AI, Finance, and the Future: A Conversation with Christopher Penn

In this episode of Behind the Curtain, Money Made Simple, Julie welcomes Christopher Penn, co-founder of TrustInsights.ai and an authority on artificial intelligence. Together, they explore how AI is reshaping personal finance, from budgeting and investment strategies to preparing for job interviews and career shifts. Christopher shares practical advice on protecting personal data, using AI as a financial planning tool, and balancing machine-driven insights with human expertise. The conversation also examines AI’s impact on jobs, industries in demand, and how individuals can leverage these tools to adapt. Listeners will walk away with actionable tips, including a challenge to use AI for a personalized financial review.

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(00:00:00) Julie introduces Christopher Penn as the episode's guest, focusing on AI and money.

(00:01:53) Christopher explains generative AI and how large language models work.

(00:03:55) Privacy concerns: "If you're not paying, you are the product."

(00:05:20) Julie asks about AI's role in everyday search tools like Google and Siri.

(00:06:13) How AI can support personal finance planning with broad data insights.

(00:09:26) Prompting AI to act like a financial advisor and ask guided questions.

(00:12:03) Christopher's recommended AI platforms and the importance of paid versions.

(00:14:55) Why finance, law, and health always require human validation alongside AI.

(00:16:31) Fields most affected by AI: healthcare needs vs. jobs being displaced.

(00:20:50) Outsourcing vs. AI disruption — speed of change as the biggest challenge.

(00:24:09) The rapid pace of AI adoption and its effects on work and personal finance.

(00:26:26) Using AI as a neutral or adversarial voice to challenge financial assumptions.

(00:27:00) Christopher shares how AI can prepare candidates for tough job interviews.

(00:29:18) The concept of ikigai and how AI can help align skills with fulfilling careers.

(00:31:15) Negotiating pay and the foundational importance of cashflow analysis.

(00:34:34) Money advice Christopher wishes he'd learned earlier: cashflow is king.

(00:35:26) Final challenge: use AI to review your financial statements critically.

Links:

Christopher Penn on LinkedIn: https://www.linkedin.com/in/cspenn 

Rockland Trust: https://www.rocklandtrust.com/

Julie Beckham on LinkedIn: https://www.linkedin.com/in/julie-beckham-05589534