The Upwind Podcast is a founder-focused, Caribbean-born global show hosted by Lily Dash—lawyer, entrepreneur, and Co Founder of ACTAI Advisors.
“upwind journeys” of founders, investors, and thinkers
Progress is rarely downwind
The Upwind Podcast is built on a simple but powerful idea: meaningful growth happens when you learn to navigate resistance. In sailing, going upwind requires skill, patience, and constant strategic pivots. The same is true for building companies, allocating capital, and shaping the future.
Hosted by Lily Dash, lawyer, entrepreneur, and Co Founder of ACTAI Advisors, Upwind explores the journeys of founders, investors, policymakers, and technologists operating at the edge of change. From blockchain identity infrastructure to tokenized real estate, from AI data systems to venture capital strategy, these conversations dive deep into how real value is created under pressure.
This is not hype-driven commentary. It is strategic analysis grounded in lived experience. Guests share how they navigated regulatory friction, market downturns, personal loss, funding constraints, and structural barriers. They discuss capital discipline, product timing, governance, network effects, and the emotional resilience required to build at scale.
Caribbean-born but globally oriented, The Upwind Podcast reflects a worldview shaped by small markets with big ambition. It highlights leaders who understand that scale is not accidental. It is engineered.
Each episode asks the same core question: how do you make forward progress when the wind is against you?
Lily Dash, the dynamic host of The Upwind Podcast, is a seasoned lawyer, accomplished entrepreneur, and Co-Founder of ACTAI Advisors. With a passion for uncovering the stories behind success, Lily brings a wealth of knowledge and experience to each episode. Her unique background and insightful questioning style make for engaging and enlightening conversations with guests from diverse backgrounds.
