Entrepreneurial Critical Thinking

Big Red Car here.  Well, another day in paradise.  Hot, sunny and glorious!

Or, so, thinks the Big Red Car.


Speaking of thinking, one of the things that The Boss recommends to all of his CEO coaching clients is to think and plan before “doing”.  As obvious as this sounds, sometimes it is received as if it were revealed truth.  CEOs, particularly startup and small company CEOs, do not spend enough time thinking, planning and committing those plans to writing.

The continuum of Vision, Mission, Strategy, Tactics, Objectives, Values and Company Culture requires a bit of thinking and this thinking must result in written plans.  Entrepreneurial critical thinking?  Yes, indeed.

Thinking, critical thinking, requires information and one of the best ways to obtain the requisite information to create well conceived plans is to read.


Reading informs the CEO on subjects upon which she may not be fully knowledgeable.  Makes sense even to a Big Red Car, no?

So what are you going to read?

1.  Read the Web.  Places like StartupManagement are a damn good start.  Look for it here.  SUM <<< link.  I particularly like this aggregation and curation site because it is owned and run by a seasoned entrepreneur, my friend William Mougayar, who has been involved in the curation business for decades.  He has damn good judgment.

2.  Read the current startup literature — search for the best books on the Web.  Many of these are trendy and should be read with a bit of skepticism but they also contain lots of real world information.  And the “real world”, well that’s the world you’re operating in, Old Sport.

3.  Read a bit of the more traditional business literature — Hell, even read a bit of Drucker.  Yes, Drucker.  Drucker had it figured out before most of the current authors’ parents were born.  Sorry.  [No, Drucker’s generation did not invent sex either and neither did yours but Drucker was closer to the time of invention than yours.  Sorry, Sport.]

4.  Read “good books” like The Checklist Manifesto, Rework, The Power of Alignment, The Northbound Train and other books which have stood the test of time but are not “trendy”.

5.  Last, and here is the one I want to talk about today — MILITARY HISTORY.

WTF, Big Red Car, military history?

Military history is particularly good for entrepreneurs because by its very nature it deals with chaos, conflict and panic.  [Hey, Big Red Car, that sounds like the startup business, doesn’t it?  Yes, Grasshopper, it does, indeed.]

Military commanders are the ultimate entrepreneurs — standing up and training their units for operations under extreme conditions, taking casualties and refitting their units on the run and achieving successes which come at a cost.  Talk about some market competition, eh?

Military successes are never complete successes.  Military commanders still have to bury their killed and heal their wounded.

Two great books to read are Washington’s Crossing <<<link here and The Bitter Woods.

Washington’s Crossing

Washington’s Crossing is the story of the attack on Trenton in the Revolutionary War in which George Washington having been chased across Long Island, Manhattan, northern New Jersey and hunkered down across the Delaware River decided to execute an amphibious double envelopment against an enemy — the Hessians — he had never bested in combat in the middle of the winter.  [Whew, George Freakin’ Washington — big brass balls or what?]

From a purely military tactical perspective, this battle plan was easily the most complicated battle plan ever conceived until in history.  And, the poorly organized Continentals, our kin, made it work.  Be proud of those soldiers.  They birthed our country that night,.

This battle was arguably the pivotal battle of the American Revolution as it showed that the American Generals — well, Washington anyway — were the equal of the Brits and could beat them in open combat.  It was ballsy, daring, creative and well executed.  It defines American military prowess to this day.

The battle was like an entrepreneurial pivot and the analogy and comparisons are very apt to what an entrepreneur would do in the same business situation.  You will see yourself in Washington’s saddle.  It may be a damn good fit for you.

The Bitter Woods

The Bitter Woods is the story of the Battle of the Bulge which had it not been turned into an Allied victory could arguably have driven the Allies off the Continent.  It is a story of intelligence failure, incredible planning and execution by the Germans and a fierce and resolute reaction and counterattack by the Allies led by American arms which absorbed, contained, turned and defeated this daring attack.

In both of these stories, one sees the American entrepreneurial spirit writ large on a canvas of challenging conditions, intense competition, forceful leadership, daring plans, exuberant execution and keen analysis.  This is what the American businesswoman and man does every day — react to a fierce and unforgiving market.

Enlightened and expansive reading arms the entrepreneur with information which supports critical thinking when you face your moments of entrepreneurial crisis and panic.

You will be like Brigadier General Anthony McAuliffe, acting commander of the 101st Airborne Division at Bastogne, who when solicited to surrender by a tremendously superior German force said the most eloquent word ever spoken by an American military commander:  “Nuts!”

At first, the Germans could not figure out what he meant but they soon understood.  They resumed their attack and learned even more.

On the strength of that determination, the 101st Airborne held Bastogne against incredible odds and German assaults forming a fulcrum against which the Allied counterattack was leveraged and the Germans were beaten back.

One man — one entrepreneur — standing firm in the face of incredible market forces.  NUTS!

That entrepreneur, Old Sport, is you!  Of course, you have to read the book The Bitter Woods written by Eisenhower’s son by the way.

But, hey, what the Hell do I know anyway?  I’m just a Big Red Car.

3 thoughts on “Entrepreneurial Critical Thinking

  1. Awesome post BRC, thanks for the words of wisdom and advice. Tough to see through the trends sometimes especially as a youngster – good to remember that many have been through this before and are ready to share their advice.

    • .
      Joseph —

      The Big Red Car likes to say — this generation did not invent sex or business. Neither did the Big Red Car’s generation.

      It is cheaper to learn from someone else’s experience than to pay full tuition this time around.

      Thanks for stopping by.


  2. There are so many parallels to entrepreneurship and the military. But, one of the downsides of the military is that it is highly structured. There are norms that are built in that take randomization out of a lot of processes which make things highly efficient.

    Managing startups is different because the employee can say “no”.

    But, the strategy piece, pivoting in the heat of battle, and the way that troops can be motivated are highly valuable to entrepreneurs.

    Another one to watch is in Band of Brothers when they take out the 88 nests. They came up with that strategy on the fly-and it became textbook strategy for the military.

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