The Upwind Podcast

In this deeply personal and expansive conversation, host Lily Dash sits down with Shontelle Layne—Barbadian singer, songwriter, and global creative force whose work has shaped modern pop music for over a decade. Best known for writing Man Down for Rihanna and her own hits like Impossible and Roll It Gal, Shontelle’s story goes far beyond chart success. It is a case study in resilience, resourceful...

What if the key to unlocking blockchain's mass adoption wasn't another crypto exchange—but reimagining how we travel, earn rewards, and spend money in the real world? In this conversation, host Lily Dash sits down with Lin Dai from SuperLogic and Oscar Diaz De Leon from Bellsonio—two visionary entrepreneurs who are merging Web3 infrastructure with the $10+ trillion global travel industry to create...

What if the key to winning in 2026 wasn't perfection—but moving so fast that your competition can't keep up? In this high-energy conversation, host Lily Dash sits down with Michelle Romanow—co-founder and executive chair of Clearco (which has funded over 10,000 companies and deployed $3 billion in capital), one of Canada's youngest Dragons on Dragon's Den for 12 seasons, and one of the most influe...

What if the key to preventing diabetes, heart disease, and chronic illness wasn't another diet or supplement—but understanding your body's ability to bounce back? In this deeply insightful conversation, host Lily Dash sits down with Dr. Taylor Sitler—physician, computer engineer, and co-founder of Color Health (formerly Color Genomics), a $4.5 billion company pioneering accessible genetic and meta...

What if the key to solving addiction, chronic disease, and aging wasn't another pill—but understanding the 37 trillion powerhouses inside your body? This episode Sean Fetcho CEO & Co-Founder, Versea Health unpacks: • What mitochondria actually are—and why they're the root of nearly every chronic disease • How 37 trillion mitochondria power your body—and why most people have no idea how theirs are...

What if the real bottleneck holding blockchain back—and quietly undermining AI—wasn’t scalability, compute, or capital, but identity? In this deeply technical, wide-ranging conversation, host Lily Dash sits down with Evin McMullen, co-founder and CEO of Billions Network, a Yale-trained computer scientist who has been working on decentralized identity since long before it was fashionable—or even pr...

In this conversation, host Lily Dash sits down with Amanda Terry—Princeton-educated investor, Wharton MBA, co-founder of Metagood, tokenizing real world assets from historic art on Bitcoin collection OnChainMonkey to modernizing capital markets, andco-founder of ACTAI Ventures alongside legendary VC Bill Tai. From digital media executive at Twitter and NBC to Web3 pioneer to venture capitalist hun...

What if buying property in one of the world’s hottest real estate markets didn’t require hundreds of thousands of dollars upfront, months of paperwork, or opaque intermediaries? In this deeply technical and timely conversation, host Lily Dash sits down with Matt Ong — founder of Ctrl Alt and one of the few builders who has actually crossed the chasm between theory and execution in tokenized real e...

What if the key to winning wasn't carrying the weight of expectations—but surrendering fully to who you are? In this deeply personal conversation, host Lily Dash sits down with Anya Ayoung-Chee—Project Runway winner, former Miss Universe Trinidad and Tobago representative, fashion entrepreneur, and one of the Caribbean's most powerful advocates for creative industry transformation. From stepping o...

In this powerful conversation recorded in Greece, host Lily Dash sits down with Eva Kaili—former Vice President of the European Parliament, blockchain pioneer and one of Europe's most visionary voices on technology, sovereignty, and the future of democracy. From navigating the Cyprus banking crisis to championing AI legislation, Eva has spent over a decade at the intersection of policy, innovation...

What if the key to fighting aging, addiction, and chronic disease wasn't a new drug—but a molecule your body already makes? In this fascinating conversation, host Lily Dash sits down with Dr. Halland—a double-board-certified medical doctor, interventional spine specialist, and longevity researcher who's been pioneering cellular medicine for over a decade. From building medical imaging software inc...

What if Africa's biggest challenges—unemployment, infrastructure gaps, and capital access—could be transformed into billion-dollar global businesses? In this powerful conversation recorded in the heart of Bridgetown, Barbados, host Lily Dash sits down with Iyinoluwa "E" Aboyeji—serial founder, ecosystem builder, and one of Africa's most visionary entrepreneurs. E is the co-founder of not one, but...

We must not give away the printing press of our time. In this powerful conversation, host Lily Dash sits down with Michael Casey—author, blockchain pioneer, and Chairman of the Advanced AI Society—to explore one of the most critical questions of our era: What happens when the most powerful technology in history becomes concentrated in the hands of a few? Michael traces his journey from covering Ar...

The Caribbean is at a crossroads. For decades we've borrowed policies, adopted foreign narratives, and shaped our economies around systems that were never designed for us. But what would happen if we finally built a future grounded in our own stories? In this powerful episode, host Lily Dash sits down in Bridgetown, Barbados with two of the region’s most respected economic thinkers: Marla Dukharan...

Danish Chaudhry brings his unique perspective from BlackRock to blockchain in this candid conversation about the evolution of crypto and what it takes to survive its brutal cycles. From buying Bitcoin on eBay at 60 cents to managing a $34 billion daily volume exchange that crashed 95% overnight during the FTX collapse, Danish shares the unfiltered reality of building in Web3. As co-founder and GP...

From 20,000 Patient job to Building a Healthcare Revolution Dr. Emma Dash didn't just witness Barbados's health crisis—she lived it, treating 40 patients a day, seven days a week, until her body forced her to stop. In this deeply personal conversation with her sister Lily, Emma reveals how a childhood spent sailing taught her that sometimes you must choose your hard: the pain in your legs and abs...

From Music NFTs to Revolutionizing Travel Rewards: The Decade-Long Journey to Bookit.com Linda's story isn't just about building in crypto—it's about feeling the subtle shifts in the wind and knowing exactly when to tack. In this conversation with Lily Dash, recorded at Token 2049 Dubai, Linda traces his journey from trying to buy Bitcoin on eBay in 2011 to launching Bookit.com, a platform where y...