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We all feel the urgency: learn to use AI, or risk falling behind at work. And we all know there’s upside: AI can reduce tedious tasks, streamline operations, and boost output. But knowing is half the battle (maybe even less) and implementing AI needs to happen across an entire organization. So what does it take to start?
Well, here at WaitWhat (the company behind this podcast!) we paused all operations for three days to find out. From editorial curation to visual design to event planning, we split into teams for an “AI Sprint.” And this Pioneers of AI episode takes you to the starting blocks on the track with us, as we test new tools, discover their limitations, and find where AI can deliver on its promise.
Learn more about Pioneers of AI: http://pioneersof.ai/
Follow Pioneers of AI on all channels: https://linktr.ee/pioneersofai
At the center of AI is people, so we want to hear from you! Share your experiences with AI — or ask us a burning question — by leaving a voicemail at 601-633-2424. Your voice could be featured in a future episode!
Reid and Aria explore how an AI-native world is reshaping trust, money, and work. Reid breaks down why crypto could power identity and transactions in an agent-driven internet, and what recent layoffs at Coinbase and Cloudflare signal about the shift toward AI-native organizations. They also examine Anthropic’s push into finance, and what it means for accuracy, regulation, and fraud. Plus, Reid responds to listener questions on “AI slop,” and why human taste and judgment matter more than ever.
For more info on the podcast and transcripts of all the episodes, visit https://www.possible.fm/podcast/
Beeple didn’t turn an 18-year daily JPEG habit into a $69 million Christie’s sale by waiting for permission. He posted, missed, learned, repeated, and inadvertently walked straight into the moment NFTs forced the art world to take digital work seriously. In this episode, Reid Hoffman talks with Mike Winkelmann (aka Beeple) about the real story behind the sale, why deadlines beat inspiration, how satire lets artists ask dangerous questions without preaching, and why AI is not a soul, a friend, or a shortcut. It is a tool that can—and should—make humans do more. From robot dogs with billionaire faces to AI-built sculptures shaped by strangers, Beeple argues the future is going to get much weirder, the bar for originality is rising fast, and artists who opt out may not like what happens next.
For more info on the podcast and transcripts of all the episodes, visit https://www.possible.fm/podcast/
Reid and Aria unpack a pivotal turning point for AI as rapid advances in generative image tools, such as ChatGPT Images 2.0, lead to deeper questions on AI usage, culture, and habits. For example, they explore how these technologies could transform creative work and visual communication, before zooming out to a global debate where voices like Pope Leo’s weigh in on AI as a fundamentally human challenge. Reid argues that while risks like isolation and misinformation are real, the future of AI depends on how actively we steer it. The episode also examines a major economic shift: the move from selling software to delivering outcomes—and what that means for jobs, entrepreneurship, and entire industries.
This week, Reid and Aria sit down with Netflix co-founder Reed Hastings. Reed has seen technology rewrite the rules of entertainment before, but AI takes him back to his beginnings: he studied it at Stanford in the late '80s, decades before it became the only conversation in tech. Few people have watched this moment build from as many vantage points: he's served on the boards of Microsoft, Meta, Bloomberg, and, now, Anthropic.
With AI moving from apps into the devices we use every day, Reid and Aria explore where the real value will be created. From Google Gemini powering hundreds of millions of devices to ChatGPT entering cars, Reid argues that distribution alone won’t decide winners but that depth of use, iteration, and personalization will. They also examine the $650B race to build AI infrastructure, the hidden bottlenecks and geopolitical risks behind it, and why U.S. capital still provides a key edge. Finally, they highlight the Trust in American Institutions Challenge and its winner as a case for how AI can help rebuild trust by making institutions more transparent and accountable.
Reid and Aria unpack the geopolitical battle over chips, from U.S. export controls to China’s push for self-sufficiency, and how the race for compute is reshaping global power. They then turn to how AI is rapidly expanding the attack surface, driving more frequent breaches and exposing new vulnerabilities deep in the software stack as speed and scale outpace traditional defenses. Finally, they explore why enterprise AI adoption has been slower and more uneven than expected, and how network effects, organizational inertia, and trust constraints are shaping the path forward. Together, these forces show how AI is not just advancing technologically, but quietly transforming the foundations of security, competition, and economic power.
In this episode of Possible, Reid Hoffman and Aria Finger talk with Sean Neville, co-founder of Circle and architect of USDC, about building the financial infrastructure for an AI-driven economy. Now leading Catena Labs, Neville is working on what he calls the first AI-native bank—designed for autonomous agents that can transact, comply, and interact without humans in the loop. The conversation explores what breaks when AI tries to use today’s financial rails, why stablecoins may power machine-to-machine commerce, and why new concepts like “Know Your Agent” could become the foundation of trust in an AI financial system.
For more info on the podcast and transcripts of all the episodes, visit https://www.possible.fm/podcast/
Is SaaS actually dead or just evolving? Reid and Aria break down why the traditional seat-based software model is under pressure as AI reshapes how products are built, priced, and delivered. They discuss how these fundamental changes have started shifting SaaS software toward customization, token-based economics, and deeply integrated AI systems. The conversation digs into what this change means for engineers, why network effects and customer relationships still matter, and how new moats will emerge as software becomes faster, cheaper, and more dynamic than ever before.
For more info on the podcast and transcripts of all the episodes, visit https://www.possible.fm/podcast/
Reid and Aria unpack three emerging fault lines in the AI era: where real power sits in the AI stack, how AI is reshaping human creativity, and whether governments could ultimately treat AI as critical national infrastructure. Reid responds to Jensen Huang's "five-layer cake" framing of AI, arguing that while compute, infrastructure, and models carry geopolitical weight, the greatest economic value tends to emerge at the application layer. The episode then turns to a broader debate over a viral NYT experiment that pitted humans against AI writing. Reid and Aria close by examining Palantir CEO Alex Karp's warning about AI nationalization, weighing the tensions between innovation, national security, and democratic values as AI becomes foundational technology.
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