Simon sits down with James Oldham, Founder and CEO at Sentry AI and one of the leading agentic developers in New Zealand, and opens with the obvious question. What's the biggest mistake brands make when they start their AI transformation?
James has never paid a dollar to learn any of this. He asked AI how to use AI, and reckons that's why he's moved faster than the people who studied first. Two years ago he was building bespoke systems for clients, until he came back a week later and found 3 people out of 40 had opened one of them twice.
We go deep into the maths behind a $400 Claude Max plan that would bill out around 4K a month through the API, and why that gap is the same trade as cheap Facebook clicks in 2015.
James walks through the work we're doing together at Nature Baby, where tracking tool calls rather than messages shows how staff actually work before anyone writes a skill file. We also get into why one odd tool in your stack triples the cost of any AI build, why the noise around OpenClaw and Mac Minis went quiet, and how to tell a capable AI partner from someone repeating a course that's two months old (which is about two years old in AI terms).
This one's about how far a brand owner can get on their own before they need to pay anybody, and how to recognise the moment they do.
Massive thanks to James for coming onto the podcast.
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