Episode 157 - Cybersecurity First, AI Second, Always

Episode 157 - Cybersecurity First, AI Second, Always

From The Number by Wendy Brookhouse

December 18, 2025 · 36 min · Season 5

About this episode

Wendy Brookhouse discusses the importance of prioritizing cybersecurity before implementing AI in business with guest Darryl Cresswell.

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.

People in this episode

Host: Wendy Brookhouse

Guest: Darryl Cresswell

Topics covered

  • cybersecurity
  • artificial intelligence
  • business risk
  • automation
  • data protection
  • entrepreneurship

Keywords

  • cybersecurity
  • AI
  • automation
  • data leakage
  • entrepreneur
  • business value
  • shadow AI

Mentioned in this episode

Organizations: myDWARE

More episodes of The Number

Explore listener stats, chart rankings, contacts and more on the The Number podcast page.