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.

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I invited Graham Barlow onto The Real Bottom Line because his founder journey is one of the wildest I’ve ever heard. He started out as a teenager selling virtual game items on eBay, scaled that “hobby” into almost six figures a month, and eventually went on to build and exit multiple companies.

In our conversation, Graham and I dig into

• How he and a group of friends used bots to farm virtual currency long before in-app purchases were normal
  
• Why cash flow, projections, and financial discipline matter far more than top-line revenue
  
• The painful lessons he learned building a game studio and raising money

• How ego and “I’m the only one who can do this right” thinking quietly caps your business

• Why community and the rooms you put yourself in can dramatically change your sense of what’s possible

• The two strategic gaps he sees in most businesses right now… outbound sales and how teams use AI

We also talk about Founder Link, the community he never planned to build, and why so many founders desperately need a place where they can ask real questions, drop the armour, and get guidance from people who’ve already walked the path.

If you’ve ever hit a ceiling, questioned your next move, or wondered what it actually takes to build something someone would buy, you’ll get a lot from this conversation.

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

FinTech leader Carrie Forbes, CEO of Rockstar Advisory, joins Wendy to unpack the shift from startup energy to running energy, the corporate habits worth keeping, and how to make AI projects succeed with tiny, low risk wins. Human skills remain the moat... and that’s the optimistic bottom line.

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