A modern-day odyssey through AI chatbot hellscape artwork

A modern-day odyssey through AI chatbot hellscape

Marketplace All-in-One

July 23, 2026

A missing package can easily ruin a day, but chasing where that package went — or even a refund — is like following Odysseus on his treacherous journey. And in the age of AI chatbots, the process is a whole lot less human.Dillon Thompson is currently on such a journey.
Speakers: Meghan McCarty Carino, Dillon Thompson, Lee Hawkins
**SPEAKER_1** (0:00)
This podcast is supported by Raymond James, a financial firm offering wealth management, banking, and capital market services that are inspired by people.
Before Raymond James' financial advisors build plans, they build relationships so they can craft individual strategies designed to achieve priorities and pursue what's possible.
That's the power of personal. Disclosures at raymondjames.com. Raymond James and Associates Inc., member NYSE, SIPIC.

**SPEAKER_2** (0:29)
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**Meghan McCarty Carino** (1:34)
The new version of customer service hold music is Chatbot Hell.
From American Public Media, this is Marketplace Tech. I'm Meghan McCarty Carino.
Four months ago, Dillon Thompson ordered two e-bikes, one for himself and one for his fiancee. But only one e-bike ever arrived. He got a notification that the second one had been delivered. But when Thompson went to look for the $1,700 package, it was nowhere to be found. His quest to find the missing bike sent him on a journey through what he calls Chatbot Hell. He wrote about it for Wired.

**Dillon Thompson** (2:21)
Over the course of the saga, over the three months plus trying to find the bike, I reached out to obviously FedEx, who claimed to have delivered the bike to me, even though I never received it. I reached out to the bicycle company that I purchased the bike from. I reached out to my bank and my credit card company, hoping to get refunds or cash for the transaction. I also reached out to my local police department, and throughout the entire process, I found it extremely difficult.
When I say that, I mean I spent hours and hours of my week for multiple weeks trying to contact these various organizations, often finding myself stuck back in this loop of talking to chatbots that would either not refer me to a real person or would make me jump through a million hoops and rings to talk to a real person. And in the end, I would ultimately just get sent back to the next organization, which would then have me talk to many more chatbots again to try to find a resolution.

**Meghan McCarty Carino** (3:17)
And when you say chatbot, are you sort of referring to like you were on a computer interface, like it directed you to a computer interface, you're talking to a chatbot, or are these like voice, AI voice agents, like what are they?

**Dillon Thompson** (3:31)
Yeah, very often both. I mean, obviously anyone who's purchased something in the last several years has had an experience that probably every version of these. More often than not though, I actually found myself on the phone with these businesses, or trying to be on the phone with them, and realizing that the first line of communication for essentially every organization that I could possibly come in contact with is an AI chatbot.
I would say the most shocking of these was with my local police department, which there's essentially no way in the city where I live and I can't speak for other places to file a non-emergency police report and speak to a real human unless you, I guess, go down to the station itself. And I would say that's when the point really got hammered home that feels, at least from the experience of the person on the other end of the phone, designed to keep you away from the possibility of speaking with a real person who might hear you out.

**Meghan McCarty Carino** (4:27)
So at this point, you said it's been more than four months. Have you ever gotten through to a real human being that would actually help you?

**Dillon Thompson** (4:35)
Yes, yeah, I was able to eventually get through with every business, including the, I would say, the most successful instance of this was contacting the bicycle company. And I was able to work with them on getting a refund for the shipping costs for the order. I also was ultimately able to get through to FedEx and speak with a real person. But they have such a convoluted customer claim system that, essentially, if you don't have an open claim with them, they won't help you with your issue whatsoever. And they just refer you to the initial shipper. And something that FedEx did in my situation was, they opened a claim for me and then closed a claim for me, all via a chatbot over the phone and then followed up over email. So there was never a real person involved in evaluating my case. Meaning, by the time I actually spoke to a real person on the phone, they basically told me that the situation was done and dusted and there was nothing they could do to help.

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