Collaborative Leadership in an AI-Driven World

Sallyann Della Casa, CEO Dubai-based "community as a service" GLEAC, joins us to share her personal journey and how collaborative leadership will thrive in our AI-drive future. She explains how access to networks, proximity to experience, and "quiet capital" are often more powerful than credentials alone in shaping opportunity, leadership, and career outcomes. We explore inequality driven by access rather than ability, leadership and gender mental models, and examines why modern society struggles to produce widely respected leaders. We also education and AI, arguing that traditional schooling is outdated, overly focused on memorization, and ill-suited for a world where AI can outperform humans on hard skills, while human skill can thrive in areas AI can't. AI will reshape leadership, investing, and management and future leaders will succeed by combining learning agility, deep expertise, strong networks, and the ability to co-lead alongside AI.

We discuss...

• Sally Ann Della Casa shares her personal story to illustrate how proximity, networks, and early access often determine life outcomes more than raw talent.
• The concept of "quiet capital" is a mix of social trust, reputation, networks, and deep domain knowledge that drives real-world success.
• The discussion examined inequality as a function of access and networks rather than intelligence or effort.
• Leadership was debated through the lens of mental models, including gender expectations, risk tolerance, and the loneliness of decision-making.
• Modern society struggles to identify and develop respected leaders across business, politics, and culture.
• Education systems are outdated, overly focused on memorization, and misaligned with how people actually learn and collaborate.
• AI was framed as a forcing function that will finally push education to prioritize human skills like judgment, creativity, curiosity, and critical thinking.
• The risks and benefits of AI are discussed, emphasizing that AI reflects human biases and represents the "gray average," not top-tier insight.
• The importance of context, storytelling, and lived experience are highlighted as something AI cannot replace.
• Leadership in the future is more agile, less hierarchical, and increasingly collaborative with AI tools and agents.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Phil Weiss | Apprise Wealth Management

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For more information, visit the show notes at https://moneytreepodcast.com/collaborative-leadership-in-an-ai-driven-world