In this episode of Drink Coffee. Do Cool Stuff., I sit down with entrepreneur and cybersecurity founder Heather Stratford to talk about why most security awareness training still fails and what it actually takes to change behavior inside organizations.

We explore the human side of cybersecurity, including:

• Why compliance doesn’t equal culture
• How behavioral change actually happens
• Leadership vs authority
• Why people are both the problem and the solution in cybersecurity
• Entrepreneurship, discipline, and resilience
• The hidden realities of building strong security cultures

Heather shares lessons from building multiple companies, including Drip7, and explains why effective security training must move beyond checkbox compliance and become something people actually understand, remember, and apply.

This conversation goes far beyond cybersecurity awareness training. It’s ultimately about leadership, ownership, culture, and the disciplined consistency required to build anything meaningful.

If you lead teams, build organizations, or care about resilience in the modern world, this episode is for you.

🎧 Drink Coffee. Do Cool Stuff.
Cybersecurity, Leadership & Life at the Edge.

Heather Stratford:

• LinkedIn: https://www.linkedin.com/in/drip7ceo/
• Website: https://drip7.com

#Cybersecurity #Leadership #Culture #CISO #RiskManagement #BehaviorChange #SecurityAwareness #ExecutiveLeadership #DrinkCoffeeDoCoolStuff

Fear gets results. But it also leaves damage behind.

In cybersecurity and leadership, we’ve used fear, uncertainty, and doubt for years to drive action.

Sometimes it works. Sometimes it creates alignment.
And sometimes, it quietly breaks trust.

I’m Jason Elrod, an executive leader, strategic advisor, author, and founder of Limitless Cyber.
I help leaders turn complexity into clarity and build resilience in high-stakes environments.

In this conversation with Bindi Dave, we unpack where communication actually breaks down, why being “right” isn’t enough, and how leaders unintentionally lose their audience even when their message is clear.

We also explore a different way to think about communication.

Not as a 50-50 exchange, but as full ownership.

Communication is a 200% responsibility.

If you’ve ever felt like your message didn’t land the way it should have, this episode will hit home.

Connect with Bindi Dave':
LinkedIn: https://www.linkedin.com/in/bindidave/

🎧 Learn more and access all episodes:
https://limitlesscyber.com/DCDCS

👉 Follow the show for more conversations like this.

Artificial intelligence is advancing faster than most leaders have time to process it.

But the real risk is not the technology.

It is the erosion of judgment.

In this episode of Drink Coffee. Do Cool Stuff., I sit down with Sol Rashidi to explore what AI can do, what it cannot do, and where leaders are getting it dangerously wrong.

Sol is a five-time C-suite executive and global AI and data leader who has built and governed large-scale AI initiatives inside some of the most recognized organizations in the world. She holds multiple patents in AI and data innovation and is a sought-after advisor and keynote speaker on the future of work, governance, and human amplification.

But this conversation is not about hype.

It is about leadership.

We unpack:

• The critical difference between using AI and doing AI
• Why AI hallucinations are a leadership and governance issue, not just a technical flaw
• The danger of mistaking confidence for competence
• How organizations should think about AI governance in practical terms
• Why outsourcing tasks is smart, but outsourcing thinking is not

Sol challenges the narrative that AI is primarily a cost-cutting tool and reframes it as something far more important: a human amplification tool that must be deployed with discipline, discernment, and accountability.

If you are a C-suite executive, board member, CISO, or leader navigating AI transformation, this episode will help you slow down, think clearly, and lead intentionally.

Because in the age of AI, the leaders who stay relevant will not be the ones who automate the fastest.

They will be the ones who think the best.

Connect with Sol and follow her work:

LinkedIn: https://www.linkedin.com/in/sol-rashidi-mba-a672291/
YouTube: https://www.youtube.com/@solrashidi
IG: @solrashidi
Newsletter solrashidi.substack.com