How I Invest with David Weisburd
E168: How I Coach The Top 0.1% CEO's in Silicon Valley w/Alexis John d'Amecourt
Fri, 30 May 2025
Alexis John d'Amecourt is the coach behind some of the most iconic CEOs in tech today—including the founders of Substack, Eigenlayer, and Booksy. In this episode of How I Invest, I sat down with Alexis to explore what really makes great CEOs tick—and what causes them to fall apart. We talked about how founders can build trust, navigate emotional turbulence, lead organizations as they scale, and get unstuck when things feel overwhelming. Alexis also opened up about his own story—from being raised by his grandmother in D.C. after a turbulent childhood to becoming a three-time founder turned executive coach. This conversation is packed with tactical frameworks, powerful analogies, and a ton of heart.
Chapter 1: What misconceptions do CEOs have about leadership?
There's this misconception out there that CEOs show some anger sometimes. You know, they got to rattle some chains. And I see it a lot of times with younger CEOs who believe that that's the persona they should have. And I'm saying is a lot of times, especially with those tech, I point out to them that when you get angry with someone, you usually have to go back and apologize immediately.
I've worked with over 80 CEOs and I watch how the most successful do it there. And I've never seen any of them go ballistic on people and scream at people to get them to move. I work with such good people, CEOs who are just really good people. Four of my first five clients I ever had, I still work with them. And so I'm watching them grow orgs from 11 people to 50 to 100 to 150.
One of them has 3,500 employees. Still the same guy. It's good to see you.
Today, I'm excited to welcome Alexis Demecourt, head of coaching at Motri Method and trusted advisor to some of Silicon Valley's most dynamic CEOs and founders. Alexis has spent over two decades as a three-time founder, C-suite leader, and now as a coach behind leaders at companies like Substack, AgentLayer, Booksy, and more.
Chapter 2: How does Alexis coach top CEOs?
In this episode, Alexis shares a rare inside look at how he helps top executives get unstuck from their biggest problems. We'll dive into his frameworks for navigating high stakes decisions, his approach to blending personal and professional growth, and what he's learned from coaching the leaders shaping today's tech landscape. Alexis, welcome to the How I Invest podcast.
Alexis, you coach some of the top CEOs and executives on the planet. Brag a little bit about your clientele and some of their accomplishments.
First and foremost, let me brag about them this way. They generally care about their colleagues. They're good human beings. They are really absolutely smart. They're absolutely focused. But I'd say the one thing is they've really figured out how to balance that focus on product for customers with also being good people and also balancing having a family.
At Substack, I coach Chris Best, who's the CEO. Substack is now in the zeitgeist. It's everywhere. And he's still just excited about his kids and their performance at school, which he shares. I'll highlight a third. Sharam Kanan from EigenLayer. I've been working with him from the very first day of their startup.
And the best photo I have of him is not the one with all of his engineers that are everyone. It's him holding his daughter who has the mouse ears on because he got to take her to Disneyland. And those are good people. And it's nice to work with those good people.
And why would the CEO of Substack or Eigenlayer or Booksy need coaching? And who is coaching really for when it comes to executives? Now, coaching is everywhere.
I think for CEOs, though, it's a little bit different. It's like, look, CEOs have their exec teams. But they can't really go to their exec teams with everything. They have their investors. Sometimes they go to their investors and their investors are like, hey, look, I want a 10x return. They go to their board. Their board looks at them and goes, that's great.
However, let me tell you how I used to do this. And what happens is everyone they go to has an agenda. And so what I like to say is, look, I just don't have an agenda with you. And two, If you tell me something, you're not going to have that awkward moment of seeing me two hours later in the kitchen or by the water cooler. And you're like, hey, how's it going? I just told you this thing.
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Chapter 3: Why do CEOs need coaching?
That's this vulnerable moment I had that I'm working through. So I also feel like, look, the best athletes in the world have coaching. I believe that, you know, there are skill sets. We're building skills. No one's born a true leader. No one's born with all the answers. So sometimes they're practicing with me. Sometimes what they're doing is they're saying, I have these personas I wear.
I have these preconceived notions or I'm just scared. And so I'm a person, I feel like I'm in the corner with them in a boxing ring. And sometimes I'm just, I'm like... you know, fixing that cut. I'm giving them some encouragement. Sometimes I'm just listening to them so they can kind of purge it out of their system.
So I think everyone in that high pressure role is learning how to be a leader, a manager. And there's one other aspect to this as well, is that it's not always, you don't pick up a skill and then that's it. You have it forever. There can be times when you go back below the line. And you need someone there who says, you know what? I'm only invested in you.
