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, 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.

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.

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

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.

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.

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 practical. Evin isn’t a tourist in crypto. She’s been in the trenches since 2010, when she first encountered Bitcoin at Yale in a class taught by Elizabeth Stark (now founder of Lightning Labs), and she has spent the last decade tackling what may be the hardest unsolved problem in decentralized systems: how to reconcile privacy, accountability, and coordination at global scale. Evin’s career reads like a roadmap of where the internet was headed long before the rest of the world noticed. From building with IBM Watson and CERN, to founding Disco (one of the first products that let users carry their own data in a portable “data backpack”), to opening ConsenSys’s first Dubai office in 2017, to ultimately merging identity research teams with Polygon to form Billions Network—her work has consistently lived at the intersection of cryptography, governance, and real-world systems. At the heart of the conversation is a simple but uncomfortable truth: if all you know about someone is a wallet address, your options are extremely limited. You can send money, or you can demand over-collateralization. That’s it. You can’t coordinate, comply, govern, personalize, or trust—at least not in any meaningful way. Identity, Evin argues, is the “genesis block” of everything blockchain claims to enable. This episode unpacks why zero-knowledge proofs are the missing primitive. Evin explains—clearly and without hype—how ZK proofs allow you to prove something about yourself without revealing the underlying data. You can prove you’re over 18 without sharing your birthday. You can prove you’re not from a sanctioned country without revealing your nationality. You can prove you’re a unique human without giving up your name, biometrics, or personal history. The three pillars—zero knowledge, completeness, and soundness—aren’t abstract math concepts here; they’re the foundation of a more private, more functional digital world. The discussion goes far beyond crypto. Evin lays out how governments today are leaking the personal data of over a billion citizens because their identity systems are effectively giant spreadsheets protected by passwords. Hospitals routinely email non-anonymized X-rays to AI startups in exchange for equity. Small businesses now dedicate entire staff just to handle privacy compliance requests. Meanwhile, Americans collectively spend over 50 million hours per year filling out forms—most of them asking for the same information, over and over again. Against this backdrop, Billions Network is building infrastructure that feels almost inevitable in hindsight. By tapping the NFC chip in your passport, users can generate cryptographically verifiable, zero-knowledge proofs on a phone in seconds—something that in 2017 cost hundreds of dollars per transaction and required a desktop computer. The implications are massive: airports, hotels, hospitals, banks, events, borders—all without forms, photocopies, or data leaks. The conversation also confronts the AI elephant in the room. Today, roughly 50% of internet traffic is bots. Trust online is collapsing. Evin introduces the idea of Deep Trust: persistent identities for AI agents that are cryptographically linked to accountable humans or organizations. Without this, we’re heading toward a world where no one knows whether they’re interacting with a person, an AI, or a malicious swarm—and where responsibility evaporates entirely. From Sybil-resistant token airdrops, to privacy-preserving medical identity across clinics, to age verification at a bar without showing ID, to search engines that respond to your preferences without harvesting your data—the episode paints a coherent picture of where identity is headed. Not surveillance. Not anonymity absolutism. But minimum disclosure: sharing only what’s necessary, exactly when it’s needed, and nothing more. Evin doesn’t pretend this is easy. Translating cryptography from academic research into production systems that governments, enterprises, and developers can actually use is slow, unglamorous work. But her thesis is clear: identity isn’t the end goal. Identity is the thing that gets you to the thing. Without it, decentralized systems stall. With it, coordination becomes possible at a scale we’ve never seen. Five years from now, Evin believes, you won’t pull out a passport, fill out a form, or photocopy an ID. The environments around you will respond to who you are based on what you choose to prove.

