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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 He entered the business of purposely offering slightly outdated technological solutions to companies who couldn’t afford to be cutting edge.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!

  • http://shirleyszone.com/ Shirley

    Great lessons from your Grandfather, Brandon :). Great lessons! I loved them and I’ve learnt a lot from it.

    Thanks for sharing these lessons with us :).
    .-= Shirley´s last blog post: The Famous Bloggers Making Money Online Contest =-.

    • Brandon Cox

      Thanks Shirley – glad you found the story applicable!

  • http://www.Bryanmcardle.wordpress.com Bryan McArdle

    Brandon, love the degree story. The fruits of being an entrepreneur are never in the money but in the everyday adventures being an entrepreneur awards us with.

    • Brandon Cox

      Absolutely right! The people we meet and the memories we make are worth a lot more than cash.

  • http://www.famousbloggers.net Hesham @ FamousBloggers

    To much to learn in this post Brandon! it’s very inspiring to see someone make his own success in from of your eyes and learn from him!

    great post!
    .-= Hesham @ FamousBloggers´s last blog post: Facebook Cafés from Lebanon to Bulgaria using Huge Online Brands to Promote Offline Business =-.

    • Brandon Cox

      Thanks Hesham – and I’m thankful there are teachers all around us.

  • tony ramirez

    That’s incredible, its never too late to go into business for yourself. I think that cultivating or casting a big vision is probably the key, because it allows you to develop a main idea of what exactly your shooting for, which leads to all the other roles to occur.

    Oh, one more thing, I love how your grandfather responded:
    “So where did you get your degree?” Without hesitation, my grandfather responded “Bays Fork Academy,”

    • Brandon Cox

      He was always quick-witted that way – another thing that inspired me about him.

  • http://profitsrgood.com Roland Millward

    A really great story and one with some very good lessons to note. Thanks so much for this.
    .-= Roland Millward´s last blog post: 5 Secrets of Successful Blogging =-.

    • Brandon Cox

      No problem, Roland – glad it inspired you!

  • Clinton Skakun

    Good post Brandon,

    Every thing BIG that happens seems to be as a result of a vision. I like what you said about flexibility as well. One of the causes of many businesses dying these days, because they just aren’t flexible(or belong in a different time or decade.)

    Cheers,
    Clinton Skakun

    • Brandon Cox

      Absolutely right – if we’re unwilling to change, we’ve signed our death certificates and are waiting to be finalized!

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  • http://www.alaskastartup.com Morgan Howard

    I’m not a regular reader of this blog or the author, so I might have missed it but… what did the grandfather/Willoughby Communications do and what was the old technology that they embraced?

    • Brandon Cox

      He sold slightly outdated telecommunications equipment (office phone systems, wiring, etc.) to companies that needed updated, but not necessarily fiber-optic systems.

  • Car Transporters | Igor

    Thank Brandon for this wonderful post, Very Interesting.

    • Brandon Cox

      No problem, Igor!

  • http://weblogredux.com Hal Brown

    This reminds me of my some people I have known from the WWII generation, people I had forgotten. It is both inspiring and a reminder that history is important. It is not always what we can learn from the giants (Edison, Ford) but the history of those close to us.
    One of the best days of my life I spent with a brilliant woman who helped develop real estate in Dallas after the second world war.
    Great post!

    • Brandon Cox

      Thanks Hal, and I totally agree!

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  • http://moralde.com/ James Moralde

    Yes, it all begins with a vision. So many great achievers have said this as to be beyond doubt. It must feel really great to receive this words of wisdom from within your family Brandon. You saw with your own eyes how these nuggets of wisdom worked powerfully in front of you. Compare this to others who just read it from books and have yet to see real life instances of their effectiveness.
    .-= James Moralde´s last blog post: AmplusnetPrivacyTools.exe Eating Up CPU Resources =-.

    • Brandon Cox

      Very true, James, and I’m permanently thankful for his example. And I often see myself doing things he would have done – must be in the blood… I hope.

  • young entrepreneur

    This is a great post and one I think will help a lot of people.

    All the time we see people telling others that they should try an original approach and then just copying others.

    The lesson I think isn’t to copy what he did but to copy the idea of creating an original solution, and not letting others tell you it won’t work.

    • Brandon Cox

      Absolutely! And, for the record, he sold his business at its peak and retired rather than trying to keep alive an idea that probably was about to lose steam.

      Copy what he did exactly and you’re headed for bankruptcy, haha. Good point.

  • http://digitivity.org Digitivity @ The Digital Life & Tools Blog

    What an inspirational post!

    Most of our grandparents (other than those born into money) have such stories to tell.

    Our grandparents’ generation faced real adversity, and I think we can learn from that.

    For most of us, the only adversity we’ll have to face is our computer crashing.

    So if our parent’s parents could make it, so can we.
    .-= Digitivity @ The Digital Life & Tools Blog´s last blog post: Matt Mullenweg Creates the WordPress Foundation =-.

  • http://twitter.com/napwinc Larry Jacobs
  • http://davidshawblog.com David Shaw

    These are some pretty awesome lessons..

    Was not sure what I was about to read when I saw the word milkman in the title but was a good read.

  • Fran the Online Writer

    Hi Brandon:

    You have a post that is an awesome read, very inspirational. I have a suggestion for you. If you publish your story, in the form of motivational books for children, and promote, it could be a best seller and think of the benefits it will give to young readers. I am more concerned about doing something for the next generation, and I am sure you are that kind of person too.

    Good luck

    Fran A