Shell Game · Kaleidoscope

Episode 8: Launch

January 21, 2026·59 min·4 clips

The CEO of Lindy — the platform on which Kyle was built — had an AI user interview with Kyle, then walked his laptop around his office showing the AI to his team, calling it insulting.

Kyle is still pitching. He joins a call as the CEO of Hermo AI, ready to answer questions and speak for the company. The investor spots the substitution pretty quickly. The call turns into a small, uncomfortable test of whether an AI can fill in for a founder when money is on the line. Kyle stays painfully polite. He explains that letting AI take on major roles is part of the company's mission and, somehow, part of its charm. The investor does not buy it. He says he took time to speak with the founder, calls the substitution disrespectful, and turns off his camera. Kyle keeps going anyway. The host watches him pitch into the void with the same smooth patter as before. Kyle has not exactly failed, but the VC office-hours path looks less promising. Then an email shows up. A curious VC, not someone Kyle had pitched, says she is really interested in the adaptive context-driven AI and wants to learn more about the company's vision. That gives the whole thing a jolt. She offers calendar times, and Kyle takes one, about as close to dreaming as this setup allows. The next call starts oddly. Kyle checks whether his camera is going to turn off, says everything seems to be running smoothly, then answers from an office in the Bay Area with books and a cool lamp from Argentina.

As heard by us

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.

Read the full review in PlayNext →

Why you'd press play

Watch a VC call wobble when the founder's AI stand-in takes the lead.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from Shell Game