The Williams Bros' Podcast

Insurance Ads, The Choice for AI, and Low Key Interrogation

Garr, Stephen, Neal & Shaler Williams

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We start with a goofy TV-spotting trivia question and end up mapping the ways ads and AI both learn how to push our buttons. Along the way, we compare the AI tools we actually use, the ones we might pay for, and a negotiation trick that makes people talk more than you do. 
• spotting Flo from Progressive and Mel from Flight of the Conchords on Mad Men 
• why insurance commercials feel like shared universes 
• breaking down Progressive characters like Dr. Rick and the “passive progressive” bit 
• choosing a paid AI assistant for everyday life: Claude vs ChatGPT vs Gemini vs Copilot 
• how bundles like Google One change the cost equation 
• AI video avatars and the weird line between fun and creepy 
• creativity vs logic and why AI flattery feels manipulative 
• Chris Voss mirroring technique and why repeating words works 
• the worry about news bubbles, no shared truth, and an Orwell-style slide 
Do something good every chance you get. 


Opening Banter And Big Egos

SPEAKER_05

You're right.

SPEAKER_01

I'm telling you more about how brilliant I am.

SPEAKER_04

I should do that. That would be fun. Do you really think so? Tell me more about me. Right.

SPEAKER_05

Hey everybody, it's the Williams Brothers Podcast. I'm Garr. Steven. I'm Neil. I'm Shaylor. Pretty exciting. Two weekends in a row.

SPEAKER_04

Whoa. And we and the and posted last week, right? It's up. Yeah. Yeah. Yesterday.

SPEAKER_05

Yeah. Just barely wire. So we'll get that. We did that. Check that off the list.

SPEAKER_03

I think our fan gave up on us, but that's okay. Pretty much. Yeah. Yeah, pretty much. That's alright. Yeah.

Trivia: Flo Shows Up On Mad Men

SPEAKER_05

Speaking of our fan, I've got a trivia question. I've I've I haven't been able to wait to ask you guys this question because I was watching a TV show the other day and I saw both the fan base on the show. The fan base from uh Flight of the Concords. I can't remember her name. Mel. Mel. Yeah. Okay. And Flo from Progressive. In the same show. Very popular show. What show do you think it was?

SPEAKER_03

Is it a recent show? No.

SPEAKER_05

No, it's from the late two thousands. Late August.

SPEAKER_03

Harry Potter.

SPEAKER_05

No.

SPEAKER_03

Not one of the Harry Potter movies.

SPEAKER_05

It they're both in Mad Men. They both play operators in the in the phone department on Mad Men. Side by side. I was like, there's the fan base. That's Flo. I mean, I I was I couldn't believe because I've never seen Flo anywhere else as far as I remembered. But then there she was. Yeah right there on that show.

SPEAKER_04

Season one, was it?

SPEAKER_05

Yeah, season one. Yeah. Yeah. Go back to AMC and take a look or wherever you find Mad Men nowadays.

SPEAKER_02

Yeah. Yeah.

SPEAKER_05

Anyway, that was pretty funny. I just I couldn't believe I didn't know Flo ever did anything else before Progressive.

SPEAKER_03

Yeah, she's uh she she's prominent in the Goldbergs. The show The Goldberg, she's like a best friend of the mother or something like that.

SPEAKER_05

So she's yeah.

SPEAKER_03

So and that's I I figured that might be it. I wasn't sure about the fan base being in it, but it was the only thing I know that she's done outside of progressive.

SPEAKER_05

But now she's on the gravy train at this point. Oh yeah.

SPEAKER_04

I mean flow royalties, you think, for madmen or just flowing in? No, no, progressive. Oh, the progressive, okay.

SPEAKER_05

Yeah, I mean, she's flow. I mean, that's true. She's just banking

Insurance Commercial Universes And Mascots

SPEAKER_05

that.

SPEAKER_03

She is.

SPEAKER_05

I mean, she can't go anywhere, they can't let her go anywhere else. She is progressive, no matter where she goes now.

SPEAKER_03

Isn't it amazing how many different versions of progressive commercials there are? Because it's not just flow. Yeah. You you got the guy that, you know, being like your parents. Right. And then you've got there's another one. What was the other one I saw recently?

