How I Missed 400 Points In Apple (aka…In Life, Always Go For The Cubans).

I am not one of those hip people who gets waived past the velvet rope right into the club, and if I do get in, I am terrible at getting the bartender’s attention. I just stand at the bar and watch as people on both sides get their drink orders taken before me, while I try to figure out what I’m doing wrong.

My brother-in-law Dan is exactly the opposite.  It’s like his hand is permanently affixed with one of those stamps you can only see under an ultraviolet light.  He always knows the doorman. He used to date the waitress.  The bartender is his best friend.  He is the essence of bar cool.

A while back he came into town and in an attempt to show him how cool I could be, I took him to a great little cigar bar I know of in Los Angeles.  I had been there a few times before and had noticed that there was a humidor “behind the humidor” if you know what I mean.  If you don’t, I mean that there were real Cuban cigars in that second humidor, which although the best in the world, are illegal to sell in the United States (thanks a lot JFK).

I had worked up a good rapport with the bar owner and was pretty sure that I had become enough of a regular that I would soon be offered “The Cubans.”  I primed my brother-in-law, who had never smoked real Cubans before, and left him with the impression that we were “all dialed in.”

We arrived and took a seat at the bar, and the owner recognized me right away. This was a great start to the night and I felt that my “cool” quotient had already started to rise.

He asked us what we wanted to smoke and I told him that I wanted him to pick up out something “special,” while doing my best “wink wink, nudge nudge, say no more” routine.

“I know exactly what you are looking for,” he said, “I’ll be right back.”

He walked towards the humidor, and not wanting to look too anxious, I kept my back to him. I leaned forward towards Dan and whispered, “is he going to the humidor behind the humidor?”

“No,” he replied.


He came back with a couple of great cigars, but they weren’t Cubans.  I was not sure where to go at this point.  I thought I had given all the correct non-verbal cues; that the tone in my voice spelled it all out.  But my fantasy of finally being part of the “cool” crowd was fading away fast.

We smoked the cigars and drank our drinks, and Dan suggested we have another round of both.

This was it. This was where I was going to make my stand. All or nothing.  Home run or strikeout. Sydney or the bush.

I called the owner over, ordered two more drinks, and then told him “we want the real special cigars.  You know ‘los mejores’,” as if using my high school Spanish on him would seal the deal.  I probably looked like I was having an epileptic seizure as I simultaneously motioned with my head, trying to convey the universal signal for “you know, the humidor behind the humidor.”

“Ah ha.  Got it!  Back in a second,” he said.

“Is he going to the humidor behind the humidor?” I feebly asked my brother-in-law, the last bit of my hip quotient hanging on life support.

“No,” Dan replied.

I was crushed.  I did not get it.  I would never get it.  What did I need to do to get this to happen?

When he returned with two more non-Cuban cigars I thought there was no choice but to accept my fate and just smoke the ones he gave us.  As I was just about to reach for one of them, my brother-in-law leaned forward and said….

“We want the Cubans!”

We want the Cubans?  Did I hear that right?

I was shocked.  I was mortified.  You can’t just blatantly say something like that!  You need to be subtle. You need to be smooth. You need to be strategic and analyze the situation, waiting for the right time to….

“Oh…..!!!,” said the owner, “You want the Cubans?  Hold on I will be right back.”

I was 42 years old, and in that moment I instantly realized that I had spent a large part of my life in the “analysis” mode instead of the “action” mode.

Looking back, how bad had it been at times?

I’m nineteen years old and my best friend and I are going over to his girlfriend’s mother’s house. She is gone for the weekend, and his girlfriend has two of her friends spending the night.


I am told one of the girls, Vicki, is a model who has been in jail.

Double schwing……!!!!

We get to the house and start to party. Everybody is hanging out in back by the pool, drinking Corona’s, and getting loose.  After a while one of the girls says she is tired and is going to bed, followed quickly by my friend and his girlfriend.  That just leaves just me and Vicki.

Vicki wants to get in the hot tub, but “oh no,” neither one of us has brought a bathing suit.  “Let’s just skinny dip,” she suggests.  At this point I can actually hear the cheesy porn sound track start to play in my head….

“Bump chicka-bump buuuump bump ba, bump chicka-bump buuuuump bump ba…!!!”

In one seamless and fluid motion she strips her clothes off, grabs her beer, lights up a clove cigarette, and slinks down into the hot tub.

Now stay with me here.  I am sitting in a hot tub, naked, alone with “hot-model-ex-con-chick,” who is drinking a beer, and smoking a clove cigarette……


And in that moment, the thought running through my head was, “I’ve got to figure out the right time to try and kiss her.”

Last week I highlighted a blog post about $AAPL that I did in December of 2008, when it was trading around $85.00.

As I re-read that post for the first time in over four years It reminded me how much thought and detailed analysis I put into it, and how much in-action it led to.

And it just wasn’t when $AAPL was at $85.00.  I remember talking to my friend when it hit $170.00, saying that we should just drop some money into it and “put it into a drawer.”

The same thing happened again and again over the years in the 200’s, 300’s, and 400’s….each time I “analyzed” my way out of buying it.  Now that I think of it, I did the same thing with $BIDU when it was at $88.00…..pre-adjusted for the split.

AAAAARRRRRRGGGGHH……!!!!  These were my market versions of the hot tub and cigar bar.

