Entrepreneurial Lessons from a Poor Milkman

My grandfather had an eighth grade education and spent the early part of his adulthood as a milkman, barely scraping by to put food on the table for his wife and four children. When he hit middle age, he caught a vision to start his own business with the goal of earning one million dollars.

His idea was somewhat radical. At a time when companies were embracing new communications technologies, Willoughby Communications, Inc. stepped in to offer smaller companies older solutions. That’s right. He entered the business of purposely offering slightly outdated technological solutions to companies who couldn’t afford to be cutting edge.

Certain stories stand out in my mind about my grandfather and though he passed away many years ago, I still hear his voice in my head reminding me of some pretty important entrepreneurial principles that are really quite timeless. For instance…

Cultivate a Big Vision

When my grandfather stopped driving his milk truck and went into business with his brother-in-law, he had in mind that he would build a communications company that would some day earn one million dollars. Shortly before selling off the remainder of his life’s work and entering retirement, he reached his goal.

The lesson for entrepreneurs? Aiming high and missing by a little is far better than aiming low and hitting the target. Think big!

Find a Niche and Own It

In the 1980′s (when I grew up), everybody wanted to be on the cutting edge. This was the decade Macintosh was born, after all! The phrase “fiber optic” was the buzz word in communications technology, but my grandfather saw an enormous number of businesses that had an unmet need. So he met it and did so quite successfully.

The lesson here? Don’t necessarily follow the crowd. Sometimes the greatest opportunities get missed by everybody on the bandwagon.

Strive to Remain Flexible

My grandfather once commented that if you always want to have something to do – do something nobody else wants to do. The example he used? Plumbers always have work because very few people want to mess with crap. The business my grandfather entered into didn’t offer the glamor of being the next AT&T, but it was his sure path to success.

This principle is simple… be ready to adapt to the voids left around you and you’ll always be in business.

Control Your Personal Brand

One of the funnier stories I remember hearing pertained to a company CEO who contacted Willoughby Communications, Inc. (which was two partners and a couple of employees) to request more information. With somewhat of a haughtiness, the CEO asked my grandfather, “So where did you get your degree?” Without hesitation, my grandfather responded “Bays Fork Academy,” which was the name of the one room schoolhouse where he’d received his eighth grade education.

This story has always inspired my own self-confidence. Be the first to set the tone for your personal brand.

Enjoy the Journey

My grandfather was able to make a comfortable living and store up a nice retirement nest egg, but I don’t think the financial gain was the biggest benefit of his work. He had the privilege of traveling to every one of the United States with the exception of Hawaii. He even managed to get frostbite in Alaska while meeting with a company executive.

My grandfather flew all over the country, and drove a couple hundred thousand miles. Imagine all that he saw! Maybe this is the biggest lesson of all… in your drive toward entrepreneurial success, don’t forget to stop and see the sights along the way. Don’t forget to enjoy the journey!