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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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In this episode of How I AI, I sit down with Jon Mest, a data scientist turned startup CEO who’s helping brands understand what visibility means in a world run by AI search.
Jon is the founder of Just Reach Out, a digital PR platform that helps businesses pitch the media and earn organic coverage, and ChatRank, a new tool that tracks how your brand shows up across AI models like ChatGPT, Gemini, and Google’s AI Overviews.
We trace the evolution of search from Ask Jeeves and AltaVista to the era of conversational agents, where the algorithms deciding what people see are no longer just search engines.. they’re language models. Jon shares how AI is reshaping SEO, what it takes to stay relevant when content discovery is automated, and what it really means to “rank” in an AI-first world.
🔥 Topics We Cover:
• The evolution of search from Ask Jeeves and AltaVista to ChatGPT
• What “ranking” means inside AI models and answer engines
• How ChatRank helps brands measure their presence in AI systems
• How PR, SEO, and AI search are converging
• What businesses can do today to remain visible as search becomes conversational
Tools Mentioned in This Episode:
Search & Visibility Tracking:
ChatRank.ai, SEMrush, HFS, Bolt.new
PR & Outreach Platforms:
JustReachOut.io, Google, Gemini
AI Discovery & Research:
ChatGPT, Ask Jeeves, AltaVista
Connect with Jon:
JustReachOut.io
ChatRank.ai
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More About Brooke:
Instagram: thebrookegram
Website: brookex.com
LinkedIn: Brooke Gramer
More About the Podcast:
Instagram: howiai.podcast
Website: howiaipodcast.com
"How I AI" is a concept and podcast series created and produced by Brooke Gramer of EmpowerFlow Strategies LLC. All rights reserved.
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