Being smart and working hard got you this far. Now you’re stuck.
On the outside, everything’s working. But you are burning out.
You’re working the longest hours but the ceiling won’t break. The efforts won’t scale.
You are thinking harder than ever, but it just gets you stuck in analysis paralysis.
You don’t know what to decide. You don’t know in which direction to move.
Your analytical mind brought you this far. Now it’s the thing standing in your way.
It’s not a technical problem. It’s a problem of meaning.
You won’t figure it out by doing more research or analyzing more options. You won’t figure it out by reading guru’s books or best practices. Not through any new technology or study. This is not an engineering problem for you to solve. It doesn’t work like that, and you know it.
You have a philosophical problem. A problem of meaning. And until you find that meaning, things will stay stuck.
Entrepreneur coaching is a one-on-one partnership between a founder and a coach who has been in that same fire. It’s not consulting: no one’s handing you a playbook. And we’re not here to fix you. It’s a safe space where you can finally stop performing and start listening to what you actually know.
I work with entrepreneurs in Berlin and worldwide who have built something real but lost the thread of meaning along the way. The work is simple: reconnect with who you are, and the decisions start making themselves.
What Entrepreneur Coaching Is
“I know who I am, therefore I know what to do”
That’s my favourite feedback from clients. Not “I studied the market so I know what to do”. Not “the team voted so I know what to do”. Deep, unshakeable confidence in your own self and in your own path – this is what finding your own truth gets you.
Entrepreneur coaching: where tactics go to die
A clear mission and a plan to accomplish it
Enough confidence to easily persuade others
Trusting your own gut and making right decisions quickly
Knowledge that the world needs you and is ready to hear you
The courage to be who you always wanted to be
Not waiting for anybody’s permission to do what you feel is right
Entrepreneur Coach vs Business Consultant vs Executive Coach
Business consultant
A consultant looks at your business and tells you what to fix.
Executive coach
An executive coach supports the C-suite to reach the company’s mission and vision.
Entrepreneur coach
I look at you and ask what’s in the way. Entrepreneur coaching is for entrepreneurs who have built something real but feel stuck.
FOUNDER journey: YOUR PATH to inner power
Let go
Safe space to be weird
Space to not know the answer. To not decide. To be conflicted. To let go of all the analysis, best practices, frameworks, and “shoulds” and accept that you don’t know.
Safe space to be scared.
Sit with your own chaos
Be understood in all of your contradictions
You are not just an invincible entrepreneur. You are a person, entrepreneur, partner, teammate, child, parent, boss, dreamer and all round human being.
Each of these identities comes with challenges, expectations and conflicts. It’s time to fall in love with all this chaos.
Finally decide for yourself
Align the pieces, your own way
Emerge with a decision – not based on what people say, numbers show, or what’s “reasonable”. A decision that is you, that you feel in your bones is right. This decision is your new grand vision, the one that was showing up as chaos.
Now all that energy that was spent on overthinking can now be poured into growth.
I know how it feels because I’ve been there
For most of my life, I believed that I was my performance.
I measured myself by my output, like a machine. I did everything right, climbing the corporate ladder at Warner Bros, then consulting for Netflix, Sony, LinkedIn.
From the outside, it looked perfect. Inside, I was exhausted. Always not good enough.
On the surface, our society praises this behavior, but in reality the world celebrates people who dare to be themselves unapologetically.
And it’s hard.
Even as I left corporate and started my own business, the old habit of asking for permission followed me. I had to burn this business to the ground twice to unlearn it.
But every time I’ve rebuilt myself, it was something more real. And now I help other entrepreneurs to do the same: find what really drives them. Build from their inner confidence.
Following no one but themselves.
I’ve been doing this work since 2019. Before that, fifteen years of workshops and masterclasses with over a thousand professionals across twelve countries.
Companies that trust Matteo
How we can work together
All prices excluding VAT
€1290 €490
One hour to start your transformation
No more over-analyzing, no more indecision. Book an online session, discover what holds you back.
Full refund if it wasn’t up to your expectations.
€3590
2 Session Deep Dive
Two 90-minutes session to emerge with a solution that can’t wait. Online.
€5990
In-person Day
We meet at the myth maker farm to solve something important.
€6990
Monthly coaching
Online coaching tailored to your needs. Weekly 90-minute sessions.
