RS363: Why Talking to AI About Your Business Is Dangerous

RS363: Why Talking to AI About Your Business Is Dangerous

Author: Craig Hewitt August 18, 2026 Duration: 32:53
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. Resources and Links from This Episode: Produced by Castos Productions  The Podcast Host: https://www.thepodcasthost.com/  Colin on LinkedIn: linkedin.com/in/colinmcgray?originalSubdomain=uk  Castos Free Tools: castos.com/tools Email me: podcast@roguestartups.com  Find me on Twitter: https://twitter.com/TheCraigHewitt  LinkedIn: https://www.linkedin.com/in/craig-hewitt-78386a66/   Email: podcast@roguestartups.com

Behind every new company is a story, and Rogue Startups digs into the real ones-the messy, uncertain, and exhilarating paths founders actually walk. This isn't about polished success tales; it's a candid look at the day-to-day grind of building a business from the ground up. You'll hear directly from entrepreneurs in the thick of it, along with seasoned experts who specialize in the crucial engines of growth: sales, marketing, and product development. Conversations focus on practical tactics, particularly around scaling productized services and SaaS offerings, exploring the real "how" behind their growth hacking strategies. The value of this podcast lies in that shared experience-hearing how others navigate the very obstacles you might be staring down, and learning what moves actually led to a win. It’s for anyone who prefers the unvarnished truth of entrepreneurship over theory, offering a sense of camaraderie and a toolbox of ideas drawn from the front lines. Tune in for authentic dialogue that skips the fluff and gets straight to the challenges and victories of building something new.
Author: Language: en-us Episodes: 50

Rogue Startups
Podcast Episodes
RS336: Claude Project Deep Dive with Alison French [not-audio_url] [/not-audio_url]

Duration: 47:43
On today’s episode of Rogue Startups, Craig continues his AI series with founder, marketer, and Claude-user Alison French. They discuss the hesitation creators feel when working alongside AI and what Alison did to overco…
RS335: Evaluating AI Model Performance with Stuart Grey [not-audio_url] [/not-audio_url]

Duration: 47:06
In today’s episode of Rogue Startups, Craig sits down with AI expert Dr. Stuart Grey to discuss how AI is transforming both his personal and professional life. Dr. Grey also shares how he educates his students and client…
RS334: How AI Saves Me 10 Hours A Week [not-audio_url] [/not-audio_url]

Duration: 15:51
Today, I’m kicking off a series on AI—how I’m using it personally and professionally to grow my business, make life easier, and operate at a higher level. Over the next few episodes, I’ll be chatting with folks about the…
RS333: Grading My Business (and yours!) [not-audio_url] [/not-audio_url]

Duration: 22:03
In this New Year's Eve 2024 episode, we dive into a framework for evaluating SaaS businesses across eight crucial criteria. Instead of doing a typical year-in-review or making predictions, we explore how to assess the fu…
RS332: Competing with Stripe and Hubspot (ft. Geoff Roberts) [not-audio_url] [/not-audio_url]

Duration: 39:14
Hey everyone! Just had an awesome chat with Geoff Roberts from Outseta (outseta.com). They're doing something pretty wild - basically smashing together Stripe and HubSpot into one platform for subscription businesses. Ho…
RS331: I'm Still Here... [not-audio_url] [/not-audio_url]

Duration: 9:23
After a 2+ month hiatus, we're back! Watch on YouTube Sorry for the pause in episodes, but thank you for tuning in this week. In this episode I talk through why the forever long break in the podcast, what I've learned in…
RS330: Product-Led Playbook with Wes Bush [not-audio_url] [/not-audio_url]

Duration: 47:52
Wes Bush is a leading authority on product-led growth (PLG) and is here to guide Craig through the playbook for implementing product-led strategies in your business. This episode is invaluable for entrepreneurs eager to…
How To Hire For Growth [not-audio_url] [/not-audio_url]

Duration: 14:20
In this episode of Rogue Startups, I dug into several pressing questions from the community. From knowing when to pull the plug on a marketing channel to the debate around hiring for support versus sales, we covered grou…
RS328: Are you Productive or Effective as a founder? [not-audio_url] [/not-audio_url]

Duration: 14:27
Running a business is both incredibly rewarding and exhausting. Over the years, I’ve experienced highs of motivation and productivity, but I’ve also hit those low points, battling burnout and loneliness. In this post, I…
RS327: 3 Traits Of Successful Founders w/ Rob Walling [not-audio_url] [/not-audio_url]

Duration: 44:07
Craig has TinySeed’s Rob Walling in the hot seat today. They’re chatting about defining, attaining, and maintaining success. What does success mean to you? How do focus, clarity, and execution fit into it? Rob, a leading…