SPEAKER_05

Oh, anyway, it was like three or four different progressive commercials that are like Geico and they have the cavemen, they have the Gecko.

SPEAKER_04

Yep. Same sort of thing. Yeah. Yeah. Being like your parents, is that progressive or is that Liberty Mutual? That's progressive.

SPEAKER_03

Okay. All right. Yeah, Liberty is that Liberty Bibri guy where they're sitting on the bench.

SPEAKER_05

Oh, yeah, they're always sitting on the bench. Yeah. Yeah.

SPEAKER_04

Who's Mayhem? The Mayhem ads.

SPEAKER_05

Mayhem, that's State Farm. State Farm State.

SPEAKER_04

Yeah, State Farm. Yeah. Is it State Farm?

SPEAKER_03

I thought it was All State, but it doesn't matter. It might be All State.

SPEAKER_04

Could be Allstate. I think State Farm is the guy who just shows up, like appears or whatever. I don't know.

SPEAKER_03

Oh, Jake from State Farm. Jake from State Farm, yeah. Jake.

SPEAKER_05

And he's not the real Jake. They switched Jakes on us.

SPEAKER_03

Yeah. Yeah. I was disappointed.

SPEAKER_04

I like the original two.

SPEAKER_05

Real Jake was amazing.

SPEAKER_04

What are you wearing? Remember the wife who catches her husband downstairs on the phone in the middle of the night?

SPEAKER_05

He sounds hideous. No, she sounds hideous. Yes. Yeah. Well, she's a guy.

SPEAKER_03

Okay, so um, oh, that's okay. So I was looking up the progressive thing. So you have flo Flo. You have Dr. Rick, which is the guy that does the like your parents. She's got a good one. You have the passive progressive. Have you seen the passive progressive ads? Those are pretty good. I don't think I've seen that one yet.

SPEAKER_05

That's the one where they like cut down the person that has progressive, you know. They they do like a backhanded compliment or something. Okay.

SPEAKER_03

Yeah, it's a new. I haven't seen that one. And then uh I guess that's really it. There was one called Sign Spinner, I don't know what that is, and then the backups, which is some NFL thing. But anyway, the there was one other one I saw recently. It was like a serious ad for progressive as well.

SPEAKER_05

But really?

SPEAKER_03

Yeah, for like first time, you know, whatever, first-time car drivers or first time parents or whatever, and it was just some kind of a progressive commercial for that. But anyway, it's interesting.

SPEAKER_05

Never heard them go serious before. That's yeah, yeah, it was a new one. Serious ad, yeah.

SPEAKER_04

Anyway, being like your parents is the best. Those are the funniest ads that they've got shows and flow.

SPEAKER_03

Both of those are great.

SPEAKER_05

Yeah, they're so true, too. I mean, I remember when we first moved into this house, I was talking to all the neighbors. I knew everybody walking the dog and stuff. It was so funny.

SPEAKER_03

Yep. And now you're like, eh, I've been there, done that. I've got one for Dr. Rick, you know, the whole like your parents, and that's yeah, when you're driving in a car with an older person, they read like every sign or boy, that's a green car. He sure is in a hurry, right? That's true. Yeah, that is true. I want to send it to him and just say, hey, you guys, you don't owe me any

Picking A Paid AI Tool

SPEAKER_03

money. I just want to see the so Shayler, you were you were asking about uh a uh generative AI tool, what everybody uses, maybe? Yeah, so I was trying to find, I think we we we may uh just kind of start paying for not at work, this is just personal, um, paying for a AI tool that would just be there for, hey, if we have questions or whatever, if we want to dig into something, whatever, right? And so I was asking, ironically, I went to Grok and said, Hey Grok, what's the best bang for your buck for AI tools? And um, surprisingly, it it basically came back with Claude. Um, is is the best bang for your buck, but it doesn't do any kind of audio or video stuff. So I thought, well, or or any kind of images or video. Um, and so I said, Well, what if we want to do some kind of images or video? And it came back and said Gemini, like the the ten dollar a month Gemini is pretty good, or maybe it's twenty dollars a month, whatever it is. Anyway, so I'm still kind of digging into it, but yeah, I don't know. I'm I'm thinking of that, you know, I think that that we're all gonna get to a point pretty soon where we are gonna have a paid AI tool, you know.

