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Charles Waugh
Structural Engineer
Bellingham, Washington
Extraordinarily helpful
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Five Business Lessons from Mark Twain

Twain was a very successful writer and publisher, who made a fortune at these pursuits. He was a technological visionary -- who lost a fortune backing an inventor. We can learn much by the lessons of his life.
Written Dec 02, 2010, read 2071 times since then.


In an age when digital media are triumphant, the release of Mark Twain’s unexpurgated autobiography published by The University of California is a triumph of the printed word.  The four pound (!) book, retailing for $35, has sold 275,000 copies.  That is truly an amazing run for a man dead 100 years.

Twain was no stranger to success in publishing in his own time, either.  He was a peerless self promoter.  Huckleberry Finn was a triumph, both critically and in terms of sales.  He also published the biography of General U.S. Grant, directed its distribution, and made large profits both for the Grant family and himself.

He was a giant in writing and publishing.  Nevertheless, he was generally an abysmal failure in business.  It was not for lack of foresight.  Twain was a visionary.  He could see changes coming to the world, though he never lived to even have an inkling of the electronic revolution.  One of his stories, “Captain Stormfield’s Visit to Heaven” was about a starship!  (Perhaps it was the basis of a Star Trek episode in which Mark Twain was a character!) 

Huckleberry Finn was the first novel written on a typewriter.  Twain certainly was not stuck with the notion that all that needed to be invented already had been invented.  He had the sort of vision that business people today would appreciate.

But while he could see the value of technology, he was not himself an inventor.  He had no business plan -- he improvised as he went along.  The result was tragic.

Those of us who are familiar with his story know that he spent a fortune on backing the development of a typesetting machine.  His vision was to be realized – but not by his machine.  He poured more and more money into his machine, whose inventor he described as a “Shakespeare of mechanical invention.” All was to no avail.  The Linotype was to prove more practical, and for more than 75 years remained the standard by which newspapers were printed, worldwide. 

He was advised to seek the protection of bankruptcy, but refused to do so, feeling that it was unethical.  So, he set off on a lecture tour late in life -- causing him great unhappiness --  to repay his creditors.

What lessons can we learn from Mark Twain?

  1. Know your skill set.  If we are inventing / starting a business / working with a business partner whose skills we understand, we have a set of instincts we can trust.  If not, we must be more careful.
  2. Set boundaries with partners.  If we are just backing somebody else whose skills are a black box to us, set firm boundaries.  Set a limit at the beginning as to how much we are willing to risk. 
  3. Get another opinion when needed.  If there seems to be a situation developing in which success is always just over the horizon, call in another opinion.  Are you nearing success, or just getting fleeced?  Biznik contacts can help with this!
  4. Learn from mistakes, don't just repeat them.  Don’t let business decisions be made the way gamblers think.  “Next time I will win big!” is a sign of distorted thinking.  Be rational!  For the great majority of us, it takes a lot of time and effort to attain success.  I think every business person can agree, we can learn from mistakes, not just repat them.
  5. Do what you know and what you love.  Most of all, do what you know best – and what you love.  Twain was a brilliant writer – William Dean Howells called him “The Lincoln of our literature.”   Kipling, who met Mark Twain, compared him to Cervantes!  Imagine what he could have done had he not wasted so much time and effort on the typesetting machine.  Imagine how much happier he would have been.

Mark Twain, the persona of Samuel Clemens, was brilliant.  But poor Sam Clemens was vulnerable to those who took advantage of him.  This was the story of his life, as reflected in the title of Justin Kapaln's brilliant biography, Mr. Clemens and Mark Twain.

Samuel L. Clemens – Mark Twain – might take me to task for my writing style.  Still, having read his edited biography (and parts of the unexpurgated autobiography) I feel certain that he would agree with the lessons to be learned from his business experience.  A sadder but a wiser man would he be.

Learn more about the author, Charles Waugh.

Comment on this article

  • Communication and Personal Coach  
Seattle, Washington 
Jenny Davidow
    Posted by Jenny Davidow, Seattle, Washington | Dec 02, 2010

    Wonderful article, Charles! Twain certainly is a great example, both of what to do, and what not to do, in business! What a talent. I take much inspiration from him. I think he would be amused that his biography, this time the unexpurgated real deal, is a best seller one hundred years after his passing.

  • Entrepreneur 
Seattle, Washington 
Michael Hartzell
    Posted by Michael Hartzell, Seattle, Washington | Dec 02, 2010


    Excellent topic. I love Mark Twain (Sam)

    A few random thoughts as I read ---

    "The greater the idea, the more resistance it will receive." Who said that?

    3 "If there seems to be a situation developing in which success is always just over the horizon, call in another opinion."

    Opinions are good but not for quashing visions... only to see the minor barriers and more quickly think of solutions.

    2 Set a limit at the beginning as to how much we are willing to risk.

    This is always true. Part of a business plan. ROI.

    4 Don’t let business decisions be made the way gamblers think. “Next time I will win big!”

    Watch the Sound of Music again and many other "dream big" movies...

    "Next time" is at the tip of every entrepreneur's tongue. The fact that "next time" exists is a sign of "never giving up".

