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Business Unplugged™
This blog features Carol Roth's tough love on business and entrepreneurship, as well as insights from Carol's community of contributors.

40+ of the All-time Greatest Leaders

Written By: Carol Roth | 2 Comments

Great leadership is one of the most important keys (if not the most important!) to having a successful business. But, what are the defining characteristics that make a leader great? In that spirit, we have asked the incredible CarolRoth.com contributor network of business owners, experts, advisors and entrepreneurs to share who they think is the greatest leader of all time and why. Their answers are presented below in no particular order.

You may notice the same leaders listed more than once, but I kept them separate, as something in the way one is framed may resonate differently with you.

1. Jack Ma- Never, Never Give Up

Jack Ma, Founder & Executive Chairman of Alibaba for his thinking, perseverance, and his vision to create more opportunities for small business owners. He places customers 1st, employees 2nd, and stakeholders 3rd. Despite countless denials from Harvard to KFC, he never gave up. His tireless pursuit led him to start Alibaba in his apartment to create opportunities for others. He is now worth $29 billion USD. Integrity, emotional intelligence, and determination makes him one of the greatest to me.
Thanks to: Alexis Davis, CEO of Hoo-Kong.

2. President John F. Kennedy

"Ask not what your country can do for you – ask what you can do for your country" may not have been an original line of JFK(*), but the way that he used it to inspire a nation truly puts him in the category of great leaders. In his inaugural speech of 1961, Kennedy inspired a world to think beyond themselves & inspired a generation of service & a man on the moon. How can you inspire others to do incredible things & bring the passions of others to bear?

*http://dailym.ai/29P5sit

Thanks to: Ben Baker of Your Brand Marketing.

3. Leading on the Edge...

Aerosmith vocalist Steven Tyler is an amazing leader whose legacy is worth examining. He has held together a business for 45 years. His willingness to duke it out with his staff is a key part of his band's success. Not one for polite corporate pretentiousness, Steven says, "I like to figure out exactly what it is that's wrong and not just say, 'Can we agree to disagree'?" Steven credits heated arguments with the band for shaping the powerful drive of Sweet Emotion, Dream On, and Walk this Way.
Thanks to: Ken Kilpatrick of kenny the k.

4. The Power of Words and Thought

Winston Churchill, Prime Minister of Britain, pled to the United States in 1938 to join them to defend freedom, speech, and thoughts. He compelled the US to join Britain to fight the tyranny of the Nazi and Communist parties that were rising up and destroying the world. His plea went beyond weapons and violence; he recognized that these parties were obliterating human sanctity of free thought. He inspired entire nations to defend those who could not defend themselves. This is a hero, a leader.
Thanks to: Kristen Fusaro-Pizzo of Bath, Body, Candle Moments.

5. MLK Was a Great Leader!

Dr. Martin Luther King Jr. knew how to control his anger. He was threatened and attacked by racist people, repeatedly jailed by state authorities, harassed by the FBI and even vilified by fellow black leaders who preferred more aggressive forms of resistance. Yet, still he rose. Great leaders do not ignore their anger, nor do they allow themselves to get consumed by it. Instead, they channel that emotion into energy, commitment, sacrifice, and purpose. They use it to step up their game.
Thanks to: Zondra Wilson of Blu Skin Care, LLC.

6. Best Leader Ever

Jamie Dunn was a Supervisor at a recreation center for the developmentally disabled. At the time, it was my dream job, but there were no openings. However, Jamie's staff of 12 were taking consecutive vacations. She hired me as a sub. One day, she approached me and said, "Jane is leaving. I spoke with everyone on the team, and we all want you." I was thrilled. Jamie inspired loyalty by consulting her entire team when a major decision needed to be made that would affect the entire team.
Thanks to: Randy Peyser of Author One Stop, Inc.

7. Walt Disney's Inspiration

I have always admired Walt Disney as a leader. Not only did he create an entertainment empire, but he popularized the idea that with dedication you can accomplish anything. When Disney first began his career in the 1920s, he was a man from Missouri with a drawing of a mouse. Similarly to how Disney started out, all I had was an idea and the motivation to move forward. Walt Disney’s story inspired me to take risks when it came to running my business and to always think outside of the box.
Thanks to: Adam Binder of Creative Click Media.

