[rank_math_breadcrumb]

Rob Caskie Legacy Project

Storyteller

About

Rob Caskie Legacy Project shares his Stories of human trials and triumphs never go out of vogue, and mesmerising storyteller extraordinaire Rob Caskie, with his walking stick and trademark shorts, brings them alive like no other.

Often in the settings where such stories unfolded, in South Africa and abroad.

Rob Caskie Legacy Project

In a world of instant gratification, the art of a powerfully told story belongs to few and relies on he who stirs the imagination. Most interested in how people behave when challenged and under pressure, he believes we only reveal our true strength in adversity – and he shows audiences how they can draw on this to thrive in uncertain times.

Contact Us at WeSpeak Global and follow us on Twitter

Interview Questions

Has your definition of it changed over the years and if so, why? | Definition of success has changed over years. In younger years, I wanted to be a hero – with 7 billion people, little chance of that! With passing years any desire for fame has receded completely.

Definition of success now a healthy balance between work, play/recreation and rest. To have enough financially to live comfortably and be able to assist others. I do NOT want it recorded on my headstone that I wished I had spent more time at work!

I am driven to do more with Life than the generation before mine. I am driven to be environmentally and socially aware. My definition of success in question 1 gives me plenty to strive for daily.

My magic, I believe, comes from considerable Life experience (much of it unhappy, with the loss of my parents at an early age), limited resources, extensive travels, being unafraid of risk, seizing opportunities, and a deep interest in human beings.

There is magic in entertaining people through storytelling. My magic, if any, would be very difficult to describe or quantify.

Confidence, and the ability to interact well with people.

What do you believe are the characteristics, actions, habits and behaviors that you both have and use, that have helped you achieve what you have been able to achieve?

 

A very good memory, humility, ability to listen and learn, good work ethic, constant desire to improve my stories and presentation, punctuality and the confidence to do it “my way” rather than mimicking somebody else.

Indecision or hesitation has caused us to get stuck on occasions. With age/experience, seizing opportunities not as easy as it was 20 years ago. The longest, darkest hour is only 60 minutes.

Remaining stuck is not an option! Being self-employed forces one to respond swiftly. Evaluating priorities, for me, usually solves these situations, and ensures they don’t keep recurring.

Honesty, integrity and transparency. In our industry, reputations are built over years and smashed in seconds. Be as good as your word (in 13 years of intensive UK lecture tours, we have never once entered into a contract), never over-promise and under-deliver. Be authentic, always. Communicate with clients, don’t leave them hanging or guessing.

Establishing my worth, still cannot believe people will pay me to tell a story. Afraid to push my rates up.

That our business may not survive Lockdown and beyond.

Try to get enough rest and exercise. Regular mountain bike rides are a wonderful time to be creative, and clear the noise from one’s mind.

Step up to the responsibility of performing for an audience – it is a show/performance.

Absolutely. When is enough, enough? If one is constantly wanting to improve one’s offering, surely one can never be fully content with it? I think most human beings struggle with being completely happy with what they have – difficult aspect of human nature. Desiderata is often referred to in these instances, for me.

Essentially I am a loner, and very happy with my own company. Storytelling/performing is not my usual comfort zone. I have a large Bonsai tree collection.

Interview Date

  • 2021-03-17

Country

  • South Africa

Gallery

Videos
[everest_form id="26923"]

View further interviews.

The Legacy Project

Alyson McGregor is a graduate of Boston University School of Medicine and Brown University Emergency Medicine Residency. Dr. McGregor is the Director for the Division of Sex and Gender in Emergency Medicine (SGEM), formerly Women’s Health in Emergency Care, at Alpert Medical School Department of Emergency Medicine and Co-Director for SGEM Fellowship. Dr. McGregor is […]

Brad Sugars Legacy Project

Brad Sugars Legacy Project came from humble beginnings and is a self-made multi-millionaire most famous for his global business coaching franchise Action Coach. Along with his family, one of the biggest influences in his life is Jim Rohn. Brad often tells audiences the tale of how as a teenager he scrimped and saved his allowance […]

  • United States
  • Keynote Speaker
The Legacy Project

Lance Brown author of “The Driver of Change” is a living testament to his “Creating Opportunities” philosophy and presentations. Growing up in Mitchells Plain, a Cape Town suburb where dreams rarely stretch beyond one’s street corner, Lance dared to reach for the stars. From a small seed of a basic job as a delivery driver […]

The Legacy Project

Dorie Clark | The Legacy Project is an Adjunct Professor of Business Administration at Duke University’s Fuqua School of Business and the author of Reinventing You (Harvard Business Review Press, 2013) and Stand Out (Portfolio/Penguin, 2015). A former presidential campaign spokeswoman, she is a frequent contributor to the Harvard Business Review, TIME, and Entrepreneur. Recognized […]

The Legacy Project

Roman Rezac is a prolific South African retail entrepreneur with 25 years experience in a constantly evolving environment. He was an International knee-board surfer before he made his passion for beach lifestyle into a career. He opened his first Surf store in 1993 in Durban with borrowed capital and with hard work and perseverance he […]

The Legacy Project

Amit Virmani’s debut, “Cowboys in Paradise”, was one of the most talked-about Asian documentaries in recent years. The controversial film was featured on CNN, BBC and various international media, and is regarded as a valuable counterpoint to “Eat, Pray, Love”. His follow-up, “Menstrual Man”, was a Netflix audience favourite at Hot Docs and will be […]

The Legacy Project

In 2008, Patrick was elected an Ashoka Fellow for his work as a social entrepreneur. At Ashoka, he was one of the first Fellows with a strong background in the for-profit corporate sector, and one of the first to have scaled a for-profit social enterprise globally. More recognition soon followed: He was named an Endeavor […]

The Legacy Project

Nolan Watson is a Canadian businessman, humanitarian, and philanthropist. He is known for his contribution to finance innovation in the mining industry. Watson began working in mine finance with Silver Wheaton Corp., where he was named the Chief Financial Officer in 2006 and was the youngest CFO (age 26) of a New York Stock Exchange […]

Disclaimer
The profiles and images embedded on these pages are from various interviews conducted by The Legacy Project.

These remain the property of its owner and are not affiliated with or endorsed by WeSpeak Global.

Our Mission

We are your partner creating memorable and engaging experiences that go beyond the event itself.

© All rights reserved 2025. Created using VOXEL THEME