Great Advice A Young Business Owner Will Never Take

Jerry Winston (not actual name at the request of the family) was a big name in Detroit back in the day. 

He had a passion for racing and bought his first stock car at 23.  His love for the sport steered him toward the automotive industry until he found his niche in trucking.  He started with a single tractor trailer in 1977 and by the mid 80s had over 300 rigs on the road.  

Winston Transportation leased trailers from Xtra Lease  (my only customer at the time) who regularly sent me out to perform mobile maintenance. 

Jerry had his own garage and I made sure I was nowhere to be seen when he came back to mingle with his mechanics;  Jerry was an intimidating guy.  One day, however, without warning he stepped up beside me at the urinal.  “Is that your truck out there?” he asked.

“Yes, sir.”

“Do you own the business?”

“Yes, sir.  It’s just me…” trying to impress, “for now.”   

“I’m gonna give you some advice,” he said.  “When I had a small company I was the happiest I’d ever been.  Makin’ good money, but still had time to appreciate it.  Then we got this deal with Chrysler and have been growing ever since.  The money’s great, but I’ve never been as happy as I was in the beginning when I was small.”

And with that, he was gone. 


What kind of advice is that to give a young, ambitious entrepreneur? The words seemed so alien to me at the time.  Here’s a guy who races cars telling me to slow down and let somebody else take the prize?  

I realize now, 30 years later, it truly was the best advice he could have offered me.  But it didn’t matter.  It was impossible to accept at the time and I’m sure he knew it.  Still, it’s one of those truths wise business owners feel obligated to warn youth about. 

Competition drives our success, but it’s virtually impossible for young business owners to know when to punch it and when to hit the brakes.  If you are pedal to the metal too often, you’re probably missing out on some of the greatest moments of your life.  If you slam the brakes at the wrong time or for the wrong reason, everything you worked for could skid out of control.  

The bottom line, hindsight is 20/20 and sometimes it’s just too risky to stay small.  The goal of the Mobile Maintenance Association is to empower independent business owners so they can remain small and still compete with the largest players in the nation.