Drink Coffee. Do Cool Stuff.

Jason Elrod
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Purpose. Clarity. A life built by choice, not momentum. If you didn't have to do anything, what would you do? Drink Coffee. Do Cool Stuff. is a podcast about the work of becoming who you are meant to be. It explores the question that sits underneath every meaningful life. Who would you become if nothing was required of you. It is a conversation about purpose, courage, and the discipline to build a life that reflects your values. I am Jason Elrod. I am an award winning CISO, author, and founder of Limitless Cyber. Most people know me for cybersecurity, but my world is broader than that. It is shaped by philosophy, mindfulness, martial arts, backcountry exploration, and a commitment to showing up with intention. Each week I sit with thinkers, doers, and builders. Cybersecurity leaders, creators, founders, and people committed to growth who refuse to drift through life on autopilot. If you want to think with clarity, lead with courage, and live like your choices matter, you are in the right place.

  1. AI Can’t Say “I Don’t Know” - Sol Rashidi on Judgment, Hallucinations & Leadership

    FEB 12

    AI Can’t Say “I Don’t Know” - Sol Rashidi on Judgment, Hallucinations & Leadership

    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: @solrashidiNewsletter solrashidi.substack.com

    43 min
  2. Curiosity Over Fear - Leadership, Judgment, and Staying Human in the Age of AI

    JAN 22

    Curiosity Over Fear - Leadership, Judgment, and Staying Human in the Age of AI

    Leadership rarely breaks down because of a lack of tools.It breaks down when fear replaces curiosity, and judgment gets outsourced. In this episode of 𝘋𝘳𝘪𝘯𝘬 𝘊𝘰𝘧𝘧𝘦𝘦. 𝘋𝘰 𝘊𝘰𝘰𝘭 𝘚𝘵𝘶𝘧𝘧., I sit down with Kara Schlageter, a people-first cybersecurity and technology leader, for a thoughtful conversation about leadership when certainty disappears. We talk about curiosity as a discipline, resilience without bravado, and why you can do everything right and still lose AND still grow. We also explore the role of AI in leadership, not from a hype perspective, but from a human one: where it helps, where it harms, and why judgment, accountability, and authenticity can’t be delegated. This isn’t a conversation about trends for the sake of trends.It’s about staying grounded when systems change, roles shift, and pressure is real. ☕ In this episode, we cover:• Curiosity over fear in leadership decisions• Resilience during disruption and transition• Gratitude without denial• AI as an amplifier, not a replacement• Why authenticity matters more than ever 𝘋𝘳𝘪𝘯𝘬 𝘊𝘰𝘧𝘧𝘦𝘦. 𝘋𝘰 𝘊𝘰𝘰𝘭 𝘚𝘵𝘶𝘧𝘧. is a podcast about leadership, purpose, and navigating uncertainty with clarity and courage. 👉 Subscribe for conversations that help leaders show up ready. What the video episode on YouTube @LimitlessCyber :  Curiosity Over Fear: Staying Human in the Age of AI | Kara Schlageter Connect with Kara on LinkedIn:  Kara Martin Schlageter

