Your Points, Your Asset: Building the First Transparent Rewards Network
What if the key to unlocking blockchain's mass adoption wasn't another crypto exchange—but reimagining how we travel...
The Upwind Podcast
The Upwind Podcast
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
Four Days in One: Michelle Romanow on Moving Fast, AI Tools & Why Speed Beats Perfection
What if the key to winning in 2026 wasn't perfection—but moving so fast that your competition can't keep up...
From Cortisol to Diabetes: How Chronic Stress Destroys Your Metabolic Health
What if the key to preventing diabetes, heart disease, and chronic illness wasn't another diet or supplement—but unde...
Stop Guessing, Start Measuring: How Mitochondrial Testing Reveals What Your Body Really Needs
What if the key to solving addiction, chronic disease, and aging wasn't another pill—but understanding the 37 trillio...
Prove You're Human Without Revealing Who You Are: The Math Behind Zero-Knowledge Identity
What if the real bottleneck holding blockchain back—and quietly undermining AI—wasn’t scalability, compute, or capita...
Blessing in Disguise: Trevor Koverko on Losing Everything, Finding Ethereum & Building in Web3
What if a catastrophic brain injury that ended your professional hockey career became the catalyst for building the f...
Where Community Meets Capital: Amanda Terry of Metagood and ACTAI Ventures on Tokenizing Real World
In this conversation, host Lily Dash sits down with Amanda Terry—Princeton-educated investor, Wharton MBA, co-founder...
Sold Out in Minutes: The Ctrl Alt Story of Dubai's Tokenized Real Estate
What if buying property in one of the world’s hottest real estate markets didn’t require hundreds of thousands of dol...
Risk Being Yourself Fully: On Winning Project Runway & Building Global Fashion Tech
What if the key to winning wasn't carrying the weight of expectations—but surrendering fully to who you are...
Eva Kaili on Principles & Resilience
In this powerful conversation recorded in Greece, host Lily Dash sits down with Eva Kaili—former Vice President of th...
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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?
Meet Lily Dash
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.