I'm not invested in the success of the company. You know, I have the equity here. So I'm only invested in you. So I'm going to point out these things. And they appreciate that. And I think that's a big reason why CEOs need a CEO coach.
You mentioned a lot of top athletes have coaches. There's obviously famous cases like Tiger Woods with a swinging coach or Shaquille O'Neal is free throw coach or a boxing coach, but which athletes actually have a overall coach and talk to me about that within the field of athletics and what are the best practices there?
Such a good question. I think what they need as well is someone who goes, look, I'm going to look at your skill. I'm going to look at your technique, but I'm not asking to help you with your mindset. And, you know, look, when top athletes, CEOs, sometimes are going into an offsite, a board meeting on all hands, or they have to have a critical conversation with somebody.
you know, they're kind of like this fight or flight feeling. Sometimes they need somebody else to just say, hey, have you thought of this? Or remember, it's not about you. It's about this. So that's why I think that corresponds well with top athletes who are going into maybe a big game. You just need someone to say, hey, these are the things to focus on. Don't worry about the rest of this.
Or let's put something around you, a framework that allows you to focus on the priorities and not those secondary things.
Sometimes it's just really good as a business leader to have someone in your corner that has no conflict of interest, but yet has high vested interest. It's kind of a paradox. Is coaching just a euphemism for therapy? How does coaching differ from therapy? And is it just another packaging?
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Chapter 4: What frameworks does Alexis use to help CEOs?
part of that startup culture where we go, I don't have anywhere else to go. So this sounds like a good place to go. So you're in this kind of battle for survival constantly. But then you transition out of that, you find product market fit, and you start realizing some of these people who started with me aren't actually able to grow with the company. So you know what I'm going to do?
We have a bunch of funding. People are telling me we're going to be huge. I'm going to go hire that person from Microsoft. Yes, we have 15 employees. Let me go see if I can hire that senior VP with 22 years experience at Microsoft. And then what you find is they get in there because actually that person has their own agenda. Their agenda was, you know what? I was at Microsoft.
I wasn't promoted fast enough. I'm really awesome. I want to be at a company now.
going to show everyone that i can do it on my own and then they get into there and they realize that it's a completely different mentality the startup mentality right is that there is no framework it is flying by the seat of your pants there is no like what are the policies um and oftentimes it's you know we're gonna work all night well no i have to go home you know my wife we have twins
And so there's that fit that kind of deteriorates over time. So what then I see is you then bring in some people who love that stage, that 10 to 100 stage, and they have self-awareness that that is the stage. Then when you get to 800 employees, that's the time when you bring in people who have run big orgs, that don't need so much handholding. It's more kind of bigger picture.
And they've seen a lot of issues. They know how to, they have their own frameworks. Nothing surprises them anymore. And they're ready to take it. But they also, they're at a certain stage of their career. And what I've seen a lot of times is they're at a stage of their career, they, at 800 people and above, this is their time to make their big mark.
This is when either they're making retirement money Or they're like, I want to accomplish that big thing in my career, and this is it.
CEOs come to you with their hairiest problems. How do you go about getting CEOs unstuck on specific problems?
First thing I ask them to do is, where are you emotionally? Where are you in your head right now? What I want to see is, what I want to sense is, are they in fight or flight or freeze? Where are they in their head? Meaning, are they in their amygdala? Which means they're back on the Serengeti. They're either sprinting away from that, I don't know, wildebeest, or they're going to attack it.
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Chapter 5: How do CEOs get unstuck during challenging times?
But when you're in that part of your mind, you're not open to creative thinking. You're reacting. So what I try to do is I shift them away from that. So once you shift them away, and it's either through acknowledging what emotions you're feeling right now, describing what the problem is, taking a moment to calm down because calmness is contagious,
is then I have a framework, which is a simple thing called issue proposed solution. So what we start doing is let's break down the issue. What simply, what is the issue? So let's block out all the noise and start typing out that issue. And I have them do it on Zoom. So we're sharing something, they're typing out the issue.
And then I ask them what I think is the critical question, which is how did you contribute to this issue? And it's because so often CEOs are like, oh, you know what? It was my head of engineering. It was my da-da-da. But I go, hey, I'm going to press you and I'm challenging you. How did you contribute to this? And so usually upon that reflection is a lot of what the solution to that issue is.
So then we write out a proposed solution, break it down into actions, and then I ask them to do the very first action. Just start. Because... Attitude follows action. And so once they start doing the actual work, I've seen the transformation. Three weeks ago, I had a CEO who's in a Series B, was closing a Series B, and his lead investor had two questions for him.