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 hunting unicorns, Amanda has built her career at the intersection of digitization, community, and impact. But this isn't your typical VC story. Amanda and Bill run one of the most strategically disciplined funds in early-stage investing— small fund sizes, massive focus, and a model that builds companies from scratch. The thesis is simple but powerful: keep the fund small enough that one or two wins can return multiples on the entire fund. This episode unpacks: • Why small funds with strategic bets outperform massive capital deployments • The power of the ACTAI Global community: from Canva to Zoom to Dapper Labs—how a network becomes fertilizer for startups • How 30% of ACTAI Ventures' deployed capital comes from companies they built from scratch at sub-$15M valuations • Why 50% of their portfolio has Bill Tai on the board—giving them direct insight and control • The venture building model: when to incubate ideas vs. when to back existing teams • How Amanda transitioned from Twitter and NBC to Web3 and venture capital • The historic creation of OnChainMonkey: the first 10,000 NFT collection inscribed in a single Ethereum transaction • Why they pivoted to Bitcoin Ordinals— becoming the first 10,000 NFT collection on  Bitcoin L1 using parent child inscriptions • How tokenization is finally ready: from corporate debt to rare earth minerals to commercial real estate • Why BlackRock, JP Morgan, and NASDAQ are all racing to tokenize real-world assets—and how MetaGood is positioned to win • The 2015 vision: how Bill and Danny created an architecture for putting Egyptian property rights on the blockchain • Why velocity of capital is what makes markets—and how tokenization unlocks global liquidity 24/7 • How fractionalized ownership could let anyone invest in commercial real estate, corporate debt, or rare earth minerals  • The current fund is deployedinto60% AI, 40% blockchain companies and the next fund is expanding into energy and longevity • Why angel investors need to ask: What's my superpower beyond capital? • How founders should think about cap table construction: bringing on investors who open doors, not just write checks • The truth about pivoting: from Ethereum NFTs to Bitcoin Ordinals to tokenized real-world assets—every step builds on the last • Why timing is everything: being 7-8 years early kills companies, but being positioned when the wind shifts creates unicorns • Standout portfolio companies: Gigaverse (live AI-powered video streaming for creators) and Dyad (semantic AI for value-based healthcare growing 10-15% monthly) Amanda doesn't sugarcoat the founder journey. She's learned that "every day in a startup, you're solving problems and trying to get to the next step." But she's also discovered that the right network, the right timing, and the right strategic positioning can turn small bets into generational wealth. Her philosophy is clear: "If you can keep a smaller fund, just one or two of these hits can produce 10, 20x on the whole fund." From working alongside Bill Tai (first investor in Zoom, seed investor in Canva, board member of 23 publicly traded companies) to building Metagood's full-stack tokenization infrastructure (marketplace, smart contracts, community), to backing companies at the frontier of AI and blockchain—Amanda is playing the long game with precision and patience. But perhaps most striking is her message about community: "A lot of our LP base are founders through the ACTAI Global network. Outside of just providing capital, we can always make ties to help our companies—whether it's customers, additional funding rounds, or strategic partnerships." From Necker Blockchain Summit to Extreme Tech Challenge to West Tech Fest—the ACTAI ecosystem has been quietly building the infrastructure for the next generation of unicorns for over a decade. This conversation goes deep on what it takes to generate returns in venture capital, why the tokenization wave is finally here, how to build companies from scratch with the right team and timing, and why staying small and strategic beats raising massive funds every time.

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 estate. For nearly a decade, tokenized property has hovered in a perpetual “almost there” phase. Whitepapers, pilots, demos — but little real adoption. What makes this conversation different is simple: Matt and his team have done what most couldn’t. They achieved full legal integration with the Dubai Land Department, enabling native tokenization of real estate at the land registry level, not just tokenized wrappers or offshore SPVs. The result? Two live residential properties. Fully compliant. Legally recognized. Sold out in minutes. Thousands of investors — many of them first-time buyers — now owning fractional interests in Dubai real estate, one of the fastest-growing property markets in the world.