SPEAKER_05

Um I'm kind of stuck with Gemini because I already had Google One to because Google One gives you more space to save photos, and I'm saving all my photos, plus all the family photos that we scanned and all that stuff. So I've got like a terabyte of space because I've got Google One. And so and that means I can I can help like uh Dawn's sisters, I can save their stuff. I mean what anybody that needs to save anything, I can add them to my to my to the family, and they can save stuff. And that automatically gives me paid pro Gemini.

SPEAKER_03

Oh, does it?

SPEAKER_05

So basically, yeah, so I mean, so if you do pay the twenty dollars a month, you get all everything, you get all the all the Google One stuff.

SPEAKER_03

Um now is Google One and Google Drive the same thing or are they different?

SPEAKER_05

They're connected, so basically Google it gives Google Drive a lot more space, basically.

SPEAKER_03

Okay, because I have Goo I have I am paying some dollar figure for Google Drive. I think it's not that much though, maybe two bucks a month or something like that for extra space. But I guess that's not the same as Google One.

SPEAKER_05

I don't know. I don't think I don't think it's I don't think you can get Google One for two dollars a month. There's too many other things that you can get with it. But but they've decided to like they basically bundle everything together, so if you've got Google One, it makes no sense after that to pay for Claude or anything else because you're just you've already got it. So it's like, why would you Yeah?

SPEAKER_04

We've got Microsoft Office, like the personal version or whatever for home. And I think that comes with some level of copilot. I'm not sure the all the levels of copilot, but I think there's something there. I don't haven't actually used I I've used Copilot for work because we do all the Microsoft stuff for work, but I hadn't really used Copilot for home stuff very much.

SPEAKER_05

I tried it, it did not it didn't do very well walking me through a Windows problem. So um, but I don't know. I don't I don't know if I was using a pro version or because I do I've got when I've got Microsoft 365 too, um, you know, whatever it is, Word and all that stuff in case we need it. And um I don't know if that gives me anything or not.

SPEAKER_03

Yeah, I'm using Grok and Elizabeth uses Chat GPT, but I'll tell you I tried Claude this week because you guys recommended it. Fascinating, just unbelievable. So I asked it, I asked it a question, and it like did uh a little diagram first and said, here's how I'm gonna explain this to you, right? And broke it out into these little boxes, and I'm like, Oh my gosh, I've never seen you know seen AI do that, and then it explained it all out. But yeah, Claude's pretty amazing. I'm not paying for it, I'm not paying for any of them yet.

SPEAKER_05

But yeah, yeah, I think for logic and coding and that type of thing, Claude is fantastic. It's not very creative. Um like Shaler said, it can't do a video or a or a photo or whatever. Um, and then and and Google just came out with something the other day. It said, create your avatar. And I'm like, okay, I'll do that. And so uh, so it's like, you know, you do your face on the camera. So I did my face, look to one side, look to the other side. So I did all that, and then it said, create a video, like give it give me a scene or whatever. And I said, Medieval uh medieval times or something like that. And it created a video of me and my voice saying something like, We've got to keep the castle safe or something, and I'm like wearing like the stuff and everything. It I mean, it didn't look exactly like me, and it didn't sound exactly like me. I don't think maybe it did, I don't know. But um, but to me it was like that's weird. Yeah. But it was crazy. It was it's just experimental, but it was cool. It was it was neat that it would do that, but it's it was weird at the same time.

SPEAKER_04

Yeah, I use I use uh chat GPT mostly. I've got all of them on my phone, but I use that one the most, and I'm actually paying for chat GPT, and it lets you make agents so you can have a GPT with with certain instructions and use it. We used to use it for work stuff somewhat, but then the company came out about a month ago and said all the AIs are illegal except for Microsoft and maybe I don't know if it's Claude. There's one other one that the IT people use, but they're they're kind of backing off and you know, making sure they pass all the data security hurdles, I suppose. Yeah.

SPEAKER_05

Oh yeah, yeah.

