Which one do you prefer?
Where were you going? And why?
The things that really attract me to this work, besides the vulnerability and besides creating space for difficult questions, are three things.
Chaos
The first is the chaos that is all around us, the chaos of having to make a million decisions.
Conflict
The second is conflict, and the fact that we’re trained to go away from it. As founders, we have to lean into conflict and even feel comfortable there.
Confidence
The third is what my clients have been asking me for ten years: confidence. How can I be more confident? How can I be more myself?
Underneath most of what looks like being stuck, there’s noise. I like working on what coping mechanisms you carry from childhood into the business you’re running now. I like to acknowledge the person as a whole, and most of the time, the work is figuring out what is the noise that right now is preventing the signal from coming to you.
Executive coaching, the way I run it, is one on one work with a founder or a CEO on the person and the mindset, not just the business plan. I ask deep questions.
Most of the time we’re dealing with fear. And when we deal with fear, there are two options. Adopt a framework: go online, and there’s a step by step guide that tells you everything you need to do to avoid feeling fearful. The only problem is you’re adopting somebody else’s way of doing things, aimed at an outcome somebody else defined. You bring your fear to the framework, and the framework won’t work for you.
The other option is confronting the fear. And it’s uncomfortable. That’s why I am there.
There’s a difference with therapy, too. Therapy has a very specific purpose: to get clear about the past and explore everything. With coaching, we’re trying to go into the future.
What executive coaching is here, and what it never is
How coaching works
There are three phases: we work on the problem, we work on the narrative, and then we work on finding your voice.
We work on the person
We work on the problem
We work on the authenticity
We find your intuitive sense
You solve the problem
Founders typically work with me for around a year. We do it at your pace, with the tools you prefer. If you like information, I send you information. If you like working one on one, we work one on one, and we get to your goal. There’s really no analytical part to it, because everybody’s journey is different.
I know in advance we’re going to encounter some recurring themes. And each time we do I will have specific resources ready to share with you. That’s what I call Founder Journey.
What changed for the people who did this
Some of my clients’s stories
Sophie: “A PARTNER THAT HELPS AMPLIFY MY WORK”
“He’s my coach, but he feels like a friend. A partner that helps amplify my work. He understands things I’m doing but don’t even know I’m doing.”
Before: Sophie left corporate and built two companies. But they felt like jobs. She’d assigned herself a job description. She hadn’t detoxed from corporate.
The shift: She learned entrepreneurship isn’t following VC rules or someone else’s playbook. It’s doing what you love. Clearing doubts. Focusing on who you are.
After: In less than a year she is running leadership retreats & masterminds in two continents.
In the process she doubled her revenue.
From “How am I going to make it?” to “I know exactly what to do: get out of my way.”
She stopped worrying. Started feeling serene. Confident. Focused.
JEN: “He spotted what everyone else missed”
“He was the only one who could spot the root cause and say: ‘Let’s follow this thread and unlock it.’”
Before: Jen ran a B2B marketing agency. She was working hard but her business wasn’t growing. Multiple coaches told her: “It’s your mindset. Fix that.” Years of coaches & masterminds, but nobody could actually help her.
The shift: They did deep work. Not just talking about feelings. Actually unlocking the block.
After: Within one month: her biggest client ever. Within one year: pivoting from marketing to M&A. Working with businesses far larger than her previous experience. Her 5-10 year dream? She’s doing it now.
“It’s like healing a broken leg you’ve been limping on your whole life. Now I can actually run.
If you’re a high-performance decision-maker and you’re not integrated, you will always be struggling.”
Mario: €5M in funding by telling the right story
“Working with Matteo was a game-changer. He helped me shape my pitch like a compelling story. I learned to direct listeners’ attention exactly where I wanted it and I closed a €5 million funding round with European investors.”
Before: Mario had a brilliant business. Solid technology. A winning idea. But his pitch was too technical. He had all the ingredients. He just didn’t know how to make them appealing to investors.
The shift: Three months of work together. Taking the technical pieces and building a narrative around them. Not changing what he had. Translating it into something investors could understand and feel.
After: €5M Series A funding.
