Exploring Prosperity- Challenging Pessimism in the US

What does it take for one of the world's largest financial institutions to adopt an entirely new technology?Morgan Stanley's Head of Digital Asset Strategy, Amy Oldenburg, joins Exploring Prosperity to discuss the hidden challenge of bringing crypto, tokenization, stablecoins, and blockchain technology into a global financial institution.Most conversations about digital assets focus on prices, regulation, or the latest market cycle. This conversation focuses on something deeper: how innovation actually moves from the outside into the institutions that society already depends upon.Drawing on more than two decades at Morgan Stanley, Amy explains why large organizations often struggle to innovate, what she calls the challenge of institutional transformation, and why understanding both emerging technology and legacy financial infrastructure has become increasingly valuable.We discuss:• How Amy's experience in emerging markets led her to Bitcoin and digital assets• Why Morgan Stanley began exploring digital assets years before most institutions• The internal resistance new technologies face inside large organizations• What "institutional grade" really means• Why tokenization is about far more than crypto investing• How stablecoins may strengthen the global role of the U.S. dollar• The infrastructure required to support 24/7 financial markets• Why user experience ultimately drives technology adoption• How AI and digital assets are accelerating financial modernization• The opportunities and challenges facing Wall Street over the next decadeOne of the most fascinating themes in this discussion is the role of the translator: people who understand both the culture of innovation and the realities of large institutions. As digital assets continue moving into the financial mainstream, that role may become one of the most important in finance.If you enjoy thoughtful conversations about technology, markets, institutions, Bitcoin, AI, and the future of financial services, subscribe and join us for future episodes.Subscribe to my Substack for more in depth analyses of these topics: https://robertdewey3.substack.com/Thank you very much to our sponsors:Foundation: Protect your Bitcoin using the latest off-line technology with easy-to-use Passport. Their next product, Passport Prime will protect all passwords off-line with even-better technology. https://foundation.xyz/River Financial: If not cold storage for your Bitcoin, I’d highly recommend River for buying and holding- River is engineered to protect your Bitcoin over the long run. Use this link for discounts: https://river.com/signup?r=T7GGAF7G#DigitalAssets #Tokenization #MorganStanley Timestamps:00:00 Highlights01:05 How Amy Oldenburg Found Crypto Through Emerging Markets07:25 Why Bitcoin Made Sense Outside the Developed World10:35 Morgan Stanley's First Digital Asset Working Groups11:25 The "Innovation Firewall" Inside Large Institutions13:00 Why Financial Firms Struggle to Innovate17:45 The Regulatory Turning Point for Digital Assets21:35 From Experimentation to Firm-Wide Strategy22:25 Amy's Role as Head of Digital Asset Strategy26:40 What Does "Institutional Grade" Really Mean?30:40 The Most Important Use Cases for Digital Assets36:20 Tokenization, AI, and the Future of Financial Infrastructure42:10 The Biggest Challenges Facing Institutional Adoption46:00 Tokenization, New Products, and the Future of Finance48:25 Closing Thoughts This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit robertdewey3.substack.com/subscribe

In this episode, I sit down with investment manager and author Lawrence Lepard (The Big Print) to examine how America’s monetary system actually works—and why its failures increasingly feel moral, not just economic.Larry breaks down the Cantillon Effect: how Federal Reserve money creation and artificially low interest rates disproportionately benefit Wall Street, large financial institutions, and asset owners, while eroding the purchasing power of wages and savings on Main Street. What emerges is a system that rewards proximity to newly created money rather than productive contribution.We discuss what Larry calls the “Gradual Print” now underway—a slow but persistent expansion of the monetary base that avoids crisis headlines while steadily debasing the currency. To illustrate the scale of this debasement, he introduces the concept of a “shadow price” of gold: a theoretical calculation showing that gold would need to be priced near $90,000 per ounce to fully back today’s M2 money supply. This is not a near-term price forecast, but a framework for understanding how far the system has drifted from monetary discipline.The conversation also explores the historical origins of central banking, the moral hazards created by bailouts and credit expansion, and why Larry believes sound money is essential to restoring fairness, trust, and long-term stability. We conclude by discussing why he holds both gold and Bitcoin as protection against monetary debasement—and what a realistic transition to sound money could look like.Topics Discussed:- The "Rigged" Game: How low interest rates and bailouts favor the elite banks.- The Big Print vs. Gradual Print: Why the Fed is trapped and what comes next.- The $90,000 Gold Calculation: What the price of gold would be if it backed today's money supply.- Bitcoin vs. Gold: Why Larry holds both to protect purchasing power.- The Solution: How we transition to sound money and a fairer system.Thank you very much to our sponsors: Truflation: BUY Truflation products/services and save 10% using code BOBDEW10. Learn about what prices are actually doing by going to https://truflation.com/Foundation: Protect your Bitcoin using the latest off-line technology with easy-to-use Passport. Their next product, Passport Prime will protect all passwords off-line with even-better technology. https://foundation.xyz/River Financial: If not cold storage for your Bitcoin, I’d highly recommend River for buying and holding- River is engineered to protect your Bitcoin over the long run. Use this link for discounts: https://river.com/signup?r=T7GGAF7GTimestamps: 00:00 - Intro 03:38 - The "Moral Crusade": Why the System is Unfair 07:04 - The Cantillon Effect: How Banks Rigged the Game 13:13 - Larry’s "Radicalization" (The GFC Moment) 17:15 - The "Gradual Print" vs. The "Big Print" 26:49 - The End of the Dollar Reserve Currency? 34:15 - The Secret Meeting at Jekyll Island (Fed History) 46:16 - The Solution: How We Transition to Sound Money 52:01 - The Michael Saylor 2032 Prediction 56:51 - The Debt-to-Gold Ratio & The $90k "Shadow Price" 1:03:14 - Volatility & The "God Candle": Why Selling is Dangerous 1:08:22 - Bitcoin vs. Gold: Which to Buy Now? This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit robertdewey3.substack.com/subscribe

