54: Leadership Advice from Winston Churchill with Randy Otto

Today, we have the honor of speaking to Sir Winston Churchill, the former British Prime Minister, as impersonated by Randy Otto. Randy has been playing Winston Churchill for the last forty-seven years, and he is phenomenal!

In this episode, you will learn about history. You will hear the great quotes of Sir Winston Churchill, and you will also get some great leadership advice.

We know you are going to love this show!

Today, we have the honor of speaking to Sir Winston Churchill, the former British Prime Minister, as impersonated by Randy Otto. Randy has been playing Winston Churchill for the last forty-seven years, and he is phenomenal!

In this episode, you will learn about history. You will hear the great quotes of Sir Winston Churchill, and you will also get some great leadership advice.

We know you are going to love this show!

Randy Otto’s background

Randy Otto’s British history professor did a spot-on impression of Winston Churchill, and Randy thought he could impersonate him impersonating Winston Churchill. The professor walked up behind him and surprised him by telling him that he might have something, and Randy’s life changed instantly! That professor became a great mentor in his life, and Randy gave him credit every day for allowing him to see the world through the prism of Winston Churchill.

You don’t know as much as you think

Randy urges you, as business people, to always remember that you don’t know as much as you think you do. Go and find the people in your life who know more than you do, or who can complement your knowledge, and ask as many questions as you can.


Throughout his life, Randy has had several great mentors. One of them was the great actor Hal Holbrook, who impersonated Mark Twain on stage for 64 years and died recently at the age of 94.

The best advice

Hal Holbrook gave Randy the best advice he has ever had, which was that he did not need a script. He told Randy that he knew enough about Winston Churchill to become Winston Churchill at any time he wanted to do so. All he had to do was to tell the stories and string them together with segues.

Randy Otto’s advice for business people

Randy Otto’s advice to business people is not to lose track. He advises you not to get so involved in the details that you lose track of the opportunities that come your way. Winston Churchill said, “The pessimist sees the difficulty in every opportunity, but the optimist sees the opportunity in every difficulty.”

Eight principles

Randy has eight principles that he does on stage for groups, organizations, corporations, and associations in a piece he calls Winston Churchill CEO. One of the things he stresses in it is that you touch the troops.

Great leadership

Winston Churchill set the standard of great leadership for Randy because he could stand up and sway the course of history. He did that by simply telling the truth and reminding the British people of who they were.


Churchill had the cooperation of the press during World War Two. Although he knew they could take it, he asked the press not to give the British people all the bad news at once.

Taking ownership

People appreciate leaders who take ownership of it when there is a problem or when something goes wrong, and asking for help is powerful.

A painter’s eye

Winston Churchill had a painter’s eye, and he used it as a leadership technique. He would choose a focal point for where he wanted to go in a meeting. He would then focus on that point. Sometimes, it was something that the audience thought of as inconsequential, but Churchill would stick to it like a bulldog for hours until they found a solution. As a result, he was very successful in the cabinet meetings when things got tough.

Mein Kampf

Churchill got quoted as saying that he was the only person who read the English translation of Mein Kampf as early as he did. He realized that it was a roadmap to disaster. Unfortunately, he had no proof at the time.


Churchill made a living by writing. When he started criticizing the Germans and the Italians, he lost the ability to be published by many magazines and newspapers. He kept on despite that, however.

Painting in Marseilles

Churchill painted at a chateau in Marseilles. You can see a beautiful painting that he did here.


When Churchill became Prime Minister, he was clever enough to invite Neville Chamberlain into his cabinet. Chamberlain was his fiercest enemy before doing so, and despite that, Churchill gave the eulogy at Chamberlain’s funeral.

He was himself

Churchill was true to himself as a leader. He was unafraid and honest, and he told the truth. He always said what he meant and meant what he said.

Winston Churchill gives some management and leadership advice for small business owners

“One must look at the past before one looks at the future.”

“History is our best teacher. Study history. Study history. Study history.”

“In history lie all the secrets of statecraft.”

“The further back that you can look the further forward that you can see.”

What is important as a leader when you are managing a team

“You must find your enemies and keep them close to you.”

President Lincoln assembled a team of rivals. He found the people who opposed his policies most assiduously and asked them to be part of his cabinet. As a leader, you must do the same thing in business. You must find those who are not afraid to take you on or disagree with you, and you must welcome it.

You must find the best men and women, and not the ‘yes’ men and women today, to help you, and to ask the difficult questions of you. Then you might learn to better run your company.

Managing a budget and finances

You should hire someone you can trust, who is good with facts and figures, to do that for you. “And don’t be afraid to spend money to make money.” (Churchill was not the greatest financier that ever lived.)

Company culture

You must have a vision for the future, and you must be able to communicate it. If you don’t, you had better figure out a way to find out what your vision is and communicate it. That vision must drive every single strategy that you have in your business.

Randy Otto’s bio as Keynote Speaker, Playwright, Academic, Actor

Randy Otto does NOT enter onstage. He explodes into your midst. The suspension of disbelief immediately immerses the audience. It IS Winston. Without doubt, Churchill.

Through Randy Otto’s astonishingly authentic portrayal of Churchill, based on decades of academic research and performance passion, the true genius of the man, the statesman and most admired leader can be fully seen, heard and even questioned!

Randy Otto, with unapologetic admiration, depicts a witty, humane, accessible living portrait of the most admired leader ever.

Randy’s KEYNOTES & THEATRICAL SHOWS (Winston Churchill: CEO, Winston Churchill: Man of the Century, and Winston Churchill: The Blitz) skillfully leads the audience on an immensely entertaining Churchillian journey, imparting WHY Churchill was a VISIONARY organizational genius who harnessed a unique MAGNANIMOUS, ACTION ORIENTED STYLE infused with boundless enthusiasm; and how today’s 21st Century leaders easily incorporate Churchill’s Timeless Principles of Leadership into their personal and professional lives.

Randy answers the questions: WHO was Winston Churchill, HOW did Churchill leave a timeless legacy of leadership and WHY Churchill is relevant and needs to be heard now more than ever in the 21st Century.

Randy Otto’s Awards/Honors/Education/Experience:

  • Has portrayed Winston Churchill professionally for over four decades
  • Honorary Archivist – Churchill Archive Center – Churchill College/Cambridge University/Cambridge, UK
  • Advisory Board – International Churchill Society – Milwaukee, WI
  • Hosted 70th Anniversary of Churchill becoming an American Citizen – Hillsdale College, Hillsdale, MI
  • Commissioned by National Churchill Museum to create “Painting as a Pastime” February 2014 – honoring the largest exhibition of Churchill paintings since 1976 in St. Louis, MO
  • Rotary 20+ Years – President of 2 Clubs, Assistant Governor
  • Randy Otto is the ONLY Winston Churchill endorsed by members of the Churchill family
  • Native of Milwaukee, Wisconsin, alumnus of the Milwaukee Repertory Theatre and numerous theatrical roles– BA graduate of the University of Wisconsin at Eau Claire
  • Missionary two years Hokkaido and Kyoto Japan
  • 20+ Years Vice-President of Investments – Fully licensed private investment management with Stifel Nicolaus Investment Brokerage – Offices in Brookfield, WI & St. Louis, MO

Connect with Randy

On Churchill Speaker

On the telephone – (920) 988-4459

See Randy as Winston in action!

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Eric Rozenberg

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