    Mark Twain quotes about success:

    A person with a new idea is a crank until the idea succeeds. Mark Twain

    A round man cannot be expected to fit in a square hole right away. He must have time to modify his shape. Mark Twain

    All you need is ignorance and confidence and the success is sure. Mark Twain

    Don't part with your illusions. When they are gone, you may still exist, but you have ceased to live. Mark Twain

    Sure enough he went to proverbial sea without much of a compass or destination in mind. His contribution to others hearts and mind is not relative to his wealth... but what he did with his mind, what he believed and how he took action on those beliefs.

    thank you for taking the time. Absolutely Helpful.

  • Structural Engineer 
Bellingham, Washington 
Charles Waugh
    Posted by Charles Waugh, Bellingham, Washington | Dec 03, 2010


    Thanks for your long reply. It shows an enthusiasm for the article.

    I have slightly revised my article to clarify and emphasize some of the points that you brought up, mostly that "he went to sea without a compass."

    I enjoyed your quotes, but I do recall (from his biography) that while he was at first quite happy with his business partner, he later became so disenchanted with him that his feelings were unprintable. He needed a reality check, and did not get it.

  • Structural Engineer 
Bellingham, Washington 
Charles Waugh
    Posted by Charles Waugh, Bellingham, Washington | Dec 03, 2010


    Thank you for your comment about how inspirational that Mark Twain was. He would be amused to think that $35 x 275,000 = $9.6 million. He would also want his share!!


  • Washington Federal Assistant Manager 
Bellingham, Washington 
Susan Templeton
    Posted by Susan Templeton, Bellingham, Washington | Dec 03, 2010

    Charles, I often reflect upon visionaries like Mark Twain and Edison who died without reaping much financial success for their contributions. We need help for those underdeveloped aspects of our vision. Thanks for this reminder!

  • Tax Professional and IRS Representation 
Blaine, Washington 
Bill Bradfield, EA
    Posted by Bill Bradfield, EA, Blaine, Washington | Dec 03, 2010


    I loved your article. Thanks for taking the time to reflect on Samuel Clemens life and relating it to today's world of business and life. I'm a firm believer in knowing what your skill sets are focusing your business around them.

    On the other hand, you may have skill sets that you don't even know you have. I have always said to my children and others, "the turtle only gets ahead by putting its neck out." Sometimes we have to get out of our comfort zone and try things. As you said, "learn from our mistakes, don't just repeat them." Frequently, very successful people are the ones who have failed miserably but have taken what they learned from the failure and applied it to a new venture.

    Thanks again for writing this.


  • Communication Coaching, Classes & Consulting 
Portland, Oregon 
Karen Mathieson
    Posted by Karen Mathieson, Portland, Oregon | Dec 03, 2010

    Charles, your article is outstanding for its insight, compassion, motivation and sheer good writing. It made my day to find it on Biznik, and I'm hoping to see many more of your bylines.

    A favorite from among Mark Twain's pithy observations: "The difference between the right word and the almost-right word is the difference between lightning and the lightning-bug." Too bad Sam Clemens couldn't distinguish between the right invention and the almost-right one!

    Thank you again for a wonderful read -- Karen

  • Structural Engineer 
Bellingham, Washington 
Charles Waugh
    Posted by Charles Waugh, Bellingham, Washington | Dec 04, 2010

    Susan, Bill, and Karen:

    Thanks for your support -- it is great to see that people read my articles, but each positive comment is worth 500 readers to me. Again, thanks


  • Bellevue Graphic Designer/Illustrator/Toy & Book Creator 
Bellevue, Washington 
Susan Straub-Martin
    Posted by Susan Straub-Martin, Bellevue, Washington | Dec 04, 2010


    I wanted to say that i loved your article. The points you made and how you broke it down were indeed successful.

    4 is my personal favorite. I tried years ago to get a business off the ground and failed miserably.

    When starting again I looked at what went wrong and made a check list. If I come close to anything on the list, I stop and do more research, ask more questions, find multiple sources, then proceed with caution.

    But the biggest lesson I learned was to ask for help. You may be great at what you do, but you are not great at everything. I have asked for lots of help this time and I am going down a much happier and more successful path.

    Mr. Twain was wise in words and for this we are all grateful. His business sense we can learn from as well. So Thank you for the article.


  • Structural Engineer 
Bellingham, Washington 
Charles Waugh
    Posted by Charles Waugh, Bellingham, Washington | Dec 04, 2010

    Thanks, Susan -- I am sure that Mark Twain would be happy to know that you -- and many of us -- are still grateful for what he wrote.


  • QuickBooks And Xero Outsourced Contractors Bookkeeping Services 
Lynnwood, Washington 
Randal DeHart, PMP, QPA
    Posted by Randal DeHart, PMP, QPA, Lynnwood, Washington | Dec 07, 2010


    Your 5 lessons are most appropriate and timely as we get ready to close out 2010 and open 2011.

    I really enjoyed the part about… “ He had no business plan -- he improvised as he went along. The result was tragic.”

    We offer to help our clients with documenting a formal Business Plan as part of our regular monthly bookkeeping service yet sadly very few take advantage of it.

    Warm Regards, Randal