“Fear isn't only a guide to keep us safe; its also a manipulative emotion that can trick us into living a boring life.”
Donald Miller - A Million Miles In A Thousand Years
'I was waiting for you to come back and run with it,' my friend said. 'That was always my hope.'
I was terrified to organise something like this - not because of the logistics or the cost, but because of a deeper fear I couldn't quite name at first.
I knew why I wanted to organise this. I was afraid that in ten years, when my kids need me less and the daily chaos of parenting subsides, I won't have enough people I can call my people. I won't have enough conversations or enough interesting things to be involved with. That's the real fear. That's why I'm here.
From Forward To Back
Ever since I made the move away from the sweaties in the scrum and joined the dashing models in the backs of a rugby team, I've worn the number 13 jersey.
The number thirteen has always had a special place in my heart. It's in my favourite username, madmorg13, I used it for my DJ name (and logo!).
My daughter was born at 4.45am (4+4+5=13). The postcode of my favourite place in France is 06250 (yes, I've checked - it adds up to 13). I'm aware this makes me sound barmy!
2 Years ago, a friend of mine - the CEO of a technology company here in the neighbourhood - came to me with an idea. Small, curated dinners. A handful of male friends from each of our circles. Good food, good wine, great connections. This wasn't networking. The point wasn't business. The point was bringing together interesting people and seeing what happened.
I loved everything about it. I love meeting new people in smaller, more intimate settings. I love organising things. I love drinking great wine.
But at the time, my confidence was shot. I didn't realise it then - or maybe I did and couldn't admit it - but I felt like I had nothing to offer.
So I did nothing. I waited for him to come back to me. To initiate the next stage. To tell me what to do.
Looking back, I can see what was really happening. I was terrified. Not of the logistics - terrified that I'd send out invites and nobody would come. Because why would they? What credibility did I have? What was I even doing with my life that would make someone want to spend an evening with me?
My friend, who'd suggested all this, has an incredibly busy life. He's trying to build his company, raise three kids, and run a foundation. Unsurprisingly, he didn't have a ton of spare time. And so the idea of these curated dinners died on the vine that year..
In the months that followed, he and I still spent many a breakfast, lunch, or walk around the neighbourhood discussing business and life. He was a staunch advocate for me to start writing. He felt I had stories to tell and that I'd enjoy the process.
It terrified me.
But, as long-time readers will know, I started writing mid-way through 2024. And much to my shock - and I suppose delight - after sending out those first few blog posts, I didn't die. The ground didn't open up and swallow me. My friends didn't disown me. And I wasn't front-page news on The Sun or The New York Post as being an idiot, a terrible entrepreneur, investor, or person.
Something about the lack of Armageddon-esque events gave me a spark of inner confidence. I wasn't chasing down a book deal or knocking on TED's door, but I enjoyed the process. I enjoyed the engagement and the responses I was getting. Somewhere, I was stoking a very small creative fire.
As some of my fears subsided, I took up another friend's offer to connect with the Harvard Business School professor who'd written the case study on Ample Hills - the company where I'd been both an investor and president in its final years before the first bankruptcy. That connection led to me scheduling a trip up to Harvard, which was life-changing. But more importantly, the momentum from writing, coupled with the boost from that Harvard conversation, set me on a more open-minded trajectory. To trying new things. To pushing boundaries and taking risks. Something I used to have but which had been significantly cowed after the Ample Hills failure and some lacklustre investment outcomes.
All this meant that as I came into 2025, I had found a new level of energy around trying things - irrespective of whether they worked or not.
In early January, I went back to my CEO friend and said, "I want to rekindle the idea we had about hosting dinners. I'd love to do it with you, but I understand this is a huge year for you and your company. If you don't have the time, I think I'm going to do it anyway."
I wasn't surprised when he told me he loved the idea. I wasn't surprised when he said he wanted to do it with me. I even felt somewhat honoured that he was happy for me to run with it and have him be the silent partner — given how much he had to deal with.
Where I was surprised - where he stopped me - was what he said next.
He'd been waiting for me to come back to it. That had always been his hope.
I'd spent eighteen months convinced I wasn't enough, that people wouldn't come to something I organised. And he'd been sitting there the whole time, waiting for me to believe in myself.
He thought my fears were ridiculous.
And so began the planning of what we'd already decided, a year previously, we would call The XIII.
An excerpt from the first email we sent to invitees:
We both wore the hallowed “13” jersey as rugby players.
A “13” must possess both defensive strength and attacking flair, must read the game's subtle rhythms and create unexpected breakthroughs.
Our coming together is intended to balance structure with surprise, intimacy with intrigue in the hope of creating new connections, sharing new ideas and putting the foundations of lifelong bonds, as fostered by the game of rugby.
XIII awaits those who appreciate the art of perfect timing, the thrill of the breakthrough, and the beauty of being in exactly the right space at exactly the right moment.
We look forward to our collective collision!
We hosted our first dinner in February in a private room at a Soho restaurant owned by a friend of mine. We brought our own wines but didn't make bringing wine a requirement.
The only thing we asked our initial invitees to bring was an answer to each of our purposefully open-ended provocations:
What are you excited about this year?
What are you afraid of this year?
What we hoped to achieve with these provocations was an opportunity for each person to answer in a way that reflected where they were in that moment and the things that had brought them there.
This sounds overly serious. In reality, I knew at least one person would show up with a sarcastic British quip that would crack the whole thing open. And he did - leading to him being declared co-MVP of the evening.
Equally, both my partner and I knew some of the other invitees would come with deeply thoughtful, cerebral answers. We couldn't have predicted how deep some of those thoughts turned out to be.
More than anything, it made for an incredibly connected conversation - a group of people willing to show honesty, vulnerability, insight, and humour.
We've now held six of these dinners and hope to continue - evolving the discussions and the group whilst never losing the core ethos of connection, presence, and vulnerability.
Almost by accident, our initial intention to have only thirteen guests has amplified the intimacy. We've added a handful of new people throughout the year, but delicately - respecting the balance and energy that's formed.
We didn't want to always control who comes, so we're experimenting. The core group will be able to add people to the roster when spots open up. Our hope is that the list grows organically and becomes more diverse in the process.
Perhaps our biggest learning so far has been this: bringing together a group of guys in a setting that's not only not business-oriented but almost anti-business, prompting them to open up, leading with our own vulnerability - it's set the group on a path to much deeper and longer-lasting relationships with each other.
The number of attendees who now tell us they look forward to these get-togethers, that they need these get-togethers, is both telling and humbling.
At that first dinner, standing in the private room waiting for people to arrive, I was still half-convinced nobody would show. Or that they'd show out of politeness and leave early.
They all came. They stayed. And they asked when the next one was.
We’ve been there for each other through guys losing their parents, having their kids go off to university, navigating challenging dynamics with families and celebrating big business wins.
The willingness of this group to come together and share - wholly and fully - has made each dinner more satisfying than I could have hoped.
I'd spent eighteen months afraid to host a dinner because I thought I had nothing to offer. Turns out, the thing I was most afraid people wouldn't show up for was exactly what they needed.
What have you been waiting for permission to start? What dinner are you afraid to host, email afraid to send, project afraid to begin - not because you lack the skills, but because you're convinced you're not enough?
And who in your life has been sitting there the whole time, waiting for you to believe in yourself?
Start it. This week.