Custom
Long-term work
Online, In-Person or Hybrid approaches for you and your team.
They embraced their chaos and found their true power
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.
Give one hour to your deeper self
Stop the overthinking spiral. Dive deep and reveal insight on your story and what’s holding you back.
Fully and immediately refundable if you don’t get any value from it.
Think about it,
but not too much
More on Matteo’s approach
How does coaching work?
No other coach will show you this. Full 2h video of a coaching session that you can watch for free.
Watch this talk
Challenges of entrepreneurs like you.
Discover what’s holding you back as a founder
Powerful personality assessment. Meet your shadow.
Founder Journey: from founder burnout to a business that fits you
This is my free course Founder Journey. Why it is free: these are the episodes that I am shooting for my highest paying tier of clients, my one-on-one clients. This is the information that I want them to have.
Decision Making Under Uncertainty: Are You Sherlock Holmes or Columbo?
“I Hate My Business”: How I Shut Mine Down and Built a Better One
How to Be Confident as an Entrepreneur: The Zero Confidence Strategy
4 Types of Entrepreneurs: Are You a Wealth Wizard or a Mythmaker?
Self Awareness for Founders: How to Trust Your Intuition in Business
Questions entrepreneurs ask before starting
About
Entrepreneur coaching is a 1:1 partnership between Matteo Cassese, a Berlin-based entrepreneur coach, and founders who feel stuck — delivering clarity, confidence, and a growth path through Founder Journey methodology.
Related
- Provider: Matteo Cassese (Person)
- Related: Founder Communication Coaching (Service)
- Related: Leadership Keynote Speaking (Service)
- Framework: Business Storytelling Mountain (Article)
How does entrepreneur coaching work?
We can start with even just one hour together. A space for you to show up with whatever is weighing on you. I listen for what’s underneath the words: the pattern you can’t see because you’re inside it. Then we find a name for it, together.
Most clients say that first session already shifts something. From there, we go deeperL weekly or however it fits your life. Your chaos is the curriculum.
Who is this for? and who is it not for?
Entrepreneur coaching is for entrepreneurs who have built something real but feel stuck. You’re smart. You’ve tried the frameworks. They didn’t fix this.
It’s not for people looking for a ready made plan. I don’t do playbooks. If you need someone to tell you what to do, we’re not a fit. If you’re ready to find out what you already know, then we’re could be a match made in heaven.
How long does it last?
The average engagement is nine months. But some clients come for a single session and get what they need. No minimum, no lock-in.
Online or only in Berlin?
Both. I’m based in Berlin and I love working in person. There’s something about sharing a space that cuts through the noise faster. But most of my clients are remote. Founders in Germany, Italy, the US, Portugal, the Netherlands, and ten other countries. A screen doesn’t change what happens between us.
How is this different from business consulting?
A consultant looks at your business and tells you what to fix. I look at you and ask what’s in the way.
The business problem is almost always a reflection of something deeper — a conflict the founder hasn’t resolved, a story they’re telling themselves that isn’t true anymore. Fix that, and the decisions start flowing.
What results can I expect?
Clarity. Not the kind you get from a strategy deck, the kind you feel in your bones.
My clients stop overthinking and start deciding. They stop performing confidence and start actually feeling it. Sophie went from burnout to doubling her revenue. Mario went from a scattered pitch to €5 million in funding. Jen found the root cause everyone else missed.
Every story is different, but the pattern is the same: when you reconnect with who you are, the path forward becomes obvious.
What does an entrepreneur coach do?
I listen for what’s underneath the words: the pattern you can’t see because you’re inside it. Then we find a name for it, together. Most clients say that first session already shifts something.
How much does an entrepreneur coach cost?
One hour to start your transformation: €490, full refund if it wasn’t up to your expectations. Two 90-minute sessions: €3590. An in-person day at the myth maker farm: €5990. Monthly coaching, weekly 90-minute sessions: €6990. Long-term work for you and your team: custom. All prices excluding VAT.
How do I choose the right entrepreneur coach?
Coaching relationships are based on trust. In every interaction with your coach, you want to feel seen and understood. What you want in a coach is somebody who has gravity, heft, depth. Somebody you would want in a seat next to you on a very long flight, or somebody with whom it will be a pleasure to be stuck in an elevator.