'Training for life' and 3 other things I learnt spending the week with Richard Branson
Sometimes you meet your heroes and they disappoint you. Sometimes you meet your heroes and they inspire you even more. And sometimes you meet your heroes and they give you a triple beatdown.
‘Necker Island...’
With that subject line on an email I had to open it. Never mind that it was the week before Christmas, I was on holiday in Patagonia, holed up in a tiny hotel with sketchy wifi, and was about to go off-grid hiking for the next 8 days. I was taking that introductory call.
Growing up our home was scattered with Richard Branson’s books. He is the inspiration behind my mum starting her own company. And famously, he lives on a private island: Necker Island.
Speaking has taken me to some incredible places - from conference stages like TEDx and SXSW, to the Paris Olympics. But an intimate speech to 100 people on a private island, with Richard Branson in the front row asking questions and making jokes... what an incredible memory. And then I got to spend the entire week hanging out with him. (Read to the bottom to see how he humbled me in 3 different sports).
I’ll save what I spoke about for another post. Instead, here is what I learnt from spending a week with one of the greatest entrepreneurs in history: Richard Branson.
Take MORE risks as you age
‘What’s the scariest moment you’ve had in all your adventures?’
It was day 1 on the island. At breakfast time I just went for it and sat down next to Richard (My friends all say ‘Of course you did!’) The person sitting opposite opened with this question.
‘Probably hot air ballooning across the Pacific ocean,’ he told us. ‘We were 1000 miles into a 8000 mile trip, and 3 of our 6 propane fuel tanks froze and then dropped into the water, gone forever. It was almost certain death.’
This was said in the casual tone you might use to say ‘pass the sugar’. Completely downplaying the tension.
‘The balloon was far too light and rising too high,’ he went on. ‘We didn’t have enough fuel to cross the ocean. And we calculated that we’d have to travel at 180 miles an hour to make it… and no balloon had ever gone faster than 70 miles per hour.’
At the table we had fighter pilots from the Marines, people who had built businesses into the billions of dollars, and I’m a former trampoline athlete who is comfortable upside down 30 feet in the air. None of those are easy things, and yet none of us would have liked to be in that balloon in that moment.
‘Everything that could go wrong did go wrong. My co-pilot was a much more experienced balloonist and he was on the floor, not responding.’
‘What were you thinking in that moment?’ We were all hanging on every word of this story.
‘Our comms weren’t working, so we had no contact with anyone, no way to get help. I was thinking of the letters I had written to my wife and kids in case we didn’t make it.’
‘And then?’
You can read the facts of this story online - Richard has told a smoother version in public settings and even has an animated video for kids. But over the table at breakfast, you get the honest version. How his co-pilot really reacted. How close to death they really were.
‘And then I just made the best decision I could in the moment - often that’s what bravery is. I took the balloon up, up, up into the jet stream. We were lucky, we got right in the middle of it, and the speed just took off. 60, 70, 80, 90, 120, 130, 140, 150, 200, 220, 230 miles an hour.’
‘For three days we didn’t sleep. We stayed in the jet stream as long as we could, covering as much distance as possible. We had no navigation. And no comms. Back at home, they called my wife and told her they’d had zero contact for days. She knew what that meant…’
Ultimately, of course, they made it. They landed 4000 miles off course - in the arctic circle rather than LA.
Later in the week, as I sailed a tiny boat together with Richard and two other people in a race around the island, I asked:
‘Do you feel the need to keep upping the ante on your adventures to have them be fulfilling? You’ve done some crazy things, do you feel compelled to do even more daring things?’
Richard didn’t hesitate.
‘If I’m willing to take those risks in my 20s and 30s, then I should be even more willing to take them in my 70s and 80s.’
‘Training for life’
My alarm went off at 5am. I slapped at my phone, groaned softly, and then rolled out of bed. 5am is an early wakeup for the very last day of vacation.
‘That’s where we are going,’ the staff member pointed up at the mountain. We had taken a boat from Necker Island to a neighbouring one.
‘That white building?’ I asked
‘No, the green one,’ she said. ‘Way at the top of the hill.’