Artificial intelligence is transforming the global economy — but will America stay ahead? In this audio edition of Exploring Prosperity, host Robert Dewey examines whether U.S. innovation can outpace regulation, comparing today’s AI revolution to past eras when new technologies reshaped productivity, jobs, and global power.From Silicon Valley’s open-source momentum to Europe’s regulatory headwinds and China’s centralized push, this essay explores the balance between freedom, experimentation, and control — and why the future of prosperity may depend on which model wins.Topics include:* The real drivers of America’s AI edge* How overregulation could slow innovation* Lessons from past technology revolutions* The global race for AI leadershipListen to understand how policy choices today could decide whether AI accelerates prosperity — or stifles it.Thank you very much to our sponsors:* Truflation: Truflation: BUY Truflation products/services and save 10% using code BOBDEW10. Learn about what prices are actually doing by going to https://truflation.com/marketplace/us-inflation-rate* Foundation: Protect your Bitcoin using the latest off-line technology with easy-to-use Passport. Their next product, Passport Prime will protect all passwords off-line with even-better technology. https://foundation.xyz/* River Financial: If not cold storage for your Bitcoin, I’d highly recommend River for buying and holding- River is engineered to protect your Bitcoin over the long run. Use this link for discounts: https://river.com/signup?r=T7GGAF7G This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit robertdewey3.substack.com/subscribe

Every generation inherits miracles that once seemed impossible. Childbirth used to be among humanity’s greatest risks—today, it’s routine. In this episode of Exploring Prosperity, I look at the extraordinary fall in infant mortality and what it reveals about the quiet triumph of modern medicine. From 1800—when nearly half of all children died before age five—to today’s rates in the US at 0.5%, this is one of history’s clearest measures of human progress. Yet our healthcare system, despite these miracles, has become a source of frustration and pessimism. Why? Costs, complexity, and bureaucracy now obscure the deeper story of achievement. This video explores both sides of that paradox: how far medicine has come—and why so many feel left behind by it. Subscribe! Explore how innovation, capitalism, and human creativity continue to shape a more prosperous future. Thank you to our sponsors! Truflation: Learn about what prices are actually doing by going to https://truflation.com/Foundation: Protect your Bitcoin using the latest off-line technology with easy-to-use Passport. Their next product, Passport Prime will protect all passwords off-line with even-better technology. https://foundation.xyz/River Financial: If not cold storage for your Bitcoin, I’d highly recommend River for buying and holding- River is engineered to protect your Bitcoin over the long run. Use this link for discounts: https://river.com/signup?r=T7GGAF7G Timestamps: 00:00 The Miracle of Modern Childbirth 02:42 The Paradox of Healthcare Progress This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit robertdewey3.substack.com/subscribe

For nearly 80 years, the world’s leading powers have avoided direct war — a stretch historians call the “Long Peace.” This video explores why peace has lasted so long, what forces have kept it in place, and how fragile it may be in the years ahead. Drawing on my essays from my research, (https://robertdewey3.substack.com/p/g...) we look first at the historical rarity of 80 years without great power conflict. Then we examine the global forces that shaped this era: U.S. hegemony after World War II, nuclear deterrence and the Cuban Missile Crisis, economic interdependence between rivals like the U.S. and China, and international institutions such as the UN, WTO, and EU. While these systems have enabled extraordinary global prosperity, each contains weaknesses — and history shows that peace is never guaranteed. Cycles described by Ray Dalio in Principles for Dealing with the Changing World Order and Strauss & Howe in The Fourth Turning suggest new challenges may be approaching. The Long Peace has been a foundation for growth and progress. But can it endure — and what happens if it doesn’t? These are questions that matter for the prospects of the next generation. Thank you to our sponsors! Truflation: BUY Truflation products/services and save 10% using code BOBDEW10. Learn about what prices are actually doing by going to https://truflation.com/ Foundation: Protect your Bitcoin using the latest off-line technology with easy-to-use Passport. Their next product, Passport Prime will protect all passwords off-line with even-better technology. https://foundation.xyz/ River Financial: If not cold storage for your Bitcoin, I’d highly recommend River for buying and holding- River is engineered to protect your Bitcoin over the long run. Use this link for discounts: https://river.com/signup?r=T7GGAF7G Timeline: 0:00 — Overview of The Great Peace. 0:26 — Modern Flashpoints: 2025, two flashpoints, Israel airstrike, Russian drones, historical precedent. 1:05 — Theories and Historical Context: Extraordinary events, global powers, extended peace, historical cycles. 3:33 — Hegemonic Stability & Nuclear Deterrence: US dominance, nuclear weapons, deterrence, global order. 6:11 — Systemic Forces & Fragility: International institutions, recent escalations, fragility of peace, looking ahead. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit robertdewey3.substack.com/subscribe