The Upwind Podcast

From Small Island to Global Stage: How Shontelle Made History with Music, Tech & NFTs

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, resourcefulness, and staying ahead of technological and cultural shifts. From her earliest years, Shontelle saw herself not just as a performer, but as a creator. Music wasn’t something she consumed—it was something she built. At just 17, while still in school, she wrote songs like “Colors” and “Roll It Gal,” which became cultural anthems across the Caribbean. Her work consistently centered themes of independence, confidence, and empowerment, driven in part by her role as an older sister and her instinct to uplift young women through her lyrics. A defining chapter in her career came when Rihanna personally called her to collaborate on the Loud album. The now-iconic Man Down was written on a tour bus while Rihanna was traveling with Kesha and Kanye West. Shontelle initially thought the track might be too bold to make the final cut, but Rihanna backed it, and it went on to become one of the defining songs of that era. Shontelle’s upbringing positioned her at the intersection of art and technology. With a musically inclined mother and a technically curious father, she developed both creative instinct and systems thinking early on. As a child, she took apart electronics to understand how they worked. As a teenager, she taught herself music production using whatever she had access to—often cracked software, a basic computer, and the internet—because traditional studio access wasn’t available. That same mindset carried into the pandemic. While the industry paused, Shontelle leaned in. She explored emerging technologies and became one of the first major female artists to release music as NFTs, well before it became mainstream. That decision opened doors into global tech ecosystems, connecting her with founders, investors, and communities far beyond the music industry. Her perspective on blockchain, crypto, and AI is direct. These are not abstract ideas. They are tools that reduce friction, expand access, and level the playing field for creators in small island states. She draws a clear parallel: AI is no different from tools already embedded in music and finance. The difference now is accessibility and scale. She sees agentic AI systems as a leapfrog opportunity for the Caribbean, particularly in solving coordination challenges across fragmented markets. The region’s biggest constraint is not talent or creativity. It is fragmentation. Data exists, capital exists, and talent exists, but they remain disconnected. Throughout the conversation, Shontelle returns to one core idea: mindset. Caribbean people often see themselves as consumers, not producers. That has to change. She reinforces this through simple examples, including a young Barbadian who turned the island’s snail problem into a business with minimal capital. Constraint forces creativity. Lack of resources forces innovation. She also points to structural inefficiencies holding the region back, from the high cost of inter-island travel to the lack of coordinated market systems. The Caribbean has the potential to operate as a unified economic and cultural bloc, but it requires alignment across governments, private sector actors, and creators. There is also a perception problem. Globally, the Caribbean is still framed primarily as a tourism destination, yet the region consistently produces world-class talent across music, education, and innovation. Genres like Soca, dancehall, reggae, and Afrobeats are deeply interconnected and influential, yet Caribbean artists remain under-recognized due to structural gaps, including low submission volumes to institutions like the Recording Academy. Her global experience reinforces the opportunity. Some of her most impactful performances have been in Southeast Asia and the Middle East, where Caribbean music is embraced at scale. Meanwhile, the region itself continues to under-leverage its own cultural exports. Her influences—Michael Jackson, Stevie Wonder, Bob Marley, Whitney Houston—reflect a lineage of artists who used their voice to move culture, not just entertain. Her philosophy is simple: use what you have. Don’t wait for perfect conditions. Whether it is using unconventional tools or adopting new technology early, progress comes from action. This conversation connects creativity, technology, and regional identity into a single narrative. The conclusion is clear. The Caribbean’s future will not be defined externally. It will be built by those willing to create, experiment, and coordinate at scale.