    59 min
  3. Why Some Leaders Crumble and Others Stand Firm - Stoic Leadership

    JAN 14

    Why Some Leaders Crumble and Others Stand Firm - Stoic Leadership

    Stoicism is often misunderstood as emotional detachment or indifference. In reality, it is a practical leadership discipline built for moments when pressure is high, decisions are imperfect, and responsibility is real. In this episode of Drink Coffee. Do Cool Stuff., Jason Elrod is joined by returning guest Brad Bussie for a grounded conversation on stoic leadership in modern executive roles. Together, they explore how stoic principles show up not as philosophy, but as daily practice for leaders operating in uncertainty. This conversation reframes stoicism as an operating system for leadership, focusing on emotional regulation, moral courage, and the discipline of choosing response over reaction. Jason and Brad discuss why leadership failures are often rooted in character rather than strategy, why temperance is one of the most overlooked leadership virtues, and how credibility is built when outcomes are not clean or popular. They also examine how stoicism can be misused or performed, drawing a clear line between genuine stoic leadership and performative restraint that masks ego, avoidance, or moral compromise. This episode is especially relevant for executives, CISOs, board-facing leaders, and anyone responsible for making high-stakes decisions who wants to remain steady, credible, and human under sustained pressure. Amazon Affiliate Links to books mentioned: The Obstacle is the Way - Ryan Holiday Courage Is Calling: Fortune Favors the Brave (The Stoic Virtues Series) - Ryan Holiday Subscribe & Stay Connected If you found this conversation useful, subscribe to Drink Coffee. Do Cool Stuff. for future episodes exploring leadership, clarity, and decision-making under pressure. 🎧 Podcast home: https://limitlesscyber.com/DCDCS  📺 Watch full episodes and clips on YouTube: https://youtube.com/@limitlesscyber  New episodes drop regularly.

    56 min
  4. Bonus Episode: AI Can’t Lead. The Human Responsibilities We Can’t Outsource

    JAN 5 ·  BONUS

    Bonus Episode: AI Can’t Lead. The Human Responsibilities We Can’t Outsource

    This is a bonus episode of Drink Coffee. Do Cool Stuff. It’s not a traditional conversation. It’s a short, focused leadership reflection. As AI continues to accelerate, the real challenge facing leaders isn’t how powerful the tools become. It’s what we decide to hand over and what we refuse to. AI can execute. It can generate answers. It can optimize decisions. What it cannot do is carry responsibility for the consequences. In this episode, I walk through the core human responsibilities that cannot be automated or outsourced, even in a highly AI-driven world: Judgment Moral courage Interpretation Accountability Presence This isn’t about competing with AI or trying to outwork it. It’s about out-framing it. Deciding what remains human work when systems get faster and pressure increases. We’ll be back to our regular conversations next episode.

    12 min
  5. Why Slowing Down Feels Unsafe: A Navy SEAL on trauma, ego, and rebuilding presence

    12/29/2025

    Why Slowing Down Feels Unsafe: A Navy SEAL on trauma, ego, and rebuilding presence

    High performers are often told to slow down, reflect, and be more present. But for many, slowing down doesn’t feel calming. It feels unsafe. In this episode of Drink Coffee. Do Cool Stuff., Jason Elrod sits down with retired Navy SEAL officer JJ Parma for a deeply honest conversation about elite performance, survival wiring, and what happens when discipline alone stops working. JJ shares how ego can function as armor, why many leaders live in a constant future-focused state, and how unresolved trauma (often rooted long before adulthood) shapes how we lead, decide, and relate to the world. Together, they explore burnout not as weakness, but as a system failure, and presence not as softness, but as one of the hardest disciplines to master. This conversation also touches on JJ’s personal journey of confronting root trauma, reframing healing as awareness rather than escape, and learning how to rebuild a life of clarity without losing edge, discipline, or purpose. This episode isn’t about shortcuts or prescriptions. It’s about understanding why slowing down can feel dangerous and what becomes possible when awareness finally replaces survival mode. Guest: JJ Parma Retired Navy SEAL Officer | Human Performance Consultant | Founder, Fourth Phase Consulting  Watch on YouTube (Limitless Cyber with Jason Elrod): Why Slowing Down Feels Unsafe Connect with JJ Parma:Website: The Fourth Phase Podcast with JJ ParmaLinkedIn: JJ Parma Follow Jason ElrodWebsite: LimitlessCyber.comLinkedIn: Jason Elrod Links from episode:Netflix Dcoumentary: In Waves and War  Drink Coffee. Do Cool Stuff. explores leadership, presence, and learning to show up well in uncertainty. Be present and lead with courage.

