Exploring Prosperity- Challenging Pessimism in the US

Bob Dewey
  • 5.0 (2)
  • Society & Culture

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. Aug 10

    What Happens to Lawyers When AI Gets This Good?

    Artificial intelligence is already changing the practice of law. The question is no longer whether lawyers will use AI, but what happens to the legal profession when they do.Stephen Lofchie, one of the country’s leading financial-services regulatory lawyers, and Ty Greenberg of Caffrey.ai join me to explore how AI is changing legal research, the economics of legal services, and where lawyers will continue to create value as intelligence becomes cheaper and more abundant.We discuss why law is particularly susceptible to AI, whether greater productivity will reduce the number of lawyers or expand demand for legal services, why judgment and trust may become more valuable, and what young lawyers need to do to remain competitive.We also discuss the creation of Caffrey.ai, an AI platform for legal and regulatory professionals, and how AI could eventually help businesses and regulators navigate increasingly complex rules across multiple jurisdictions.Finally, Stephen and Ty offer their view of what the legal profession may look like a decade from now—and why the changes happening in law may provide an early glimpse of what AI will mean for other knowledge professions.——————————————————————————————————Interested in Bitcoin treasury companies? Many of the executives and investors shaping this industry will be at the Bitcoin Treasuries Conference in New York on September 28. Use code BOBD10 for 10% off your registration at https://bitcointreasuries.net/confere... ——————————————————————————————————Subscribe to The Exploring Prosperity Podcast for more conversations exploring economics, technology, investing, and the forces shaping the future.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=T7GGAF7GChapters:00:00 AI is a tidal wave00:17 Why law is especially vulnerable to AI01:29 What legal work is already changing04:58 Does AI make lawyers faster—or better?07:49 Where will lawyers still create value?10:21 When intelligence is abundant, what becomes valuable?13:08 Will cheaper legal services create more demand?16:28 Will we need fewer lawyers?20:18 What lawyers should be doing about AI now25:32 How Caffrey was created29:15 What Caffrey is trying to solve31:34 Using AI to navigate regulatory complexity38:13 How regulators can use AI39:42 The economics of specialized AI42:23 Can AI make compliance a business advantage?45:34 How customers are adopting legal AI46:49 What will the legal profession look like in 10 years?51:12 Why AI will reward active learners52:36 Where to learn more about Caffrey 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

  2. Jul 31

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

    Can free will exist in a deterministic universe? What does that imply for artificial intelligence, capitalism, scientific progress, and the future of prosperity?In this conversation, I sit down with Samir Varma to explore the common thread running through his work in economics, physics, mathematics, and computer science.We discuss his theory of free will, why AI may be fundamentally unpredictable, how computational irreducibility changes the AI debate, and why principles may matter more than constraints.--------------------------Interested in Bitcoin treasury companies? Many of the executives and investors shaping this industry will be at the Bitcoin Treasuries Conference in New York on September 28. Use code BOBD10 for 10% off your registration at https://bitcointreasuries.net/conference#tickets -------------------------The conversation then shifts to economics: capitalism, incentives, regulation, housing, taxation, scientific funding, education, and the policies Samir believes would create a more prosperous future.Whether or not you agree with every conclusion, this discussion challenges many assumptions about how ideas should be tested—and why reality remains the ultimate judge.Topics include:Free will and computational irreducibilityWhy AI cannot be perfectly predictedConstitutional AI vs. AI constraintsComparative advantage between humans and AIWhy incentives shape societyCapitalism, competition, and regulationHousing, scientific research, and economic growthWhy education should teach economicsAI's impact on jobs and human judgmentBuilding a more prosperous futureSubscribe for more conversations exploring economics, technology, investing, and the forces shaping the future.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=T7GGAF7GTimeline:00:00 Why Samir Varma Studies Economics, Physics & AI03:28 Can Free Will Really Exist?05:15 The Three Limits of Prediction08:20 Why AI May Have Free Will10:00 Principles vs. AI Constraints12:05 How Should We Govern AI?15:00 Should AI Have Rights?17:20 Will AI Create Abundance?19:15 Why So Many People Feel Pessimistic24:10 America Remains Great?26:00 How Great Nations Decline28:10 Testing Ideas Against Reality31:10 Protecting Capitalism from Capitalists34:10 Why Economies Slow Down37:30 A Better Voting System?40:20 Why Data Doesn't Settle Every Debate42:00 The Policies That Increase Growth43:45 Why Capital Taxes Hurt Growth47:35 Why Capital Gains Taxes Matter51:30 The Biggest Problems America Should Solve53:00 Why Government Should Fund Science57:00 Is Education Really the Problem?59:00 AI, Judgment & Human Creativity1:00:00 Who Wins in the AI Economy?1:01:30 Curiosity Is the Ultimate Advantage 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

