Keynotes · Conferences · Guest Lectures

The Speaker Who Got There
Before ChatGPT

I was making and selling AI work eight months before ChatGPT launched — so my talks come from the early side of the wave, not the commentary box. Practical, honest, and built to hold a room.

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Rupert Chesman showreel — poster frame

The showreel — two minutes. Plays via YouTube's privacy-enhanced player; nothing loads until you press play.

The Talks

Three Talks, One Rule: No Hype

Every talk is adapted to your audience and industry on a call beforehand. These are the three I'm asked for most.

Flagship

The Artist's Door

How I got to AI 18 months early — and what your team should do now

In February 2022, nine months before ChatGPT, I was renting cloud GPUs to make and sell AI artwork — and by June, OpenAI had invited me into their DALL·E 2 early artist access programme. This is the view from the early side of the wave, told with dated receipts: what I got right, what I got embarrassingly wrong, and the pattern I'd already watched once before, when digital cameras ate the film industry I trained in. Your audience leaves with a practical answer to the only question that matters — what does "early" look like right now?

AI Tools That Actually Stick

The gap between the demo and Monday morning

Most corporate AI enthusiasm dies somewhere between the impressive demo and the following Monday morning. This talk closes that gap. Live, unscripted demonstrations of the tools teams actually keep using — and an honest account of the ones they quietly abandon, and why. Drawn from teaching 700+ students this year and training teams at Thomson Reuters, Downer and Just Eat Takeaway. Your audience walks out with two or three workflows they can try before lunch.

AI for Leaders

Strategy and governance without the hand-waving

Boards and executive teams don't need another "AI will change everything" talk. They need to know what to allow, what to block, and what to invest in — this quarter, with the staff they actually have. A calm walk through the decisions leaders face, drawing on the Australian policy landscape, real shadow-AI case studies, and the governance material from my AI for Defence course. No computer-science degree required; no doom, no breathless optimism either.

Past Stages

Where I've Spoken

Getty Images — "Prompt Battle"

SXSW Sydney · October 2024

On stage at one of the world's biggest image libraries' own AI event — live prompt-craft in front of a festival audience.

West London Business

London · 2023–2026

My first corporate AI briefing, ten weeks after ChatGPT launched — and they've kept inviting me back ever since, most recently for their 2026 team retreat.

Australian Institute of Management

Ongoing facilitator

Regular AI course facilitation for one of Australia's most respected training institutions.

Corporate Keynotes & Sessions

2023–2026

Sessions and training for organisations including Thomson Reuters, Downer and Just Eat Takeaway — from executive briefings to hands-on team days.

A packed modern auditorium during a keynote, warm stage light washing over the audience
Fees

Keynotes (30–60 minutes) from $8,500 + GST, plus travel. Guest lectures for universities and associations (1–2 hours) from $2,250 + GST. Virtual where it suits your event.

Running a community event or non-profit? Ask — rates by discretion.

Speaker Kit

Everything Your Programme Needs, Ready to Paste

Rupert Chesman — headshot

Headshot

Print-friendly headshot for programmes and event pages.

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Intro Bio — copy and paste into your programme

Rupert Chesman is an AI educator, filmmaker and creative technologist based in the Blue Mountains, NSW. He was working commercially in AI nine months before ChatGPT existed, and was invited into OpenAI's DALL·E 2 early artist access programme in June 2022. He has taught AI continuously since February 2023 — more than 700 students this year, plus corporate training for organisations including Thomson Reuters, Downer and Just Eat Takeaway, and facilitation for the Australian Institute of Management. He is the author of The AI-Native Playbook. Before AI: twenty years of film production for SAP, Getty Images and KPMG among others, filmed in 30+ countries.

Short Version — for tight layouts

Rupert Chesman is an AI educator and filmmaker who was working commercially in AI nine months before ChatGPT launched. Author of The AI-Native Playbook, he has taught more than 700 students this year and trains teams at organisations including Thomson Reuters and Downer.
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Photo, bio, talks, past stages and contact — on one page for your events team.

Got a Date and an Audience?

Tell me about the event and I'll tell you honestly whether I'm the right fit for it. Twenty minutes, no pitch deck.

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Or email ru@rupertchesman.com