Why I'm building Skin in the Game
A community for men building ambitious lives and figuring out how to be a better man along the way
Being an entrepreneur can be the most beautiful journey of self-discovery but it can also be the loneliest road you’ll ever walk.
On the outside, it looks like freedom, autonomy and excitment. But on the inside, it feels like pressure, self doubt and can be incredibly isolating.
Most founders carry it quietly. Friends don’t quite understand. Partners try but they can’t fully feel it. And for men especially, vulnerability still sits uncomfortably in the room. So we carry it, the responsibility, the fear of failure of getting it wrong.
Because no one teaches you this part. It’s not in business books, definatly not in the highlight reels. The part about leadership and loneliness. About ambition and identity. About success and what it quietly costs you and the people around you.
I’ve been there and more times than I’d like to admit.
Over the last few years of building I’ve never felt more connected to my work and never felt more alone in it. When I started saying that out loud, something unexpected happened. The men around me said the same thing.
Then, something happened last November.
I put together a campaign called I Love You Mate.
We brought 11 real men into a room, handed them a phone, and asked them to call a mate and tell them they love them. No script. No retakes. Just real men saying real words.
The reactions were priceless. Some awkward, others funny, it was pretty emotional. and healing at the same time.
The campaign went further than I expected. Over a million views across platforms. hundreds of messages. You can watch the video below
First came the men. Guys reaching out saying they were having a hard time. Real stories, men who had picked up the phone after watching the film and ended up having the most honest conversation they’d had in years with a friend. Some said it turned into a mini breakdown they didn’t know they needed. Others just said thank you. Some men just messaged and we had a chat - about life, about love about how hard it can be
Then came the women.
Mothers worried about their sons. Partners worried about their husbands. Sisters watching the men they love carry something heavy and silently. Message after message saying some version of the same thing:
“I’ve been trying to get him to talk for years. I didn’t know it was this hard.”
Because I know that man. I’ve been that man. And I know a lot of men just like him -builders, creators, leaders, doing incredible things in the world and struggling in ways they’d never say out loud.
Why men only.
I want to be honest about this because it’s a fair question.
I’m not building something that says women don’t belong in these conversations. They absolutely do and some of the most important voices in men’s wellbeing are women. My wife Amanda is the best entrepreneur I know. She has pushed me, supported me, and called me out more than anyone. The women in our lives matter enormously to this conversation.
But I’ve noticed something. Men show up differently in a room without women present. Not better. Just differently. There’s a specific kind of shame men carry around vulnerability, ambition, and identity that surfaces more easily when the performance pressure drops. When you’re not managing how you appear. When you’re just with other men who are facing the same things.
There are brilliant female-only communities for leaders and I support that movement completely. This is the equivalent, built for a specific need that I keep seeing go unmet.
Because the need is real. In the UK, 8 million men experience loneliness every week. Almost half don’t feel they can confide in friends. Three in four suicides are men. And for men running businesses, over 72% of entrepreneurs report mental health challenges — most of which they never talk about publicly.
We are at a moment where men need better spaces. Not the manosphere. Not hustle culture. Not toxic positivity.
Real rooms. Real talk. Real support.
I don’t have all the answers. This is a passion project and I’m figuring it out as I go. But I know that when I’ve been around other builders, creators, leaders, men in the arena something shifts. You feel seen. You feel understood. You remember you’re not mad for caring this much.
That feeling shouldn’t be rare. So I’m trying to build it.
Our last event at The ministry in London bridge
About the name. Skin in the Game.
In business, it means having a stake in the outcome. Real investment. Real risk. But for me it goes deeper than that.
This was about getting under the skin of men. Understanding the scars that success brings. Getting more comfortable in our own skin, which for a lot of us is something we’ve never been taught to do.
The game is what we’re all playing. No matter what level we’re at, we’re all trying to win - in life, in love, in work. This community is about how you play bigger without losing yourself in the process. How you level up without leaving behind the things that actually matter.
That’s what Skin in the Game means to me.
Right now I’m starting with two things: real life events and a small WhatsApp community for ambitious men who want to connect and support each other.
Most of the men in the group so far are founders, CEOs, business operators and leaders in their field. Not because I want it to be about perceived success but because of the specific situations, challenges, and pressures these men face.
The events are not networking nights. Not a room full of ego and business card energy.
A small, private gathering. Space to actually arrive, not just show up. A guided session to open the room. A fireside conversation with someone who has built something meaningful and is willing to talk about what it really cost them. Then we break bread together, family style. Then music and good energy to close the night.
Previous fireside guests have included Dhiraj Mukherjee, co-founder of Shazam, and Arian Kalantari, co-founder of LADbible. Men who built extraordinary things and are willing to share the scars behind the success.
It’s connection. With real talk, depth. And yeah, maybe a little bit of a bass.
The next gathering is April 15th in King’s Cross, London and we’re opening up a few spaces for ambitious men to join us Get your ticket → lu.ma/shbcyloa
Why now.
I’ve spent 20 years building brands. Reboxed. Disrupt Marketing. GRM Daily. Creating campaigns, communities and shaping culture.
And somewhere along the way I started noticing the gap.
The gap between what founders talk about publicly and what they actually feel privately. The gap between the LinkedIn highlight reel and the 3am anxiety. The gap between the ambition and the cost of it.
So I wanted to build something real, something that gave back value and created connection.
Skin in the Game is that something. A space for the conversation that actually matters can happen. About ambition and identity. About what it really takes to build a life you’re proud of without losing yourself in the process.
If you’re a man building something a business, a life, a family, a vision - and you’ve ever felt like you were carrying it alone, this is for you.
You don’t have to have it figured out. None of us do. You just have to be willing to show up and do the work…the real work.
Hopefully I see you in the room or at least subscribing to the content. 🖤 If you’d like to apply to be in the group, attend the events or connect drop me a mail at hello@philkemish.com and we can connect the dots.
Up next week - The messy middle - and what they don’t teach you to get through it.
Skin in the Game is built by Phil Kemish - Entrepreneur, creator, and speaker. Co-founder of Reboxed® and Disrupt Marketing. 20 years building brands across media, technology and culture.
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