The Part Nobody Teaches You About The Messy Middle

Five years into building Reboxed, I found myself questioning something I hadn’t doubted in a long time.

Not the market. Not the team. Not even the model.

My belief.

From the outside, people see the progress. The partnerships. The awards. The momentum. And I’m proud of what we’ve built, genuinely. But there’s a version of this story that doesn’t make it onto the highlights reel. The one that happens at 11pm when the spreadsheet doesn’t quite add up, you can’t sleep and you’re lying alone with the weight of it. Nobody teaches you about that part.

Startups have seasons.

There are moments of pure beauty in this game. Early traction. The first customer who really gets it. The team growing and firing on all cylinders. The feeling that you’re building something that actually matters.

And then there are the other moments.

The model evolves. The market shifts. Cash gets tighter. People leave. Expectations get heavier. And somewhere in the middle of all of it, a question appears that you weren’t expecting:

Are we still on the right path?

This is the loneliness of leadership that nobody writes about. Not the sexy kind of hard — the grinding, unglamorous, keep-showing-up-anyway kind. The responsibility of other people’s livelihoods sitting on your shoulders. The weight of investor capital. The fear of getting it wrong quietly living alongside every decision you make.

You keep moving. You keep building. But the conviction that carried you through the early years gets replaced with something else.

Not certainty. Just persistence.

What I’ve come to understand is that this phase “The Messy Middle” is actually very common in companies that survive long enough to matter.

There’s a brutal stretch between early traction and real scale. Scott Belsky calls it the messy middle (he literally wrote the book on it). The space between finding product market fit and building something that actually scales. The first model stops working perfectly. The new model isn’t fully proven yet. You’re operating without a map, navigating by feel, trying to hold the team’s confidence while quietly rebuilding your own.

The problem is that what got you to £5m will kill you on the way to £30m.

You know that intellectually. But do you really know it? In your body, in your decisions, in the way you show up every day?

Early growth runs on founder energy. Hustle. Duct tape. Scrappy conviction and sheer force of will. And that works, for a while. It gets you off the ground. It proves the concept. It builds the early momentum.

But it doesn’t scale.

Getting through the messy middle is a different game entirely. It requires a different version of you. Less doing, more deciding. Less hustle, more clarity. Systems that work without you in the room. Leadership that multiplies rather than depends. A story you can tell with conviction even when you’re still living through the uncertainty of it.

That’s the transformation nobody puts in the business books.

As a founder, you carry things you can’t always put down.

You can’t share every doubt with the team - their belief is part of the fuel. You can’t always be transparent with investors about the wobble as confidence is currency. And you can’t always explain it to the people closest to you, because unless they’ve been in the arena, the words don’t quite land the way you need them to.

So you carry it.

And in carrying it, you can start to confuse the weight with failure. The doubt with weakness. The uncertainty with being on the wrong path.

But I’ve started to think about it differently.

The doubt isn’t a sign that something is broken. It’s a sign that something is being rebuilt.

The messy middle isn’t a crisis - it’s a transformation. And transformation, by definition, is supposed to be uncomfortable.

The mission wasn’t wrong. The business isn’t broken. The next chapter just looks different from the first one. And that’s not a problem to solve — it’s a reality to lead through.

So right now, I’m reminding myself of a few things.

We’ve built something real. Something with genuine impact and a reason to exist beyond the numbers. The team we’ve put together is the best we’ve ever had. The model we’re evolving is stronger than the one we’re leaving behind.

If you had offered me where we are today, this time last year — would I have taken it?

And none of that is certain. But it’s worth fighting for.

This is what being in the arena actually looks like. Not the highlight reel. Not the award on the shelf. Just a founder, in the middle of the game, choosing to keep showing up.

The job of the founder is not to have all the answers. It’s to keep showing up until they do.

And for now, that’s enough.

If this resonates, Skin in the Game is where I share the real journey, the lessons from the arena on business, leadership and what it really takes to win without losing yourself. Subscribe below.

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I first met Sach during his days of building Secret Sales one of the UK’s first flash sale fashion platforms, co-founded with his brother Nish at just 22, six months out of university.

