Exploring Prosperity- Challenging Pessimism in the US

Bob Dewey

Challenge Pessimism. Explore the Complexity of Progress. Headlines and survey results scream pessimism, but is it warranted? Join us on Exploring Prosperity as we delve into the complexities of human progress with leading thinkers across markets, economics, history, philosophy, and more. Discover how economic and societal factors shape our world, and gain a deeper understanding of the drivers of individual and societal prosperity and a fulfilling life. Our in-depth conversations may leave you empowered and optimistic about the future and equipped with insights to navigate the challenges and opportunities that lie ahead. Bob Dewey brings his expertise in investing and his network in the investment community and beyond to address the big issues of the day and whether we can solve problems faster than they grow. robertdewey3.substack.com

  1. VOR 6 TAGEN

    AI Is Rewiring Markets, Energy & Bitcoin | Matthew Sigel

    Why are stocks hitting new highs during war and geopolitical instability? Why are Bitcoin miners suddenly becoming AI infrastructure companies? And could sovereign nations eventually adopt Bitcoin as a reserve asset?In this conversation, Matthew Sigel, Head of Digital Asset Research at VanEck and portfolio manager of the Vaneck Onchain Economy ETF (ticker: NODE), explains how AI, de-globalization, energy infrastructure, Bitcoin mining, stablecoins, and sovereign debt are converging into a massive new investment cycle.We discuss:• Why markets continue rising despite war and political instability• The US investment cycle• The AI-driven electricity and infrastructure boom• Why Bitcoin miners may become major AI data center operators• How sovereign nations are accumulating and mining Bitcoin• Why stablecoins could transform the global payments system• The future of Bitcoin treasury companies like MicroStrategy• Why Matthew believes Bitcoin could eventually reach half the market cap of gold• How VanEck’s NODE ETF approaches digital asset investing differentlyThank you to our sponsors:Foundation: Their new prioduct Passport Prime helps secure your digital life by moving passwords, authentication keys, Bitcoin, and sensitive data into a secure offline environment. Visit www.foundation.xyzRiver 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 to sign up: https://river.com/signup?r=T7GGAF7GThis discussion connects macroeconomics, digital assets, energy infrastructure, and the future of global finance.Tmestamps:00:00 Why Markets Keep Rising During War02:25 AI and Deglobalization Are Reshaping the Economy04:45 Why Cloud Growth Is Accelerating05:35 Bitcoin Miners Become AI Infrastructure06:40 How NODE Invests in Crypto and AI08:30 Why Bitcoin Sentiment Was Extremely Bearish10:40 What Institutional Bitcoin Activity Really Looks Like12:55 Why Bitcoin Now Trades Like Tech Stocks16:00 The Energy Bottleneck Driving AI18:20 Why Bitcoin Miners May Be Undervalued21:10 What Happens if Miners Leave Bitcoin?23:50 Why VanEck Reduced Altcoin Exposure27:20 Corporate Blockchains vs Public Chains28:15 Matthew Sigel’s Bitcoin Outlook30:15 Sovereigns Are Quietly Accumulating Bitcoin33:30 Has El Salvador’s Bitcoin Experiment Worked?34:30 The Problem With Bitcoin Treasury Companies39:00 Stablecoins and the Future of Payments43:50 Sovereign Debt and Bitcoin’s Long-Term Role 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

    46 Min.

  2. 25. APR.

    Is Digital Security Ready for What’s Coming? (Zach Herbert)

    AI is changing cybersecurity—and it may be increasing the scale of digital threats beyond what banks, platforms, and institutions can manage. In this video, I break down how AI-driven attacks could expose vulnerabilities in financial systems, online accounts, and digital identity infrastructure. Based on real-world fraud experiences and insights from Foundation CEO Zach Herbert, we explore why traditional security models may be insufficient and what individuals can do to protect themselves. Key topics: * AI cybersecurity risks and vulnerabilities * Digital identity theft and account breaches * Bank fraud, SIM swaps, and social engineering * Why institutions may struggle to contain large-scale attacks * Self-custody and personal digital security tools Thank you very much to our sponsors: * Foundation: Secure your digital life—from passwords, 2FA, files and Bitcoin with Passport Prime, an all-in-one personal security platform. Visit them at https://foundation.xyz/ * 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 * 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 Introduction to Digital Security Vulnerabilities 02:49 Zach Herbert’s Journey into Security 05:56 The Evolution of Bitcoin and Security Breaches 08:57 The Shift from Bitcoin to Overall Digital Security 12:08 AI’s Impact on Security Landscape 15:00 The Risks of Centralized Security Systems 18:09 Shared Infrastructure and Individual Vulnerabilities 20:58 The Concentration Risk in Custodial Security 24:06 Future Vision for Digital Security Solutions 28:14 Enhancing Security with Hardware Solutions 35:07 User Experience and Ease of Use in Digital Security 40:17 Advanced Security Features of Passport Prime 45:00 Quantum Computing and Future Security Challenges 52:59 Empowering Individuals in Digital Security 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

    57 Min.

  3. 19. APR.