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, 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 something that has never existed before. From building blockchain rails for Fortune 500 companies to acquiring the tier-one domain Bookit.com, to pioneering the first fully transparent, on-chain rewards network backed 1:1 by stablecoins, Lin and Oscar are building the bridge between digital assets and real-world commerce. This episode unpacks: • How Bill Tai connected the dots between SuperLogic's Web3 expertise and Bellsonio's 23 years of travel industry experience • Why 99% of blockchain activity is still digital asset trading—and how Bookit is changing that • The reimagined vision for Bookit.com: Expedia meets Ticketmaster meets premium Amazon—all powered by blockchain • How Oscar went from software engineer to digital strategist at Marriott to early Bored Ape holder—and why NFT culture unlocked his vision for Web3 commerce • Why community, identity, and belonging matter more than the JPEG—and how that insight shaped Bookit's strategy • The brutal truth about traditional rewards points: you're losing money faster than fiat currency through corporate-controlled inflation • How Marriott Bonvoy points lost 40% of their value in a single year—and why consumers have zero protection • The Spree Network breakthrough: the first decentralized, transparent rewards system where 100 points = $1 USD stablecoin, locked in a smart contract, forever • Why smart contracts eliminate the conflict of interest between brands and consumers—no more broken promises or bankruptcy risk • How Bookit is giving nearly all margin back to consumers as rewards—an unheard-of model in the travel industry • Why direct brand relationships (not aggregators) give Bookit access to exclusive upgrades, amenities, onboard credits, and loyalty matching • The white-label play: how major crypto exchanges with tens of millions of users are exploring partnerships to integrate Spree and Bookit infrastructure • Why rewards points are legally exempt from money transmission regulations—making them the perfect entry point for blockchain adoption • How earning points is tax-exempt by law—and why attacking from the rewards angle unlocks regulatory advantages • The watershed moment for crypto: when your mom can tap her phone, pay with crypto, earn rewards, and never know blockchain is running in the background • Why Spree takes only 0.75% from merchants compared to Visa and Mastercard's 2.5% to 4%—and how blockchain makes this possible • The shocking stat: Visa and Mastercard run a 50% profit margin business on trillions in transaction volume—and why that's unsustainable • How charging merchants less and rewarding consumers more grows the entire travel market—a rising tide lifts all boats • Why transparency and eliminating conflicts of interest could disrupt traditional finance, government systems, and legacy rewards programs • The biggest challenge ahead: educating consumers that they can own the digital equity of their travel experiences—not just earn points trapped in a corporate ledger • How changing behavior requires showing people the secret sauce behind the travel industry—and why transparency is the catalyst Lin and Oscar don't sugarcoat the journey. This is 5 to 10 years of sailing upwind—waiting for regulation, infrastructure, and consumer readiness to align. But they're also clear: the wind is finally at their backs. From acquiring Bookit.com, to building Spree as a decentralized rewards network, to partnering with major crypto exchanges, to launching a commerce DeFi protocol that reimagines credit—they're not just building a travel platform. They're building the infrastructure for a future where blockchain powers real-world commerce, rewards are transparent and fair, and consumers finally own their digital equity. Their philosophy is simple: "Give people purpose, give them outcomes, give them resources—and let them go do what they're good at. They will surprise you." From working with American Express and the biggest banks, to pioneering tokenized rewards, to making crypto payments accessible for your mom without her ever knowing blockchain exists—Lin and Oscar are proving that the future of commerce isn't about perfection. It's about transparency, fairness, and giving value back to the people who create it. If you care about blockchain mass adoption, the future of travel, transparent rewards systems, decentralized finance, or building real-world utility in Web3—this conversation is essential.

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? 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 influential entrepreneurs and investors in North America. From building one of Canada's first e-commerce companies in 2010, to pioneering revenue-based financing for founders, to navigating the AI revolution as both investor and builder, Michelle brings a relentless, no-nonsense perspective on what it actually takes to build, scale, and win. This episode unpacks: • Why Michelle's entire investment criteria has changed in the last 15 years—and what she's looking for in 2026 • The brutal truth: AI has made it easier than ever for founders to move fast—and harder than ever for big companies to keep up • How one AI agent is now doing the work of four people: sales, support, operations, and collections—all in one conversation • The Kavak example: how Mexico's Carvana is using AI agents to transform customer experience and eliminate departmental silos • Why founders now have a bigger opportunity than ever—if they know how to use AI tools to build fast and iterate faster • The four days in one day framework: how elite founders structure their time to move 4x faster than everyone else • Why taking 100 shots on goal beats 10 perfect shots every time—speed compounds, perfection stalls • The Cal AI story: how high school students built a calorie tracking app using AI, scaled to millions in ARR, and got acquired by MyFitnessPal—all while attending classes • Why traction is now accessible with $150 in AI credits—when it used to cost $30,000+ just to get an app off the ground • How low barriers to entry also mean low barriers to competition—and why brand, PR, and early traction are the only moats left • The three investment themes Michelle is betting on: AI applications, health and wellness, and defense technology • Why people are drinking less alcohol, doing more cold plunges, and spending serious money on natural health solutions • How the defense and military tech sector has exploded due to global conflict—and why it's a major opportunity • The truth about SaaS: why companies