The lesson:
To create a winning pitch, you need to be vulnerable, believe in yourself, find your confidence, tailor a story for your audience, and then have the guts to go out there and change the world.
And that’s exactly what Mario did.
Two decades across tech, film, and consulting
I’m Matteo Cassese. During seven intense years at Warner Bros. Pictures, I helped launch more than 140 films. And then I switched it up again and left corporate for my own consulting business. It served clients like Netflix, Sony, LinkedIn, and Heineken. It thrived, but something didn’t feel right. So I burned it down.
After two decades working across tech, film, and consulting, I saw a pattern: founders with big visions and sharp minds kept hitting the same wall. It wasn’t lack of knowledge, or a wrong strategy, or a wrong market situation. It was something deeper blocking them.
Every time you have a call with me, I could give you a solution, a framework, a paint by numbers solution. It’s pretty simple. But you won’t hear it.
Instead we can work together and figure it out from your point of view.
Not for people who want a ready-made plan
What executive coaching costs here, in plain numbers
I really want to be transparent with you, so this is the whole ladder. All prices excluding VAT.
start here
Intro call
Tell me where you want to go. I’ll tell you how we get there.
monthly coaching
A custom coaching journey
Two 60-minute calls a month
Unlimited emails and messages in between calls
1:1, Online
Bring the mess you can’t show your team. Let the chaos in, sit in it with me, and sort it into what matters and what can wait. You leave thinking clearly under pressure, with a plan you believe in.
From 1,000 Eur a month
in real life
In-person intensive
A beautiful location immersed in nature. No phones or computers. An active day with time to brainstorm, exercise, hike, eat and relax. My undivided attention, curiosity and care. You leave connected to your world and yourself.
From 10,000 Eur
What I try to do with any of these packages is make sure you don’t worry about hours: do we have enough hours, are we out of hours. I want to bring you to a certain goal. That’s my job, to bring you there.
Start with the intro call
Tell me where you are stuck. I listen for what is underneath, and I tell you whether I am the right coach for you.
Coaching for your whole leadership team is a different scope and a different page: request a quote.
Not ready yet? Start with the free Founder Journey course, or take the Leverage Assessment to see where you actually stand first.
Questions founders and CEOs ask before hiring an executive coach
About
Executive coaching with Matteo Cassese is 1:1 work with a founder or CEO on the person and the mindset, not the business plan. Working with founders worldwide, he runs a full time practice built on deep questions, not frameworks. Engagements run about a year, in three phases: the person, the authenticity, then the client’s intuition.
Related
- Provider: Matteo Cassese (Person)
- Related: Entrepreneur Coaching (Service)
- Related: Founder Communication Coaching (Service)
- Resource: Founder Journey free course (Course)
How executive coaching works
There are three phases: we work on the problem, the narrative, then finding your voice. Founders typically work with me for around a year.
We do it at your pace, with the tools you prefer. If you like information, I send you information. If you like working one on one, we work one on one, and we get to your goal.
Who this is for, and who it isn’t
This is for founders and CEOs with big visions and sharp minds, hitting the same wall over and over.
It’s not for people who want a ready-made plan. I could give you a solution, a framework, a paint by numbers solution. But you won’t hear it. We figure it out from your point of view instead.
What executive coaching costs
Start with an intro call. Monthly coaching: from 1,000 Eur a month, two 60-minute calls a month, unlimited emails and messages in between calls, 1:1, online. In-person intensive: from 10,000 Eur. All prices exclude VAT.
Why won’t you just give me the answer?
I can give you the answer, but it won’t resonate if you hear it from the outside. It’s better to do the deep work: understand why you feel how you feel, where your confidence went.
Therapy has a specific purpose: get clear about the past. With coaching, we’re trying to go into the future.
What happens in the intro call
Most people arrive saying, I’m stuck. Good, that’s self awareness.
Then I ask: where were you headed, and why? That’s where I make space for a long silence.
Someone less talented than you is growing faster & charging more.
The 3-minute Founder Assessment shows you exactly what kind of founder you are, the blind spot that’s costing you revenue, and one clear move to make first.