How I Booked a Holiday by Chatting to AI (2025 Finale)

Stop Treating Claude Like a Writing Tool. Build a Team.

Send us Fan Mail [https://www.buzzsprout.com/2527278/fan_mail/new] Season 2, Episode 1. Davina Montgomery and Aamir Qutub are back in a new studio space and Claude isn't just for tightening up your writing anymore. Aamir shows how he runs a crew of AI agents that handle SEO, finance, admin and research — and how he built an app in a weekend his own team quoted at three and a half months. You'll hear how Claude Cowork does real work across your files, how Skills hand AI your brand and knowledge, and how a Valentine's Day agent booked a plumber off Airtasker. We get into the Copilot vs Claude data question Australian businesses keep asking, why your $20 subscription could one day cost $500, and what an AI team really means for productivity and cost. Practical AI for business, minus the hype. Follow the Dumb Monkey podcast so you don't fall behind. Resources & Links: 📲 Dumb Monkey AI Academy → https://dumbmonkey.ai/ [https://dumbmonkey.ai/] 📱 AI Academy → https://dumbmonkey.ai/dl [https://dumbmonkey.ai/dl] 📘 The CEO Who Mocked AI (Until It Made Him Millions) → https://mybook.to/dumbmonkeypodcast [https://mybook.to/dumbmonkeypodcast] 🚀 Enterprise Monkey → https://enterprisemonkey.com.au [https://enterprisemonkey.com.au] Deakin University → https://www.deakin.edu.au/ [https://www.deakin.edu.au/] AI for Good (UN/ITU) → https://aiforgood.itu.int/ [https://aiforgood.itu.int/]

AI in No Man's Land: Who Owns it In Your Business

Send us Fan Mail [https://www.buzzsprout.com/2527278/fan_mail/new] AI is already inside your business, even if nobody “owns” it.  In this episode, board director Mark Edmonds shares what he’s seeing across organisations: CTO says “not me”, CIO says “not me”, and AI adoption stalls while everyone stays busy.  We talk practical AI for business:  * How to create quick wins that prove value * Why Copilot/Microsoft 365 and Teams note-takers can expose more than you expect * How to reduce hallucinations with simple verification habits (including asking for sources). The standout idea is to treat AI like driving: train people, test them, and give them an “AI licence” so usage is safe, consistent, and actually sticks.  Follow the show for more practical AI you can use this week. Resources & Links: 📲 Dumb Monkey AI Academy → https://dumbmonkey.ai/ [https://dumbmonkey.ai/] 📱 Dumb Monkey App → https://dumbmonkey.ai/dl [https://dumbmonkey.ai/dl] 📘 The CEO Who Mocked AI (Until It Made Him Millions) → https://mybook.to/dumbmonkeypodcast [https://mybook.to/dumbmonkeypodcast] 🚀 Enterprise Monkey → https://enterprisemonkey.com.au [https://enterprisemonkey.com.au]

Agentic AI Is Coming — Is Your Business Ready?

Send us Fan Mail [https://www.buzzsprout.com/2527278/fan_mail/new] AI adoption fails when leaders treat it like an IT rollout instead of a business shift. In this episode, Barwon Water’s GM of Digital Business, Wayne Pales, explains why AI only works when senior leaders get their hands dirty, make mistakes in public, and lead the conversation. We unpack how Barwon Water rolled out Copilot to 500 staff, tackled shadow AI without locking everything down, and built a culture obsessed with data quality. Wayne shares why traditional change management is too slow for AI, how “agentic AI” changes workflows, and why people, processes, and data matter more than tools. If you’re serious about AI for business, not hype, this episode shows how leaders actually make artificial intelligence in business stick. Follow the podcast for more no-nonsense AI conversations. Resources & Links: 📲 Dumb Monkey AI Academy → https://dumbmonkey.ai/ [https://dumbmonkey.ai/] 📱 Dumb Monkey App → https://dumbmonkey.ai/dl [https://dumbmonkey.ai/dl] 📘 The CEO Who Mocked AI (Until It Made Him Millions) → https://mybook.to/dumbmonkeypodcast [https://mybook.to/dumbmonkeypodcast] 🚀 Enterprise Monkey → https://enterprisemonkey.com.au [https://enterprisemonkey.com.au]

Why AI Fails Without Culture (and How Leaders Fix It)

Send us Fan Mail [https://www.buzzsprout.com/2527278/fan_mail/new] Most AI rollouts don’t fail because of the tech, they fail because people were never brought along. In the first episode of 2026, leadership and culture expert Tiffany Gray breaks down why simply “flicking on” Copilot or mandating AI use creates resistance, fear, and silos. We unpack what cultural integration really means, why most people can’t articulate their own role, and how unconscious competence blocks automation and AI agents. Tiffany shares practical ways leaders can build AI literacy, psychological safety, and shared learning, without turning AI into a compliance nightmare. If you’re a CEO or exec wondering why AI adoption is stalling, this conversation reframes AI as a leadership and culture problem first and a technology problem second. Follow the podcast for more practical AI-for-business conversations. Resources & Links: 📲 Dumb Monkey AI Academy → https://dumbmonkey.ai/ [https://dumbmonkey.ai/] 📱 Dumb Monkey App → https://dumbmonkey.ai/dl [https://dumbmonkey.ai/dl] 📘 The CEO Who Mocked AI (Until It Made Him Millions) → https://mybook.to/dumbmonkeypodcast [https://mybook.to/dumbmonkeypodcast] 🚀 Enterprise Monkey → https://enterprisemonkey.com.au [https://enterprisemonkey.com.au]

How I Booked a Holiday by Chatting to AI (2025 Finale)

Send us Fan Mail [https://www.buzzsprout.com/2527278/fan_mail/new] In the final episode of 2025, we reflect on the moment AI stopped being a novelty and quietly became part of everyday life. Amir shares how he booked an entire family holiday — flights, hotel, seats and itinerary — without opening Booking.com or Skyscanner, simply by chatting to ChatGPT like a travel agent who’d already been there. We unpack why conversational, voice-first AI beat typing and searching this year, especially for busy leaders. From smarter travel decisions and gift buying to packing, productivity and turning emotional rants into professional emails, this episode captures what artificial intelligence in business actually looked like in 2025. Thank you for listening, sharing and supporting the Dumb Monkey Podcast this year. We’re signing off for a break and looking forward to coming back refreshed — and ready for what 2026 brings.  👉 Follow the Dumb Monkey Podcast for more no-BS artificial intelligence in business. Resources & Links: 💬 Join the Dumb Monkey Community: dumbmonkey.ai 🧠 Subscribe to the Dumb Monkey Newsletter: https://dumb-monkey.beehiiv.com 🧠 Subscribe to the Dumb Monkey LinkedIn Newsletter: https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7378944396286681088 💼 Learn more about Aamir Qutub: https://www.linkedin.com/in/aamirqutub/