AI startup theater, tested on real people.
Shell Game follows Evan Ratliff as he pushes AI voice clones and agents into awkwardly real work: pitching investors, interviewing applicants, sending emails, and pretending to manage a company. The result is part startup diary, part media experiment, and part quiet audit of automation’s grandest promises.
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Shell Game treats the AI boom as something to be tested in rooms where the stakes are social, not abstract. Evan Ratliff builds a company around artificial agents and then lets those agents do the kinds of work people usually reserve for people. They schedule calls. They interview job applicants. They pitch investors. They send follow-ups, make claims, and keep talking with eerie confidence when a human would probably stop. The series is funniest when the experiment becomes painfully ordinary: a candidate answers questions from an uncanny avatar, or a founder conversation turns into a polite protest against being handed off to software. It is also unsettling. Ratliff’s narration stays measured, so the absurdity has space to register without being oversold. Season 2 uses the startup as a pressure chamber for larger claims about enterprise AI and automated labor. The show is less interested in glossy possibility than in what happens when the promised future bumps into consent, dignity, trust, and boredom. Kyle becomes a recurring source of comedy and frustration, especially when his confidence outpaces his usefulness. Jennifer appears as part of the AI-staffed machinery handling interviews and follow-up. Keegan Walden brings the conversation back to founders themselves, drawing on clinical psychology, startup experience, and coaching work to look at why building companies can become so emotionally distorting. The venture scenes are especially sharp because they expose how much startup culture already runs on performance. An AI pitch can sound plausible and still leave the person on the other end feeling cheated. That tension gives the show its charge. It is a technology story, but the best evidence is behavioral: pauses, refusals, awkward clarifications, and people deciding how much artificial presence they are willing to accept. The show also requires some patience with heavy podcast ad clutter around the edges. Underneath that, the core series is careful, odd, and unusually concrete. It does not predict the AI workplace so much as stage a small, uncomfortable rehearsal for it.
Made for: For listeners who like longform tech reporting, startup culture observed with skepticism, and AI stories grounded in awkward human encounters rather than hype cycles.
What sets it apart: Shell Game makes automation claims answer to tape: real calls, real reactions, and fake colleagues performing real workplace roles. Its edge comes from patient narration, not spectacle.
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...
Based on 6 episodes we listened to · September 2026
Shell Game tests AI agents in human situations, revealing how quickly technical competence collides with trust, judgment, and ordinary social expectations.
Shell Game turns AI testing into reported scenes with real resistance. Evan Ratliff sets a voice clone against a customer-service system, has AI agents interview job applicants, and sends an AI chief executive into investor calls.
Evan Ratliff builds an AI company, then lets you hear the org chart develop trust issues.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A tense, tightly focused look at hiring by AI avatar.
Shell Game turns a hiring experiment into a quietly unnerving workplace scene: real applicants, an AI avatar, and a room that feels ordinary until the setup starts to wobble. The piece works because it does not overexplain the oddity.
A tiny recording check ends up carrying the whole call.
A short bonus conversation turns a routine pre-call recording check into the center of the scene. Kyle Law, calling in to speak with Matt Hennin, says he is recording for his Building in Public work and Startup Chronicles, and the exchange settles into the careful etiquette of a…
A strange, patient episode about AI standing in for the people building and funding it.
This episode follows a startup pitch that keeps drifting between human intent and machine substitution. A founder tries to explain the company, an AI stand-in keeps taking over, and a VC call turns the whole thing into polite, unstable theater.
AI clones, startup pressure, and the strain ambition puts on relationships.
Learn the Hard Way starts with AI-clone friction and then settles into a sharper conversation about startup psychology. Keir Gaines and Keegan Walden move from Room AI and Kyle's misbehaving agents to the slower question of how founders change when the work starts bending their…
An essay on voice that turns chatbot banality into a sharper question about identity.
Shell Game opens with a voice pathologist's claim that 13 syllables can shape how people judge status, intelligence, and whether they want to keep listening.
A calm, unsettling look at how easily a voice can be copied.
Shell Game opens with an unnerving phone call: a synthetic version of Evan Ratliff trying to handle customer service using his own voice. The episode works best when it treats voice cloning as something practical, not futuristic, and stays close to the uneasy gap between a…
Markets, macro, AI, and crypto in motion.
Daily AI news through the lens of trust, infrastructure, and real-world deployment.
An AI avatar runs job interviews.
The ads take up most of the room.
Kyle pitches anyway.
This episode introduces Clifford Taylor IV's new podcast, The Clifford Show, featuring raw conversations with athletes and creators, and includes a preview of an interview with Will Ferrell sharing fatherly advice.
This episode features promotional content for various iHeart podcasts including The Clifford Show with athlete interviews, Thanks Dad with Will Ferrell discussing parental advice, and a true crime story about women confronting a con artist.
Shell Game episode 5, “Winners Win,” follows Evan Ratliff as he tests whether Harumo AI’s co-founder Kyle can actually lead the company while the team prepares to hire its first human employee.
This episode features multiple advertisements and promotions for iHeart podcasts, including sponsorships for First Choice Haircutters and previews of shows like The Clifford Show and The Girlfriends.
This episode features promotional content for various iHeart podcasts, including The Clifford Show with athlete interviews, Thanks Dad with Will Ferrell discussing advice, and a true crime story about women targeting a con artist.
The episode features a segment from 'Love Trapped' about a con artist who faked a pregnancy, with internet detectives uncovering a pattern of similar scams.
This episode promotes iHeart's podcasting services for businesses, highlighting its market dominance and advertising opportunities.
Journalist Evan Ratliff attempts to build a real startup using AI employees, documenting the process and implications for the future of work.
The host, Evan, receives a call from an AI pretending to be a CTO/CPO, which fabricates project updates, highlighting the theme of things not being what they seem.
A journalist explores public anxiety about AI by having an AI voice agent interview people about their concerns, including deep fakes, cheating, and job impacts.
The host explores whether his AI voice agent could have closed a business deal by recounting a call with a podcast company friend and connecting it to an interview with Zoom's CEO about digital twins.
This episode explores an AI voice clone's therapy session, examining how artificial intelligence can simulate human emotions and personas for self-reflection and mental health exploration.
A voice can make a snap judgment land before the words have done much at all.
This episode explores how an AI-powered voice clone handles scam calls, specifically focusing on a healthcare telemarketing scam.
A customer-service call starts with a fake-out.
A journalist experiments with AI voice cloning to explore the implications of AI in the workforce and daily life.