Founder Journey: Conversation with Matteo Cassese

    Matteo Cassese is a business coach for entrepreneurs and keynote speaker with over twenty years of experience across corporate, startup, and creative worlds. He has worked with Warner Bros., Netflix, Sony, LinkedIn, and Vinted, and spoken on stages like SXSW and Gitex. During seven years at Warner Bros. Pictures, he helped launch more than 140 films. Based in Berlin, he helps founders and executives build businesses on their own terms.

In this conversation, Matteo speaks about his post, Founder’s Journey.

Geetesh: Matteo, you’ve moved from corporate storytelling to keynote speaking over the years. What shifted in how you show up in front of people along the way?

Matteo: Over the last few years I transitioned from trainer and facilitator to keynote speaker and coach. And I transitioned from hard skills to soft skills.

I moved from believing that the solution is learning something new, learning the craft, to seeing that the craft is just part of the solution. From believing that the solution is outside in (I come in as a trainer, teach you a technique, and then you are going to apply it flawlessly) to thinking that everyone is complete in every possible way, and that my job is to make you want to unearth your innate abilities. So the work is done from the inside out.

And after you have done the work from the inside out, obviously the technique will help. You need the hard skills, you need the craft, you need the repetitions. But if we have started from the inside, then whatever you do will have so much more power.

Geetesh: You’ve spoken about the difference between confidence and courage, saying confidence is something you decide rather than something you have. How does that idea show up for you when you’re about to walk on stage?

Matteo: In the five minutes before I go on stage I do a small meditation. I focus my thoughts on the audience, and on the gifts that I have for the audience. And then I focus on the idea of having fun together with the audience. I decide that what is going to happen is: we are going to have fun.

Then I do my little run up the stage. Hopefully the stage is big enough. And lo and behold, that inner intention of having fun, and that confidence that we are going to have fun, is already in the room. The people are already smiling. I haven’t said a thing. I just enter the room with a certain energy.

It does take courage to step on stage. But it takes confidence to do that in a way that is intentional. The intention can also be: scare everybody, or be gloomy, or be boring. But that you embody that intention: that is confidence. And that is a decision.

Geetesh: In your Founder Journey post, you describe a “zero-confidence strategy,” where you invest your confidence in yourself rather than in whether a specific talk or video succeeds. Can you talk about how that plays out for you when a presentation doesn’t go the way you hoped?

Matteo: I am privileged that after a presentation I always have another presentation. After a talk, I always have another talk. After a video, I always have another video. So, if the presentation, the talk or the video bombs, it provides a learning opportunity for the next one. At the talk level, I want to have zero confidence. Zero, on purpose, because then I can allow the talk to fail. That is what I call the zero-confidence strategy. I can allow a video to fail miserably without becoming a failure.

However, there is an enormous amount of guilt and shame in failing, especially when you fail at the very human job of inspiring, entertaining, motivating and moving an audience in front of you. And most of the time it boils down to not being enough in the moment. Whenever you sense that something is off, that is where you should change your plan. Oftentimes speakers have their big narrative arc, and I myself, I find myself carried away: oh, they are going to get into it, they are going to understand it, I only need to get to that peak, I only need to get to that idea. And instead, the most excellent speakers realize in real time that the feedback is not good. They slow down. They stop. They involve the audience. They change their plans.

The more I learn about the art of stagecraft, the more I realize that what you prepared is in the background, something you can go back to. What you are doing is something unique for the audience in front of you. Your senses are heightened, and if you feel that something is off, this is the moment for you to go off script.

In the broader sense, obviously you learn a lot from every failure, and you can bring that failure into your confidence. You say: okay, now I know that I shouldn’t do that, so I can be more confident the next time. You use experience as a proxy for confidence. But in reality, what a real keynote speaker is trying to do is to disappear. To disappear into the room and just be in the hearts and the minds of the people in the room. And to do that, you not only need a compelling story, but you also have to be in the moment.

Geetesh: Over the years you’ve gone from storytelling to myth-making. What does that look like when you’re preparing a talk or a message for an audience, and what is the difference between the two?

Matteo: Three years ago, I was on a plane coming back from a retreat. And I kept thinking: I have defined my career through storytelling, but what is bigger than storytelling? And it struck me that stories are usually parts, little fragments of something bigger, which is a myth.

You don’t have to think of Christopher Nolan’s The Odyssey to think about myths. We live in a society of myths. AI right now is a myth. Cybersecurity is this mythological threat.

Apple as a whole is a mythology, right? Linux is the rising mythology of a way of tech that is free and open source. All the big movements have story points, but then they are part of a mythology.

Now, if I think of a talk simply in terms of story, what I want to do is take the audience somewhere. I want to bring them to another place, and by bringing them somewhere unfamiliar, I am going to change them. Then they go back to their day changed.

If I think of this as a myth maker, I am going to try and have them not go back to the world where they were living before but actually enter a new world from there. So I am going to have not just one story, but maybe ten stories, and these ten stories will represent a mythology. Let’s say these ten stories are ten products for Apple: the iPhone, the Mac, the HomePod, the Apple Watch and so on. You see how there are building blocks to a mythology. And then everything is under the same symbol, the bitten apple. Symbolism today is expressed by design. So we want a powerful brand that determines a design style, and this design style determines the look and feel and the vibe that everything has.

But ultimately, why do we design stuff? Because we want people to say: I’m a Mac, I’m a PC. That is the ultimate goal of myth making, for people to say: I subscribe, I belong to this myth. I wear Nike because I believe in performance, and I believe that with enough repetitions I will make it big.

So, whenever I am thinking about my little story, I am thinking: where does this keynote belong in the mythology that I am creating, in the brand that I am creating, in the product lineup that I am creating? And what sense of belonging is it giving to the ones who are going to listen to it?

Geetesh: Matteo, where can readers go from here?

Matteo: Three parting gifts. First, I have three premium courses free for everybody to take. Mindset, Pitch and Story. Second, if you want to follow me and get all my insights, subscribe to my YouTube channel. And third, if you don’t believe in the algorithm and want everything in your email, this is my newsletter.

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