AI Over 50: Personalize Your AI So It Finally Gets You

Hosted by Brett Bouchard

Thu, Jul 9, 2026

4:00 PM UTC (45 minutes)

Virtual (Zoom)

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What you'll learn

Personalize any AI to stop generic answers

Set up your AI to answer with your background and goals every time, instead of the same reply it gives everyone.

Build your own context file in 10 minutes

Use a guided set of questions to create your personalized file, so you never face a blank page.

Reuse it across ChatGPT, Claude and Gemini

Set it up once and use the same file in any tool, so you stop re-explaining yourself in every new chat.

Keep your setup working over time

Update your context file as your work and goals change, so it keeps fitting you.

Why this topic matters

AI gives generic answers until it knows you, and that setup is the piece nobody shows you. Fix that and the vague, unusable replies turn into answers you can actually use. For professionals over 50, this is where your experience pays off, because good context is just judgment, and you have plenty. You build it once, reuse it in any AI, and every answer comes back sharper and sounds like you.

You'll learn from

Brett Bouchard

Ex-Google Director, 20+ yrs in tech, helping people over 50 thrive with AI

I spent more than 20 years in tech and go-to-market, including time at Google and multiple startups. When AI started changing everything, I began using it to augment my own solo practice, and I learned it the way a skeptic does, by testing it on real work. Along the way, one thing was missing: hardly any of the AI advice out there is focused on experienced professionals who have spent decades building real judgment.


That gap is why I started AI Over 50, and I'm on a mission to help experienced folks thrive in this new AI era. There is a real need for those of us between 50 and 65 to put AI to work, skeptically, practically, on our own terms, with no hype and without the overwhelm. My job is to make it genuinely useful, peer to peer, without the jargon.


Everything I teach comes back to three beliefs I developed working with these tools:


  • Be the skeptic who uses AI. Stay wary of the technology and get proficient enough to question it firsthand. The person who uses AI and still asks the hard questions is who we should all be right now.


  • Bet on your foundation. Learn the fundamentals that do not change with every new model release, and look past the noise to the systems underneath.


  • Your experience is the edge. Decades of work and change gave you judgment, pattern recognition, and the instinct to push back. That is the one thing AI cannot supply on its own and it is exactly what makes it work well.


If you have been curious about AI but unsure where to start, you are in the right place. Let's put your experience to work.

Previously at Google, Ancestry, AOL

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