I Co-Hosted a Retreat With Richard Branson—Here’s What I Learned
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I Co-Hosted a Retreat With Richard Branson—Here’s What I Learned
Last week, I had a pinch me experience:
I spent five days co-hosting a retreat with Richard Branson, Adam Grant, and a group of incredible entrepreneurs and thinkers on Necker Island, Richard’s private island in the Caribbean.
The opportunity came about in the most unlikely way...
The day after my book launch in February, I got a cold DM on X:
I assumed it was a practical joke—it seemed too good to be true—but replied just in case it was real. A week later, I met Noah (the sender) at my hotel in London during my book tour and told him I was “100% in” on the spot.
It was an easy decision: I’m a big believer in placing myself in rooms where I don’t feel I belong. The discomfort is a sign of growth. I always leave with new learnings and reflections, feeling inspired to think bigger and differently about my life.
In today’s issue, I’d like to share those learnings and reflections—my best attempt to bring you into the room with me, to spark a ripple effect in your life.
Here are 7 learnings from a week with legends…
1. Intuition is earned.
There was a lot of talk about the value of intuition in business. Not overthinking decisions. Allowing your gut to guide you in the big moments.
But one silent theme I noticed:
Very few people appreciate just how much of that intuition is honed through thousands of hours of experience.
Intuition is earned, not given.
You aren’t born with good business instinct. You build it through reps. Through showing up when nobody’s watching. Through taking action.
Anyone can become a great business decision maker, but few are willing to put in the work to make those decisions look effortless.
2. You’re judged by your peaks, not your sums.
One of the highlights of the experience was getting to spend time with Adam Grant, an author whose work I have admired for more than a decade.
During a discussion he led, he talked about changing his mind on the importance of brute force hard work.
His message was simple, but powerful:
You’re judged by your peaks, not your sums.
In other words, it’s not about your sheer output, but about the quality of your output. It’s a power law.
I wrestle with this topic a lot, because part of me still thinks that focusing on sums is what allows you to increase the likelihood of producing impressive peaks.
Upon reflection, I think my model has adapted:
Create a lot at first. This allows you to refine your thinking. To earn your intuition. Then, slowly start to focus your creation on the most interesting opportunities.
Sums first, peaks later.
3. We need to look back more often.
The entire retreat was built around a series of physical challenges. The most significant was a 2 mile open water swim from Necker Island to nearby Moskito Island.
As someone who has never swam more than a couple of laps in a pool, let alone in open water, this was terrifying to me.
Once I got comfortable with the safety precautions—dozens of kayakers in the water, wearing an inflatable safety buoy—I decided to give it a shot.
After about 30 minutes of swimming, I grabbed my safety buoy and paused to take a look at my target. I felt my heart sink. It was so far away. I felt the panic set in. It was too far. I was never going to make it.
But then I turned my head and looked back. My starting place was way off in the distance behind me.
Suddenly, I felt rejuvenated. I’d made serious progress. I just had to keep going.
So, I put my head down and kept swimming. 1 hour 35 minutes later, I walked onto the beach at Moskito Island—exhausted, but thrilled.
It was a lesson for life:
If you find yourself discouraged by the daunting journey ahead, look back. You may have a long way to go, but you’ve come much farther than you realize.
When your head tells you that you’ve got nothing left, you probably have another 50% left to give if you tap into your heart. Keep going. You can do it.
4. Most people don’t know what they want.
I remember seeing this viral tweet from Naval:
My view is that there’s actually a more important foundational layer:
The only real test of intelligence is if you know what you want out of life.
I’m constantly blown away by how rare it is that someone can clearly articulate what they want their life to look like.
From college graduates just starting out to billionaires we write books about, very few have taken the time to answer that foundational question.
What do you want out of life?
Once you answer that, you can create a plan and take action to get there. But if you never answer the question, you may climb to the top of a mountain only to realize you never wanted to be on it in the first place.
5. Stop doubling down on a losing hand.
Escalation of commitment is a human tendency to continue down a given path even when facing increasingly negative outcomes rather than adjusting course.
An observation on extraordinary entrepreneurs:
They avoid the trap. They cut the line. They never double down on losing hands.
In many ways, it’s about a willingness to be wrong. If you fear embarrassment, you’ll stick to a losing plan. If you embrace it, you’ll adapt.
6. Vulnerability is contagious (and breeds strength).
In a group setting with 30+ high performers, it’s easy to imagine people hiding their insecurities to try to impress others in the group.
But early in the retreat, a few people opened up to share the raw stories of their journey, struggles, and challenges.
Leading with vulnerability, rather than bravado, immediately created a ripple effect throughout the group. Everyone let their guard down. No pretenses. No masks.
We all assume that covering our insecurities is the way to be strong, but it couldn’t be further from the truth. Opening up about these insecurities breeds strength. It encourages others to do the same and brings everyone together in a web of support and love.
No one has it all figured out. We’re all struggling through this journey together. When you open up more, you start to struggle a bit better.
7. Maybe you can have it all.
I gave a talk about The 5 Types of Wealth during the retreat. The next morning, Richard Branson pulled me aside to tell me that it had him thinking about his life.
My response to him was direct:
“I think you’ve lived by these principles without having a name for it.”
He seems to have designed a life of abundance across all five types of wealth:
Freedom to pursue interesting projects
Deep, loving connection with his family (many of whom were there during the retreat!)
Purpose-driven pursuits
Health and vitality (he kicked my butt in the bike ride!)
Financial success
While I’m sure there were times when it wasn’t perfectly in balance, he clearly never turned anything off for extended periods. He understood that anything above zero compounds. And now, he’s living the rewards of those actions.
For me, and many others, it was an inspiring example:
Maybe you can have it all.
When I reflect on the experience, I just feel an immense gratitude.
Five years ago, I had never written or shared anything with the world. And here I am, having the opportunity to sit in these rooms and share my learnings with all of you.
My lost younger self would definitely smile at the things I get to call “work” today.
And believe me: If I can do it, so can you.
I’ll close with one of my favorites from Dr. Seuss:
You have brains in your head.
You have feet in your shoes.
You can steer yourself
any direction you choose.
You're on your own. And you know what you know.
And YOU are the guy who'll decide where to go.
There’s a great big world out there. Let’s go shape it.
Most people haven’t clearly defined what they want—which is why their effort toward longevity often feels vague or reactive. If you haven’t defined what a longer life is *for*, it’s hard to design how you age.
This made me think of longevity not just as lifespan, but as *life range*—how much capacity you preserve to do what matters.
The earlier you integrate your values, the more range you can sustain. Direction compounds