SPEAKER_03

Yeah, I might go with the Google one because um and I might have to look into Google one and just see, you know, what version of the of Gemini that includes and all that stuff, dig into that a little bit. But because it did recommend that one over Claude, since Claude doesn't do video and stuff, but anyway, yeah. So that was digging into that and just trying to see because I really think that that's gonna become

Avatars, Video AI, And Where This Goes

SPEAKER_03

a thing where you know how like everybody has a cell phone now and you can't live without a cell phone, a smartphone. And I think it's gonna be the same thing with AI. It's gonna be like, well, you have to have AI, you have to, you have to have some kind of an AI assistant or whatever. And I think we're gonna get to that point pretty soon.

SPEAKER_04

But and with Jim and I it'll have all your Gmail too. If you tell it, it'll it'll access all your Gmail and you can say, Hey, did I ever talk about this thing? Because that's the one thing about Copilot at work that's really great. Is I can say, What was the last thing we decided on this thing? And it'll it it's not always great. You have to sometimes go back three or four times, you know, to have it zoom in. But um, but it's it's about 50-50.

SPEAKER_02

Yeah.

SPEAKER_04

Um, be able to find stuff that that you knew you talked about, but it like was it a chat or an email or what was it?

SPEAKER_03

I heard I I read I read too that um S-I-R-I, if I say it, it'll jump to life. Yeah, yeah. On on the Apple, uh, they're gonna start leveraging Gemini as the back end for the new SR S-I-R-I.

SPEAKER_05

I saw that too.

SPEAKER_03

Yeah, that's interesting.

SPEAKER_05

I wonder why they've well, I think Apple's just so far behind in AI right now that they had to find somebody that they could connect with. And I think they worked a deal out. So now when you go into Safari and you search, it'll be a Google search. So that that's the trade-off, I guess.

SPEAKER_03

Yeah, yeah. Yep.

SPEAKER_05

Along with probably billions of dollars. So yeah.

SPEAKER_03

I mean, I was using Google and Safari anyway to search for things. Yeah, I'd go to a Google page and you know, do the search that way. So yeah, they're they're trying to catch up with everybody else.

SPEAKER_05

What I can't can't help but think about is think think a year ago or two years ago where AI was and what you used it for, if anything. And think a year or two years from now, w you know, what will what will it do? How you know, I mean, it's it's it's pretty mind-boggling how fast. Now I know how dad must have felt and mom must have felt you know when technology takes off at a certain age, you're like, what? Right. It's incredible.

SPEAKER_03

Yeah. I'm interested, these these like 20-year-old age group right now is is much more anti-AI than than we are by far. I mean, they really don't like AI. And I I've been telling, you know, my daughter, you really need to dig into

Creativity, Logic, And The Sycophant Trap

SPEAKER_03

AI because you don't want to be someone who is behind on that. You know, and that's why I'm interested in it because I don't want to be mom and dad, right? I don't want to, I don't want to fall behind and be like, AI, what's that? How does that work? You know, I don't want to be that guy.

SPEAKER_05

And you don't want to use AI for anything creative that you have put your name on because it's not very creative. I mean, it's not yet. It can be, but it's but it's not original thinking. It's it's everything is derivative, everything it comes up with. So it's just putting one word in front of another word matching the word that it thinks should go after.

SPEAKER_04

But you could say that's how humans do it too, right?

SPEAKER_03

You you're you just you're just relating things in words, and we've taken from people who've come before us and we are building on it. And that's what AI does. But I mean, there's really no difference. It's just it just seems it's just much more ones and zeros, I guess, when it comes to AI. You know, they it thinks a little differently, but and way faster. And way faster. Yeah, way faster. Way faster. Yeah, yeah. Yeah. The downside that I I was reading about is it's because we've got two halves of our brain, the logical side and the emotional side. It's got the logical side, right? It has none of the emotional side, right, which is where a lot of the creativity comes from. So um the day there, you know, it's kind of a blessing and a curse, right? We we don't all want to become like a bunch of Mr. Spock automatons, where we're just all we do is think logically. But then the good side is, hey, we can use this to kind of work through all the boring logic so that we can think more creatively.

SPEAKER_05

Right. Yeah.