    Credit Stress Is Back: What Happens When Markets Stop Clearing?

    Credit stress is beginning to reappear in parts of the economy—especially in private credit markets where institutional capital has surged in recent years.In this episode of Exploring Prosperity, I sit down with veteran distressed real estate investor Bill Landis, co-Founder and Managing Partner of Raith Capital Partners, to break down what actually happens when markets stop clearing. We explore how distressed capital restores liquidity, how assets transition into stronger hands, and why this process becomes essential when traditional lenders pull back.If the current strains in credit markets continue to build, understanding this overlooked part of the financial system may be key to understanding what happens next.Topics include: * Early signs of stress in private credit markets * How distressed investors provide liquidity * What happens when financing disappears * Why long periods of calm create hidden risks * What a true credit cycle looks like Subscribe for more conversations on markets, macroeconomics, and what drives long-term prosperity.Read about this episode: https://open.substack.com/pub/robertd...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:00:05 – Introduction: Why Credit Stress Is Reappearing01:05 – Are Cracks Forming in Private Credit Markets?02:45 – The Hidden Risk: Liquidity Mismatches & Redemptions04:15 – How Credit Stress Spreads Across Markets05:45 – Mini-Crises vs Major Crises (Post-2008 Reality)07:30 – The “Medicated Economy”: Government Backstops Explained09:00 – What Distressed Investors Actually Do12:00 – How to Invest When There Is No Distress16:00 – Finding Opportunity: Housing, Industrial, and Demographics20:00 – Institutional Capital: Stabilizer or Distortion?24:30 – How Government Intervention Restores Liquidity30:30 – Why Real Distress Has Been Scarce (Even After Rate Hikes)33:30 – Where the Edge Comes From in Real Estate Investing38:30 – New Opportunities: AI, Data Centers, and Mispriced Assets43:30 – Case Study: San Francisco Real Estate Recovery49:30 – The State of Distressed Investing Today56:00 – Macro Risks Ahead: Oil, Debt, and the Next Downturn 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

    1 Std.

  4. 4. APR.

    What AI Can Actually Do — And What It Can’t

    Artificial intelligence is changing finance, healthcare, education, and the future of work — but what is it actually doing under the hood?In this conversation, I sit down with Albert Berdellans, Global Head of AI at Invenium, for one of the clearest explanations I’ve heard of how large language models actually work, what AI can and cannot do, where the risks are overstated, and how it may reshape society in the years ahead.We discuss:• how large language models generate answers• why AI does not actually “think”• hallucinations, context rot, and why AI gets things wrong• whether AI will replace jobs• how AI is already changing finance• the future of healthcare and education• why fears of rogue AI may be overblownIf you’re trying to build a clear framework for understanding AI beyond the hype and fear, I think you’ll find this conversation to be invaluable.Subscribe to Exploring Prosperity for conversations on technology, economics, markets, and the forces shaping human progress.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 Introduction — what AI actually is beyond the hype01:04 Albert’s background and how he entered AI04:55 Where AI impresses most — and where it doesn’t07:31 How AI is used in finance and large institutions12:11 Context rot and why too much information hurts AI14:05 How large language models actually work17:44 Hallucinations and false answers19:25 Can you trust AI outputs?22:31 Can AI reason and make predictions?27:21 Which jobs AI will change first31:13 How AI is transforming private markets and due diligence37:36 Tokenization, liquidity, and real estate40:49 How AI could improve healthcare and education47:12 AI in medicine, diagnosis, and surgery48:16 The future of education and personalized learning52:08 Will AI go rogue? The real risks55:15 Real-world examples of “rogue AI” explained59:23 Final 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

