Drink Coffee. Do Cool Stuff.

Jason Elrod
  • 5.0 (1)
  • Self-Improvement
  • Updated Weekly

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. Bonus Episode: The Father’s Day Ride

    16h ago ·  Bonus

    Bonus Episode: The Father’s Day Ride

    This bonus episode of Drink Coffee. Do Cool Stuff. was recorded during a motorcycle camping trip through the Nevada backcountry with my son, Luke. We were almost 700 miles into the ride, with around 200 miles on dirt. We chased thunderstorms, found a remote hot spring, camped by a lake at the end of a trail most people could not get to, and recorded part of the conversation from a truck stop on the final ride home. Luke is an AI engineer who builds automation and agent-based solutions, so the conversation naturally turned toward AI: where it is useful, where people are rightly concerned, what happens to work and identity, why local models matter, and why not everything needs to become AI just because it can. But this episode is really about more than technology. It is about getting away from the noise. Being present. Sharing hard miles with someone you love. And remembering that sometimes the best way to get out of your head is to get back into your body. Father’s Day. Motorcycles. AI. Nevada dirt roads. Hot springs. Thunderstorms. And a conversation I will remember for a long time.

    47 min

  2. 5d ago

    When a season ends before you are ready

    A season does not send you a notice when it ends. The light shifts. The air changes weight. Something that was true last month is quietly less true this month, and you feel it before you can name it. The same thing happens in a life. Specifically, it happens to the definition of winning you have been carrying, the one that formed early, got rewarded, and slowly stopped feeling like a belief and started feeling like reality. For a season, maybe a long one, that definition was exactly right. Then the season turned, and nobody told you that releasing it would feel less like relief and more like loss. This episode is about that moment. The low-grade friction underneath the competence. The grief of putting down a version of yourself you built deliberately. The question of what you were actually trying to get at underneath every scoreboard you ever kept. And what it means to update a definition of winning instead of abandoning it. Not a motivational episode. Not a therapy episode. Just an honest conversation about something most people are inside right now and almost nobody names. SHOW NOTES:  YoutTube Channel: https://www.youtube.com/@LimitlessCyber Podcast catalog: https://limitlesscyber.com/DCDCS LinkedIn: linkedin.com/in/thejasonelrod

    18 min

  3. Jun 18

    When You Become the Container

    When someone asks you who you are, what is the first thing that comes to mind? For most people, the answer is a function. A title. A role. And that reflex tells you something important — not just about how you introduce yourself, but about where your identity actually lives and what happens to it when the function changes. This episode is about the container problem. The slow, unannounced process by which we stop being the person inside a role and start being the role itself. What causes it. What it costs. And the work of maintaining the distinction before pressure makes that question urgent. No frameworks. No list of habits. Just an honest conversation about something most people feel and almost nobody names clearly. TIMESTAMPS 00:00 — The question nobody answers honestly: when asked who you are, what actually comes to mind first? 01:00 — How the fusion happens: capability to skill, skill to craft, craft to reputation, reputation to identity — and why nobody notices while it's occurring 02:00 — The container concept: what a role actually does for you, and the moment it stops being useful shorthand and becomes the definition of self 03:00 — What pressure on the container reveals: why professional disruption lands bigger than it should, and what that tells you about where the weight was resting 06:00 — The first thing that gets lost: curiosity — and why the most experienced people often become the most defended 07:00 — The second thing that gets lost: range — the parts of you that existed before the role arrived, and what happens when they go quiet for 20 years 08:30 — The third thing that gets lost: resilience — not the performance of it, but the settled kind that does not require external validation to hold its shape 09:00 — The harder question: who are you when you are not performing the role? The version that exists in the quiet, when the container is temporarily set aside 11:00 — The work: separation, not distance — what it actually means to know the difference between yourself and the container you carry 13:00 — The close: don't wait for the pressure to tell you whether the person inside the container is still there YouTube:  https://youtu.be/el7uozmoSXwYour Title Won't Save You | The Three Traps Destroying Security Leaders LinkedIn: linkedin.com/in/thejasonelrod

    16 min

  4. May 14

    Cybersecurity Is a People Problem with Heather Stratford

    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

    48 min
  5. Why Communication Fails Even When You’re Right

    Apr 13

    Why Communication Fails Even When You’re Right

    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.

    1h 5m
  6. 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
  7. 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
  8. 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
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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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