AI is everywhere — in your inbox, your office tools, your phone, and probably in places your business never approved.

In this episode, Alyson and Omar break down what AI really does behind the scenes, how “shadow AI” sneaks into organizations, and the red-flag risks business leaders must understand before adopting any AI technology.

Omar and Alyson dig into:

• Why tools like Gmail, Google Workspace, LinkedIn, and meeting transcription bots are training on your data by default
• What “shadow AI” actually means and why it can quietly put your organization at risk
• Real examples of data exposure, privacy breakdowns, and AI systems behaving badly
• The business and legal dangers of using AI-generated contracts, customer service tools, or code
• A practical checklist to evaluate ANY AI vendor before you deploy them inside your company
• How mis-trained or garbage-in-garbage-out models can cause catastrophic business mistakes
• Why your vendors’ use of AI directly becomes your risk
• The future: data governance, transparency, and the uncomfortable imbalance of power between tech giants and consumers

This episode blends expertise, humor, and blunt honesty; it's a human conversation about a technology that affects every business decision today.

👉 If this episode helps you, please like, subscribe, and share. Sharing really fuels our mission to make cybersecurity more human, accessible, and resilient. Chapters:

00:00 – Intro & disclaimers

02:30 – Why tough conversations matter

03:30 – What is Shadow AI?

04:30 – Unmonitored AI and business risk

05:00 – Gmail, Google, LinkedIn & default AI training on your data

08:50 – AI listening devices & privacy concerns

11:00 – Meeting transcripts, confidentiality & inappropriate recording

14:45 – Celebrity privacy, consent, and the “ask before you film” principle

19:20 – Do you really need AI? Machine learning vs actual intelligence

21:00 – Garbage-in, garbage-out models and data poisoning

24:00 – Business risk when you don’t understand the tool you’re using

26:00 – AI customer service gone wrong

28:00 – What to look for in AI contracts: training rights, data deletion, shared models

31:00 – Web grounding, enterprise use, and user revolt

37:00 – IP concerns, AI art, music models & stolen datasets

43:00 – Vendor management & why your supplier’s AI becomes your risk

49:00 – Consumers, opt-in vs opt-out defaults & unfair advantages

55:00 – Insurance, data scanning & the terrifying future of personalized underwriting

1:02:00 – Why businesses must ask vendors how they use AI

1:10:00 – Free book giveaway & closing thoughts

What happens when you leave the military and step into the civilian cybersecurity world? In this episode, Air Force veteran and cybersecurity consultant Jose Toledo joins us to talk about the real (and often overlooked) challenges of the military-to-tech transition.

Jose’s career spans defense contracting, OT security, and strategic consulting with Google. He shares honest insights into identity loss, translating military experience into corporate language, navigating communication differences, and finding purpose after leaving a mission-driven environment.

In this conversation, we explore:

• why the military-to-civilian transition can feel disorienting • how veterans can turn leadership under pressure into an advantage • the challenge of “translating” military jargon into business value • soft skills veterans bring to cybersecurity and tech roles • communication differences: directness vs. corporate nuance • how office politics land for people trained in no-excuses environments • what veterans miss most after the uniform comes off • where to find purpose, meaning, and community after service • networking strategies for introverts, ambiverts, and those who hate small talk • the truth behind: “The tech is easy. The people are hard.”

Whether you're a veteran transitioning into cybersecurity, a hiring manager looking to understand veteran talent, or a cybersecurity leader navigating identity and career growth, this episode offers clarity, perspective, and actionable guidance.

00:00 – Intro & Welcome 01:12 – Meet Our Guest: Cyber Consultant & Air Force Veteran Jose Toledo 04:20 – How Jose Entered Cybersecurity Through the Military 07:58 – The Military Mindset: “Do More With Less” 10:45 – Why Translating Military Experience Is So Difficult 15:28 – Veterans Undervaluing Their Skills and Accomplishments 18:40 – The Interview Moment That Changed Jose’s Career 23:04 – Stress Leadership, Soft Skills & Mission Focus 27:52 – Responsibility at a Young Age: The Veteran Narrative 32:10 – The Mission-Shaped Hole After Leaving the Military 36:58 – Communication Style Differences: Directness vs. Corporate Culture 42:21 – Office Politics, Expectations & Emotional Intelligence 46:30 – Networking for Introverts and Ambiverts 51:12 – Teaching, Volunteering & Finding Purpose After Service 55:44 – Legal vs. Cyber: Translating Meaning Across Disciplines 59:20 – Final Advice: Reframing Your Value as a Veteran 01:02:10 – Closing & Subscribe

New episodes of The Cyber Mettle Podcast drop every other week.

Follow The Cyber Mettle for conversations on cybersecurity, leadership, law, business resilience, and the human challenges behind the keyboard.

Avoiding tough topics doesn’t protect your business — it weakens it. This episode reveals how confronting death and incapacity builds lasting strength, resilience, and continuity.

We all say we value resilience, but few of us talk about the moments that truly test it.

In this episode of The Cyber Mettle Podcast, hosts Alyson Laderman, Esq. and Dr. Omar Sangurima confront one of the hardest leadership topics: what happens when the leader or teammate is suddenly gone? From death and incapacitation to business succession and legacy planning, this conversation blends personal stories, legal insights, and cybersecurity strategy to explore what real resilience looks like — in life and in business.

💬 “Avoiding the conversation doesn’t protect anyone. It just leaves chaos for the people you love.”

Whether you’re a founder, executive, cybersecurity professional, or anyone responsible for others, this episode will challenge how you think about continuity, preparedness, and legacy. Because the best leaders don’t just protect their businesses, they protect the people behind them.

• How death and incapacitation fit into resilience planning

• Why avoidance is the biggest threat to business continuity

• Real stories of unpreparedness and the lessons they teach

• How to create a “resilience playbook” for your life and organization

• The crossover between estate planning and cyber resilience

• What legacy really means for modern leaders

• How to start difficult but necessary conversations

• How to plan for continuity and protect your digital assets

• Why transparency and documentation matter for teams and families

• How to turn uncomfortable topics into acts of love and leadership

🔥 Chapters: 00:00 – Welcome & Intro

03:00 – Why “tough conversations” matter

06:00 – Real-world stories of loss, chaos & resilience

12:30 – Probate nightmares and legal lessons

19:00 – Alyson’s personal story: from courtroom to caregiver

35:00 – The Gift Box: A blueprint for peace of mind

42:00 – Digital continuity and shared secrets

57:00 – Power of Attorney, living wills & 18-year-old planning

1:00:00 – Even the Muppets get it: Have the talk

1:04:00 – Closing thoughts on resilience & legacy Hosts: 🎙️ Alyson Laderman, Esq. — CEO of AKYLADE, attorney, and cybersecurity strategist 🎙️ Dr. Omar Sangurima — Cybersecurity and GRC leader, educator, and speaker

Together, they explore the human side of technology, leadership, business, and law, and what it takes to thrive when things get tough.

Keywords: business succession, leadership, resilience, business continuity, incapacitation planning, estate planning, cybersecurity podcast, GRC, risk management, continuity planning, digital legacy, resilience podcast, crisis management, The Cyber Mettle Podcast, Alyson Laderman, Omar Sangurima, leadership development, cybersecurity awareness, resilience strategy #Leadership #Resilience #Cybersecurity #BusinessContinuity #SuccessionPlanning #EstatePlanning #GRC #Podcast #TheCyberMettlePodcast

Listen now on: 🎧 Apple Podcasts | Spotify | Podbean | Amazon Music | iHeartRadio

Subscribe and follow for new episodes exploring how to lead, adapt, and build real resilience in a digital world.