    1 Std.

  5. 27. MÄRZ

    Are We Getting Weaker? Hard Money, Harder Virtues

    Are we actually progressing—or quietly getting weaker?In this conversation, I sit down with Aleks Svetski, author of The Bushido of Bitcoin, to explore a deeper question that sits beneath economics, technology, and politics: what actually drives long-term human progress?Many believe that fixing money—through systems like Bitcoin—can restore discipline, align incentives, and solve structural problems in society. But as Aleks argues, that’s only part of the story. Human nature, culture, and values ultimately determine whether societies rise or fall.We discuss:- Why hard money is necessary—but not sufficient- The role of character, virtue, and “nobility” in shaping civilization- Whether democracy strengthens or weakens societies over time- How AI and technology may widen the gap between disciplined and undisciplined people- Why pain and suffering may be essential to growth and progressThis is a conversation about incentives, power, culture, and the uncomfortable possibility that no system alone can fix what is fundamentally human.This episode will challenge how you think about progress.Subscribe for long-form conversations on markets, macro, technology, Bitcoin, and the future of prosperity.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:00:05 – What actually drives human progress?00:47 – Bitcoin doesn’t fix human nature03:33 – Culture, virtues, and the “20% that matter”04:22 – Are we entering a new era of leadership?08:40 – Bitcoin as an accelerant, not a solution10:55 – What defines a new aristocracy?13:57 – “Hard times create strong men” — where are we now?16:44 – The hidden flaw of democracy20:17 – Why democracy may be a historical anomaly22:10 – Leadership vs political short-termism24:50 – What Bitcoin actually enables27:15 – Incentives, savings, and generational wealth30:12 – AI: tool or crutch?34:08 – Productivity vs dependence in the age of AI38:39 – The role of pain and suffering in growth44:11 – Why avoiding hardship creates weakness47:45 – Will AI widen the gap between people?48:29 – Writing, thinking, and the discipline of ideas52:06 – Why Svetski wrote The Bushido of Bitcoin56:05 – From pessimism to responsibility and action1:00:30 – The difficulty of writing and rewriting ideas1:04:57 – A book that challenges everything you believe 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

    1 Std. 7 Min.
  6. OpenAI’s Trillion-Dollar Obligations: Can the Math Work?

    20. FEB.

    OpenAI’s Trillion-Dollar Obligations: Can the Math Work?

    In this episode of Exploring Prosperity, I sit down with investor Ram Ahluwalia to examine one of the most important — and least discussed — risks in the AI buildout.OpenAI reportedly has nearly $1 trillion in committed obligations tied to data center capacity and compute infrastructure. With revenue far below that scale, the key question is simple:Can the math foot?This conversation is not anti-AI. AI is clearly transformational. But the expansion of AI depends on capital markets. If funding conditions tighten, what happens to the trillion-dollar commitments already in place?We discuss:• OpenAI’s revenue performance obligations and data center exposure• The capital markets dependency of the AI buildout• Why tech stocks may continue to lag• The rotation into energy, commodities, and real assets• Software valuations and whether this is truly a “COVID-style” opportunity• Bitcoin’s current bear market psychology• Quantum computing risk and institutional hesitation• The role of KOLs and narrative investing in late-cycle marketsRam argues that this moment resembles past cycles where crowded themes detach from balance sheet reality — and markets begin to demand discipline again.If you care about AI, tech stocks, Bitcoin, or the direction of capital markets in 2026, this is a conversation worth watching.Subscribe for more long-form interviews on markets, technology, and economic reality.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 Intro00:48 OpenAI & “Sam Altman Broke the World”01:54 OpenAI’s $1 Trillion in Committed Obligations03:41 Why the AI Revenue Math Doesn’t Foot04:40 Microsoft, Oracle & Revenue Performance Obligations (RPO)06:45 What Happens If OpenAI Can’t Raise Capital?08:47 The AI–Capital Markets Dependency10:59 Does This Slow Down AI Development?12:50 Investment Implications: Tech Rotation Begins14:40 Inflation-Resistant Sectors Outperforming16:50 Why Tech May Continue to Lag18:20 Is Software a COVID-Level Bargain?23:25 Bitcoin, Software & the “Tech Bro Portfolio”24:45 Satoshi Conference: Institutional Bitcoin Debate29:58 Tokenization & Crypto’s Strategic Misstep34:10 Why Crypto Ignored Small Business Capital36:14 Venture Capital Overvaluation & Private Market Marks38:34 Quantum Risk to Bitcoin41:45 Is Bitcoin in a Bear Market?49:00 Real-World Investing vs. Techno-Optimism51:57 Tribalism, KOLs & Market Cycles55:36 The Four Phases of a Market Rally58:07 Was the Bitcoin Top Already In?59:45 What Capitulation Might Look Like 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

    1 Std. 2 Min.

  7. 9. FEB.

