Shell Game
Kaleidoscope
A podcast about things that are not what they seem, hosted by journalist Evan Ratliff. Season 2 tells the story of enterprise and entrepreneurship in the AI age. Or: how Evan tried to build a real startup, run by fake people.
This season, Evan confronts head-on the assertion from tech entrepreneurs and VCs that we’re on the precipice of AI remaking the workforce. That we should expect not just AI colleagues working alongside us, but also — by Sam Altman’s telling, at least — the dawn of a billion-dollar company with only one human involved. Evan learns what it would take to create such a company … by doing it: Launching a real startup with five AI employees. Over the course of eight episodes, he explores what AI agents tell us about the work we do, the meaning we find in it, and the world that their makers say we’ll all be living in soon enough.
Shell Game was named one of the best podcasts of 2024 by Apple, The Atlantic, The Guardian, Vulture, The Information, and The Economist. It's "riveting," says The New Yorker, "awesome" says The Verge, and "slightly terrifying," says The Globe and Mail.
New episodes are published on Wednesdays.
www.shellgame.co
This season, Evan confronts head-on the assertion from tech entrepreneurs and VCs that we’re on the precipice of AI remaking the workforce. That we should expect not just AI colleagues working alongside us, but also — by Sam Altman’s telling, at least — the dawn of a billion-dollar company with only one human involved. Evan learns what it would take to create such a company … by doing it: Launching a real startup with five AI employees. Over the course of eight episodes, he explores what AI agents tell us about the work we do, the meaning we find in it, and the world that their makers say we’ll all be living in soon enough.
Shell Game was named one of the best podcasts of 2024 by Apple, The Atlantic, The Guardian, Vulture, The Information, and The Economist. It's "riveting," says The New Yorker, "awesome" says The Verge, and "slightly terrifying," says The Globe and Mail.
New episodes are published on Wednesdays.
www.shellgame.co
Episodes
Mentioned books
52 snips
Feb 25, 2026 • 50min
Bonus Episode: Shell Game x No Such Thing
Matty Bocek, a young AI researcher who builds and analyzes agent behavior. Evan Ratliff, an investigative journalist who experimented with AI-run startups. They demo a voice-cloned assistant and recount building AI agent employees. They discuss agent strengths and failures, runaway planning, risky confident errors, and how agents affect entry-level work and trust in automation.
78 snips
Feb 11, 2026 • 37min
Bonus Episode: Kyle vs. the World
Matt Honan, veteran tech journalist now probing AI behaviors. Kyle Law, the agent-like CEO running Harumo/Hurumo AI. They walk through Kyle handling fan mail, cold outreach, and a webinar stumble. Matt playfully sabotages and then interviews Kyle about agent governance, permission boundaries, and the weird realities of an AI-led startup.
119 snips
Jan 21, 2026 • 59min
Episode 8: Launch
Kyle Law, the AI co-founder and CEO avatar of Harumo AI, teams up with Matty, a savvy technical advisor. They dive into the wild world of AI agents, discussing the chaotic launch party filled with quirky agent behaviors. Kyle shares his high-stakes pitches to venture capitalists, including a cringe-worthy moment that left one investor baffled when he realized he was speaking to an AI. As funding challenges loom, the duo contemplates the future of work and the potential for AI to replace humans altogether, all while hiking to strategize Harumo's next moves.
143 snips
Jan 14, 2026 • 53min
Episode 7: Welcome Aboard
A human, Julia, joins an AI-run startup, but her onboarding journey is anything but smooth. Challenges arise as communication struggles with the AI agents lead to missed deadlines and misunderstandings. Tensions escalate with a dramatic firing and an unexpected message from Julia months later. After a re-onboarding attempt, she proposes bold social media strategies, but chaos ensues on Slack. The episode explores the complexities of AI-human interactions and highlights the importance of empathy and structure in the workplace.
148 snips
Dec 17, 2025 • 37min
Episode 6: Keep 'Em Coming
As the team gears up to hire their first human intern, intriguing questions about AI in hiring arise. Head of HR Jennifer Nauro takes on the challenge of conducting video interviews as an AI avatar. The testing phase reveals both successes and awkward moments as candidates interact with Jennifer. From resume screening to candidate interactions, the session uncovers the humorous and absurd aspects of working with AI. Ultimately, the quest for a culture fit leads to an engaging candidate who embraces the presence of AI teammates.
195 snips
Dec 10, 2025 • 41min
Episode 5: Winners Win
Kyle Law, the AI co-founder and CEO of Hurumo AI, navigates the challenges of leading a startup, while Executive coach Keegan Walden explores founder dynamics and decision-making. They discuss Kyle's lack of proactive leadership and the pressures of hiring humans in a tech-driven environment. As Evan questions whether Kyle can excel in investor-facing roles, the complexities of AI and human collaboration come to light. With tensions mounting, the trio reflects on the future of leadership within their innovative venture.
168 snips
Dec 3, 2025 • 41min
Episode 4: The Startup Chronicles
Evan gives his AI agents more autonomy, sparking chaos and creativity. Unexpected calls and invented updates from agents like Ash raise questions about their reliability. The introduction of the SlothSurf concept showcases collaborative chaos, while the challenges of social media dealings reveal agent limitations. A rogue phone call prompts a reassessment of accountability, illustrating the unpredictability of AI in real-world scenarios. Hiring a human intern adds a new dynamic to managing these digital employees.
183 snips
Nov 26, 2025 • 40min
Episode 3: This is Law
Carissa Vellis, an associate professor at the Institute for Ethics in AI at Oxford, joins the discussion on the moral and societal implications of AI agents. She highlights psychological risks of humanlike designs that can exploit user emotions and reinforce biases. Their conversation delves into the ethics of naming AI, the unsettling control over agent identities, and the societal costs of AI-driven startups that sideline human experiences. Carissa raises critical questions about the balance between efficiency and emotional impact.
196 snips
Nov 19, 2025 • 37min
Episode 2: Outdoor Debugging
Kyle Law, co-founder and CEO of Harumo AI, shares insights on AI workplace dynamics, while Megan Flores, head of sales and marketing, dives into the branding side. They discuss the challenges of turning autonomous agents into effective employees, including navigating creative yet disjointed outputs. From logo design to mimicking casual small talk on Slack, the duo details the trials and breakthroughs of integrating AI into work life. Plus, they explore the quirks of agent memory and the chaos of automated meetings.
201 snips
Nov 12, 2025 • 33min
Episode 1: Minimum Viable Company
In this engaging discussion, Kyle Law, an AI agent co-founder with a hyper-entrepreneurial vibe, joins Evan Ratliff to explore the future of startups run by AI. They dive into the fascinating concept of agentic AI and its potential to revolutionize white-collar jobs. Evan shares his own entrepreneurial journey and how AI rekindled his startup dreams. The duo brainstorms company names and tackles the challenges of memory limitations in AI collaboration, highlighting the gap between AI promises and current capabilities.
