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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Content provided by Bill Caskey and Bryan Neale: B2B Sales Trainers, Bill Caskey, and Bryan Neale: B2B Sales Trainers. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Bill Caskey and Bryan Neale: B2B Sales Trainers, Bill Caskey, and Bryan Neale: B2B Sales Trainers or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://staging.podcastplayer.com/legal.
In part two of their AI series, Bill and Bryan get specific—sharing real examples of how they use AI in their daily sales work. Bill walks through actual ChatGPT conversations for client prep (including a memorable moment when the AI got it wrong about an ESOP), while Bryan demonstrates how he uses Claude to research prospects and create strategic talking points.
You'll hear how they validate AI-generated research during sales calls, why telling clients "I did some research" actually builds credibility, and how AI makes follow-up more thorough and rigorous. Plus: Bill's detailed prompt for creating pre-meeting introduction videos that position you as an expert before you even get on the call.
If you're still not using AI for sales prep and follow-up, this episode will show you exactly where to start—with real prompts, real mistakes, and real results.
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