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