The Upwind Podcast

Lily Dash

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.

  1. 9 FEB

    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 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.

    1h 36m
  2. Blessing in Disguise: Trevor Koverko on Losing Everything, Finding Ethereum & Building in Web3

    31 JAN

    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 future of global finance? In this deeply personal and technically rigorous conversation, host Lily Dash sits down with Trevor Koverko—serial founder, early Ethereum pioneer, and one of the few builders who coined the term "security token" before the world's largest banks were talking about tokenization. From playing for the New York Rangers to surviving a life-threatening accident that left him with a catastrophic brain injury and paralysis, to becoming one of crypto's earliest infrastructure builders, Trevor's journey is a masterclass in resilience, reinvention, and seeing around corners. Before most people knew what crypto was, Trevor was already there—not as a speculator, but as a builder. In 2017, he founded Polymath and created what is widely considered the first security token, years before BlackRock, JP Morgan, and NASDAQ began racing to tokenize real-world assets. Today, he's building Sapien—an open protocol for AI training data that's empowering millions of people globally to earn wages by refining the fuel that powers the next generation of enterprise AI. This episode unpacks: • How a highway collision with a transport truck ended Trevor's NHL career at 23—and forced a complete reinvention • Why he had to escape from the hospital (literally) after losing power of attorney over himself due to brain injury • The New Year's resolution that changed everything: choosing entrepreneurship after hitting rock bottom • How being okay with both the height of success and the depth of failure gave him nothing to lose • Why Toronto became an early incubator for Ethereum—and how Trevor crossed paths with Vitalik and the founding team • The pattern he saw in 2016: protocols got tokenized, then cash (stablecoins), then NFTs—so why not securities? • How Polymath raised $60 million and pioneered tokenization before it became a Davos buzzword • The brutal secular bear market for tokenization—and why they survived when others didn't • Why Larry Fink and the "gatekeepers" went from enemy to evangelist on tokenization • How legacy financial rails (SWIFT, DTCC, T+2 settlement) are built on 1980s COBOL code—and why that's about to change • The future: tokenized money market funds, fractionalized real estate, programmable assets, 24/7 global liquidity • Why emerging markets will benefit most from tokenization—leapfrogging legacy systems entirely • How velocity of capital unlocks when you remove intermediaries and automate compliance on-chain • Why Trevor believes one Caribbean stock exchange built on tokenization could unite the region's fragmented markets • The AI data bottleneck: why all the open internet data has been trained on—and what comes next • How Sapien is building the "data refinery" for enterprise AI—turning crude data into high-quality training fuel • Why JP Morgan is terrified: threats from AI-powered startups below and foundational models like ChatGPT above • The iceberg analogy: open internet data is the tip, but private enterprise data beneath the surface dwarfs it • How human-powered data labeling is creating millions of jobs globally—not replacing them • Why anyone with a $30 Android phone and internet can now earn a living wage structuring AI data • The proof-of-quality protocol: how Sapien uses crypto primitives to decentralize Scale AI's model • Why they got product market fit and millions in revenue before launching a token—the right way to build in crypto • How companies like Cursor are reaching $100M ARR in 18 months—the fastest revenue growth in startup history • Trevor's investing philosophy: why giving money to wealth managers is "low IQ" and index funds beat 95% of pros • The Rich Dad Poor Dad framework: only assets that put cash in your pocket monthly are real assets • Why he's a San Francisco maximalist • The AI application layer opportunity: infrastructure is built, now it's time to monetize with consumer-facing products • How lovable and Cursor let non-technical founders build and deploy AI apps in hours, not months • Why Barbados is "Dubai in 1995"—and the most strategic place in the Western Hemisphere that's not on the map yet Trevor doesn't sugarcoat the founder journey. He's learned that rock bottom isn't the end—it's the beginning of something new. From trying to escape the hospital with a catastrophic brain injury, to buying student rental houses in college, to spending time in Silicon Valley learning from the best, to recognizing the tokenization wave before anyone else, to now building the data infrastructure that powers enterprise AI—Trevor has consistently been early, disciplined, and relentless. His philosophy is clear: "I've been at the height of the highs and rock bottom. I'm okay with both. So I have nothing to lose.

    1h 3m
  3. Where Community Meets Capital: Amanda Terry of Metagood and ACTAI Ventures on Tokenizing Real World

    24 JAN

    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 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.

    52 min
  4. 31/12/2025

    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? 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.

    1h 1m
  5. Eva Kaili on Principles &  Resilience

    23/12/2025

    Eva Kaili on Principles & Resilience

    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.

    40 min
  6. The NAD Revolution: How Dr. Halland Uses Cellular Medicine to Fight Aging, Addiction & Disease

    15/12/2025

    The NAD Revolution: How Dr. Halland Uses Cellular Medicine to Fight Aging, Addiction & Disease

