The Freestyle Entrepreneur

I’ll get to the title in a minute.  First, I must start by saying that I love to hit the floor running hard every day in the quest for business.  I also love to end the day exhausted, spent, without anything left to give.  Family and friends have told me there’s only one thing worse [...]

 
You don’t “stand” your business.
You don’t “walk” your business.
You “run” your business!
Ready?  Set? Go!
        –    John R. Ingrisano
               The Freestyle Entrepreneur
 

The nature of being an SBO invites burnout.  That’s because, if we’re doing it right, we come home every night on empty – bedraggled, worn out, totally spent.  That can take its toll over time.
I know I’m approaching burnout when I begin having weird fantasies.  In addition to the one about two showgirls and Las [...]

 
On a quick day trip to Milwaukee yesterday, we scheduled dinner out with my son, his wife and their three children.  Jonny (Jonathan to the rest of the world) is a successful, 35-year-old partner in a mid-sized law firm, who maintains a good balance between super-long work weeks and family time. 
 
During dinner, he apologized for being distracted, explaining [...]

 
It has been my experience that there are two kinds of people in this world:  those who dare to dream big and exciting and wondrous dreams … and those who live in little boxes waiting for someone to tell them what to do.
 
Where do you want to be in a year?  In two years?  In [...]

Hard Work Trumps Brains
 
My dad was a plodder … but he plodded his way to become an MD and picked up the title of “Nassau County Family Physician of the Year” two years in a row.  I also know a couple of millionaires.  I can beat the pants off them in a game of poker [...]

 
When I launched an ill-fated business in the Caribbean years ago, I never quit working to find ways, each and every day, to cut my costs by a fraction here, raise my sales by a smidge there, etc.  It was a daily challenge upon which I thrived.  (The business did fail, but that had more to [...]

[ A verion of this article first appeared in the June 2009 issue of Corporate Report Wisconsin.]
 
(This could be titled, “How John Lost His ‘Blink Factor’ … and How He Got It Back Again.”)
 
Like the cat that always lands on its feet, some entrepreneurs consistently seem to stroll through the mine fields of potential disaster and come [...]

[A version of this article first appeared in the May 2009 edition of Corporate Report Wisconsin]

Note to the university professor at last fall’s business conference:  The following is an attempt to explain why I slipped out early during your presentation on “The New Economics.”
 
As a business writer, I send out biz-tip email blasts periodically [...]

States Offer Voluntary Disclosure Programs to Help With Delinquent Tax Returns
By Jonathan Medows, CPA
Medows CPA, PLLC (www.medowscpa.com).
Despite the obvious benefits of being your own boss: flexible hours…stimulating daily work…the opportunity to make more money than you can working for someone else, small-business owners and freelancers face challenges unique to self-employment. Along with the likelihood of [...]

 [A version of this article first appeared in the April issue of Corporate Report Wisconsin.]
 
Who has the entrepreneurial spirit?  Not everyone, that’s for sure.  While many people dream about the romance of being self-employed (I know, romance?), most folks aren’t cut out for the life.  So, here’s a tale of two guys and a gal.
Tom [...]

People who know me tell me I’m unemployable.  There’s some truth to that.  I’ve been self-employed since 1985.  I’ve been borderline wealthy and down to my last 17 cents.  I’ve had a handful of employees and had a staff of just me … unless you count Rocky the Boxer and Toni the Golden Retriever.
 
I [...]

I’m a draft horse.  I can plug along for hours upon hours when put to a task.  My brother, on the other hand, is off running the Boston Marathon this weekend.  I admire him and others who work and sweat and train their bodies so they can actually run 27+ miles.  I love them because they not only [...]

Let’s not confuse small business owner with entrepreneur.  Yes, by definition, an entrepreneur is a business owner.  However, I think of entrepreneurs as wildcatters who roam the landscape looking for investment and business opportunities.  Most of us aren’t all that glamorous.  You could say we’re usually mostly downright usual.  For example… 
  
We’re usually amateurs when it [...]

The award goes to Badger Wholesale in Green Bay, Wisconsin.  Here’s why:
 
I was chatting with Dean Tenor last week, when his phone rang.  Dean is the owner of Dairy Deans, a small ham ‘n egger eatery overlooking Lake Michigan in Algoma, Wisconsin.  Dairy Deans is the kind of place where the coffee is strong, the [...]

I am unemployable.  People laugh when I say that, but it’s frighteningly true.  I escaped from corporate America in 1984 (exactly at midnight, December 31st), when I took the plunge into ruining my own life (rather than letting some quasi-competent manager do it for me). 

I never looked back. 
 
No, I’m not all that bright, [...]

 
I’ve been called a control freak and an egoist.  I generally reply, “Thank you.”  I’ve also had people try to get me to make decisions by committee.  The result has always been warm and fuzzy failure. 
 
Any entrepreneur must have a healthy dose of self-love, confidence, a my-way-or-the-highway sense of conviction, and an instinct for [...]

I hadn’t seen Marty in a few weeks, not since his restaurant failed.  The news had left me sad. It’s never fun to watch a hard-working fellow lose not only his money, but also his dream.  Fortunately, he still had his base business: a small tavern, with quarters upstairs for him and his wife.  But [...]

 
Let’s call it like it is:  Tough times ahead!  No, I’m not a doom-and-gloomer.  Far from it.  I am an optimist.  Besides, I truly love the challenge of tough times.  They seem to bring out all the best business instincts in me.  
 
All I’m saying is that it pays to be ready … mentally ready.  I know some [...]

 
It’s early in the downturn, and I’m already seeing some companies — mostly the new kids on the block — going under.  It’s a shame.  How can you guarantee you won’t be next?  You can’t.  There are no guarantees in business!  But there is one thing you can do — work like a dog.
 
That’s my [...]

 
Odds are that business will get a whole lot tougher before it gets easier.  And that doesn’t matter who wins the election. 
 
If McCain pulls off a miracle, let’s face it, the Republicans today are ill-equipped to truly lead. 
 
If Obama strolls into the White House in January, you as a business owner can begin thinking of [...]

(The following article first appeared in the August 2008 edition of Corporate Report Wisconsin.) 
If challenging times bring out the best in people, then these are great times for small business owners.  Those who thrive amid today’s darkening economy are those who are prepared. 
Fortunately, if you’re a small business owner, you’re in a unique position to not [...]

Dissatisfied?  Far from content?  Good!  Leave the search for that warm ‘n fuzzy safe place for the cubicle-dwelling wage slaves. 
 
As a business owner, your dissatisfaction is your motivator, the lifeblood that gets you up and out in search for a new product, a few pennies saved per item on expenses, a new market and a [...]

I know a family in Algoma — a husband and wife team — who are true entrepreneurs.  They have ten ideas, find that three are worth pursuing and end up with one that works.  They explore, they dream, they probe, they learn … and they have no time for naysayers who point out their failures [...]

 Mort, an accountant, stomps the snow off his boots after a day of skiing in Colorado, stokes the fire, pours a cup of coffee and settles down at the kitchen table to work on tax returns for his clients back on Long Island.
John, a business writer living in the Caribbean, punches a button and sends [...]