8. Everybody Loves Oprah

My favorite leader of all time is Oprah. During the last season of her talk show, she had a behind-the-scenes series that gave me insight into her leadership skills. Not only does she guide her team to make shrewd business decisions, but she treated them as humans and not workhorses. People were able to cry without feeling ostracized, as well as being able to tell her if something didn't align with their values without being punished.
Thanks to: Marissa Russell of The High Achieving Woman.

9. The Master Negotiator

One of the greatest leaders of all time would be Subhas Chandra Bose, an Indian freedom fighter. He was a master negotiator and managed to build an army with the representatives of many countries like Germany, Italy, Japan, etc. while facing immense opposition. He was the major influence which ultimately led to the freedom of India from the British. He was extremely passionate and could command thousands of people. He challenged the status quo, dared to dream and had the fire to fulfill his goals.
Thanks to: Srajan Mishra of TSI International.

10. Unf*ckwithable Ash Ambirge!

Unf*ckwithable Girlfriends is small monthly fee entrepreneurs' group and private Facebook group, run by Ash Ambirge of "The Middle Finger Project" blog. She is a bold, no-holds barred woman who is extremely transparent and lets it all hang out for anyone lucky enough to dive into her writing, which is creative genius. Her main goal for the Unf*ckwithable group is the empowerment of women (and men) to find their own greatness and go for it. To me, that is the sign of a truly great leader!
Thanks to: Roberta Perry of ScrubzBody Natural Skin Care.

11. Undaunted

Franklin D. Roosevelt was not discouraged by the Great Depression, the Second World War or his confinement to a wheelchair. He had great faith in the American people and his own ability. By his up-beat attitude, he restored confidence in the people that if he could handle polio, they could rise to their challenges. He led with bold actions and determination. From a wheelchair, he displayed boundless energy and the willingness to face any crisis head-on. The people drew courage from his strength.
Thanks to: Mitch Carnell of --None--SPWC.

12. Nothing Could Stop Her

I've been greatly inspired in my art and personal life by Frida Kahlo -- the Mexican artist of early 20th century. Despite great physical injury and chronic pain, she stopped at nothing to achieve great goals as an artist, a woman, and a cultural leader of her day.
Thanks to: Arlissa Vaughn of Portrait Artist & Live Painter.

13. How the Steelers Won the '70s

When discussing how late Pittsburgh Steelers Coach Chuck Noll mastered work-life balance, Bill Livingston said, “Noll didn't live and breathe X’s and O’s. He was a man as comfortable with opera glasses as a headset, who was also an amateur pilot and experienced sailor.”

Today’s leaders can learn from Noll’s legacy. Your job needn't define you. While a strong work ethic is noble, Chuck was just as proud of his role as a grandfather, wine connoisseur, and classical music aficionado.
Thanks to: Jason Myers of The Content Factory.

14. The Need to Be Purple

My favorite leader is the business author, Seth Godin. The thing that makes him a great leader is he inspires us to be great leaders. He stresses the importance of being uniquely you (a Purple Cow) and shows us the path to lead others by creating Tribes. To me, bringing out the best in others is the mark of a great leader. Seth Godin does that in numerous ways in all that he does.
Thanks to: Bill Gluth of Creative Thinking for Business.

15. The Zen of Micro Managing

The best biz leader I knew shared his management style with me: Listen to team members. Working for him was great, as we accomplished lots and it didn't feel like working. He gave us a very long leash. He told me once he had a boss who micro managed everything. The end result is that no one accomplished what they needed or wanted to do. Moral was poor and people wanted out. The micro manager ended up managing himself! The listener works for a top 50 corporation. The key to life is listening!
Thanks to: Mark Alyn of Mark Alyn Communication, Inc.

16. Leading Youth into Governance

At 19 years old, I belonged to a not-for-profit organization that produced community theatre. The President at the time, Jane Barnett, soon co-opted me onto the committee, of which half were young people under the age of 25. Jane taught us how to run meetings, philosophies underpinning governance and leadership, and gave us responsibilities - all while making it fun! It was her leadership and mentoring 3 decades ago that gave me the skills and confidence to pursue later career roles.
Thanks to: Jenni Murphy-Scanlon of Strategies Direct Limited.

