The AI Proposal That Lost Us a Client (with Duncan Isaaksen-Loxton)

Send us Fan Mail Duncan Isaaksen-Loxton used AI to write a 13-page proposal for an eight-website job. The research that used to take two days took 30 minutes. The proposal was done in a couple of hours. Then the client wrote back: "It sounds like you did this proposal with AI." The trust they'd built on the discovery call was gone, and so was the job. Duncan runs sixfive.io, a fractional CTO for small businesses. He looks after the tech so owners can get on with the work they're actually good at. In this episode we get into why business owners DIY their tech until it bites them, what happens when your team pastes client data into personal ChatGPT accounts, why AI without solid foundations just speeds up the mess, and why the human relationship still wins the work. In this episode: The "this will only take half an hour" myth, and what DIY tech really costs you Staff using personal ChatGPT accounts with business data (and whose problem that is when it leaks) A hospital that handed a government RFP to ChatGPT How to sell backups and security without scaring people Why you've shared an API key in Slack (yes, you have) and how to stop Onboarding, offboarding and why most businesses only need three tools Google Workspace vs Microsoft, and the Teams rant AI is a power drill: it doesn't make you a tradie What to do when a client sends you a 30-page AI document The AI proposal that lost Duncan a client, and what he changed Chapters: 0:00 Cold open 0:25 Intro 2:58 Who is Duncan and what sixfive.io does 7:11 From web developer to fractional CTO 9:33 Why business owners DIY their tech 12:45 Staff putting business data into personal ChatGPT 14:14 Data breaches and how AI amplifies bad decisions 17:00 Selling protection without the fear 21:11 Slack Connect, API keys and secrets hygiene 23:17 Onboarding, offboarding and the three-tool stack 26:09 Google Workspace vs Microsoft 29:31 Techies, builders and designers: where websites fit 31:40 AI content and the power-drill problem 35:09 The 30-page AI document policy 39:40 Human connection can't be automated 43:15 The AI proposal that lost a job 46:40 How to reach Duncan 49:08 Outro Connect with Duncan: sixfive.io: https://sixfive.io (book a 15-minute chat) LinkedIn: https://www.linkedin.com/in/loxton/ Mentioned in this episode: Viktor: https://mvrx.link/get-viktor Doppler: https://doppler.com Every episode of The Agency Hour: https://theagencyhour.com Got a question you want answered on the show? Email me: [email protected]. I read every one myself.