The Paradox of Leadership: Ego and Psychopathy

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.

Highlights:

• Why even the best CEOs need coaching—and what coaching actually looks like
• The most common problems CEOs face at every stage of company growth
• What to do when you’re stuck, overwhelmed, or panicked as a founder
• The difference between managing and leading—and how to do both effectively
• The one skill that top 10% employees all have in common
• A powerful tactic for giving and receiving feedback that builds trust
• What ego looks like when it helps vs. when it hurts
• How childhood experiences shape founders—and how to turn that into fuel

-- Guest Bio: Alexis John d'Amecourt is the founder of Mishory Method, an executive coaching firm that works with top CEOs and venture-backed founders around the world. His clients include the CEOs of Substack, Eigenlayer, and Booksy, among many others. A three-time founder himself, Alexis brings deep empathy and real operating experience to every conversation. I’ve seen firsthand how effective he is—and I’m excited to share this episode with you.

Alexis was born into a lineage of remarkable minds and bold innovators. His great-uncle was Stanislaw Ulam, the renowned mathematician who made foundational contributions to nuclear physics—including a vital role in the development of the hydrogen bomb—and who pioneered the use of Monte Carlo methods.

On his maternal side, Alexis was the great-great-great-grandson of Gustave de Ponton d’Amécourt, the French inventor and engineer who advanced early helicopter technology and coined the very term “helicopter.” Alexis was also the son of Joanna Harcourt-Smith, who was married to Timothy Leary—a relationship captured in Errol Morris’s documentary My Psychedelic Love Story. But his mother left when he was just two years old. Alexis was raised instead in Washington, D.C., by his Austrian grandmother, a sharp and self-made entrepreneur who became his greatest influence.

Raised between two continents—with one foot in European tradition and the other in American dynamism—Alexis was shaped by the paradox of abandonment and deep mentorship. That duality has become central to his work with CEOs today, offering a perspective grounded in resilience, heritage, and the power of reinvention.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

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LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexis John d'Amecourt: https://www.linkedin.com/in/alexisdamecourt/

Links: Mochary Method: https://www.mocharymethod.com/

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (1:39) The role and need for CEO coaching (5:08) Coaching vs. therapy for CEOs (8:08) Overcoming scaling challenges (11:57) Strategies for getting CEOs unstuck (16:11) Coaching dynamics with young CEOs (19:40) CEO misconceptions and role balance (22:33) Hiring challenges and skills of founders vs. traditional CEOs (25:02) Leadership styles: carrot vs. stick and anti selling (29:04) Managing and motivating top performers (31:20) CEO's organizational influence (33:31) Common mistakes and leadership styles of experienced CEOs (37:31) Encouraging employee peak performance (39:18) Feedback dynamics in personal and professional spheres (45:02) The role of psychopathy in scaling businesses (47:02) Ego balance for effective CEO leadership (54:32) Alexis John d'Amecourt's backstory and the power of vulnerability (59:34) Childhood trauma and its influence on founders (1:02:24) Transitioning from insecurity to vision-driven leadership (1:04:22) First principles thinking and immediate CEO improvements (1:08:17) Client profiles and contacting Alexis John d'Amecourt (1:09:19) Closing remarks