"PROMPT This Rapid Fire Smackdown"

December 17, 2025

Episode Summary

This episode changes up the usual format. Instead of long interviews, Clint and Greg host the first ever Prompt This Rapid Fire Smackdown.

The rules are simple. Every guest previously answered the same five AI-related questions. Clint and Greg draft teams, go head to head, and let ChatGPT decide which answer wins each round.

What follows is part debate, part comedy, and part truth serum for the AI industry. The conversation cuts through hype and surfaces how experienced operators actually think about AI adoption, buzzwords, onboarding, and real use cases.

The result is fast, opinionated, and surprisingly revealing. You hear where leaders agree, where they clash, and where AI itself struggles to be decisive.

Guest Introductions

This episode features a stacked lineup of returning Prompt This guests from previous episodes spanning sales, marketing, product, healthcare, and technology. The main event is hosted by Clint and Greg, who step into the ring as team captains with AI is the judge.

Across five rapid fire questions, insights come from leaders including Margaret Freitag, Deepak Deolalikar, Ben Taft, Jason Green, Mark Bautista, Charles Hicks, Ganesh Iyer, Christian Wettre, Gabe Larsen, John Sasson, and Chris Angus. Each brings a distinct, experience-driven take on how AI is actually being used, misused, or misunderstood inside real organizations.

This Week’s AI Challenge

This episode’s AI Challenge is timely, practical, and immediately useful.

The Challenge

Use ChatGPT to scan your email for purchase receipts, identify items you recently bought, and run price comparisons across other retailers to see if you overpaid and should return or rebuy items.

Why It Matters

It is a simple example of using AI as a personal operations assistant, not a science project. It saves money, reduces friction, and proves that useful AI does not need to be complicated.

Try It Yourself

Visit https://www.promptthis.ai
Join the Prompt This community
Share how you used AI to save time or money this week

Chapter Breakdown

00:00 – Welcome to the Smackdown
High energy intro sets the tone for a competitive, no fluff episode.

01:00 – The Rules and the Draft
Clint and Greg explain the format and draft their teams from past guests.

04:47 – Round 1: Most Underrated AI Use Case
Healthcare data analysis versus AI skepticism. ChatGPT makes its first call.

06:46 – Round 2: The Biggest AI Mistake Companies Make
AI for AI’s sake versus understanding the problem first. Accents may influence judgment.

08:59 – Round 3: The Most Annoying Tech Buzzword
Personalization, GPT, AI agents, and cognitive transformation all take hits.

12:45 – Round 4: The AI Tool You Wish Existed
Sales commission visibility versus daily AI-powered content summarization.

14:29 – Round 5: Getting New Hires Started With AI
Structured onboarding plans clash with a blunt reality check.

17:45 – The Winner Is Declared
Bragging rights are claimed and remembered.

18:00 – AI Challenge and Closing
A practical holiday use case for AI and a wrap on the Smackdown format.

Episode Transcript

AI Announcer (00:04.706)
Hello and welcome folks. We are live for the electrifying prompt this Smackdown, where business titans collide for the ultimate crown. In the red corner, we have the unstoppable Greg Rosenthal, master of scaling sales teams and the Silicon Valley playbook, bringing that undeniable swagger. And in the blue corner, it's the scrappy innovator, Clint's startup veteran and genius at transforming big dreams into

Thriving realities. Together they're ready to unleash bold strategies and fierce competition in the AI arena. It's Brains vs Hustle, Greg vs Clint. Ladies and gentlemen, strap in tight. It's time for Prompt This Smackdown.

you

Greg (01:04.662)
Okay, it's time for the first annual prompt this rapid fire smackdown. Let's get started. So each guest answered the same five questions and we have answers from all of them. So now Clint and I are going to draft teams.

guess.

and we're going to put their answers up against each other and have chat GPT decide who has a stronger answer.

That's right. You got to figure out who's on whose team. You starting to think about who your ringers are?

yeah, yeah, I got a, I hope you don't pick a couple of my special, special players, man. I got, I'm going to put together a game.

Greg (01:47.96)
Good team here.

And how are we deciding who goes first?

Hmm, let me think here.

Pick a number. I picked a number. You pick a number.