    27 Million Reports: Will Congress Scale Back Financial Surveillance?

    More than 27 million financial reports are filed each year under the Bank Secrecy Act, flagging ordinary banking activity as “suspicious.” Yet, as the data shows, only 370 investigations were tipped off by these reports. In this conversation, Nick Anthony of the Cato Institute explains how U.S. financial surveillance expanded quietly over decades, why routine cash transactions now generate government reports, and how banks have effectively been deputized as law enforcement investigators. We discuss the real-world consequences for individuals, including account closures, the "sense of confusion" that comes with debanking, and the steady erosion of financial privacy.The interview also examines current legislation in Congress, including proposals to reform the Bank Secrecy Act and the Saving Privacy Act. These proposals aim to raise outdated reporting thresholds that haven't been adjusted for inflation since 1970. At stake is whether Congress will meaningfully scale back financial surveillance or allow the status quo to continue.This discussion covers:– The $10,000 threshhold- Why inflation has expanded surveillance far beyond its original intent.– The Investigative Gap- Why 27 million reports result in only ~370 investigative tips.– Confidentiality Laws- Why banks are legally forbidden from telling you why your account was closed.– CBDC Update- The shift from voluntary pilots to "force mandates" in international digital currencies.Nick Anthony is a policy analyst focusing on financial regulation, privacy, and central bank digital currencies. He is the author of the CBDC Tracker and writes extensively on banking surveillance and civil liberties.Read the full report by Nick Anthony "Understanding Debanking" at: https://www.cato.org/policy-analysis/understanding-debanking-evaluating-governmental-operational-political-religiousThank 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 Legislative Changes and Government Surveillance06:30 The Impact of the Bank Secrecy Act12:17 Debanking and Its Consequences17:07 The Future of Surveillance and Privacy20:37 The Importance of Financial Privacy23:05 Raising Awareness on Financial Issues24:12 The Challenge of Debanking25:20 Congress and Financial Reporting28:02 Central Bank Digital Currencies (CBDCs) Overview28:37 Global CBDC Developments32:20 The European Central Bank's Push for Digital Euro37:33 Adoption Challenges of CBDCs40:10 Government Mandates and CBDC Adoption43:40 The Political Landscape of CBDCs 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

    47 Min.

  8. 24. JAN.

    The One-Hour Problem: How High School Counseling Fails Families

    Families navigate the college decision process rarely—but the consequences can last decades.In this episode of Exploring Prosperity, I speak with Jon Carson, CEO of College Guidance Network, about why the traditional college guidance system no longer works—and why rising costs, declining ROI, and information asymmetry have made the decision riskier than ever.We break down the real math behind high school counseling, why most students receive only about one hour of guidance per year, and how parents are left without the tools they need to make informed decisions. We also explore how colleges market to families, how student debt reflects systemic failure, and why confidence in higher education has collapsed over the past decade.The conversation then turns to technology and AI—where it helps, where it falls short, and why scalable, expert-anchored guidance may be the missing piece. Jon explains how AI can augment human judgment, rather than replace it, and how better incentives and better information could dramatically improve outcomes for students and families alike.This episode examines how a high-stakes decision process broke—and what it would take to make it work again.🎧 Exploring Prosperity focuses on the forces shaping long-term economic outcomes: education, technology, incentives, and growth.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 The State of High School Guidance04:45 Other Destinations after High School06:01 Technology's Role in Guidance Solutions19:09 The Need for Personalized Guidance21:12 Building a Tech-Enabled Guidance System23:53 Personalized Project Plans for Students26:21 AI-Powered Guidance Counseling28:27 Transforming Counseling with AI Data31:21 Creating Comprehensive Resource Centers34:14 Live Programming and Community Engagement35:36 Building a Public Mission in Education37:39 Navigating Challenges in K-12 Education41:38 The Importance of AI Talent42:35 First Mover Advantage in AI Education46:33 The Value of School Partnerships 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

    50 Min.
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Challenge Pessimism. Explore the Complexity of Progress. Headlines and survey results scream pessimism, but is it warranted? Join us on Exploring Prosperity as we delve into the complexities of human progress with leading thinkers across markets, economics, history, philosophy, and more. Discover how economic and societal factors shape our world, and gain a deeper understanding of the drivers of individual and societal prosperity and a fulfilling life. Our in-depth conversations may leave you empowered and optimistic about the future and equipped with insights to navigate the challenges and opportunities that lie ahead. Bob Dewey brings his expertise in investing and his network in the investment community and beyond to address the big issues of the day and whether we can solve problems faster than they grow. robertdewey3.substack.com

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