like PagerDuty are now trading at 1x revenue multiples when they used to trade at 10x forward • How legacy software companies are struggling to adapt to AI—and why founders who build AI-first will win • Why founder risk is the #1 risk in startup investing—and how co-founder breakups can destroy billion-dollar companies • Michelle's philosophy on co-founders: she's never been a sole founder, and pace alignment is more important than skill alignment • The power of Dragon's Den: how it creates a natural tension between capital and ideas—and why the Caribbean needs its own version • Why community is the #1 tool for founders—and how shared knowledge from other entrepreneurs changes everything • The mistake of building for local markets first: how someone in a bigger market will copy your idea and win with a head start • Why Groupon started in Asia, got copied in the US, and became a cautionary tale for geographic strategy • How the Caribbean could become a global hub for ocean tech, tourism innovation, and food security solutions • The food security problem: why Barbados imports 70% of its food when it has incredible soil, proximity to major food producers, and year-round growing conditions • Why AI and systems thinking could solve coordination problems in Caribbean trade, agriculture, and supply chains • How motherhood changed Michelle's perspective: the superpower of prioritization, thinking about the world her daughter will live in, and using AI to be a better parent • The cooking unlock: how ChatGPT turned Michelle into a 10/10 cook by giving her authentic recipes, perfect portions, and substitution hacks • Why she fixed her car and fridge with ChatGPT—and how AI is making everyone superhuman in daily life • The tacking analogy: how entrepreneurship is like sailing upwind—you have to pivot with the same enthusiasm you started with, even when the wind shifts • The $12,000 ad bet: how Michelle had $15,000 left in the bank, spent $12,000 on one ad, and it worked—launching one of Canada's first e-commerce companies • The Clearco pivot: how they spent two years and $30 million building products for Uber drivers and Airbnb hosts—then pivoted entirely to e-commerce financing • Why it's harder to pivot when things are going okay than when your back is against the wall—but that's when the biggest opportunities emerge

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 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 metabolic testing. From bridging medicine and technology to redefining health as resilience rather than the absence of disease, Taylor brings a unique perspective on what it actually means to be healthy in the modern world. This episode unpacks: • Why resilience is the new definition of health—and how it unifies mental and physical wellbeing • The concept of allostasis: how your body dynamically adapts to challenges rather than returning to a fixed set point • Why hormesis matters: how regular, low-level challenges (lifting weights, cold plunge, sauna) make you more adaptable • How heart rate variability (HRV) measures your cardiovascular resilience and tells you whether to push hard or rest • The brutal truth about cortisol: how chronic stress directly increases insulin resistance and creates the pathway to diabetes • Why we massively underrate the mental component of metabolic disease—and overrate food alone • How metabolic switching (your ability to burn glucose vs. fat) is a core measure of resilience • Why fasting works—and how it gives your metabolism the break it needs to switch fuel sources • The critical differences between how men and women should approach fasting—and why 16:8 doesn't work for everyone • How flooding your body with glucose (sugary drinks, refined carbs) prevents metabolic switching and reduces resilience • Why inflammation is both essential for healing and the root cause of aging, Alzheimer's, and cardiovascular disease • How immune dysfunction leads to "trash buildup" in the body—senescent cells, amyloid plaques, sugar accumulation • The role of CRP, IL-6, TNF alpha in measuring chronic inflammation—and why fatty liver is a metabolic red flag • How social connection reduces all-cause mortality by 30%—making loneliness as deadly as smoking • Why resilience is built better in groups: accountability, perspective, and shared health challenges create stronger outcomes • The North Karelia study: how a Finnish community reduced cardiovascular death by 85% through collective behavior change • Why stoicism and mental resilience are the unlock to every other health behavior—exercise, sleep, diet • How Navy SEALs are selected based on mental resilience: the ability to adapt and recover from failure • Why lashing out, holding grudges, and chronic anger triple-tax your resilience (cortisol spikes, burned bridges, isolation) • The three starting points for resilience: find an exercise you like, call a friend, throw away your alarm clock • Why sleep, social connection, and movement come before diet changes—because mental resilience enables behavior change • How genetic testing is evolving: from identifying cancer risk (BRCA mutations) to preventing diabetes in future generations • The ethical frontier: prenatal genetic testing, CRISPR gene editing, and deciding which genes to pass on • Why COVID opened the door to new testing modalities—and how platforms like Function Health are making comprehensive testing accessible • How genome testing programs (like the UAE's initiative) aim to eliminate metabolic disease genes across populations • Why mitochondrial function is the energy plant of every cell—and poor metabolic health is the root of most noncommunicable diseases • The future of healthcare: proactive, preventative, personalized—not reactive, symptom-based, and standardized Taylor doesn't sugarcoat the complexity of health. He's learned that "resilience is the ability to bounce back from any challenge—whether it's a triathlon, a night out, or a stressful work sprint." But he's also discovered that health isn't about perfection. It's about adaptability. It's about doing something slightly difficult every day. It's about building mental toughness that unlocks the rest. His philosophy is clear: "If you want to go fast, go alone. If you want to go far, go together." From working on genetic testing infrastructure that's now valued at $4.5 billion, to studying how communities like North Karelia eliminated heart disease through collective action, to understanding that your mental state directly impacts your insulin resistance—Taylor is building a framework where health is measurable, adaptable, and achievable.