‘Oh…’
I was handed a bike and a helmet.
‘You should probably just keep the bike in the easiest gear the entire time. The entire ride is uphill,’ she told me.
Meanwhile, Richard was pulling on elbow pads and knee pads.
What exactly had I gotten myself into.
I am an athlete. But I’m a power athlete. Sprints, heavy lifts, maximum intensity intervals of 45 seconds or less - that’s my jam. Non-stop uphill riding for an hour and a half…
Not my jam.
My strategy is to put the bike in a hard gear on the gentler incline parts. Sprint towards the steep hills with as much momentum as possible. As I climb the hill, switch into easier and easier gears. Until eventually I’m riding so slowly I think ‘it would be faster to walk’. And so I do.
Richard didn’t get off his bike once. He’s 74.
My quads were relieved to make it to the top. We had started with 7 fit people who’s idea of vacation is exercising at 6am. 3 of those people had abandoned biking and decided to hike instead.
Richard? When we got to the top he asked:
‘Anyone want to ride a little further up the road?’
I politely declined in favour of spending some time enjoying the view (ie. resting my legs). It turns out ‘a little further’ was all the way down to the water on the other side of the island and back up the entire hill.
I’m so devastated to have missed it 😅
The downhill ride was done at full speed (now the elbow pads made sense!) Shouts of joy, a view of brilliant turquoise water dotted with islands, and the tropical sun on our faces. Magical.
On the boat ride back, when I had enough breath to speak, Richard asked me for advice in the gym. Squat technique, injury prevention, strength training - he wanted to know it all.
‘What are you training for?’ I asked. Your goals determine your program after all.
‘I’m training for life,’ he said.
Compete, compete, compete
‘The lightest boat usually wins,’ said Richard. ‘So I only want women on my boat.’
He wasn’t kidding. 50 people were milling around on the beach, with 10 Hobiecat sailing boats pulled up on the sand. We were about to race around Necker island.
One of the event organisers came up to us with a heterosexual couple, asking if they could join the boat with Richard.
He said no. 😂
Richard has an entire team of water sports professionals who work on the island. Teaching guests sailing, kite surfing, e-foiling and more. In their spare time some of them compete in these sports.
But out on the water with Richard, the focus was on winning. And you could see the intense joy competing gave him.
(For the record we didn’t win.)
The pickleball tournament was a Pro-Am. A pro player is paired with an amateur.
Guess who I drew to play against in the first round?
‘This is my chance’ I thought.
Earlier that week my mum had and I had this text exchange. The stakes were high. I figured I wasn’t going to beat Richard at his sports - biking or kite surfing or tennis…
But pickleball? We were both amateurs.
Richard had picked Jessie Irvine - a pro with a lovely smile, and an absolutely killer instinct.
I was paired with Beth Bellamy - a former top 50 tennis player.
Our court was surrounded by photographers, videographers, and a ton of other competitors. All there to witness our incredible pickleball skills.
‘Let’s crush them,’ I said to my partner. ‘And feel free to steal balls from my side of the court.’ I knew my strengths lay more in being the Chief Cheerleader in our partnership. She’d have to bring the actual pickleball skills.
‘No, we can play nice,’ she said. I was horrified. This was a competition. There is no playing nice. And after my sailing experience with Richard, I knew just how much he would want to win.
The joke in my family is that when I was 12 and going off to sporting competitions my mum would say ‘have fun’. I would reply ‘winning is fun’.
Anytime the score got close, Jessie served a couple of aces.
Anytime I hit a smash, I got the next ball back from her twice as hard.
We were the ones that got crushed.
‘Sorry about your loss,’ Richard found me after the game. ‘Can I get you a hot chocolate to commiserate?’
‘Thank you,’ I said. ‘But I know you’re not really sorry. You’ve already humbled me on both the bike ride and the pickleball court today.’
‘I know’ he said, a giant smile stretching across his face. ‘Now come over here and let’s play some chess together.’
‘You just want to beat me again,’ I said. From one ultra competitive person to another, we both knew it was true.
‘Absolutely.’