All right, what's in between? One and ten, all right.

Clint (02:01.198)
1 in 10

Greg (02:06.08)
Okay. Seven.

Co-pilot has picked

Now you lost. All right, so I go first.

Clint (02:17.194)
We can paper scissors rock. you want to paper scissors rock? I'm taking John Sasson out of the gates. First pick.

Alrighty

I'm remembering that I want on my

Alright, well I'm taking Margaret Freytag.

Margaret had some good ones. That's okay. Let's see. I'm going for Mr. Intellectual, Jason Green.

Greg (02:54.606)
Ooh. All right, I'm going. Mark Batista.

with.

Clint (03:04.11)
All right. I remember a couple of marks. Those were funny. OK. Then let's see here. Next up, I'm going for a different take on things. Deep Pop.

Greg (03:17.678)
then I'm going to take.

Ben Taft.

All right. Then, let's see up next in mind. I gotta tell you, my team's gonna crush your team. Just absolutely crush your team. I've got Christian on my team now.

bastard.

I've got John, got Jason, I got Christian, got Deepak. You've got no chance. No chance.

Greg (03:44.504)
Well, I've got Ganesh now on my team. My team. Watch out the equal.

Okay.

Clint (03:52.334)
was letting you gonna take this one, right? But since you haven't picked him yet, I'm going for our international flavor with Chris.

I was hoping you didn't scroll down.

see that one. Okay, okay. taking Charles, the guy that was brave enough to come on the very first episode. Yeah, I'm him man.

on six.

Clint (04:19.022)
Okay, well I'm gonna, I'm gonna, I'm That's a winner. I'm gonna conclude my dream team with Gabe Larson. There's no way, no way you can.

I didn't see you the list! I scroll down!

down. All right. Teams.

think that completes our.

Excellent. Let's get into it.

Greg (04:47.65)
Round one.

What's one AI use case you think is still massively underrated?

All right, let me see here. I got a strong team when it comes to this question. I'm putting up Margaret Frye tag. She comes from a different industry and she has a really strong answer in this one. So go ahead. Let's hear it Margaret.

got it, I got it.

Margaret Freitag (05:13.378)
find ways to analyze their patient charts and mine for insights on correlations between people's health status, their demographics, the medications they're taking, their underlying pathology, their genetics, all of those sort multivariate type analyses.

Yep, that was pretty good. All right, I've got a few good ones to choose from here. I'm looking across my list of Clint team participants. I can't tell you, I gotta go with Christian. He's got the best non-answer.

Christian Wettre (05:40.378)
You know, in this environment, I don't think there's a problem of underrating any AI use case or tool. think it's a situation of everything is just massively overhyped and it's tough to figure out, you know, what's real and what's not real. I'm sure there's some of them that are quite not real, but it's tough to get a grip on.

Wow, all right, good pick, good.

Let's see what ChatGPT's got to say. Yeah, that's pretty obvious that Margaret had to win that one. I don't think Christians, everything's hype. Nothing's underrated answer quite compares to Margaret's answer on, I think a topic we all care a lot about,

Greg (06:19.756)
All right, who?

That it.

Greg (06:34.67)
All right, prompt this takes round one.

Greg Rosenthal.

Duh.

Greg (06:46.552)
Round two.

Finish this sentence. The biggest mistake companies make with AI is...

I'm...

God be with you.

that implement AI for a living. So I'm putting up char.

Greg (07:06.389)
Hicks.

Thanking.

that they can add it to their existing processes without understanding why their existing processes are the way they are.

Hmm.

You know, I'm curious what your team came up with, because my team kind of landed around the same type of answers. But I love Chris Angus's accent, so I'm going to put Chris in on this one.

Greg (07:33.44)
That throws a twist in it. All right. All right.

Throwing AI in for AI's sake. Organizations believe that they need to have AI, but they haven't fully understood the problem they're trying to solve. So they shoehorn AI where traditional tools could perhaps do the job better and are more appropriate.

We gotta go with the awesome British accent. He just sounds better when he says it. Just simple as that. Sorry Charles, but you gotta work on your British accent,

Don't.

call for the accent making things sound, sound more intelligent. It's an accent.