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 onto the Project Runway stage without knowing how to sew, to raising $5.5 million in grant funding to build sustainable fashion infrastructure across the region, to creating SVÜL—a platform matching Caribbean makers with global clients—Anya's journey is a masterclass in authenticity, resilience, and the courage to keep starting over. This episode unpacks: • Why Anya deliberately chose NOT to carry the weight of representing the Caribbean on Project Runway—and how that freed her to win • The brutal lesson: when she tried to design for New York instead of being herself—until she dug deep into her Caribbean identity • How losing her 18-year-old brother tragically taught her to strip bare and find her true purpose • Why the future of fashion is custom—and how technology is making bespoke accessible to everyone • The hidden matriarchy of the Caribbean: how women run households, communities, and now governments • How SVÜL is bridging the digital divide by teaching seamstresses and makers to access global markets through platform-based education • Why problem-solving is built into Caribbean DNA—and how that's the ultimate entrepreneurial skill • The power of hybrid identity: being born in New York, raised in Trinidad, and bringing both worlds together • How she raised $5.5 million locally through strategic partnerships with IDB, CDB, UN, EU, and Massy—without traditional VC • Why grant financing forces discipline that seeds sustainable businesses • The truth about being a woman in Caribbean business: navigating toxic male-female dynamics while staying bold • How body scanning, AI, and virtual try-ons are finally making frictionless custom fashion possible • Why designing what YOU love always outperforms designing what you think people want • The mantra that changed everything: "Risk being yourself fully—faster" • What she would tell the Caribbean if it were a person sitting across from her Anya doesn't sugarcoat the journey. She's built 16-18 small businesses over 20 years. She's navigated devastating loss and euphoric wins. She's learned that "when you try to please everybody else, you're chasing something inherently unattainable." But she's also discovered that every time she surrenders to her authentic voice—whether in design, business, or motherhood—magic happens. Her philosophy is clear: "I dug very deep into the actual identity of who I am, and it just so happens to be a very Caribbean girl. That was the only reason I won at that stage—because I showed up as me." From working on 200 entrepreneurs across Trinidad, Barbados, and St. Lucia, to building digital capacity through her platforms, to naming her son Kairi (the indigenous Amerindian name for Trinidad) as a declaration of commitment to home—Anya is living proof that your greatest strength is your truest self. But perhaps most striking is her message to the Caribbean: "You are the most incredibly complex and diverse combination of skill and talent that the world has ever seen. You are what the world has been waiting for. And your time is now to bring that power and that unique capacity for creativity and innovation and your particular lens on what the world needs right now. The world is waiting for just exactly who you are." This conversation goes deep on what it takes to build sustainable creative economies, why indigenous practice must merge with cutting-edge technology, how motherhood amplifies purpose instead of limiting it, and why the Caribbean's cultural richness—our diversity, our joy, our problem-solving resilience—is our greatest export. Anya also shares her transition from designer to fashion-tech entrepreneur, why she's building with AI and blockchain to democratize luxury, and how staying rooted in Caribbean authenticity while operating globally creates unstoppable momentum. Her superpower? Channeling something divine, starting over with courage, and trusting that alignment always wins. If you care about Caribbean innovation, creative industry transformation, authentic leadership, or the future of fashion, this conversation is essential. 👉 What does "risk being yourself fully" mean to you? How has authenticity (or lack of it) shaped your journey? Share your thoughts in the comments—your voice shapes the future we're building together. If this episode inspired you, share it with someone who needs to hear that their truest self is their greatest asset. 📌 Don't forget: • Subscribe to the channel for more conversations about the founders, technologies, and ideas driving the world forward—one pivot at a time.

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, and global transformation. This is a deeply personal conversation about resilience, motherhood, principles, and what it takes to fight for change when the system resists. This episode unpacks: • Why Eva turned to blockchain during the Greece and Cyprus banking crises—when people lost their life savings overnight • The philosophy of decentralization: restoring trust through technology, not institutions • Why you can't innovate inside the box—and the brutal resistance trailblazers face • How Europe's fragmented regulatory landscape is killing innovation—and why that's finally changing • The wake-up call: why the US administration shift is forcing Europe to reclaim sovereignty • The critical need for quantum-resistant encryption and digital sovereignty in an AI-powered world • Why sandboxes take forever—and how that kills innovation before it starts • The narrative problem: how innovators who self-regulate get targeted instead of supported • How mission-driven investing and cross-border collaboration can solve global challenges • The truth about motherhood and ambition: why becoming a mom made Eva 100 times stronger—not weaker • Why women shouldn't wait: the myth that family disrupts career is a lie • How principles become your compass through any storm • The power of soft power: nurturing before running, emotional intelligence, and building resilience through community • Eva's new frontier Eva doesn't sugarcoat the journey, navigated public scrutiny as a young woman in tech and politics, and learned firsthand that "when you try to change the system, you feel the resistance grow." But she also knows that resilience is the ultimate skill—and every experience, no matter how brutal, builds it. Her philosophy is clear: "If you have your principles in the right place, you have a compass to navigate through any storm." From working on AI legislation that requires deep fake identification and human oversight, to championing blockchain as a trust protocol for democracy, to ensuring Europe doesn't fall behind in the quantum computing and data center arms race—Eva is building the infrastructure for sovereignty, innovation, and freedom. But perhaps most striking is her message to women: "Don't wait. Having a family doesn't disrupt your career, it makes you stronger. You don't have to choose one role. You can be a mother and achieve anything you want." Eva's daughter travels with her everywhere, learning, adapting, experiencing, proof that the narrative of sacrifice is outdated. This conversation goes deep on what it takes to legislate the future, why Europe must wake up to the AI and quantum revolution, how collaboration across borders creates transformative impact, and why staying true to your principles is the only way to survive the storms of innovation and public life. Eva also shares her transition from policy making —connecting missions, solving problems, and building bridges between traditional sectors and cutting edge investors. Her superpower? Seeing what others don't—and bringing the right people together to make it happen. If you care about blockchain, AI sovereignty, European innovation, motherhood and ambition, or the future of democracy, this conversation is essential. 👉 What principles guide you through life's storms? How do you balance ambition and family? Share your thoughts in the comments—your voice shapes the future we're building together. If this episode inspired you, share it with someone who needs to hear that resilience, principles, and community are the ultimate superpowers. 📌 Don't forget: • Subscribe to the channel for more conversations about the founders, technologies, and ideas driving the world forward—one pivot at a time.