17. Leading With Chocolate!

Milton Hershey: He was already a millionaire, but decided to use his money to make a difference in people's lives. Thus, he started a chocolate company, but more than that he created a whole town and jobs for people to give them a higher quality of life. He even used the proceeds from his business to fund one of the largest schools for orphans in the world today. Then, he gave away his entire fortune when he was still alive. If leading is by example, then this is a life to emulate!
Thanks to: Craig Wolfe of CelebriDucks.

18. Lost Lessons of Marshall

One of the best leaders is hardly known today: George C. Marshall, “The Architect of Victory” of WW2. He persuaded a reluctant Congress to prepare for war. His strategic insight ensured the US supplied its allies in two hemispheres while overseeing the expansion of the US Army by a multiple of 50. And his devotion to his shareholders, the American people, empowered him to replace more than 600 senior leaders. No wonder FDR, Truman and Churchill said he was the greatest man they ever knew.
Thanks to: Kevin Black of Executive Command.

19. One Giant Leap for Mankind

Imagination captured the hearts and minds of almost every American as they were riveted to their televisions in 1969. Neil Armstrong was the first astronaut to take an actual walk on the moon. His proclamation was, “One giant leap for mankind.” Almost 50 years ago, there were no desktop computers, mobile phones or internet service. The bravery of Armstrong and his team is something to always be remembered and embraced. It was a giant leap for mankind and of true leadership.
Thanks to: Elinor Stutz.

20. Pat Summitt

"Responsibility equals accountability equals ownership. And a sense of ownership is the most powerful weapon a team or organization can have." – Pat Summitt, who accrued the most wins in NCAA basketball history during her tenure as coach of the University of Tennessee women's basketball team.
Thanks to: Brandon Bruce of Cirrus Insight.

21. Mother Teresa

I have always defined a leader as someone who takes people where they want to go, but don't know it. That's what she did. She took those who were ready to serve and led them. She didn't complain. She didn't say it can't be done. She just did it, and others followed. And she slept on the floor with the rest of the nuns.
Thanks to: David Leonhardt of THGM Ghostwriters.

22. Steve Jobs (Inspires Loyalty)

The most important trait of a leader is that they inspire loyalty (to the point of blind ignorance). The best example of a leader achieving this would be Steve Jobs. He managed to convince millions of people that every single Apple product was revolutionary, when in reality there were plenty of better and more affordable options on the market. Since his passing, many have claimed that the quality of Apple products has declined, but in reality their leadership is what has suffered.
Thanks to: Sam Williamson of Mister Singh's India Restaurant.

23. A Legacy in the Making

Gary Vaynerchuck is a thought leader and industry expert who has created an empire around storytelling. But, true leadership isn't about what you do, it's about how you treat the people who work beside you. Gary's company has been created around the ideologies of providing value to others. Many believe that the greatest asset a CEO can donate is cash. The reality is that the most valuable asset they can give is their time. Gary does this not by giving others a fish, but rather, teaching them how.
Thanks to: Kyle Reyes of The Silent Partner Marketing.

24. He Hired a Chief Heart Officer

When I think of leaders, Gary Vaynerchuck is the first face I see. Not because he's so successful, not because I love his style and knowledge, but because he truly cares for his employees and his audience and it's apparent in everything he says and does. Like a true leader, he knows to listen first and react second, he makes people feel valued and cares more about his team than his clients (which quickly translates into happy clients.) Those kills allow him to lead anywhere and anyone.
Thanks to: Bobbi Baehne of Think Big Go Local, Inc.

25. Should Be a National Hero!

The leader I will name here has done more for the common person than anyone else I can think of. Just one short sentence in just one of his books saved my husband and me many thousands of dollars and a lot of angst. He tells it like it is, and there are many who want him stopped. They are always trying. He is our hero.

Who is he? Kevin Trudeau.
Thanks to: Sheila Van Houten of New Light Consulting.