We know that as market participants we have to do analysis (even if we don’t want to), and that we can’t just randomly “go for it” without using risk management.  But I let over-analysis get me so micro-focused that even though I could see the overall macro picture unfolding, I couldn’t act on it.

I am not saying that I would have held $AAPL from $85.00 straight up to the current low 500’s, but surely I could have taken some 50 or 100 point chunks out of it, instead of trying to day trade it for crumbs here and there.

This revelation is particularly painful given the fact that my friends and I used to joke in the late 90’s that someday our kids would ask us, “daddy, didn’t you have a computer in the 80’s, and didn’t it have Windows on it?”  We would then have to rationalize to them some contemporaneous excuses for not buying $MSFT.

Nobody can expect to catch and act on every opportunity that presents itself in life, but taking yourself out of the game before you even have a chance to play is just wrong.

I know someday I will have to answer the “didn’t you have an iPod back when…” question to my kids, just like I had to answer the “weren’t you in a hot tub with…..” question to my friend.

My goal though going forward in life, is to never have to ask myself the “why didn’t YOU go for the Cubans….” question again.

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  • Pingback: How I Missed 400 Points In Apple (aka…In Life, Always Go For The Cubans). | HIA Research()

  • Edward H. Tran

    I just wish I have stories like you to tell folks! You’re so damn funny!

  • NT

    I love it… thanks for a good healthy LOL… both cuban cigars and ex-con chick are all good 🙂

  • Could be worse

    You could have been in ‘action’ mode and bought Sino Forest, and why not what a great stock. Real Assets AND China exposure? And co invested with the great John Paulson?

    For every great should have could have there must be a dozen thank god i didnts, no?

  • I think the same thing applies to the Facebook ipo that everyone is over analyzing but will clearly rise in value for a long time

    • Could be worse

      like linkedin and groupon and zynga is up 36% since ipo so to the moon!

  • gregorylent

    you are lucky … your spiritual journey, with all its pain, its confrontation with limiting self-concepts, is clearly seen … it is your daily and professional life.

    the downside is that there are no gurus for the deep stuff, or better, no vocabulary for the healing that has to happen. just gurus for trading. not quite enough to get free.

    maybe expand your circle a bit?

  • J

    Funny- I know exactly which cigar bar you’re talking about.

    • bclund

      Really….do you live in LA?

  • Lone_hand

    Wait a second. You need to finish the story. what happened to the clove cigarette.

  • Chris

    I’m guessing the hot tub was when you learned about “risk management” and “mental stops”.

    • bclund


  • Conrad

    I’m normally a non-action analyzer, but for some strictly intuitive reason starting in 2006 every time I got a bonus at work I’d buy 10 or 20 Apple Shares. I stopped buying when the shares hit $140, but have held them since then. I now have 300 shares worth $522 a piece. Not bad for a small timer! I think I’ll hold on to them for a while longer. My only regret is that in the spirit of ‘diversifying my portfolio’ I bought a couple other things that have done poorly. I look back and wish I had put it all in Apple.

  • Offgrid

    Just be happy that you didn’t but 100 shares at $70, watch it climb to $200, only to watch it drop back to $90 in 2008 (when the Stock Market was collapsing) . SELL everything …. and then sit on the sidelines while it climbs to $520 !!! That hurts.

    • I bought it at $79 after it crashed – sold it 2 weeks later at the same price, and watched it go to $525…..

      • bclund

        I so relate….

        I have to say, I was actually starting to get interested in doing some homebrew of my own (have no experience in it but love beer). However I saw one of your recent posts about a batch you did, and it totally intimidated me. It just looks so complex. If I did decided to try it, any suggestion on the best way to ease into it?

  • Great story!! I’ve ridden AAPL and BIDU both since $120 & $600 (pre-split) for some nice profits, but just wished I’d put them in a drawer back then and didn’t obsess day-in/day-out over entry and exit points.

    I, too, want to know what happened in the hot tub – but being a chick, I can pretty much guess….

    • bclund

      “I, too, want to know what happened in the hot tub – but being a chick, I can pretty much guess….”

      Your guess may differ depending on if you are as you say a “chick” or a “hot-model-ex-con-chick”….LOL!!!!

      Let’s just say I was on over-analysing dork at that time…..but not THAT MUCH of an over-analysing dork 🙂

      Thanks for reading, I appreciate it.

  • John Mc

    Same story here. Bought Chipotle @$170 Sold @ $286 now its $386 … More importantly what happened in the hot tub?

    • bclund

      “More importantly what happened in the hot tub?”

      Hah….I will have to wait until Playboy picks up my blog to reveal that one… 😉

  • wait wait wait.. I was reading along, enjoying this Quality Post, and then I got to this part:

    “And in that moment, the thought running through my head was, “I’ve got to figure out the right time to try and kiss her.”

    Last week I highlighted a blog post about $AAPL that I did in December of 2008, when it was trading around $85.00.”

    did you have an error where you cut out a few paragraphs by accident? WTF HAPPENED IN THE HOT TUB?

    • bclund

      Yeah, sorry for the “storius interuptis”…lol.

      Some night when you are I are halfway through a six-pack of your homebrew, I promise to tell you the conclusion 🙂

  • Great story! This one certainly resonates, as a scientist I tend to overthink and over analyze big time. Its a tough thing to integrate, an overall grand scheme that requires a “go for it” attitude with a near term plan set with rules and process. Great work Brian.

    • bclund

      Thanks. This is what I was saying to you the other day about “transitioning”. It’s all good stuff though. Thanks for your support buddy.