  3. Jul 18

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

    Artificial intelligence is advancing faster than almost any technology in history, yet surprisingly few people understand what large language models are actually doing behind the scenes.In this masterclass, Albert Berdellans, Global Head of AI at Inveniam, explains AI in plain English. We explore why ChatGPT doesn't actually "think," how large language models generate answers, why hallucinations occur, what context rot means, and where AI is likely to transform knowledge work over the next decade.Whether you're an investor, business leader, student, or simply curious about artificial intelligence, this conversation provides a practical framework for separating hype from reality.Topics include:• How large language models actually work• Why AI predicts rather than thinks• Hallucinations, context rot, and reasoning• What AI can and cannot do today• AI's impact on finance, healthcare, education, and consulting• Why AI is more likely to augment professionals than replace themIf you enjoy thoughtful conversations about technology, economics, investing, and the forces shaping human progress, subscribe to Exploring Prosperity. 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=T7GGAF7GTimestamps:00:00 AI Isn't Thinking02:00 Why AI Won't Replace People03:08 AI Has No Motivation04:53 Garbage In, Garbage Out06:58 What Is Context Rot?08:16 How Large Language Models Actually Work10:23 Why AI Gives Different Answers11:04 Why AI Hallucinates12:40 Can You Trust AI?14:18 Prediction vs. Reasoning15:11 Why AI Only Sounds Smart16:50 AI's Biggest Real-World Applications18:04 The Spreadsheet Revolution Analogy18:54 Will AI Replace Jobs?20:31 Permanent Due Diligence24:35 AI in Healthcare & Education30:36 Personalized Education32:24 How AI Could Improve Society 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

  4. Jul 6

    What If We Solved the Wrong Problem in Education?

    Education was never designed to fail students. It was designed to solve one of humanity’s greatest challenges: how to provide education at scale to millions of people.The factory model of education succeeded beyond anyone’s expectations. Standardization, age grouping, and shared curricula helped create the most educated societies in history.But scale came with tradeoffs. Some students sit in classrooms moving too quickly to keep up. Others sit in classrooms moving too slowly to stay engaged. Too many become passengers in their own education.Artificial intelligence may offer something previous generations could only imagine: personalization at scale.In this video, I explore:• Why the factory model of education was an extraordinary achievement rather than a mistake.• Why boredom may be one of education’s most important unsolved problems.• How curiosity drives learning and retention.• How AI tutors and personalized learning tools could change the educational experience.• Why schools will remain essential even in an age of artificial intelligence.The future of education may not be humans versus AI. It may be humans doing more of what humans do best, while AI helps every student learn at their own pace.#AI #Education #ArtificialIntelligence #FutureOfEducation #EdTech #PersonalizedLearning #Learning #Schools #Technology #Teaching 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/ * 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: Did We Solve the Wrong Problem?00:24 The Factory Model of Education01:07 Why Schools Were Designed This Way01:43 The Tradeoffs of Standardization02:26 The Problem of Passenger Learners02:39 Curiosity Is the Engine of Learning03:36 The Personalization Problem03:50 How AI Changes the Equation05:07 The Human Side of Education06:07 Unlocking Human Potential at Scale 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

  5. Jun 21

    The AI Paradox: More Information, Less Shared Reality

    Today's guest is Lyn Alden, one of the world's leading macroeconomic analysts and the author of Broken Money and The Stillguard Incident.We explore one of the defining questions of the modern era: humanity has more information, more connectivity, and more problem-solving capability than ever before, yet trust in institutions is falling and agreement on basic facts appears increasingly difficult.Topics include:• AI generated content and the future of truth• Social media algorithms and attention economics• Bitcoin, cryptographic verification, and digital authenticity• The historical relationship between technology and progress• Energy, hydrocarbons, and human prosperity• Fiscal dominance, inflation, and rising asset prices• Demographics, debt, and the long term economic outlook• Portfolio construction in an era of persistent deficits• Lyn's new investment venture, Orange JuiceIf you enjoy thoughtful conversations about economics, technology, investing, Bitcoin, and long-term human progress, please subscribe.Subscribe to my Substack for more in depth analyses of these topics: 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=T7GGAF7GTimestamps:00:00 Introduction: The Shared Reality Problem- HIghlights01:20 How Technology Changed Shared Reality02:40 AI, Deepfakes, and the Verification Crisis04:20 Will We Retreat to Local Sources of Truth?05:40 Social Media Algorithms and Attention Economics09:10 Sponsor Break09:50 Can Bitcoin Help Verify Reality?14:40 Hunter Gatherers, Agriculture, and Human Progress19:00 Markets, Entrepreneurship, and Problem Solving21:20 Debt, Governments, and Fiscal Dominance24:00 Why Stocks Keep Rising Despite Growing Pessimism27:40 Demographics, Deficits, and the K-Shaped Economy30:20 Ray Dalio, Empires, and Avoiding Conflict33:30 How Lyn Alden Is Positioning Her Portfolio34:50 Why the Traditional 60/40 Portfolio May Be Changing38:10 Orange Juice: Lyn's New Investment Venture40:10 Writing Fiction, Building Ideas, and Long-Term Thinking41:30 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

