Ideal Outcomes

Why I’d Love to Have Lunch with Sir Richard Branson

By Jason Richmond, Founder and Chief Culture Officer at Ideal Outcomes, Inc.

Someone asked me the other day to name the business leader I’d most love to have lunch with. The answer that immediately sprung to mind: Sir Richard Branson. He would be a fascinating lunch companion.

The self-made billionaire’s businesses straddle the globe. He’s a visionary in many ways, whose love of life is contagious and whose exploits have inspired thousands of headlines. But once I said Richard Branson I had to stop and think of the reasons why. Here’s what I came up with:


I remember reading an article where Sir Richard said that his motto in life was “The brave may not live forever, but the cautious do not live at all.” After dropping out of high school he wrote and published that motto in the pages of Student magazine, his first business endeavor. He was sixteen years old, and his headmaster told him he’d either end up in prison or become a millionaire. That was his first of many big risks in a career of pushing the envelope.

I’m also not risk averse. Quite the contrary. I’ve taken risks all my life, like early in my career moving to the other side of the world—Australia—and ultimately starting my own business. Of course, it doesn’t always pay off, but you learn something from every risk you take. I’d like to explore how Sir Richard weighs risk in everything he does.


Richard Branson’s approach to business is anything but ordinary. After the youthful magazine enterprise, he set up a mail order record business followed by a chain of record stores and then the Virgin Records label, which became the largest independent label, and catapulted the iconic brand into the stratosphere.

Sir Richard has disrupted more industries than most people would dare to touch—from airlines and trains, to finance and fitness, to hotels and spaceships. His ability to leap into industries that are either stagnant or ripe for change, and then turn them upside down, is unparalleled. The Virgin brand is synonymous with the disruption of the status quo. Over lunch, I would seek to understand his instinct for identifying industries that are ready for transformation. What drives his choices? How does he spot the right opportunities? These insights would be invaluable.


Sir Richard is one of the great adventurers in and out of this world. His life is a testament to the belief that one should live fully and fearlessly—qualities he seamlessly integrates into his business ventures.

Whether it’s attempting to circle the globe in a hot air balloon, kite surfing across the English Channel, or soaring to the edge of space on board his Virgin Galactic spacecraft, he embodies the spirit of adventure. Discussing how he translates this daredevil spirit into his creativity and problem-solving skills would be intriguing to say the least.


Another quality I love about Richard Branson is that he never gives up. He finds exciting new opportunities hard to resist. And he’ll overcome all obstacles and fight to the bitter end.

He told the TV series To Dine For with Kate Sullivan. “If I’m in a ballon and I’m crossing the Pacific, and everything goes wrong, and it really looks like we have no chance of surviving I will not curl up and give up. I will fight tooth and nail to survive. Once I’ve done everything I can, only then I be willing to accept the inevitable. And the same applies to business.”

The determination goes back to when he first launched the Virgin brand and the powers to be in England resisted his chosen company name Virgin. “The registry office thought the word Virgin was rude and they wouldn’t register it,” he said. He wrote back pointing the English dictionary definition. Virgin meant pure, untouched, unblemished—the opposite of rude. They acquiesced.

But he also embraces failure. He has written, “I suppose the secret to bouncing back is not only to be unafraid of failures but to use them as motivational and learning tools. There’s nothing wrong with making mistakes as long as you don’t make the same ones over and over again.”

Learning firsthand about his most challenging moments and how he turned those into opportunities for growth would be remarkably motivating.

Master Brander

Virgin is more than just a logo; it’s a global powerhouse that represents a lifestyle of fun, fearlessness, and customer focus. Branson’s ability to weave his personal brand with his corporate one, maintaining integrity and public trust through various ups and downs, is nothing short of masterful.

A conversation over lunch about the challenges of building and sustaining a brand in the digital age, where every consumer is a critic with a public platform, would be extremely insightful.

Corporate Culture

I also like Sir Richard’s thinking when it comes to corporate culture and starting a business: “A company is just a group of people, and a business is simply creating something that makes a positive difference in other people’s lives. You need to surround yourself initially with a small team of people that passionately believe in your idea and are willing to work day and night to get that idea up and running and not listen to all the naysayers. If you fall flat on your face you will have had the best education ever. And then you can start all over again.” Amen to that. And the basis for a stimulating conversation.


I admire and agree with Sir Richard’s approach to philanthropy and giving back, which is as dynamic and varied as his business pursuits. His involvement in various charitable activities includes climate change, global health, economic empowerment, oceanic preservation, and wildlife conservation.

He was instrumental in the founding of The Elders, an independent group of global leaders working together for peace and human rights, originally brought together by Nelson Mandela. He has pledged to donate the majority of his wealth to philanthropic causes, joining initiatives like The Giving Pledge. He has said, “I would be mortified with myself if I got to the end of my life and wasted the position I found myself in.”

And Then There’s Necker…

I share Richard’s love of the Caribbean, and particularly the Virgin Islands. Of course, he owns his own 74-acre island, Necker Island, and I have a more humble abode on St. Thomas. But we both appreciate the culture, the scenery, the turquoise waters, and sandy beaches, and enjoy all the water sports on our doorstep. What a conversation we could have about that!

A Masterclass in Entrepreneurship

In conclusion, a lunch with Richard Branson would not just be an opportunity to meet a celebrity entrepreneur; it would be a masterclass in entrepreneurship, resilience, and the art of living. It’s about learning from someone who has repeatedly ventured into the unknown and emerged victorious, someone who finds the true north in chaos, and keeps pushing the human experience to its limits. Such a lunch would not just satiate the appetite but would feed the soul with courage, inspiration, and boundless curiosity.