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 


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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.
 

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