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 ultimate freedom and autonomy over your business, time and life. But on the inside, it’s a constant pressure, doubt and damn, it can be isolating.
Most founders carry it quietly. For me it’s become something I feel will only lighten by sharing with a community who just get it. See the thing is, friends just don’t get it, partners try but it’s not always fair to take it home with you - and for men especially, our vulnerability silents us. So most of the time we keep it inside, the responsibility, ambition, fear of getting it wrong - alone.
No one warns you about this part, it’s often left out of the business books, and is definitely not in the highlight reels - the part about leadership and loneliness, the fight between ambition and identity. And, about how the long battle to success can more often than not quietly cost you the people around you.
I’ve been there and more times than I’d like to admit.
Over the last few years of building reboxed, I’ve never felt more deeply connected to my work but I’ve also 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, to be honest it was a pretty emotional day of filming - and healing at the same time.
The campaign went further than I expected, we gained over a million views across platforms, and received hundreds of messages. (You can watch the video below.)
I knew there was a problem, but I wasn’t prepared for how many men reached out to me saying they were having a hard time. Some even shared moving stories, of how they picked up the phone after watching the video and ended up having the most honest conversation they’d had in years with a friend. Some said it tumbled them into a mini breakdown they didn’t know they needed. Before I knew it my LinkedIn DMs were busy with chats about life, about love, about how hard it can all be.
I also received an incredible amount of messages from women.
Mothers worried about their sons. Partners worried about their husbands. Sisters who’ve identified their brothers silently carrying something heavy.. Most said 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 open about this because it’s a fair question.
I’m not building something that says women don’t belong in these conversations, as they absolutely do. Some of the most important voices in men’s wellbeing are women. My own 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 and enormously impact 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 pressure to perform drops. There’s much work to be done, many conversations to be had, without the ego and between men who are facing and feeling the same things.
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.
I think it is clear, men need better spaces. Not more hustle culture, or toxic masculinity, and definitely not the manosphere.
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. And, to be totally honest - I need this too. I just know, when I’ve leaned into my vulnerability and shared my feelings with other men in the arena - something shifts I feel seen, understood and things become clearer. 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 with 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 that these men face.
The events are not networking nights. Not a room full of ego and business card energy.
A small, private gathering. A safe 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 (above) , 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 Apply for 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 for the people you love, 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 or following on Linkedin and instagram. 🖤 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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