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What I Learned From Richard Branson

04/24/2015 11:26 am ET | Updated Jun 24, 2015

In April of 2015, I joined a group of 25 entrepreneurs from Maverick1000 for a week on Necker Island, Richard Branson's legendary private island and an idyllic place to cook up bold ideas while meeting in the same room as leaders like Nelson Mandela once have.

Richard makes himself available to this group for most meals, several strategy sessions and some fun adventures and parties, at least partially because he believes that entrepreneurs -- especially the out-of-the-box maverick types -- can truly change the world.

While I had just a few personal conversations with Richard, I nonetheless soaked up many stories and witnessed him at work and at play. One of my main motives in coming on the trip was to receive a template for enlightened business and life leadership from someone who has forged a wildly unorthodox path to success and global service.

I want to share with you 12 key insights for life and business I got from being in the presence of this truly remarkable man.

  1. Good leadership is about listening - Richard is like a sponge soaking up information and ideas, always asking penetrating questions long after most people would be bored. He is deeply curious and makes it clear that he feels he can learn from anyone. His staff comments that he's always asking questions so that whatever decision he makes is informed by the maximum amount of information. Richard said that Nelson Mandela, Jimmy Carter and the majority of the others on the council of Elders he helped create agree with him on this point: The art of good leadership requires excellent listening. Richard even commented that he can spot a good leader by the quality of his or her listening.
  2. Treat everyone as an equal - As a global jet-setter hanging out with the world's elite, it would be easy for Richard to see himself as above others, but the veteran entrepreneurs who had spent time with him for years said that he truly sees us far-smaller entrepreneurs as peers. We're dealing with the same challenges, he says, just with a different number of zeroes attached. And this applies not just to the guests but to the staff on the island, who are remarkable because they don't act servile to guests even while they still deliver great service. They become your friends, an attitude that begins with the way Richard treats them all as equals rather than second-class citizens.
  3. Find what is amazing in people - One fellow at the retreat had a company that creates robots for optimizing traffic signal, which has an impressive effect on reducing accidents. While I had thought this was moderately interesting, Richard became very animated talking to him, emphasizing just how many lives it would save globally and that he ought to get the Nobel Prize for it. His excitement was genuine and he brought the entrepreneur back into the conversation later to make key points using his example. Underneath this is a real desire to find what is unique and wonderful about people. This relates to his philosophy of trying to praise people as much as possible rather than critique them, which brings out their natural gifts.
  4. Master the art of delegation - If there is one thing most business leaders are bad at that Richard has mastered, it is delegation. It's simply impossible to create the number of companies (more than 300!) and influence the number of industries that Richard has, all while living an extraordinary lifestyle, without becoming very, very good at delegation. He said the key is to find great people and then give them a lot of slack. Let them make mistakes without criticizing them (they know they made them), and let them do things their own way. If they do 80 percent as well as you at first, that's good enough. Most of all, "Get out of the building, because people always want to talk to the highest ranking person in the building." By refusing to make decisions for people and literally leaving the building, he creates a power vacuum in which others can stand up. So his philosophy is really about creating the space for other leaders and not trying to sculpt how they do things too closely, just providing useful ideas and input. With that said, there are strong guidelines for things like branding and principles for deals that everyone follows, but there is a lot of latitude for creativity within those parameters.
  5. Get extremely fit - On the day that Richard seemed to have the heaviest load of work, he played tennis for an hour with his resident "pro" at 6:00 a.m., and again in the afternoon, and also did a few laps of pre-dinner kiteboarding to relax. In between, he managed a very full load of decisions and activities while still hanging out with the Mavericks for meals. His is not an average level of fitness. One 35-ish-year-old kiteboarding instructor I talked to said that Richard had challenged him to race to an island 17 miles away and back, and proved that he was actually in better shape at 65 than the instructor. While the younger man needed time to recuperate afterwards, Richard went on to play a match of tennis. To get to this level of fitness, part of Richard's strategy is to create audacious, almost impossible goals, from kiteboarding the English Channel to summiting Kilimanjaro, that serve to rally his family and focus his training. This keeps his daily energy and enthusiasm extremely high.
