While we weren’t looking, AI has quietly embedded itself into the coaching world. Today Craig sits down with new cohost Colin Gray, founder of Alitu and The Podcast Host, to unpack the current state of the industry.
They dig into why coaching is shifting from information delivery to accountability and thinking-partner work, how Colin built an AI system using Granola transcripts to track patterns across coaching clients and surface his own best ideas for content, and whether "everyone is a media company" still holds up for B2B, legal, and SaaS businesses that swear they're different.
It's a candid, practical conversation about personal brand versus business brand, one-on-one versus group coaching, and using tools like Claude not to get answers but to get better questions - a must-listen for coaches, consultants, and any solo founder trying to figure out where human expertise still beats a chatbot.
Highlights from Craig and Colin’s conversation:
AI can't coach you. It can only answer you.
The "how-to" business is dying, and courses are the first casualty.
Why one podcaster treats Claude like a co-founder (and where that backfires).
Coach or mentor? The real spectrum nobody talks about.
Selling a podcast editing app for millions, then figuring out what's next.
"Personal brand" is a dirty word. Here's the better way to think about it.
The one B2B industry everyone assumes content can't touch (it can).
Coaching's new job: not answers, accountability.
One-on-one vs. group coaching: which one actually makes people feel heard.
Turning client call transcripts into an AI memory system that spots patterns humans miss.
Mining your own coaching sessions to find your most original ideas.
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