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
RS326: 5 Things Most Founders Struggle With [not-audio_url] [/not-audio_url]

Duration: 19:12
Today’s a solo episode with Craig where he’s talking through the 5 common topics and themes that he helps most of his coaching clients through. Whether it’s through his 1:1 coaching with private clients or in serving as…
RS325: Stuck? Ask Yourself These 3 Questions [not-audio_url] [/not-audio_url]

Duration: 10:00
Are you a SaaS founder feeling stuck, unmotivated, or unsure about your next move? In this video, I dive into three powerful questions that can help you break through mental barriers and gain clarity on your business’s d…
RS324: $100 Million Bootstrapped SaaS with Adam Robinson [not-audio_url] [/not-audio_url]

Duration: 41:34
In this episode of the Rogue Startups podcast, Craig sits down with Adam Robinson to explore key topics such as founder psychology, overcoming self-limiting beliefs, and avoiding self-sabotage. They delve into how to ide…
RS323: Breaking Through Plateaus with Josh Ho [not-audio_url] [/not-audio_url]

Duration: 51:33
Today on the Rogue Startups Podcast, Craig chats with Josh Ho from Referral Rock about the peaks and valleys of being a founder. When is the right time to sell? Is there ever a right time? How do you break through a plat…
RS322: Marketing, in 2 hours a week [not-audio_url] [/not-audio_url]

Duration: 16:17
In this episode Craig descirbes his current SaaS marketing approach. Balancing Active and Passive marketing, he’s got his marketing time down to just a few hours a week. Using a video-first, AI-assisted workflow he’s rea…
RS321: B2B Lead Gen on LinkedIn [not-audio_url] [/not-audio_url]

Duration: 47:30
If there’s one thing Craig loves more than podcasting, it’s sales. In this episode, he shares his enthusiasm with tech sales coach Peter Ahn. They discuss everything from bridging the gap between creating content and dri…
RS320: The Psychology of Sales [not-audio_url] [/not-audio_url]

Duration: 43:26
Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly.Design for a discount on his monthly design subscription service. Tell him that Rogue Startups sent you. What gets…
RS319: Mastering LinkedIn Video Content [not-audio_url] [/not-audio_url]

Duration: 50:21
Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly.Design for a discount on his monthly design subscription service. Tell him that Rogue Startups sent you. Danny Del…
RS318: LinkedIn Content That Converts [not-audio_url] [/not-audio_url]

Duration: 44:17
Clearly Design works in every aspect from branding to marketing, from product to promotion. Go to Clearly.Design for a discount on his monthly design subscription service. Today Craig is chatting with Nemanja Zivkovic ab…