Greg (08:10.318)
Later.

what are you talking about? That's what Hollywood has trained me for the last 50 years to understand. British accents are just better, period.

I put this.

one through chat GBT. Let's see what the actual machine that doesn't have emotions.

in this.

Clint (08:28.814)
All right, I'm to put it through chat GPT and see what the all knowing mystical LLM has to say. And there it is. There is the answer. I win. win. win.

Chat GPT fell for the accent.

All right, well, here we go. We're tied, one-one.

Greg (08:59.564)
Round three.

What tech buzzword makes your eyes?

Greg (09:09.646)
This was fun seeing everybody's pet peeve buzzword. I love it.

This is a great question. So I'm going to go with Ganesh on this one, Ganesh Iyer. He's got...

He's got a pretty good one.

personalization but nobody does it

I think everyone talks about that.

Clint (09:29.262)
You know, on my team, this was a funny one. actually, I had one of my team members say, I just can't think of anything. Just can't think of a single one. And, know, and I disagree because there's so many tech buzzwords that drive me crazy. But I'm going to go with the one that I think I just, you know, I hear over and over and over again. And I'm going to submit this one and it's Jason Green. Let's hear what he has to say.

Any time.

Margaret Freitag (09:59.49)
GPT

thinking it's a technology.

and not a change in work.

guess you could call that off, yeah.

Yeah, we do say GPT

Greg (10:12.354)
Yeah. Yeah. He wouldn't make it during our meeting.

Clint (10:17.982)
Let's see what chat GPT says about these two answers. This is weird It gave us a tie said both of them were it was unclear which one is better

Yeah

Greg (10:37.422)
I thought the LLM had to make a decision.

Yeah, is chat GPT allowed to not be definitive with an answer?

Well, hey, hey, we got we got other people on our team. Let's do a tiebreaker. All right. I'm going to pick a second one. All right. Get ready. I'm going with Ben.

This is a great.

Somebody used cognitive transformation with me the other day. It sounds like the two Bobs from the Office movie would come in and talk about what's my cognitive transformation policy and process and I'm not even sure if I know what that means.

Clint (11:18.51)
That is hilarious. That's a good one. Ooh, I'm hard pressed. Any office space reference just gets an extra point or two just by itself. Okay, all right. I'm looking through my list here. see I'm kind of handicapped on it. One of my teammates did not even give an answer. I'm gonna go with Gabe Larsen's and let's have a listen here.

Yeah, great one.

That's a great-

Ganesh Iyer (11:46.29)
The buzzword, it's AI agent. I just feel like it's used for everything. I think it's misused sometimes in my opinion. It's on everybody's website. Sea of sameness. We have an AI agent, you have an AI agent. so, yeah, I'm pretty annoyed and bothered and bored of the word AI agent.

Mm-hmm.

Yeah, the gentic AI, you know, everybody's talking about a gentic AI. Let's see what chat GPT has to say And it's a clear winner for you and

Alright.

Greg (12:20.234)
Yeah. Thanks. Then comes through with office space. I love it. That's it. I think that would be two wins in one.

All right,

Clint (12:27.502)
That's a pretty good take on his part, yeah.

Well, it's for me, for you.

It means I gotta win the next two to take the cup. All right, here we go. Let's see what we got.

Greg (12:45.57)
Round four.

That's an AI tool you wish existed but doesn't yet.

All right, all right, let me shuffle the deck here. I know. All right. Mark Batista. I'm putting up Mark Batista. Here we go.

my an- exist just to know it.

Maybe

Greg (13:03.886)
I guess it comes down to

I'd like

to see.

see accurate

Like up to the

Greg (13:14.016)
second commission data from

reps.

sales guys are gonna like this.

on.

I hope chat GBDs is in.

Greg (13:24.93)
else guy.

Alright, I'm gonna bring my product manager sneak pic on this team here out and and I think he's gonna crush this one This is from Deepak a five minute music

bite of the day. I don't have time to read everybody's blog articles.

I just want that. What'd think of that one? Pretty good, Yeah, Deep. Deep Posh is gonna nail that one. We gotta see. All right, here we go. Let's see what Chatgy BT has to say.