I haven’t played chess since I was 10 years old. He made half of my opening moves for me while I remembered how all the pieces move.
There was a brief moment where I got him to check. And then the smile disappeared and the focus ramped up. Then I lived through a slow death as he stole all my pieces and another victory.
Which is how I got a triple beatdown from Richard Branson. Losing on the bike, the pickleball court, and the chess board all in a single day.
‘How about we go and do some of my sports now?’ I asked. ‘Let’s play some beach volleyball, then go on the trampoline, and then work out in the gym together.’
Mysteriously, he disappeared.
Humanity first, business second
Sometimes you meet your heroes and they disappoint you with their humanity. They don’t live up to the standards they talk about.
Sometimes you meet your heroes and they inspire you with their humanity. They quietly live by a strong moral code, and do the right thing without an audience.
There were two moments that did the latter.
First, my presentation on the island was based on investing in women’s sport. We structured it as a game where everyone was the owner of a team and had to make choices on whether they’d prefer to put their money into the ‘story’ (media) or the ‘stadium’ (real estate) to grow their team.
One of the choices was between putting $5M into either:
A community program that gives back as a way to build grassroots fandom
Increasing the sponsorship assets in your stadium to grow revenue
There is no right answer - teams are testing these strategies as we speak. Usually the answer is that you want to do both, but you have to decide on what order to do them.
But Richard was clear ‘I’ll go for the community program because if I’m wrong at least I’ve helped the community’.
Humanity first.
The second moment was hiking around the island. When you get a group of Americans together, inevitably someone talks about politics. And so as we walked past lakes full of flamingos and pet giant tortoises, someone asked what he thought.
Richard is in the unique position of having spent one-on-one time with many of the politicians we only see in the media. I won’t share the details here, but he told us exactly what the experience was like. He doesn’t weigh in with strong opinions often. But on when he does he is clear.
Most people who support the current leadership of the USA say something along the lines of ‘I don’t support him as a person, but he’s effective in getting things done.’
‘I couldn’t disagree more,’ he said. ‘If you aren’t a good person, I don’t trust you to lead.’
Humanity first.
Bonus: How to up your dating game
What do you normally plan on a third date? Dinner and drinks? A pickleball hit out? A show or movie?
‘I was 28 and in NY at the time. I had seen this girl Joan a few times. Technically, she was dating another guy and so I was trying to find a way to win her over,’ he started.
‘At the same time, a friend had asked me why my company was called Virgin. He asked if it was named after the Virgin Islands. I’d never heard of them so I looked them up, and saw that you could buy one.’
‘My business wasn’t making much money yet, I was a nobody, but I called up the broker for the islands and pretended I was important.’
At this point, we’re all laughing. Who goes from discovering an island chain exists to calling the broker as a next step? It’s classic Richard Branson.
‘They invited me down to tour the islands. Private plane, helicopter tour, nice hotel - the works. I agreed on one condition. I could bring a guest. I left the plane ticket for Joan and hoped she would show up.’
‘She did.’
‘The broker is showing us around all the islands, and I’m finding ‘fault’ with each one because I can’t afford any of them. ‘A bit small’ or ‘the view isn’t good enough’ or ‘too close to other islands’. Eventually the broker takes us out to see one more island: Necker Island, which is far more remote than the rest of the islands.’
‘It’s beautiful, but the asking price is $6M. I offer $100k - it’s all I think I can scrape together. The helicopter and plane and hotel all disappear instantly. The broker leaves us to find our own way back to NY.’
‘But a year later, they come back to me because the owner really needs to sell. ‘How much can you offer?’ they ask. I say ‘$100k’ again.’
‘Ultimately we settled on $180k to buy the island.’
‘And you got the girl,’ I chimed in.
‘And I got the girl’ Richard agrees.
Same time next year?
They say you win or you learn.
Honestly, if I’m going to get a triple beatdown, having it be from Richard Branson isn’t a bad way to lose.
Next year I’ll corner him on the beach volleyball court.
P.S. This trip was put on by Necker Island Pickleball Forum if you want to sign up for 2026.