  6. Practice acts of generosity - Stories from veterans from the island were striking in illuminating just how often Richard would go the extra mile to be generous. From offering to have a 10-minute, life-changing talk with a dyslexic teen just before going on-stage in front of 5,000 people, to offering to have one person's wife and kids come down to the island for their 10th anniversary, to his asking one Maverick repeatedly, "What can I do to help you?" and ticking things off one by one (all of which were done within a day), it's clear that Richard takes many opportunities throughout the day to just be helpful. One morning at breakfast, someone mentioned there was a shocked bird in their room that was under a bed and he immediately said he'd go personally handle it. Another woman had confessed she didn't know how to swim a previous year and he personally took the time to teach her. With everything I heard and personally witnessed, it's clear he practices servant leadership and real generosity.
  7. Keep your mischievous side alive - I was truly struck by just how playful and sometimes silly Richard would be. He was game for anything, from a first night demonstration of "twerking" to throwing people in the ocean to planting incriminating evidence on the opponent's team after our "Amazing Race" and making them "walk the plank" so his team could win. Richard was always looking for a good laugh and a bit of mischief. At lunch one day, he called up staff and leaders in our group to dance down the center of the table and revealed that all the tables on the island have been designed for table dancing. He laughed that you could never get away with this in America. They had Greek music put on one night for table dancing and handed out iced "plates" that we could break on the ground in a satisfying but ecological way.
  8. Don't take yourself too seriously - I expected a bit more seriousness and gravitas from such a powerful leader in the world but he's much more self-parodying than I would have imagined. The boat driver told me that while he was driving the boat one day that he was buzzed by Richard's private jet, and when he looked up, Richard was mooning him from the plane. I can't imagine there are a lot of other billionaire global leaders mooning folks!
  9. Follow your own rhythm, graciously - In his younger years, Richard said that he was often one of the last people standing at the end of a party. Now, though, he tends to bow out early most nights so he can get a good night of sleep and play early tennis. He never draws attention to his exits, just slips out graciously. He would just melt away without drawing any focus, even while he was clearly a main attraction for attention and conversation. He has a very natural way of following his own rhythms without seeming rushed or pressed, always having a good time but also not lingering if it isn't in his rhythm. This clearly applies to his life as well, as he doesn't make a strong line between work and play and service, letting them all seamlessly blend together. In the middle of a "work" day, he might abandon what he is doing to watch the flamingos on the island nest or the giant tortoises lay eggs, or spend time with the 96 lemurs preserved on the island. In this way, he follows a much more natural, instinctive rhythm.
  10. Seek entrepreneurial solutions for everything - One thing I love about Virgin Unite, the non-profit wing of the Virgin Group, is that they are very focused on empowering the businesses that can change the world. Richard is quite optimistic that we can address the major planetary challenges we face, setting bold goals like being off carbon in the global economy by 2050 and putting his confidence in entrepreneurs to drive the solutions I was struck by the staff saying that "everything Richard does is a business." The island itself, while perhaps the most spectacular private retreat in the world, is itself a breakeven business. His other residences around the world are all businesses. By turning his private homes into businesses, he frees up more resources for the non-profit work as well. I loved the story of how he started Virgin airlines. A plane in the British Virgin islands was grounded and he needed to get to Puerto Rico, as did others. He created a sign for Virgin Airways and started selling tickets and once he had sold enough he chartered another plane to take them. A new company was born through a spontaneous entrepreneurial solution to a long delay.
  11. Think ahead of the curve - Several years ago, when the Great House on the island was struck by lightning and burned to the ground, the Necker Island manager said they literally had not even been able to put out the fires before Richard was calling an architect out to the island to start drawing up plans for the next Great House. While it seemed a bit crazy at the time to get the next plans in motion so quickly,, it allowed them to minimize downtime in the long process of rebuilding. His focus is on the next innovation and what's possible in the future rather than the limitations of the present.
  12. Put family first - When asked about legacy, Richard emphasized that family is our most important and lasting legacy and to always put family first. From all accounts, his children are quite remarkable and they are a very tight-knit family, with his kids working at Virgin Unite. In this way, I also found Richard modeling a very new-paradigm way of doing business and living a lifestyle that is balanced with deep relationships.

There were, of course, many other lessons besides these 12, both from witnessing Richard in action and hearing stories from others who knew him much better.

What I came away with perhaps more than any other single thing was his humanity: his playfulness, his care for others, his generosity, his curious mind, his attitude of service, and his indomitable optimism about what is possible if we put our minds to it.

It offered me a beautiful glimpse into how to change the way business is done and build breakthroughs in industry after industry, all while having a rockin' good time.