    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 incubated by GE Healthcare to running university-based stem cell research, Dr. Halland brings a rare combination of tech innovation, clinical expertise, and deep scientific rigor to the longevity space. This episode unpacks: • How NAD was originally used to detox people off opiates and alcohol—without medication • Why NAD levels drop by more than 50% by your 40s—and what that means for aging • The difference between IV NAD, oral precursors (NMN, NR), and liposomal delivery • Why going slow with IV NAD is critical—and how pumps revolutionize the experience • The real physiological effects: increased energy, mental clarity, improved sleep, enhanced recovery, and detoxification • How NAD flushes toxins from your liver, kidneys, and even your brain's lymphatic system • Why mitochondrial resilience is the foundation of longevity—and how NAD powers it • The surprising link between metabolic dysfunction and mental health conditions like anxiety and depression • Why functional medicine testing (gut health, hormones, heavy metals) should start in your 30s—not your 60s • How early cancer detection tests and full-body AI scans are changing preventative care • The future of stem cell therapy: autologous vs. donor cells, cloning to 250 million cells, and why DNA integrity matters • How one tablespoon of fat can create over 1,000 doses of your own stem cells—enough for 250 years • Why Florida's new legislation (as of July 1st) is making stem cell therapy more accessible and compliant • The four key domains of FDA-approved stem cell research: long-haul COVID, neurodegenerative disorders, autoimmune conditions, and orthopedics • What exosomes are—and why 100-400 billion exosomes might deliver stem cell-like benefits • The truth about GLP-1s (Ozempic): who should take them, why low-dose might support longevity, and the power of combining them with NAD • Why peptide therapy is becoming a consumer-driven revolution—and what that means for the future of medicine Dr. Holland doesn't just talk theory—he's patient number one. Everything he recommends, he's tested on himself first. From daily oral NAD supplementation to monthly IV infusions using precision pumps, to banking his own stem cells as an "insurance policy" for future health challenges, he practices what he preaches. But perhaps most striking is his philosophy: "We weren't healing people. We were just controlling symptoms with procedures or medication. I fundamentally believed we should heal the body." That realization sent him down a 15-year journey into regenerative medicine, cellular therapy, and metabolic optimization—long before longevity became a buzzword. This conversation goes deep on what actually works: why younger people (30s and 40s) are driving the longevity movement, how environmental toxins and microplastics are accelerating disease, why early menopause in your 30s isn't normal, and how cellular medicine can help your body become metabolically resilient in a toxic world. Dr. Holland also shares the science behind why compact, high-integrity stem cells can pass through the lungs and cross the blood-brain barrier—something most cloned cells can't do. He explains why mesenchymal stem cells from fat are superior for tissue regeneration, and how exosome therapy helped save a patient in full liver failure who couldn't get a transplant. With collaborative research at the University of Miami, IRB-approved protocols heading to the FDA, and a mission to make longevity accessible (not just for the ultra-wealthy), Dr. Halland is building the future of medicine—one cell at a time. If you care about longevity, cellular health, metabolic optimization, or the future of regenerative medicine, this conversation is essential. 👉 What's your biggest question about NAD, stem cells, or peptide therapy? Have you tried any cellular medicine approaches? 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's curious about what's possible when we work with the body's natural healing capacity. 📌 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.

    37 min
  7. From Andela to Flutterwave: How Iyinoluwa "E" Aboyeji Built Two Unicorns to Prove Africa Could

    08/12/2025

    From Andela to Flutterwave: How Iyinoluwa "E" Aboyeji Built Two Unicorns to Prove Africa Could

    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 two African tech unicorns: Andela and Flutterwave. But this isn't just a victory lap. This is the story of a relentless builder who spent a decade proving that African founders could build world-class companies—and then set out to build the infrastructure so the next generation wouldn't have to fight as hard. This episode unpacks: • How Andela "imported an economy over the internet" to solve Africa's 40% youth unemployment crisis • Why Flutterwave was built with an all-Nigerian team—and what that proved to the world • The brutal truth about internalized limitations and breaking glass ceilings • How E turned down Silicon Valley VC offers to build Future Africa—a fund, platform, and movement • The evolution from family office to collective investing to $20M institutional fund • Why E is building Itana: a 2,000-hectare free zone with 576 housing units and the world's largest startup campus • The three pillars of ecosystem building: community, infrastructure, and policy • How to work with government over 10 years to change colonial-era laws—without disrupting the system • Why Barbados is "Dubai in 1995"—and the most strategic place on the planet that's not on the map • The controversial truth: you can't build Silicon Valley in three years—it takes a hundred-year march • How legal frameworks in the Global South were designed for extraction, not value creation • Why bringing talent first—not building infrastructure—is the key to ecosystem success • The future of work: discounting degrees and training for skills the world actually needs • How small nations can leapfrog traditional systems and become digital economy hubs E's journey is a masterclass in patience, persistence, and strategic vision. From working with a former deputy governor of Nigeria's central bank to navigate regulatory gray areas, to spending seven years (and counting) getting free zone policies approved, to raising $80 million from Africa Finance Corporation for infrastructure development—E plays the long game. And he's winning. But perhaps most striking is his thesis on Barbados. With direct flights to Africa, the US, Europe, Latin America, and the Caribbean, Barbados sits at the center of five major Black populations globally. It has strong property rights, 300 years of political stability, a highly educated population, and progressive leadership. As E puts it: "If you were looking for Dubai for the Western Hemisphere, you wouldn't find a better candidate." This conversation goes deep on what it actually takes to build ecosystems, why most charter city experiments fail, how to turn unemployment into opportunity by importing economic activity, and why the Global South must stop waiting for permission to build the future. E doesn't sugarcoat the founder journey: "It's the worst job ever. You could be high one day and the next day about to go out of business." But he also knows that the only way to change systems designed for extraction is to work within them—slowly, strategically, and with unwavering commitment. If you care about Africa, the Caribbean, ecosystem building, or the future of the Global South, this conversation is essential. 👉 What do you think it takes to build a thriving startup ecosystem in the Global South? What role should government play? 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 see what's possible when vision meets persistence. 📌 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.

    59 min

About

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.