Know When Told Hold Them, Know When To Fold Them

So the other night I was talking with a good friend and colleague Steve Swedler, who is also Chief Product Guy at Gangplank.  We were talking about product development, the state of things in Phoenix and a myriad of other topics.  I tend to be a fairly hard core pragmatist.  I generally tear ideas apart (including my own), even when I really like them.  This has earned me a little bit of a reputation as the dream killer.  I have agreed to only “kill one dream per day” in the spirit of innovation.  I remain oft conflicted as I am also a staunch idealist.  Always believing and fighting for the underdog in most fights, especially when a great idea/ideal is at stake.

Steve mentioned he had been thinking about “how children believe anything is possible and that we tend to try to be realists as we grow up.  No matter how much of dreamers we think we are, but the truth is that anything is possible…”.  Oddly this is something I think about intensely on a regular basis.  I think we crush the creativity out of our children and limit our potential daily because we don’t “believe”.  However, I also think that dreaming big without having the capability is ultimately frustrating and so at some point there has to be honesty within ourselves and others.  This is my notion of practicing “pragmatic idealism”.

If I wanted to become a professional soccer player, when I’m on the verge of turning 35 and being overweight by 100lbs.  I might be pushing the limit of pragmatism, but it might not be entirely impossible either.  However, I suspect it would end in frustration.  However, there are many dreams that are not likely possible in fact even highly improbable, but attainable given the right circumstances.  For example creating a search engine to displace Google.  While not likely and highly improbable for most people it is certainly possible, despite what others may think.

I think the pragmatic part comes in being honest with yourself and in your pursuits.  Too often we continue down paths that aren’t going to happen far too long.  I definitely think it’s worth STARTING down the path, but knowing when it’s becoming fruitless is the hard part.  I have observed over time that people generally fall into one of two buckets when pursuing their dreams (self included).

  1. They keep going down the path long after they have passed the law of diminishing returns.
  2. They turn and go back (give up), just before they are really ready to hit stride.

*Note this would be similar to Seth Godin’s concept of “The Dip”

Overall, when I look at those that have come out as the dream catchers and successfully hit their goals, I see a pattern, a wisdom.  I think perhaps my mother’s favorite singer (Kenny Rogers) nailed it best.

You got to know when to hold em, know when to fold em,
Know when to walk away and know when to run.
You never count your money when youre sittin at the table.
Therell be time enough for countin when the dealins done.

Now evry gambler knows that the secret to survivin
Is knowin what to throw away and knowing what to keep.
cause evry hands a winner and evry hands a loser,
And the best that you can hope for is to die in your sleep.

You see dreams are kind of like a poker hand.  Regardless of what you are dealt you stand a chance to walk away a winner.  It’s all a matter of knowing the game, the players and when to go all in and when to quit.  I encourage you to at some point watch professional poker players.  They usually know their strategy the minute they see their first two cards for a hand.  Sometimes they fold before placing a bet and other times they will ride what appears a miserable hand to glory.

They are able to quickly assess their hand, their competition and the situation.  Calculate the odds based on all three factors and make a gut decision.  When I get pitched an idea, I kind of think of that as the first two cards dealt.  I have to take a hard look at what those cards are and what I think the competition is holding as well as the situation and the odds.  Sometimes it is time to fold them and other times it’s worth putting some ante on the table to see the flop.  Generally I see the prototype as the flop.  This gives a good indication on how the other players are perceiving the market and how strong the hand really is.

Remember there are many factors that go into folding or calling.  Including how many chips you have on hand (are you playing a short stack or leading the table?), the presence of the players in the game and how you are feeling at the moment.  Life circumstances dictate how aggressive you can be in taking risks on your dreams.

Moral of the story?  The best way to get good at poker is to play a lot.  I think the same goes for pursuing dreams.  Invest in yourself and your dreams.  Teach yourself through trial and error to know when to hold them and know when to fold them.  When you think have it down, start to go after your really big dreams, but above all don’t get caught up in the game.  Be honest with yourself and know what your odds are and what you are risking and bet accordingly.  Most of all, have a blast doing it.


  1. Yes,

    I have had a few projects and businesses I rode into the grave.. should have bailed sooner. But others I thought were dead, came back to payoff huge. Timing is always the Wild card.

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