
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
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 69 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 8 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 6 days ago, with 24 episodes already out so far this year. Published by Bob Dewey.
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 69 episodesAI Can Solve Math. But Can It Ask a Good Question? | Steven Strogatz
Extinction Is the Wrong Test
Bitcoin Treasury Companies: The Rise of Digital Credit | Tim Kotzman
What Happens to Lawyers When AI Gets This Good?
Where Disciplines Intersect: Free Will, AI, Economics, and Prosperity
The AI Masterclass: How ChatGPT and Large Language Models Really Work
What If We Solved the Wrong Problem in Education?
The AI Paradox: More Information, Less Shared Reality
The Hidden Challenge of Bringing Crypto to Wall Street
What Happens When Everyone Has Institutional Investing Tools?
Can AI Really Go Rogue? Why Today’s AI Fears May Be Overstated
Money Is Political | Bitcoin, AI & the Future of Markets
Are We Running Out of Economically Valuable Problems to Solve?
AI Is Rewiring Markets, Energy & Bitcoin | Matthew Sigel
Is Digital Security Ready for What’s Coming? (Zach Herbert)
Credit Stress Is Back: What Happens When Markets Stop Clearing?

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

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

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

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