I got it

Greg (13:46.136)
Who's a spark?

Greg (13:53.494)
Alright.

and I called it. There you go. Deepak takes the round.

Wait a minute, summarization over commission payments? Come on, man. How have you been training your child?

to your audience, Greg. Play to your audience. Chat GPT. What do you think they're gonna...

And all right, well, sorry, Mark. Anyways, points thanks to the judge.

Greg (14:17.57)
I'm sitting with. You can have the.

Greg (14:29.154)
Round five, the final round.

For this round's question, we put it to our guests a little bit different for each one of them. Basically, the gist of the question for each one of them was, how do you get somebody new to the business started with AI when they don't already know AI?

This was a great one. People got so creative.

is when I like it. But I want to win. So I'm pulling Ben Taft out of the answer pile and you're going to hear something groundbreaking. Here we go.

First thing I would do is I'd ask them to fire up GPT and I would ask them to tap into the, I'm a new hire in this industry. This is my territory. These are the type of accounts I'm going to be going after. These are my solutions. Help me formulate a 30, 60, 90 plan that will ramp up my productivity by 20%.

Clint (15:37.006)
That was legit. Good answer, Ben. Absolutely. Good answer. Good answer. But I got to tell you, I'm feeling lucky here, Greg. You got it. What are you talking about? I have John Sassen who's going to come in with his take on it. Yeah, this is why I recruited him to the team is for this answer, for the win. Here it is.

You got nobody.

Charles Hicks (16:01.358)
Fire them. No.

Greg (16:10.552)
Well, some truth.

Sometimes it hurts. It's all right.

Before they even come into the job, they're leveraging AI. Through the hiring process, AI is being leveraged. The young folks that are coming around out of college and their new SDRs, those folks are already well entrenched in the leveraging of AI in their tools because they're growing up with it.

What do you think about that?

Yeah?

Greg (16:39.532)
guess when you want to win you pick somebody that is highly focused on winning.

Hey, I thrown a couple.

You got a twist by the judge already.

All right, let's see what chat GPT has to say. And.

Look at that. Guess you came in for the win. Oh. Yeah.

Greg (17:01.955)
this guy.

no. Glenn Orff takes the win.

There you go. I win the first annual.

Devastating I had the better

This is devastating.

Clint (17:13.582)
I've been fire smack down We this is this is it for all of the street cred for the year. I've got the bragging rights

that.

So for those listening, have no idea how competitive Clinton is. This one, this one is going to last for a while. Let's just say.

I will be making sure that you don't forget it too.

Greg (17:45.774)
All right. Well, it's the holidays and we have got a AI challenge that, that Ben tabbed actually, and it was brilliant. Put it into a challenge and it's something that you can use AI for to help you throughout the holidays. Clint, why don't you tell us a little bit about it.

brought up. So we put

Clint (18:04.814)
This week's AI Challenge is all about using ChatGPT to go through your email, find all of the receipts for things that you've purchased, and then go out and do price comparison against those things that you bought, letting you know if, well, if you might have found it at a cheaper place somewhere else and it's time to return what you bought. How about that for a very timely holiday AI Challenge?

Clint (18:32.846)
All right, folks, we appreciated everybody spending a little bit of time with us as we had some fun. We've got a couple more episodes coming up before the end of the year, but I hope you appreciated the a little bit of a twist that we brought to prompt this on today's rapid fire Smackdown episode.

So we had a lot of smart people on here with a lot of smart answers. all right. And don't forget to be prompting out there.

you guys have a good week.

Clint (18:59.98)
And that's another episode of Prompt This.

you

Hello and welcome folks, and that's the bell. After a fierce battle of brains and bold ideas, today's Prompt This Smackdown Champion is Clint.

What a fantastic performance we witnessed here today! But don't count out Greg just yet, he'll be back swinging in the next round, ready to reclaim that crown. Now if you're hungry for more epic showdowns and deep dive insights, you need to head over to www.promptthis.ai every episode and in-depth articles that will keep you ahead of the game. And remember...

Folks hit that follow button below so you never miss the next clash of titans. The SmackDown may be over, but the rivalry lives on. Until next time, this has been Prompt This SmackDown.