And he was literally in a state of panic. You and me, if we saw those questions, we would have been like, that one's a yes, and the second one is two sentences. But he was caring so much more. He was like, four months I've been working on this. I can't believe I've been away from the product. And I just said, you know, it took about 20 minutes to get him out of that state.
And I said, just answer those two questions. Let's start with the first one. He typed it out. And it really was. He typed out the word yes. And then the second one he did, you know, I said, just where are you mentally? He wrote it all out. And I said, let's send it to him. And I mean, David, the lift, the emotional heaviness that was around him just lifted.
And he actually, within a minute, was cracking jokes. And it was the most remarkable thing.
Sometimes you just need somebody by your side helping you, guide you through your process that you trust and that you feel like you could rely on. Absolutely.
We all go through it. The irony here is that... Right before this podcast, I was on a coaching call with someone who I, a CEO that I greatly admire. I've been to his offsites and I sit next to him at offsites while he speaks to the whole company. And afterwards he comes to me and goes, what did you see? And I told him all these things like this and that.
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Chapter 6: What are the characteristics of top 10% performers?
And if I drop my mask and I share who I am and, you know, look, one of the quickest ways I do that is by saying this kind of quip I have about my CEO career. Look, I'm a three-time founder and I successfully drove all those companies off of cliffs. And I would say about 75% of founders go, Oh yeah. And they laugh and they go, I know what that feels like. And 25% don't react.
And so it's my way of opening up and being look and looking for genuine understanding and empathy.
And does that ever backfire being so vulnerable and transparent about your background?
It has a couple of times and it used to hurt because I would say, I wouldn't understand. Like, are you, are you reacting to me as a person? Um, And I've just opened up. I was being vulnerable. Recently, I had a powerful clarifying moment around this, which was, you know, a CEO once told me openly he had less respect for me after hearing my story. And that stung initially.
But instead of retreating or becoming defensive, I faced it head on. And I asked him directly why he felt that way. And in that conversation, I realized he was reaching for the content and not the context of what I was sharing. The abandonment struggle, that's not what he was talking about. And I was reacting to his judgment of my vulnerability. That shifted everything for me.
is when I realized I could confidently and with curiosity and openness ask him about that. I was able to turn that into an authentic connection with him, which far outweighed the discomfort I initially felt.
When it comes to what's driving founders, the story is always this grand mission. My suspicion is that there is a lot of childhood trauma that's driving top founders, a lot of being unseen, being unappreciated, unloved, that leads them to take such incredible risks and go contrarian on a specific space.
What percentage of founders are trying to overcome this insecurity, this abandonment or lack of love in their childhood? Honestly? Probably about 150% of them.
It's a high number. Look, none of us arrives in adulthood perfectly polished, right? We have baggage. What we went through in childhood, even if it has this kind of stereotypical or this, what society tells us is a perfect upbringing. I think it's human nature. We pick up on things as we're growing, as we're aging, things that are limiting to us. Even subtle moments shape us.
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Chapter 7: What common mistakes do CEOs make in management?
But take a moment to realize what it's saying to you because it's about you, not the person across from you. And then two, fear is so limiting. I'm not saying the fear that says I can walk into a busy intersection and that truck will not hit me. I have no fear. Now that's stupidity, right? You know what's going to happen. But there are other fears that are limiting.
Like I can't go have this conversation, this tough conversation because my CTO will quit immediately. Here's the fear. I'm telling you, it'll be the 180 degree difference. One is having that difficult conversation with your CTO is actually going to be liberating for you. Now, if your CTO leaves or not, you're going to be okay. But the story you're telling yourself around that is limiting.
So in conclusion, it's make people feel heard. Learn how to ask questions. And accept or not accept feedback and put actions to it. And then three, understand the power that anger or fear has over you as a CEO.
In terms of your clients, do you work with just CEOs? Do you work with fund managers, VCs?
I work with primarily founders. Okay. I work with a couple of VCs and a couple of PE firms as well. And I find the same issues across the board.
And what would be the best way for people to get in contact with you if they're interested in potentially being coached?
You can go to masharimethod.com, our website, and we have a big website. Click here if you want to work with us. You can also reach out to me on LinkedIn and email me or my colleagues. And you'll find that on our website.
Alexis, I want to really thank you for taking the time to delving deep and even helping me, even delving deep into my relationship drama and my conversations as well. Thank you, David.
Really appreciate being on here and sharing everything and hearing what's going on in your life as well. Thank you, Alexis.
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