26. The Cream of the Crop!!!

The individual that has inspired me is First Lady Michelle Obama. The characteristics I noticed were: She constructs a vision for the future and has follower support. She searches for opportunities and takes rational risks. She fosters collaborations and allows others to shine. She sets a good example and helps others break down large goals into step-by-step accomplishments. She has given us the picture of what the “image of a female leader” is and should be.
Thanks to: Dr. Madeline Ann Lewis of Executive Women's Success Institute.

27. Powerful and Inspirational

The leader who inspires me now is Dr. Joanna Martin, Shift Speaker Training. She is strong, yet still very feminine, she is authentic and true to herself and her family. She is inspiring in that she is willing to stand up and say what it is she is aspiring to. She has created and run a 7 figure business from nothing and whilst still keeping that business going has now gone into partnership with a number of other highly successful business women and set up two new ventures focused on women leaders.
Thanks to: Maggie Georgopoulos of MAG Inspires.

28. A Model for Our Second Act

Dr. Marjorie Blanchard is the co-founder of The Ken Blanchard Companies. She has worked with her husband, Ken Blanchard, to develop one of the most successful management consulting and training companies in the world. She's the co-author of Leading at a Higher Level and co-recipient of Cornell University's Entrepreneur of the Year Award. Mentor at heart, she's an example of resilience, nurturing vital, long term relationships, and how to reinvent oneself to have significance in one's second act.
Thanks to: Maria Keckler of Superb Communication.

29. All Time Greatest Leader

The greatest leader is Tony Hsieh the CEO of Zappos. I consider him the greatest leader of all time because of his leadership style and philosophy on business. He believes in delivering happiness to his customers and his employees. Hsieh has a very unorthodox approach to leadership; he gives his employees the creative freedom to express themselves. Not only that, there are no managers who constantly breathe down the necks of every employee, creating a very unique and positive company culture.
Thanks to: Lisa Chu of Black N Bianco Kids Apparel.

30. Winston Churchill's Endurement

Churchill was known for his optimism and never say die attitude during WW2 that gave confidence for Britain to push on and help win the war. One of his best quotes was "I have nothing to offer but blood, toil, tears and sweat." His witty nature, passion, and ability to inspire and lead his countrymen to victory during the war is an example how a leader should immerse his or herself to their cause. Churchill never gave in, and would go through hell and back to defeat the evil of the time.
Thanks to: Nathan Barber of digitaladvertisingWorks.

31. Aung San Suu Kyi

Aung San Suu Kyi has demonstrated that peaceful opposition and consistent messaging can lead to positive change. For years, she was oppressed and silenced in Myanmar. Her message of progress and peace, however, never altered.

Aung San Suu Kyi was able to mobilize an entire country without all of the sophisticated communication tools we use today. Her leadership stems from the core belief of love and equality and this message has resonated throughout the world.
Thanks to: Sacha Ferrandi of Source Capital Funding, Inc.

32. The Inner Strength

Tony Robbins is one of the true leaders of this world. He inspires and lives his values. He has developed inner strength and determination. He interacts with people from all walks of life without prejudice and connects with them, in terms of the person they are inside. This, to me, is the epitome of a great leader – one who sets an example for others, one who is engaging and engages, and one who instills a desire to be the best and to achieve an extraordinary life of continual growth.
Thanks to: Suzanne Duncan of DiscoveryWithin.

33. No Justice? No Peace!

Bishop Desmond Mpilo Tutu is a joyful social rights activist and ex-Anglican priest who formulated his objective as “a democratic and just society without racial divisions” to oppose apartheid in his native South Africa and received the 1984 Nobel Prize for Peace for his work.
Thanks to: Ryan Phillips of Bioclarity.

34. Ted Turner

Ted Turner is a visionary and doer, who defined how much one dedicated, driven person can achieve. Maybe, "getting things done," was easier for him because he is also known for his ethical work style and hiring the best, who will work toward making his vision a reality. I don't know of anybody who succeeded in more diverse fields: Turner founded CNN, the Nuclear Threat Initiative, saved the American bison, won the America Cup, and there isn't enough room to list everything else he has done.
Thanks to: Gisela Hausmann of email evangelist Gisela Hausmann.