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 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 functioning • Why every non-communicable disease—cancer, diabetes, heart disease, neurodegeneration, inflammation, fertility issues—has ties to mitochondrial dysfunction • The breakthrough: how MitoScreen simplified mitochondrial testing from invasive muscle biopsies costing thousands of dollars to a simple finger-prick blood test anyone can do at home • Why professional athletes and bodybuilders often score poorly on mitochondrial health—despite looking physically fit • The fight-or-flight balance: why rest is just as important as activity for mitochondrial resilience • How stress, anxiety, and depression directly impact cellular health—and why mental health is inseparable from physical health • Why intermittent fasting works for some people and not others—and how personalized data reveals what actually works for YOUR body • The 80-20 rule: why balance matters more than perfection, and why partying occasionally won't destroy your health • The brutal truth about alcohol: it's poison, but so is drinking six Pepsis a day—context and moderation matter • Why the opioid epidemic killed 80-100,000 Americans annually—and how it's now shifted to fentanyl smuggled through China, Canada, and Mexico • Sean's firsthand experience losing friends, colleagues, and mentors to prescription drug abuse and opioid addiction • How Purdue Pharma and the Sackler family created a mass addiction crisis—and why doctors weren't educated on proper titration • Why mixing prescription meds (Xanax, Adderall, Ambien) with alcohol is deadly—and how it's killing people in their 30s and 40s • The power of plant medicine: ayahuasca, ibogaine, psilocybin, and how they're being studied for PTSD, depression, and addiction recovery • Why meditation, breathwork, massage, and sound baths should be tried before reaching for a pill • How Joe Dispenza's research (9,000+ subjects) is proving meditation creates measurable physiological changes at the cellular level • The future of healthcare: proactive, preventative, and personalized—not reactive, symptom-based, and standardized • Why governments and nonprofits need to fund preventative testing instead of waiting until people are sick • How the VA (Veterans Association) should be the first to adopt mitochondrial testing for Gulf War Syndrome and long COVID • Why small populations like the Caribbean (270,000 in Barbados) are ideal testing grounds for government-backed wellness programs • The 3P model: proactive, preventative, and precision medicine—and why personalized care is the only path forward • How Hamilton Souther became the world's leading ayahuasca shaman after drinking it 720 days straight to decode the safest protocols • Why MitoScreen is running studies on ayahuasca and ibogaine to measure what's happening at the cellular level during plant medicine retreats • The truth about supplements: taking 60 pills a day might be overstressing your mitochondria—not optimizing it • Why younger generations are drinking less alcohol and turning to mushrooms, edibles, and plant medicine instead • How travel, stress, and building a business tax the body—and why even founders need to measure their cellular health • Why blood work, gut health, hormones, and mitochondrial testing together create a complete picture of health—not just one data point • The bullshit detector: how mitochondrial testing reveals whether your diet, fasting, supplements, NAD, or biohacking protocols are actually working His philosophy is clear: "We're all different. Your 37 trillion mitochondria operate differently than mine. Why not assess the individual and let them trial and error what works—instead of following blanket protocols that don't apply to everyone?" From working with Dr. Patel (molecular biologist at UC San Diego and lead researcher for Joe Dispenza), to building the first mitochondrial health lab in the United States, to making testing accessible through a simple finger-prick blood card—Sean is building the infrastructure for a future where health is personalized, preventative, and precise. If you care about mitochondrial health, personalized medicine, addiction recovery, plant medicine research, or the future of preventative care, this conversation is essential.