By the time we connected, the business was already flying. £48 million in annual sales. £18 million raised from venture capital. Ranked in the Sunday Times Tech Track as one of the fastest growing companies in the country. The kind of numbers that get you on lists. And he was on plenty of them — Debrett’s 500 Most Influential People in Great Britain, Entrepreneur of the Year, top BAME leaders in business. A genuine champion in the arena.

But we didn’t bond over any of that. We bonded over music. And that small detail tells you everything you need to know about the man.

Most men building companies at his level are quietly unravelling somewhere. The pressure is relentless, the identity gets swallowed by the company, the relationships take the hit. Sach has lived all of that. He exited Secret Sales in 2017, then rebuilt — launching 7879, a sustainable luxury jewellery house that secured £6 million in seed investment, landed a pop-up in Harrods, and is redefining what it means to own gold and platinum. Two decades of building. He’s got real scars. Had some tough times and by his own admission, still figuring it out.

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After 40. During the intensity of everything he was building - something shifted. A conversation with a man in South Africa changed the way he looked at his body, his stress, his age. He rebuilt from the inside out. Fasting, health resets, a whole new playbook for the mind and the body. Not as a trend. As a philosophy.

What makes Sach worth sitting across from isn’t the exits or the accolades. It’s what he does alongside all of it. His Instagram bio says it better than I could: “Building brands. Biohacking life.” He moves, he connects, he makes music, he supports others.

Every years he maintains a tight circle of men he’s been retreating with every year for nearly a decade, five friends from different industries, no agenda other than honest conversation about what’s working, what isn’t, and what actually matters.

That’s not a habit. That’s a philosophy. And it’s the kind of thing most founders are too busy, too proud, or too isolated to build.

That’s the kind of space I’m building. And on April 15th in King’s Cross, we open the door for a few men to join us.

25 tickets. Only few spots still remaining. If you’re building something a business, a life, a version of yourself you’re proud of - this one’s for you.

Secure your place here → https://luma.com/shbcyloa For more follow @philmckemish and to learn more about Sach connect on social media @secretsach

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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.

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.

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.

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.

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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I watched the Louis Theroux Manosphere documentary this weekend.

I watched it with my Mum.

She sat next to me on the sofa, quietly taking it all in. Not angry. Just genuinely shocked. Not at the men selling this stuff. At the fact that millions of young men are buying it. That this world exists, is enormous, and until now had been completely invisible to her.

To be honest, even knowing what I know, a lot of it was invisible to me too.

By the metrics of the manosphere, I am a catastrophic failure of a man.

I’m probably a solid 3 out of 10 on whatever value matrix these guys are running. My jawline is heading south. My waistline is going with it. I don’t have a Lamborghini. I have what you might generously describe as complex emotional needs. I cry at films. I love Bridgerton. I talk about my feelings. I have days where I struggle and I say so out loud to the people I love.

I also have a wife who is, by any measure, a 10 out of 10.

And she doesn’t love me despite those things. She loves me because of them. She has told me, more than once, in more than one way, that my willingness to be soft, to be vulnerable, to show up emotionally present rather than armoured up and performing, is exactly what makes her feel safe. That’s the foundation our relationship is built on.

So I watched this documentary and I thought: what are these men actually selling? And why are so many young men buying it?

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The psychology of selling pain.

Here’s something worth understanding. Because it’s much older than the manosphere.

Every one of us, at some point, has bought into this. Felt insecure about something — our body, our success, our relationships and reached for something that promised to fix it. The self-help book. The course. The programme. The supplement. We all want to grow. That impulse is healthy and human.

The problem is what happens when people weaponise that impulse.

The playbook is simple: find the fear, amplify it, sell the cure. You’re not fit enough, here’s the stack. You’re not rich enough, here’s the course. You’re not man enough, here’s the community. These men aren’t selling fitness or money or status. They’re selling relief from pain and insecurities. And they’re very good at it.

We’ve always had men selling shortcuts to other men. Get rich quick. Get fit fast. Get the girl. That dream has always been for sale. What’s changed is the reach and the speed. What used to travel by late night infomercial now lands in a teenage boy’s feed before he’s finished breakfast, optimised by an algorithm that has learned exactly which fear to poke.

