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Exploring Prosperity- Challenging Pessimism in the US

Exploring Prosperity- Challenging Pessimism in the US

A newsletter about what thought-leaders have to say about our American condition and whether we should be so pessimistic about the future.

Bob Dewey

67 episodesEN

Show overview

Exploring Prosperity- Challenging Pessimism in the US has been publishing since 2024, and across the 2 years since has built a catalogue of 67 episodes. That works out to roughly 40 hours of audio in total. Releases follow a fortnightly cadence.

Episodes typically run thirty-five to sixty minutes — most land between 9 min and 1h — with run-times ranging widely across the catalogue. None of the episodes are flagged explicit by the publisher. It is catalogued as a EN-language Society & Culture show.

The show is actively publishing — the most recent episode landed yesterday, with 22 episodes already out so far this year. Published by Bob Dewey.

Episodes
67
Running
2024–2026 · 2y
Median length
41 min
Cadence
Fortnightly

From the publisher

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

Latest Episodes

View all 67 episodes

Bitcoin Treasury Companies: The Rise of Digital Credit | Tim Kotzman

Aug 24, 20261h 18m

What Happens to Lawyers When AI Gets This Good?

Aug 10, 202653 min

Where Disciplines Intersect: Free Will, AI, Economics, and Prosperity

Jul 31, 20261h 4m

The AI Masterclass: How ChatGPT and Large Language Models Really Work

Jul 18, 202634 min

What If We Solved the Wrong Problem in Education?

Jul 6, 20267 min

The AI Paradox: More Information, Less Shared Reality

Jun 21, 202642 min

The Hidden Challenge of Bringing Crypto to Wall Street

Jun 14, 202649 min

What Happens When Everyone Has Institutional Investing Tools?

Jun 7, 202627 min

Can AI Really Go Rogue? Why Today’s AI Fears May Be Overstated

May 29, 20267 min

Money Is Political | Bitcoin, AI & the Future of Markets

May 26, 202654 min

Are We Running Out of Economically Valuable Problems to Solve?

May 21, 20266 min

AI Is Rewiring Markets, Energy & Bitcoin | Matthew Sigel

May 10, 202646 min

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

Apr 25, 202657 min

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

Apr 19, 20261h 0m

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

Apr 4, 20261h 0m

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

Mar 27, 20261h 6m

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

Feb 20, 20261h 1m

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

Feb 9, 202647 min

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

Jan 24, 202649 min

Crypto’s Institutional Reset: Why 2026 Changes Everything | Zach Pandl (Grayscale)

In this episode of Exploring Prosperity, I’m joined by Zach Pandl, Head of Research at Grayscale, to explore why 2026 may mark the true beginning of crypto’s institutional era.We discuss how regulatory clarity — including the impact of Grayscale’s successful challenge of the U.S. Securities and Exchange Commission — shifted crypto from the margins into mainstream finance, and why Bitcoin ETFs were only the first step.Zach explains:* What the “institutional reset” really means for crypto markets* Why privacy is non-negotiable as institutions move on-chain* How AI increases the need for cryptographic identity and authenticity* Why quantum computing and digital asset treasuries are likely red herrings for 2026- * How staking, tokenization, and issuance could reshape capital marketsRead my essay about this topic on Substack here: 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/If you are interested in the Bitcoin Blockchain Traded Fund, you can find infornation here: https://truflation.com/blog/quantamm-...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 Institutional Reset in Crypto02:20 Regulatory Clarity and Its Impact05:42 The Evolution of Financial Systems11:11 Democratization of Finance13:35 Legislative Developments and Market Structure16:13 Consumer Experience and Blockchain Integration18:33 Institutional Needs in Crypto21:25 The Importance of Privacy in Crypto23:53 Market Dynamics and Competition25:11 Analyzing Blockchain Fundamentals28:13 Market Pullbacks and Future Outlook34:00 Emerging Topics: Quantum and DATs37:48 Staking and Its Significance 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

Jan 19, 202638 min
Bob