The Upwind Podcast

By Lily Dash

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Image by Lily Dash

Category: Entrepreneurship

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Episodes: 17

Description

The Upwind Podcast is a founder-focused, Caribbean-born global show hosted by Lily Dash—lawyer, entrepreneur, and Co Founder 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.

Episode Date
From Small Island to Global Stage: How Shontelle Made History with Music, Tech & NFTs
May 04, 2026
Your Points, Your Asset: Building the First Transparent Rewards Network
Apr 10, 2026
Four Days in One: Michelle Romanow on Moving Fast, AI Tools & Why Speed Beats Perfection
Mar 20, 2026
From Cortisol to Diabetes: How Chronic Stress Destroys Your Metabolic Health
Mar 06, 2026
Stop Guessing, Start Measuring: How Mitochondrial Testing Reveals What Your Body Really Needs
Feb 19, 2026
Prove You're Human Without Revealing Who You Are: The Math Behind Zero-Knowledge Identity
Feb 09, 2026
Where Community Meets Capital: Amanda Terry of Metagood and ACTAI Ventures on Tokenizing Real World
Jan 24, 2026
Sold Out in Minutes: The Ctrl Alt Story of Dubai's Tokenized Real Estate
Jan 09, 2026
Risk Being Yourself Fully: On Winning Project Runway & Building Global Fashion Tech
Dec 31, 2025
Eva Kaili on Principles & Resilience
Dec 23, 2025
The NAD Revolution: How Dr. Halland Uses Cellular Medicine to Fight Aging, Addiction & Disease
Dec 15, 2025
From Andela to Flutterwave: How Iyinoluwa "E" Aboyeji Built Two Unicorns to Prove Africa Could
Dec 08, 2025
Who Will Control the AI Economy: Decentralization vs. Totalitarianism with Michael Casey
Nov 23, 2025
The Caribbean NEEDS a New Story: Decolonizing Economics, Democracy & The Future
Nov 16, 2025
From BlackRock to Blockchain: The Hard Truth from Crypto VC Danish Chaudhry
Oct 29, 2025
Healing a Country One Clinic at a Time: The Live Well Story with Dr. Emma Dash
Oct 28, 2025
The Super Logic Story: From Warner Music NFTs to Revolutionizing Travel with Blockchain
Oct 27, 2025