35. All-time Best Leader

I can't imagine any discussion of leadership that doesn't include Abraham Lincoln. He upheld our collective principles despite the danger and kept America together during its only true existential crisis. His sacrifice is obvious, but even had he not been assassinated, he essentially gave his life to the presidency, aging what seems like decades in the span of only four years. He wouldn't have lived much beyond the expiration of his term in office.
Thanks to: Brett Bastello of Community Tax.

36. 217 Rejections, 1 Starbucks

Howard Schultz is one the greatest leaders of all time. Classically entrepreneurial, I admire his power of perseverance and vision despite repeated rejections. 217 of the 242 investors he talked to rejected him. Most people, myself included, would give up after 1 or 2, or even 100, rejections. However, Shultz’s vision went beyond that. It proved so strong that he was able to shape reality around it, with Starbucks’ now ubiquitous on every street corner and more than just a household name.
Thanks to: Stacy Caprio of Accelerated Growth Marketing.

37. Walt Disney the Visionary

Walt Disney’s determined spirit has influenced our leadership. Despite overwhelming odds, we must keep our tenacity and continue to do the impossible. The hard truth is failure can easily break your dream. Nevertheless, like Mickey Mouse so plainly encourages: “We live every moment as not to regret what we are about to do.” It is the strong willed and determined who thrive as leaders. Every moment of failure is a thread that weaves your pattern of success.
Thanks to: Michael Wenger of Quality Logo Products, Inc.

38. Making Magic

Walt Disney is one of the greatest leaders of all time. His customer service model is the gold standard which other companies follow. He led by example with unbridled passion. We started MickeyTravels several years ago. We are a recognized leader in the Disney travel industry. We have 100 agents that work for us around the country. The work we provide & the smiles brought to our clients’ faces wouldn’t be possible without the leadership exhibited by Walt Disney throughout his great career.
Thanks to: Greg Antonelle of MickeyTravels, LLC.

39. German Leadership Lessons

I think the greatest leader of all time was 19th century German chancellor Otto von Bismarck. He unified Germany in the late 19th century, but his greatest leadership trait was making peace with his enemies once he had achieved his goals. This allowed him to focus on building up Germany's economy, rather than fighting endless wars. The same goes in business, once you've achieved one goal, make peace with any former rivals so that you can focus all your efforts on your next goal.
Thanks to: Ian Wright of Merchant Machine.

40. The Grace to Lead By Example

There are many who aspire to stand on the center stage of greatness, yet fail to recognize the agony of sacrifice that dwells behind the curtains of obscurity. Nelson Mandela was an exemplary leader who demonstrated the power of humility, grace and forgiveness after being imprisoned for 27 years. In his words, "There is no easy walk to freedom anywhere, and many of us will have to pass through the valley of the shadow of death again and again before we reach the mountaintop of our desires."
Thanks to: Kristie Kennedy of KKEE, LLC.

41. Having the Magic Touch

Ervin "Magic" Johnson is one of the All Time Greatest Leaders. Magic has been successful in basketball and as a businessman. His competitive nature and his way of motivating others to succeed is why he is among the Greatest Leaders of All Time. Magic won championships in the NBA by helping his teammates play at their best potential and he does the same with those who he does business with.
Thanks to: Vid Lamonte' Buggs Jr of VLB/VBJ Enterprises, LLC.

42. My Father, My Inspiration

The leader that inspires me is my father, John Sumrell. He spent 28 years in the Air Force and fought in the Vietnam War twice during a time when our country was dealing with segregation. He taught me four very specific lessons as it pertains to leadership:
1. Always protect your team.
2. Learn how to confidently make decisions.
3. Don’t jump to conclusions; always remember there are two sides to every story.
4. Treat people the way you’d want to be treated.
Thanks to: Stephanie Chung of Stephanie Chung and Associates.

43. Moses - The Leader Isreal Need

I would say the greatest leader of all time is Moses. He overcame great adversity to become the world's most important leader. He remained humble and grounded during his leadership. Only once did he lose his temper with his people. He never gave up.
Thanks to: Patrick Henry of QuestFusion.

