Apple, Adobe and beyond: how Matt Strain became an ‘AI whisperer’
Episode 44
Episode overview
In this episode, the Forbes‑dubbed “AI whisperer” Matt Strain joins Dave Allen to unpack his journey from Apple and Adobe to The Prompt, where he’s advising non‑technical leaders on the human side of AI.
They explore career pivots, why relationships and culture still matter more than ever, and how CEOs can move from AI anxiety to practical, people‑first adoption.
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It became clear the real challenge wasn’t technical, it was: how does the average person who’s not a technologist understand and adapt to something that feels like a threat to their identity?
Matt Strain Founder, The Prompt
Forbes has labelled Matt Strain the “AI Whisperer”.
But what connects him to the world is not the technology he uses, but the people he keeps closest.
Matt is a man of great ambition, always willing to leave comfort in search of something new. His departure from prestigious roles at Apple and Adobe should be proof-enough of that.
For leaders trying to find the balance between the safe play and the ambitious one, between embracing technology and prioritizing humanity, Matt Strain gives us the roadmap.
What was going to be nine months in Asia turned into about nine years, just being open and saying yes to things that weren’t 100% defined, but were directionally where I thought I wanted to go.
Matt Strain Founder, The Prompt
You will learn:
- How Matt Strain navigated pivotal career moves from Apple and Adobe to becoming an “AI whisperer”.
- Why culture and relationships often matter more than strategy.
- What an “AI Readiness Audit” looks like in practice, and the hidden gaps it tends to reveal.
- How CEOs and executives can start using AI in their own lives and work to model healthy, responsible adoption.
- Practical ways to use AI to become a more thoughtful, creative, and effective human.
If I was doing it all again, I would spend more time focusing on developing and adding value to that network, because those are the people you can pick up the phone and call 30 years later.
Matt Strain Founder, The Prompt
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