Lily Dash
The Upwind Podcast
The Upwind Podcast is a founder-focused, Caribbean-born global show hosted by Lily Dash—lawyer, entrepreneur, and CEO of ACTAI Advisors. It captures the “upwind journeys” of founders, investors, and thinkers who navigate resistance, adapt, and create lasting value across technology, finance, and culture. Core Concept The title Upwind comes from sailing—progress made against the wind through strategy and continual pivots. Each episode examines how exceptional individuals confront economic, personal, and structural headwinds to reach scale, impact, and purpose.
The Upwind Podcast
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