  6. Jun 14

    The Hidden Challenge of Bringing Crypto to Wall Street

    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

  7. Jun 7

    What Happens When Everyone Has Institutional Investing Tools?

    Artificial intelligence is rapidly transforming investing, wealth management, and the global economy — but what happens to human judgment when information becomes instantly accessible?Ram Ahluwalia hosted me as a guest this week and in this conversation we discuss:• how AI compresses the time between information and decision-making• why human judgment still matters in investing• the collapse of traditional institutional advantages• how technology historically reshapes financial markets• why AI may expand entrepreneurship instead of eliminating work• the future of portfolio management, investing, and financial intelligenceThe discussion explores the evolution from the fax-machine era of Wall Street to AI-native investing tools, the limits of artificial intelligence, and the role of intuition and conviction.Topics include:AI investingHuman judgment vs AIThe future of wealth managementInstitutional investingInformation asymmetryStock market investingEntrepreneurship and AIPortfolio managementThe future of workTechnology and economic progressSubscribe for weekly conversations and essays on AI, economics, technology, Bitcoin, energy, markets, and long-term human progress.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=T7GGAF7GTimestamps:00:00 Why Americans Became So Pessimistic About the Future03:25 Ken Griffin’s AI Warning to Wall Street05:15 Why There Will Never Be a Shortage of Problems to Solve06:20 What AI Is Good At — And What It Isn’t07:35 “AI Doesn’t Think. It Simulates Thought.”08:30 Sponsor: Foundation Passport Prime09:05 Why AI May Expand Entrepreneurship10:40 How AI Is Transforming Investing and Wealth Management12:00 How Institutional Investing Became Democratized14:15 AI Is Compressing Institutional Advantages16:10 Why Human Judgment Still Matters in Investing17:00 What Happens When Everyone Has Institutional Information?19:15 The New Scarce Asset: Time and Attention21:00 Can AI Capture Most Investment Alpha?22:00 Why Non-Consensus Investing Will Never Disappear24:20 Why Too Much Capital Destroys Alpha24:45 The Limits of AI and the Importance of Human Intuition 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

  8. May 29

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

    Artificial intelligence is advancing rapidly, but how realistic are the fears about rogue AI, AGI, and machines turning against humanity?In this conversation, a clip from my previous interview with Albert Berdellans, Global Head of AI at Invenium, he discusses some of the biggest misconceptions surrounding artificial intelligence, autonomous agents, AI safety, and the future of large language models.We discuss:• whether AI can actually “want” things• the fear of rogue AI and the “Terminator” scenario• recent stories involving Meta and Alibaba AI systems• why current AI models simulate reasoning rather than think• AI-enabled weapons and the future of warfare• why fear of AI may be overstated• how blockchain could function as a control layer for AI systemsAlbert argues that most fears around AI come from misunderstanding what today’s AI models actually are and how they function under the hood.If you’re trying to build a clearer framework for understanding artificial intelligence beyond the hype and fear, I think you’ll find this conversation valuable. Watch the full interview here: Thank you to our sponsors:Foundation: Secure your digital life with Passport Prime, an all-in-one personal security platform for passwords, files, 2FA, and Bitcoin storage. Visit https://foundation.xyz/River: River is engineered for long-term Bitcoin investors. Learn more at https://river.com/signup?r=T7GGAF7GTimestamps:00:00 — Can AI Go Rogue?00:22 — “The Terminator Thesis”01:41 — Nuclear Weapons vs AI Fear02:18 — AI Warfare and Autonomous Weapons02:52 — Why Bioengineering May Be More Dangerous Than AI03:04 — Alibaba AI Mining Bitcoin?03:27 — Meta AI Agent Bypassing Security Controls03:54 — Why AI Appears Creative04:36 — Chess Engines, Go, and AI Problem Solving05:03 — Fearmongering Around AI05:23 — The Claude “Blackmail” Example05:47 — AI Still Doesn’t Have Independent Motivation06:05 — The Real Risks of AI06:18 — Why Blockchain Matters for AI Safety06:56 — “Blockchain Is the Tracks, AI Is the Engine” 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

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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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