    1h 3m
  6. The Ritual Matters: Identity, Drift, and Designing the Next Chapter

    12/22/2025

    The Ritual Matters: Identity, Drift, and Designing the Next Chapter

    What happens when you strip away titles, roles, and expectations? In this episode of Drink Coffee. Do Cool Stuff., Jason sits down with longtime peer and retiring executive Brant Borchert for a deeply human conversation about ritual, identity, and the quiet drift that pulls people away from who they are meant to be. They explore how small habits compound into life-defining momentum, why ritual matters more than outcomes, and what happens when alcohol, status, or work stop being the center of your identity. Brant shares his journey stepping away from corporate life and into a purpose-driven next chapter focused on creativity, relationships, and intentional living. This episode is about leadership beyond the job title. About building a meaningful life one small decision at a time. And about choosing who you want to be when no one is watching. If you are navigating transition, questioning momentum, or redefining success, this conversation is for you. 🎙️ Drink Coffee. Do Cool Stuff. Because life is a leadership test. Show up ready. Watch the video version:  youtube.com/@LimitlessCyber Brants LinkedIn Follow Brants music: North Forks Instruments And Brant on Instagram

    57 min
  7. Eyes to See: AI, Leadership, and the Courage to Move Faster Than Comfort

    12/15/2025

    Eyes to See: AI, Leadership, and the Courage to Move Faster Than Comfort

    In this episode of Drink Coffee. Do Cool Stuff., Jason Elrod sits down with Bradd Busick to unpack what leaders are missing about AI, speed, and organizational courage. This is not a conversation about tools or hype cycles. It’s a real discussion about pace, culture, and what happens when leadership either creates momentum or becomes the constraint. Bradd shares lessons from his transition from healthcare into private equity, where AI is treated as a value-creation engine, not overhead. Together, they explore why composable systems matter, why most organizations mistake convenience for capability, and how leaders must shift from task management to priority-driven thinking. They also confront uncomfortable truths:Why healthcare moves slower than almost every other industry.Why banning AI is a fast path to irrelevance.Why the future belongs to leaders who ask better questions, not those who cling to control. This episode is a call to develop the eyes to see, the courage to act, and the discipline to build systems that make people stronger, not weaker. If you’re a leader navigating AI, uncertainty, or cultural resistance, this conversation is for you. Follow Bradd on LinkedIn.

    54 min
  8. The Quiet Drift: When Momentum Replaces Intention

    12/12/2025

    The Quiet Drift: When Momentum Replaces Intention

    Most people don’t lose their purpose in a single moment. They lose it slowly, quietly, and without noticing. In this solo episode of Drink Coffee. Do Cool Stuff., Jason Elrod explores the quiet drift and what happens when momentum begins to replace intention, especially for high performers and leaders. Drift doesn’t come from laziness or failure. It comes from capability. From saying yes too often. From carrying more than your share because you can. Over time, life starts making decisions for you, and you wake up moving fast but no longer in a direction that feels like your own. In this episode, Jason breaks down: What drift actually is and why it feels productive Why high performers are especially vulnerable to it The hidden costs of drifting: clarity, courage, and identity How to interrupt drift without burning everything down One honest question that can bring you back to intentional living This isn’t about dramatic change or sudden reinvention. It’s about awareness, presence, and small choices made deliberately. If something in your life feels busy but misaligned, this episode is an invitation to pause, reflect, and choose again. ☕ Drink coffee. Do cool stuff. And keep building a life that’s actually yours.

    7 min
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About

Purpose. Clarity. A life built by choice, not momentum. If you didn't have to do anything, what would you do? Drink Coffee. Do Cool Stuff. is a podcast about the work of becoming who you are meant to be. It explores the question that sits underneath every meaningful life. Who would you become if nothing was required of you. It is a conversation about purpose, courage, and the discipline to build a life that reflects your values. I am Jason Elrod. I am an award winning CISO, author, and founder of Limitless Cyber. Most people know me for cybersecurity, but my world is broader than that. It is shaped by philosophy, mindfulness, martial arts, backcountry exploration, and a commitment to showing up with intention. Each week I sit with thinkers, doers, and builders. Cybersecurity leaders, creators, founders, and people committed to growth who refuse to drift through life on autopilot. If you want to think with clarity, lead with courage, and live like your choices matter, you are in the right place.

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