*Technology moves at the speed of light. Humans don't. Let's talk about that.* Out on the digital frontier, the rules are still being written. And the cowboys who dare to explore this territory - the innovators, the skeptics, the builders, and the cautionary voices - have stories worth hearing. This podcast explores what happens at the cyber-physical boundary. Where cutting-edge capability meets the messy, beautiful, stubborn reality of the human condition. We're here to explore what happens when innovation outpaces wisdom, when automation meets emotion, and when the future arrives faster than we can make sense of it. **For the curious, the concerned, and the committed to getting this right.** Whether you're a CTO grappling with AI ethics, a leader navigating digital transformation, or simply a human trying to stay human in an increasingly algorithmic world- saddle up. **New episodes every week. Join the roundup.** **Subscribe wherever you wrangle your podcasts.** digitalcowboystudio.substack.com
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Contact path
Public web form
Booking probability
36%
Guest openness
Selective
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Signup to Generate a Pitch*Technology moves at the speed of light. Humans don't. Let's talk about that.* Out on the digital frontier, the rules are still being written. And the cowboys who dare to explore this territory - the innovators, the skeptics, the builders, and the cautionary voices - have stories worth hearing. This podcast explores what happens at the cyber-physical boundary.
Recent episodes include "S2EP1 - I’m Back From the 2030 Interregnum" (14 January 2026, 7 minutes), "S1 EP9 - 2030: The Interregnum" (17 December 2025, 21 minutes), and "S1 EP8 - AI Anchored in Mediocrity" (10 December 2025, 7 minutes).
Digital Cowboy Roundup publishes roughly weekly, with episodes averaging 15 minutes.
Booking probability for Digital Cowboy Roundup is 36%, and the host is rated Selective on guests. Digital Cowboy Roundup requires a Pod Score of 80 or higher. Digital Cowboy Roundup's contact route on record: public web form.
The strongest fits for Digital Cowboy Roundup are IT Services & Software Development.
Digital Cowboy Roundup is a general podcast.
Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.
Digital Cowboy Roundup
<p>This is the first episode of Season 2!</p><p>I’m back from the 2030: Interrugnum and ready to go.</p><p>In this episode, I observe my migration to Substack and the content I am corralling there for you.</p><p>I’ve...
Digital Cowboy Roundup
<p>Welcome to Digital Cowboy Roundup.I put my AI tools on a sleep timer, fired up my time machine and posted this episode from the EOY 2030. This is 2030: The Interregnum</p> <br/><br/>Get full access to Digital Cowboy...
Digital Cowboy Roundup
<p >In this episode, we look at the potential issue that AI is quickly approaching. It's not necessarily an AI bubble. It's more like an evolutionary stall. </p> <p >With all the focus of energy, $ and time on...
Digital Cowboy Roundup
<p >In this episode, we look at the continuing issues that the group of companies, the Digital Strugglers, are having in adapting to emerging technologies, such as AI. They continue to fail at realizing significant...
Digital Cowboy Roundup
<p >In this episode, we look around the corner at true Human & AI Collaboration aka Collaborative AI, and ask the question:</p> <p > "How do we move closer to achieving Collaborative AI?"</p> <p >I introduce a 3-part...
Digital Cowboy Roundup
<p >In this episode, I continue my conversation with Christopher McCune in the Roundup! This is part 2 of the interview. Check out Part 1 to get a great grounding in what Christopher and I discuss in this episode.</p>...
Digital Cowboy Roundup
<p >In this episode, I invite Christopher McCune to the Roundup! This is part 1 of the discussion.</p> <p >Christopher is the CEO of Twelve33 Solutions and an expert in Innovation tools, techniques, and training.</p> <p...
Digital Cowboy Roundup
<p >Still no red carpet at the Digital Cowboy Studio, but another red-hot topic.</p> <p >In this episode, we turn up the lights and ask</p> <p > "Are we getting what we want – and NEED – from the current generation of...
Digital Cowboy Roundup
<p>No red carpet at the barn door of the Digital Cowboy Studio for this premier episode.</p> <p>And that's just fine 'cause we're talking about function over form right now.</p> <p>In this episode we put the hot iron on...
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