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Ray Shefska

Things Ray Says on Podcasts

Where to Find Them

Ray Shefska has been a guest on Rich On Tech .

Recently: “Free AI dictation, rideshare horror stories & a smarter way to buy a car (198, Oct. 31, 2026)” on Rich On Tech (October 2026).

What They Said

“In July of 2025 we rolled out our AI agents that will negotiate anonymously on behalf of paying customers when it comes to wanting to buy a car. And since that time our agents have been involved in excess of 160,000 conversations, which has allowed us to rate dealers on how transparent they are. And we have rated nearly 26,000 dealers with a grade from A to F, depending upon how easy it is to obtain the information we ask for and how complete that information is when they finally do provide it.” — Ray Shefska, Rich On Tech

Rich asked how AI is changing car buying. Ray describes his company's AI negotiating agents and the dealer transparency grades built from their conversations, the data behind his claim that dealer behaviour is starting to change.

Rich On Tech · 2026-10-31 Permalink → Listen →
Rich On Tech Around 1:40:11 into the episode
Ray Shefska

Yeah. Salespeople are trained to, to use every psychological ploy that they can and to extract every dollar out of your wallet that they possibly can. And our job at Car Edge is, well, to help mitigate all that.

Rich DeMuro

So tell me about how AI is affecting this industry, because I am sure it is.

Ray Shefska

Well, there's AI both on the dealer side of things, and now we're starting to see it on the customer side of things. Obviously, you can go to chat GPT or Gemini or whatever, and ask pretty generic questions to try and get some answers. I can tell you that at Car Edge in July of, 2025 we rolled out our our AI agents that will negotiate anonymously on behalf of paying customers when it comes to wanting to buy a car and since that time our agents have been involved in excess of 160,000 conversations which has allowed us to rate dealers on how transparent they are And we have rated nearly 26,000 dealers with a grade from A to F, depending upon how easy it is to obtain the information we ask for and how complete that information is when they finally do provide it.

Rich DeMuro

Interesting. Okay, that's fascinating. Because one time I was buying a car and I rushed out. I told my wife, like, we got to rush to this place. They got a great deal. It was like an hour away. We get there. And the price was great. It was lower than all the other prices I'd gotten, but they're…

Ray Shefska

The AI agent actually gets involved in texting and mostly emails back and forth with the dealership using whatever pseudonym you give it. And your information isn't shared with the dealership until you've agreed that the price is where you want it to be. So the AI agent is doing all the work. You…

Rich DeMuro

How open are the dealerships to this? I mean, is a sale a sale? They're just like, okay, fine. We don't care if we're chatting with AI or chatting with a person. We just want the money.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“My father was a dentist. And I would tell you, as someone who spent 43 years in retail automotive, it is worse than a root canal. And it is set up that way by most dealerships because the idea behind it is it's like psychological warfare.” — Ray Shefska, Rich On Tech

Rich asked whether buying a car is tricky and frustrating for the average consumer. Ray, who now runs a consumer advocacy group after decades in dealerships, says the stress of the process is deliberate.

Rich On Tech · 2026-10-31 Permalink → Listen →
Rich On Tech Around 1:37:41 into the episode
Ray Shefska

…my son and I to help level the playing field when it comes to navigating the car buying experience. I spent 43 years in retail automotive, and when my son had to buy his first car, he had me in his back pocket, and he thought, well, the rest of America should have me in their back pocket as well.

Rich DeMuro

So do you agree that the car buying process can be tricky to navigate for the average consumer and frustrating and makes people cry?

Ray Shefska

My father was a dentist. And I would tell you, as someone who spent 43 years in retail automotive, it is worse than a root canal. And it is set up that way by most dealerships because The idea behind it is it's like psychological warfare.

Speaker 9

Yes.

Speaker 5

Okay.

Speaker 6

Yes.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.