in every breath.” -Ma Jaya
    And a very good song (on a topic of our time): 
    And lyrics + translation:
    PS: I’ve fallen into the sheer terror but I intend to grow wings and learn how to fly…