Inspire•Educate•Empower
I've been building, scaling, and selling companies since 1992. I ran FMG through the 2008 crisis as a first-time CEO. I founded Ceros in 2012 and led it for thirteen years, from fifty grand in revenue to just under sixty million, until it sold to Sumeru in 2020.
Now I coach a small group of founders through the same shifts I lived through, while running a handful of ventures of my own and co-leading the rebuild of Rhapsody Media into an AI-native agency.
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. Most of my best work has been helping founders find their own balance.
Creativity lives between order and chaos, between art and science, between human instinct and logic. Getting that balance right is the hard part.
Creativity lives between order and chaos, between art and science, between human instinct and logic.Getting that balance right is the hard part.
Move your cursor to understand the approach
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.
Nearly every operational problem is a human problem wearing a logical disguise. We decide on feeling and dress it up in logic. The work is helping you see the real driver, name it, and act.
Strategy, hiring, fundraising, product, AI... all of it flows easier once the inner stuff is moving. Most founders bring me a tactical problem and we're two layers down within an hour. That's where the leverage is.
I'm not a playbook coach. The world is too chaotic for that right now. But there are four things I lean on so consistently 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.
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.
My personal AI, Jony, lives in my Slack and ships real work daily. He built the page you’re reading. He runs my calendar, my research, my newsletter, the back end of my coaching practice. I’m running six agents at a time most days and it feels like a team of thirty.
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.
Retainers sit around five thousand a month. Sometimes more, sometimes less, sometimes equity, sometimes nothing because I just want to help. I'd rather have a real conversation about the right shape than quote a price you'll negotiate against.
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