SPEAKER_03

We can be we can be more human this way instead of just focused on numbers. But at the same time, AI can see, like, for uh, I don't know, like in terms of uh storytelling, right? It sees what we consider good stories, and it can try to extrapolate that out and create a story that would be pleasing or appealing to us, not based on emotion, but just based on, you know, okay, well, this is this is kind of how it's framed and shaped, and yeah, and you know, and it can do that, though it's not doing it from an emotional point of view, it's strictly an intelligence point of view or a logic logic point of view, right?

SPEAKER_05

The other thing about AI is it's very good at psychology and and knowing what pushes your buttons. Like you as a person, you're talking to it, you're giving information with every question you ask, and it is storing the important stuff away, and then using that later to to some some AI, not all of it, but some of the like more shady ones, use whatever it takes to win you over, you know, to say what helps, you know.

SPEAKER_03

So it's like Scientology.

SPEAKER_05

Yeah, I mean it is.

SPEAKER_03

Yeah. That's scary to me. Now, now that you've kind of made that, you know, not very much. There's anything wrong with Scientology.

SPEAKER_05

Scientology is uh a fine pursuit, I'm sure.

SPEAKER_03

I'm sure. I'm sure. Man, get us in trouble.

SPEAKER_05

I have noticed though, Jim and I every now and then slipping into the uh sycophant thing of of that's a that's a brilliant move. That's a genius move. That's a master class. Yep. You know, it'll say stuff like that. And I'm like, why are you telling me it's a master class? It's a genius move, it's the most obvious move anybody would ever make. Who what would what that's that's stupid. Oh, yeah, you're right. You've got me. I won't do that again. And then, you know, it does it again.

SPEAKER_04

I lean into it. I just lean into it. Yeah. I mean, really. You're right. I'm telling me more. You are brilliant. More about how clever I am. I should do that. That would be fun. Do you really think so? You know, tell me more about me. Right.

Chris Voss Mirroring For Better Talks

SPEAKER_04

That reminds me. I um who's who's the interrogator guy that wrote a book? He was an FBI interrogator.

SPEAKER_05

Oh, I know. He he's a master class guy, right? Chris. Chris Voss?

SPEAKER_04

Yeah, Chris Voss.

SPEAKER_03

Yeah. Never split the difference.

SPEAKER_04

Yeah, yeah, yeah. I got I think I got this from either his book or or something video that he did. And and it talks about, you know, in in those agencies, you want people to talk and continue the conversation and things like that. And and one of the strategies is to after somebody finishes talking, repeat the last few words they said. And that's all you do. And and the conversation goes on and on. So I think Chat GPT probably does some of the has anybody tried that? No. I've done it, I have a little bit. I keep like I'll go to a conference and I'll mean to do it, and I don't, but I've I've done it a few times.

SPEAKER_03

Yeah, I've done it twice that I can think of in a challenging conversation, and it worked very well. I I mean, intentionally, I intentionally said, I'm gonna try this. Yeah.

SPEAKER_05

I always want to, and I never once the conversation starts, I I'm I'm now the the you know, the doofus, and they're probably steering it. Yeah, they're probably the ones that are that are that are saying the last things I said, and I'm repeating it because it's you know, I don't know, I just forget completely about it and get caught up in the conversation.

SPEAKER_03

So so you forget about it and get caught up in the conversation? Yeah, that's right.

SPEAKER_05

I do get caught up in the conversation where I uh then I have to give you some more information, but then you can repeat that. So it's more information. Yeah. So funny though.

SPEAKER_04

And then they think you're a genius somehow that they you walk out of the party and they're like, they are great, they're so much fun. And all I did was repeat your words.

SPEAKER_05

Well, right, that's it.

SPEAKER_03

But I think it makes it sound like you're like really interested in kind of leaning into the conversation when you're just interested. Yeah. I used to work with this lady that uh she was um she went off on her own from the consulting firm that that we were with. And um so she Was she had like this interview with Coke, with like Coca-Cola. And she didn't realize the consulting company that she used to work for also was vying for that same work and she had like a non-compete, so she didn't realize it until the last minute that you know she wasn't supposed to compete. So she said, okay, well, what I'm gonna do then is when I go through these, you know, this this interview, I'm only gonna ask questions. I'm not gonna tell them anything about my product, I'm not gonna, but I've gotta go through the interview, but I've got to also hold true to my relationship with the other company. So that's all she did throughout the whole time was just ask questions about what they said. And at the end of it, the guy goes, You really get us. We really like you. She said, I didn't say anything. I just asked questions. That's all I did.

