Work with me.

Order & Chaos.

This diagram has lived on my wall for ten years. It’s the most honest version of how I see the work.

On one side, science. Logical, structured, orderly. On the other, art. Emotional, instinctual, playful. Most founders pick a side. Most coaches do too. The real work happens in the middle... just enough order to keep the wheels on, just enough chaos to make something new.

I sit about sixty/forty toward the art. This isn’t a philosophy exercise. It’s the lens I use for everything... leadership, building companies, working with AI, creative decisions, when to push and when to wait. Most of my best work has been helping founders find their own balance.

The burning building.

It's the picture I draw most often.

You're on the top floor of a burning building. Ten doors in front of you. You stall, terrified you'll pick wrong. Check temperatures. Gather data. Pretend it's analysis. Meanwhile your team is behind you saying which door, boss? and the smoke is coming.

The winning move is picking a door, convincing your team you have a feeling about it, and working out the rest in the stairwell. Most founder coaching avoids this conversation. I lean into it.

The thing beneath the thing.

People don’t hire me because I know things. They hire me because I see things. Patterns. Blind spots. The human dynamic under the operational one. The connection between a sales problem and a hiring problem and a story the founder is telling themselves.

Nearly every operational problem is a human problem wearing a logical disguise. We decide on feeling and dress it up in logic. Most founders bring me a tactical problem and we’re two layers down within an hour. That’s where the real shift happens.

What I actually know.

I scaled Ceros from nothing to something real. Built FMG before that. Hired well, hired badly, kept some people too long, learned the difference. Performed certainty in board rooms I didn't feel, and learned when that was the job and when it wasn't. Scaled GTM until it stopped scaling, and figured out what came next. Rebuilt the company more than once, and rebuilt the version of myself running it more than once too. I know how this works, and I know how it breaks... mostly because I've done both.

The list, if I had to name it:

• Hiring, firing, and the years it takes to get a feel for either.
• Building leadership teams. Rebuilding them when they stop fitting.
• Culture. Inspiring large groups of people around something they can actually feel.
• GTM that worked at twenty people and stopped working at sixty.
• Scaling and growth, and the scar tissue you collect along the way.
• Reinvention. Rebuilding companies, teams, and identities when the ground moves under them... which, right now, it is.
• What AI is actually doing to the work, the team, and the way you think.
• Founder identity, and the way it fuses with the company without anyone asking permission.

That's most of what I bring.

I don’t work alone.

AI isn’t a tool I use. It’s the way I operate. I build with it every day. I write with it, design with it, think with it. It runs my calendar, my research, my newsletter, the back end of my advisory practice. I’m running six agents at a time most days and it feels like a team of thirty.

My personal AI, Jony, lives in my Slack and ships real work daily. He built the page you’re reading. This isn’t a demo. It’s how I already operate.

When it makes sense in our work, I install the stack with you and we learn to operate this way together. Not a side service. Part of the work. Most founders I work with start out curious about AI and leave operating in a fundamentally different way.

The frameworks I actually use.

I'm not a playbook coach. The world is too chaotic for that right now. But there are certain frameworks I lean on consistently enough that I should name them.

Lencioni. The Five Dysfunctions of a Team. A coach introduced me to it sixteen years ago and it felt less like a framework and more like someone finally articulating how I already operated. I've been teaching it for thirteen years. I know it cold.

Business Sprints. A framework I built with my old CTO, borrowed from software sprints. Theme. Why. Mission. Alignment. Rallying cry. If you have an army of seventy going over the hill and they're not aligned, the plan is irrelevant. The plan never survives. The alignment does.

Hard Thing About Hard Things. Ben Horowitz. On making decisions when there's no right one. The line I come back to most: the great CEOs are the ones who decide when there is no right decision to make. That's the whole burning building.

Play Then Apply. My own. The shift happening right now is so big that most of what you knew about how to operate just got rewritten. The honest response is to become a curious child again. Play with the tools, treat AI like a thought partner, notice the patterns, connect the dots... and only then, apply.

Sandler. On the sales side. My CRO at Ceros lived and died by it, took us from twenty people to nearly sixty million in ARR running it. I don't know the mechanics intimately, but I sat next to it for years and came away convinced the specific methodology matters less than the fact of having one. Sandler just happens to be a more human one... less ego, more honest conversation. Big fan, deep network in it.

The kind of founder I'm built for.

Pre-seed, seed, and Series A is where I light up. I can help later-stage operators too, I got Ceros there myself, but the joy is earlier.

Good fit if you...

• can sit in the room when I tell you something you don't want to hear
• are stuck in the no right answer trap
• care about creativity as much as execution
• know something fundamental is shifting because of AI, and want a thinking partner more than a coach
• are trying to build something that matters, not optimise a machine
• lean a little chaotic, a little artistic, and want a partner who’s done it

Probably not me if...

• you want validation for decisions you've already made
• vulnerability isn't on the table
• you’re late-stage, near-PE, and terrified of losing what you’ve built... staring at the doors waiting for the building to burn down

The shape.

I’ve spent most of my career creating value first and capturing it later. Not a complaint, just context. It’s why retainers, advisory equity, and flexible structures all sit naturally inside how I work.

Sometimes retainer. Sometimes advisory equity. Sometimes a conversation because the situation matters more than the invoice. I choose intentionally, and the joy of this work is real when the fit is right.

Always month to month. Locking someone into a long contract for this kind of work feels misaligned to me. The value should be obvious enough that month to month works for both of us. It can evolve into something longer eventually, but only the way a good marriage does... not to secure the person, but because the fit is undeniable.

I keep a tight book. Three to six clients at most, and right now I have room for two to four more. The work is thinking together... when it comes to building, I'll help you find and brief the right people for that.

— Simon