44. Boudicca

The Celtic Queen, Boudicca, may not have made it into your history books as a great leader, but her fearless sense of honor brought 80,000 Roman soldiers in Britain to their knees in 60 CE. Following her husband, King of Iceni’s death, an agreement for their land was not upheld by Rome. The Queen was flogged and her daughters raped, fueling the tribe’s anger at the injustice and causing her to lead one of the bloodiest revolts in British history.
Thanks to: Michael J. de Waal of Global IQX.

45. A Diamond in the Rough

You may or may not have heard of Michelle Dale from Virtual Miss Friday, but she is a true diamond in the rough. She is one of the best leaders & sources of inspiration. She's a woman determined to achieve goals & works tirelessly to make a difference in the lives of her clients & colleagues. Her wisdom & creativity is endless & she keeps no secrets. She shares every bit of knowledge she can to ensure others achieve success. If she is a stranger to you, I highly encourage you to look her up!
Thanks to: Megan Dixon of Rescue Me.

46. Leading the World With No Legs

Not only did Franklin D Roosevelt, who became President of the United States of America at the height of the Great Depression, help the American people regain faith in themselves and their country, he fought his handicap, poliomyelitis, where he lost the use of his legs, with determination. In 1932, with 13,000,000 unemployed and almost every bank closed, he brought relief by bringing in a new program of reform.
Thanks to: Jacob Singer of www.jacobashersinger.com.

47. Lee Iacocca Could Work Magic

Lee Iacocca, creator of the Mustang, was fired as Ford's president. Instead of retiring, he saved Chrysler from bankruptcy. Chrysler had a bloated payroll and Iacocca set the tone by working for $1 a year! And in exchange for workers’ wage concessions, he promised profit-sharing. Revamping its line-up would cost Chrysler millions. But Iacocca convinced the public that Chrysler's junk bonds were good investments. With funding secured, a new line of FWD cars hit the market, saving the company.
Thanks to: Timothy Wiedman of Doane University.

48. All-time Best Leaders

Dr. Martin Luther King, Jr. had a dream, but he awakened America by using main street media through the television set. He didn’t need a gun or bomb to change America. Every night on the evening news, the civil rights movement was viewed by millions of people watching Black children and adults being beaten by police sticks, bitten by police dogs and arrested during non-violent protests for equal rights. As his dream continued to magnify, we saw Blacks assuming leadership positions.
Thanks to: Ruben Britt, Jr. of Rowan University.

49. Jack Welch

Jack Welch in my opinion is one of the greatest business leaders of all time for his emphasis in rigorous candor with his leadership style.

Jack pioneered a leadership process by which the bottom 10% of performing team members in the General Electric organization were dismissed on an annual basis.

While it may seem non-sympathetic, real leadership takes courage and the leader must be willing to take steps that are better for the team even though they may be uncomfortable and unpleasant.
Thanks to: Bryan Clayton of GreenPal.

Do you know any great leaders that weren’t included? Please share your thoughts below. And as always, many thanks to everyone that contributed to this article!

And if you would like to become a part of the CarolRoth.com contributor network and find out about opportunities to contribute to future articles, sign up here: http://www.carolroth.com/carolroth-com-blog-contributor-sign-up/

Article written by
Carol Roth is a national media personality, ‘recovering’ investment banker, investor, speaker and author of the New York Times bestselling book, The Entrepreneur Equation. She is a judge on the Mark Burnett (Shark Tank, The Voice, Survivor, The Apprentice) produced technology competition series, America's Greatest Makers, airing on TBS and Host of Microsoft's Office Small Business Academy show. Previously, Carol was the host and co-producer of The Noon Show, a current events talk show on WGN Radio, one of the top stations in the country, and a contributor to CNBC, as well as a frequent guest on Fox News, CNN, Fox Business and other stations. Carol's multimedia commentary covers business and the economy, current events, politics and pop culture topics. Carol has helped her clients complete more than $2 billion in capital raising and M&A transactions. She is a Top 100 Small Business Influencer (2011-2015) and has her own action figure. Twitter: @CarolJSRoth