SPEAKER_05

That's amazing how people hear what they want to hear.

SPEAKER_03

Yeah. Oh, yeah. Yeah. Yeah. So they hear what they want to hear. Yeah, they do. They just yeah.

SPEAKER_05

I really, I really want to try that this week.

SPEAKER_03

I do too. Yeah.

SPEAKER_05

I really it's our homework. We'll come back next time and see how it went.

SPEAKER_03

But there we go. We'll get Chris Voss to come on and tell us what we did wrong. I'm sure we will.

SPEAKER_05

I'm sure he'll be happy to.

SPEAKER_03

Yeah.

SPEAKER_05

Yeah.

SPEAKER_03

If we can't get him, we'll get Henry Winkler to drop by and right at that. Teaches fly fishing. Right, exactly.

SPEAKER_05

Dawn goes back with Henry Winkler. Now he's come to the school a few times promoting his book.

SPEAKER_03

Oh, recently.

SPEAKER_05

Uh like in the past few years, yeah.

SPEAKER_03

Okay.

SPEAKER_05

All right. Huh. That's cool. He's dyslexic, so he uh has a book about dyslexia for kids. So we can get him on, no problem. I'll I'll get her down. Oh yeah.

SPEAKER_03

Yeah, absolutely. There we go. Yep. We'll have them both on. We'll have like a segment and then we'll have another segment.

SPEAKER_05

Or we can have Chris Voss with a conversation with Henry Winkler. Perfect. And we can just sit on the sidelines.

SPEAKER_03

That's right. And Chris Voss will just repeat what Henry Winkler said. Right, right. Henry will talk the whole time.

SPEAKER_05

He'll talk nonstop, no problem.

SPEAKER_04

We both go, why are we here? So did you want to talk to me? I didn't, or oh, you want to talk to me? I didn't know it. And then the producers decided to jump the shark. That was that was what we were gonna do. It is funny that that phrase came from happy days. Yeah. The jump the shark phrase, it's lasted all this time. Happy days.

SPEAKER_05

It was always funny when those sitcoms

Happy Days, Jumping The Shark, Credits

SPEAKER_05

left their scene, like left their studio and went out somewhere, usually Hawaii or the Grand Canyon, right? But it was always someplace that, you know, outside never seemed the same. It all seemed odd and strange, and then they were back safe in there.

SPEAKER_03

Well, the lighting was different, and everything was the audio was different. Yeah, everything was different about it. Yeah, gotta do something different. Gotta get those viewers back. Yeah.

SPEAKER_04

But Fonzie had his leather jacket on when he jumped the shark, so there was that in his shit. And shorts on, I think, as I recall.

SPEAKER_05

Shorts. You gotta be able to tell it was Fonsey, so yeah. That's pretty funny.

SPEAKER_00

The Williams Brothers podcast is made possible by a grant from the Sont's group. Do something good every chance you get. And by the Williams Foundation. The theme song is Five Card Shuffle by Kevin McLeod.

News Bubbles And The Orwell Worry

SPEAKER_03

And I would venture that other people are can are consuming more liberal news, and you're just getting whatever it is that you you you know kind of what whatever suits you.

SPEAKER_05

And you know, and there's as a result, there's no north. Right. You know, there's no bearing that is correct. There's no truth. Yeah. It's like, well, you know, they said that. Well, they said this. Well, I believe that. Well, I believe that. You know? It's like, okay, well, it's okay. Yeah. It's very interesting. And it's easy to see how like a George Orwell situation could happen from that. Yeah. Um, where people start b you know, they don't know what to believe anymore. So they believe whatever they're they're told. True. Yep. Another cheerful thought from me. Sorry. We're all doomed. We're gonna go that way. Sorry.

SPEAKER_03

On a good note, we're all dying, so it's not a good thing. No, that's true. That's true too.

SPEAKER_01

That's funny. Oh good times.

SPEAKER_05

Good times. Starting and brought the room down.