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
RS346: What 11 Years in SaaS Really Looks Like [not-audio_url] [/not-audio_url]

Duration: 48:49
In this episode of the podcast, Craig sits down with longtime entrepreneur Colin Bartlett, cofounder of StatusGator, to explore what it really takes to build, and sustain, a SaaS business over the long haul. With more th…
RS345: The State Of Search 2025 [not-audio_url] [/not-audio_url]

Duration: 18:27
- LLMs.txt article: https://www.quoleady.com/llm-txt-files/ - Craig's YouTube channel: https://youtube.com/@thecraighewitt
RS344: 12 Years to Overnight Success with Amar Ghose [not-audio_url] [/not-audio_url]

Duration: 47:27
What does it really take to lead a company for over a decade—and still be growing? In this episode, Craig chats with Amar Ghose, founder and longtime CEO of ZenMaid, about the challenges, lessons, and evolution that come…
A Caffeine Infused Diatribe [not-audio_url] [/not-audio_url]

Duration: 46:59
Hello, remember me? Sorry that it's been 6 weeks, but I'm back. In this episode I talk through what I've been up to recently, what's going on with Castos, with myself personally, and things I'm learning growing the busin…
RS342: SaaS Survival Mode - AI, Niches & Navigating Chaos [not-audio_url] [/not-audio_url]

Duration: 45:12
In this episode of Rogue Startups, Craig chats with Jesse Hanley, marketer, self-taught developer, and founder of Bento, a powerful email marketing platform for modern teams. With today’s economy in flux and global event…
RS341: Microconf 2025 Recap [not-audio_url] [/not-audio_url]

Duration: 17:48
Craig recaps his biggest takeaways from MicroConf 2025, reflecting on lessons in positioning, lead generation, conference ROI, and the power of going all in on what’s working. From tactical marketing insights to personal…
RS340: Is AI Killing SaaS w/ Tim Schumacher [not-audio_url] [/not-audio_url]

Duration: 43:00
In this episode of Rogue Startups, Craig sits down with founder and entrepreneur Tim Schumacher to discuss his insights on AI, the future of SaaS, and what makes a company successful. In 2001, Tim co-founded Sedo.com, th…
RS339: AI Skeptic, or Believer [not-audio_url] [/not-audio_url]

Duration: 47:49
In today’s episode, Craig chats with Anthony Eden from DNSimple about how they use AI in their businesses and their personal lives. As early skeptics of AI, they do a deep dive into what made them change their minds, wha…
RS338:  Balancing Your Use of AI with Aaron Francis [not-audio_url] [/not-audio_url]

Duration: 52:12
Ever wonder what's happening behind the scenes when your dev team says they're "leveraging AI"? As a non-technical founder, you don't need to understand every line of code, but knowing how AI is actually being used in yo…
RS337: Building AI Native SaaS w/ Jordan Gal [not-audio_url] [/not-audio_url]

Duration: 48:06
Today, Craig chats with Jordan Gal from Rosie about starting a business centered solely on AI. While many of us use AI to help with our work tasks and streamline certain jobs, Jordan’s whole business is AI. They discuss…