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President Obama's Entrepreneurial Mindset

Posted: Updated:

I can give you
anything but time


I'm  sometimes critical of President Obama because it often seems to me that he doesn't understand people like me – an owner of a small
business in a small town.  

I have not seen much evidence of Obama being in touch with
Kentucky, but
after reading David Plouffe's new book, The
Audacity to Win
, I have become
convinced  that he knows what it takes to run a business.

I'm a devoted student of  Dan Sullivan, the “Strategic Coach" for
entrepreneurs.  I went through Sullivan’s program in Toronto.  Dan has devoted
his life to helping entrepreneurs become better at their craft.  I am convinced that President
Obama operated his 2008 Presidential
campaign with a classic entrepreneurial mindset.

traits of successful entrepreneurs include setting
seemingly impossible goals and challenging conventional wisdom.

Planning to be President of the United
States is a pretty high goal.
 Especially for a guy who had been an Illinois state legislator just five years

When history goes back to studying the Obama
campaign, it will compare it to the William Jennings Bryan campaign of 1896 or
Ross Perot's in 1992.  Those unconventional
styles of
campaigning set the standard for every
campaign after them.

No one focused on Larry King before Ross Perot did.
all candidates find their way to Larry, Leno, Dave, Ellen, Tyra and Oprah.

Now, every campaign is going to organize and raise
money using the
Obama model.

Like a Steven Jobs or Bill Gates, Obama changed the dynamic.  

But unlike
Bryan and Perot,
Obama won.

And he
did in classic entrepreneurial fashion.  He developed a campaign plan that
opportunities that seemed crazy to "Washington insiders.”

It was the same way Steven Jobs and Bill Gates seemed crazy to IBM and Xerox.  Or the way that Google seemed crazy to Microsoft.

A good entrepreneur takes what "the
professionals" see as disadvantages and turns them into advantages.  

Jimmy Carter had one of the most innovative
campaigns of
the modern era.  People laughed when an unemployed, former governor of a Southern
state decided to be president.  Carter understood that being unemployed
allowed him to campaign full time, and that being Southern allowed him to connect to a large segment of
the population who didn't want George Wallace as the primary symbol of southern

Obama took the unconventional candidate theory to a new
extreme.  We have not had many senators become president, and especially not many one-term senators.  I can't think of another president who was raised by an unmarried,
single mother.  I’m sure
Obama is the first president born in Hawaii.  He’s younger than all but a
handful of presidents and has an unusual name. 

 Also, did I mention that
he is African-American?   

As Plouffe's book points out, Obama's
"negatives," like Jimmy Carter's negatives, turned out to be

Plouffe noted that among people who voted in the 2004 George W. Bush- John
Kerry election, Obama beat McCain by only a 50% to 49% margin.  Depending on how
the electoral votes would have played out, Obama could have narrowly won, narrowly lost or faced the
same fate as Al Gore.

Instead, a huge turnout by African-Americans and younger voters propelled Obama to a landslide victory.

Obama did not run the
campaign by conventional rules.  He
developed his own rules and made them work for him.

It’s tough to challenge conventional wisdom.  Everyone wants to tell
you what you are doing wrong.    

Programs like the Strategic Coach teach
entrepreneurs to develop written goals and to have ways to measure how people are progressing
towards those goals.

Plouffe noted the discipline exhibited
by the Obama campaign in sticking to their game plan.
 The early campaign was roundly criticized by "experts" who didn't see the same
vision that the Obama people saw.  

I was impressed by how they were able to use matrices to measure
every aspect of the campaign, like fundraising, organizing and coordinating, to track how successfully the campaign was meeting its plan.

It has been said that anything that
can be measured, can be obtained.  In Obama's case, that
included the Presidency of the United States.

 Dan Sullivan built most of his
coaching philosophy around something called the "entrepreneurial time
system."  An entrepreneur's time is the
most precious resource of any business, and it needs to be treated as such.

I've seen way too many political candidates and business people
try to be everywhere, doing everything, and who wind up being nowhere and
getting nothing much done. 

Until I read The Audacity to Win, I had no idea how
much campaign focus was directed
to proper use of Omaba's time.  Time was also scheduled for the
candidate to relax and spend time with his family.  There was a lot of pressure
to have Obama go to outside  debates and rallies, but the plan called for him to stay focused on the Iowa primary and never to waver from
his central message.   

His highly favored primary opponent, Hillary
Clinton, did not manage her time as
well and had a litany of campaign messages.  Obama against Clinton was like
watching an energetic start-up go against a bureaucratic

We all rooted for David over Goliath.  Entrepreneurs are those who
can look at Goliath and recognize
that a giant can be taken down.

Just like Barack Obama took the Presidency. 

Don McNay, CLU, ChFC, MSFS, CSSC is
one of the world's leading authorities in helping people deal with
Money” issues.


is an award winning
,  syndicated financial columnist and
Huffington Post Contributor.

You can read more about Don at

founded McNay Settlement Group, a structured settlement and financial
consulting firm, in 1983
and Kentucky Guardianship Administrators LLC
in 2000. You can read more about both at

has Master's Degrees from Vanderbilt and the American College and is in the
Eastern Kentucky University Hall of Distinguished Alumni.  

has written two books.  Most recent is Son of a Son of a Gambler: Winners, Losers
and What to Do When You Win The Lottery

is a lifetime member of the Million Dollar Round Table and has four
professional designations in the financial services field.