The difference now is the scale. And the damage that comes with it.

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Back to the men themselves.

I get it. I really do.

Men are struggling. The stats are real. Isolation, mental health, falling behind in education, a loss of purpose and identity. The old scripts for what it means to be a man have been ripped up without anything coherent put in their place. And into that vacuum walks someone with a camera, a six pack, and a simple message: you’re not the problem. The world is. I can fix you.

These aren’t confident men. They’re performing confidence. There’s a difference, and the camera catches it even when they don’t.

The tragedy isn’t that these men are bad. It’s that they’re in pain and they found a way to sell that pain as a product. And millions of young men, who are also in pain, are buying it because they’re desperate.

The numbers are hard to ignore. According to Movember’s global research, nearly two thirds of young men aged 16-25 regularly engage with masculinity influencers online. Those same young men report higher levels of psychological distress, are less likely to prioritise their mental health, and are more likely to engage in risky behaviours. And according to Equimundo’s State of American Men report, two thirds of young men feel that no one really knows them. That’s not a crisis of masculinity. That’s a crisis of connection.

I think about my two teenage nephews growing up online, algorithms already learning their insecurities, content finding them before they even know what they’re looking for, and I find that genuinely terrifying.

What they’re actually selling.

The courses, the supplements, the membership communities. Those are almost incidental. What these men are actually selling is identity. Belonging. A story about who you are, why your life looks the way it does, and who’s to blame for it.

That sells because identity is exactly what a lost, isolated young man is desperate for.

But the identity on offer is a cage. It tells you that softness is weakness. That emotion is failure. That the measure of a man is his jawline, his bank balance, his ability to dominate. That the women in your life, your mum, your sister, your partner, are obstacles or objectives. Never allies.

I think about my own life and I know with complete certainty that is wrong.

This is exactly one of the reasons I started Skin in the Game. To build something that goes in the opposite direction. A community for men who want to lead better, live fuller, and play bigger without losing themselves or the people they love in the process. Not a red pill. Not a quick fix. The real work.

What these men actually need.

This is going to sound reductive. I mean it sincerely.

I think most of them just need a hug.

Not because they’re weak. Because they’re human.

Because underneath every man performing dominance online is a person who learned somewhere along the way that needing things from people was dangerous. That asking for help was failure. That softness would get you hurt.

And instead of healing that, the manosphere monetises it. Fuels it. Amplifies it and feeds it back to them as identity. And in doing so it’s creating a generation of young men whose role models are performing pain as power.

That’s not a movement. That’s a crisis.

A final thought. Maybe instead of the red pill, try listening to the women already in your life.

Instead of paying a stranger on the internet to tell you how to be a man, what if you asked your mum? Your sister? Your partner? The women who actually know you, who have watched you your whole life, who want you to be well?

I know what mine would say.

Stop performing. Start feeling. The people who love you aren’t waiting for you to be dominant. They’re waiting for you to show up.

If you’re looking for a quick fix, a shortcut to the man you want to be, I understand the appeal. We live in a world that sells shortcuts to everything. But the work that actually changes men’s lives doesn’t come in a course or a supplement stack. It looks like therapy. Honest friendships. A partner you let in. A relationship with your own fear that’s curious rather than hostile.

It looks like finding a role model who has the success and the drive but also shows up for his friends, his family, his partner. Who is willing to be honest about the hard stuff. Who measures himself by the depth of his relationships, not the size of his yacht.

Do the slow work. The deep work. That’s how you get out of the matrix. Not into a smaller, lonelier version of it, but into something real.

You deserve a bigger, better life.

If you haven’t watched it yet, Louis Theroux: Inside the Manosphere is on Netflix now. Watch it. Then have a conversation with the people around you about what you saw.

You can watch the Louis Theroux Manosphere trailer below:

That conversation is probably more valuable than anything in the manosphere ever will be.

Skin in the Game is where I share the real journey. The lessons from building, leading, and figuring it out without losing yourself and becoming a better man along the way. If this landed, subscribe below.