Episode 157 - Cybersecurity First, AI Second, Always

AI is showing up everywhere in business.

And a lot of owners are turning it on without realizing what they just gave access to.

In this episode, Wendy sits down with Darryl Cresswell, CEO and founder of myDWARE, to talk about why cybersecurity has to come before any AI rollout.

They dig into real world examples entrepreneurs can actually relate to.

AI agents running under owner level access.

Sensitive data leaking through email, CRM systems, and shadow AI tools.

And why flashy automation without guardrails can quietly destroy trust, value, and deal readiness.

Darryl breaks down the difference between AI bots, AI agents, and agentic AI in plain language.

They talk about shadow AI, third party tools, and how employees accidentally create risk.

And why buyers and auditors are now paying close attention to cybersecurity when valuing a business.

If you are experimenting with AI, thinking about automation, or planning to sell your business one day, this conversation will change how you think about “just turning it on.”

Cybersecurity first.
AI second.
Always.

Join The Freedom Files
Tired of money advice that feels complicated or out of touch?
Discover Freedom Files from Black Star Wealth — a bi-weekly dose of smart financial insights and real stories about building a life on your own terms.
Because freedom isn’t someday — it’s something you design.
Subscribe now at blackstarwealth.com/freedomfiles

Creators and Guests

Wendy Brookhouse
Host
Wendy Brookhouse
The Financial Planner for ambitious growth oriented Entrepreneurs
Shaun Whynacht
Editor
Shaun Whynacht
I’m the founder of Blue Cow Marketing and father of an amazing little boy. helping other business owners overcome challenges is my passion.
Episode 157 - Cybersecurity First, AI Second, Always
Broadcast by