All Episodes
Episodes
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...
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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 â not just about how you...
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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...
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Why Communication Fails Even When Youâre Right
Fear gets results. But it also leaves damage behind.
In cybersecurity and leadership, weâve used fear, uncertainty, and doubt for years to drive action.
Sometimes it works. Sometimes it creates alignment. And...
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AI Canât Say âI Donât Knowâ - 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...
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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 đđłđŞđŻđŹ đđ°đ§đ§đŚđŚ. đđ° đđ°đ°đ đđľđśđ§đ§., I sit down with Kara Schlageter, a...
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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...
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Bonus Episode: AI Canât Lead. The Human Responsibilities We Canât Outsource
This is a bonus episode of Drink Coffee. Do Cool Stuff.
Itâs not a traditional conversation. Itâs a short, focused leadership reflection.
As AI continues to accelerate, the real challenge facing leaders isnât how...
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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 doesnât feel calming. It feels unsafe.
In this episode of Drink Coffee. Do Cool Stuff., Jason Elrod sits down with...
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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...
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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...
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The Quiet Drift: When Momentum Replaces Intention
Most people donât 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...
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