*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 (https://digitalcowboystudio.substack.com?utm_medium=podcast)
This is the first episode of Season 2!
I’m back from the 2030: Interrugnum and ready to go.
In this episode, I observe my migration to Substack and the content I am corralling there for you.
I’ve done a lot of research, made a bunch of observations, and provided a good amount of guidance and hopefully entertained a bit.
Am I on track for what you want and need?
In this episode, I ask you the question:
"What topics interest you, out there on the Digital Frontier?”
Digital Cowboy Roundup (https://digitalcowboystudio.substack.com/)
Untraveled Road Companion (https://untraveledroadguide.substack.com/)
Crafting Competitive Cadence (https://competitivecadence.substack.com/)
Get my Book The Pivotal Tech Leader's Guide to the Untraveled Road (https://www.amazon.com/dp/B0FTSGCLQL?ref_=cm_sw_r_ffobk_cp_ud_dp_MJR2M9GP67PKPTX0YZTG_1&bestFormat=true) on Amazon
Get full access to Digital Cowboy Roundup at digitalcowboystudio.substack.com/subscribe (https://digitalcowboystudio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
17 Dec 2025
S1 EP9 - 2030: The Interregnum
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
Get full access to Digital Cowboy Roundup at digitalcowboystudio.substack.com/subscribe (https://digitalcowboystudio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
10 Dec 2025
S1 EP8 - AI Anchored in Mediocrity
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.
With all the focus of energy, $ and time on Transactional AI solutions, we are not advancing Collaborative AI at all.
This has a broad impact, potentially delaying advancements in Collaborative AI for decades as well as any chance of sensibly managing the approach to Artificial Super Intelligence at all.
We ask the question:
"Are we anchoring AI in mediocrity?"
LinkedIn articles:
AI Bubble or Not, we Need a Reframe (https://www.linkedin.com/posts/iamthedigitalcowboy_ai-bubble-or-not-40-60-of-companies-continue-activity-7401290024601825280-9JvK?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAChDPkB8Zm59XJWOvu0MUsGRLhHOpBR9Lw)
Website Blogs:
AI Bubble or Not, We Need a Reframe (https://digitalcowboystudio.com/#56cd3c51-fd5d-42db-b308-b56e3496e701)
Get my eBook The Pivotal Tech Leader's Guide to the Untraveled Road (https://www.amazon.com/dp/B0FTSGCLQL?ref_=cm_sw_r_ffobk_cp_ud_dp_MJR2M9GP67PKPTX0YZTG_1&bestFormat=true) on Amazon
Follow me on LinkedIn (https://www.linkedin.com/in/iamthedigitalcowboy)
Get full access to Digital Cowboy Roundup at digitalcowboystudio.substack.com/subscribe (https://digitalcowboystudio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
3 Dec 2025
S1 EP7 - Value Capture Gap
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 value at scale.
We ask the question:
"What's up with the Value Capture Gap?"
LinkedIn articles:
AI Bubble or Not, we Need a Reframe (https://www.linkedin.com/posts/iamthedigitalcowboy_ai-bubble-or-not-40-60-of-companies-continue-activity-7401290024601825280-9JvK?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAChDPkB8Zm59XJWOvu0MUsGRLhHOpBR9Lw)
Website Blogs:
AI Bubble or Not, We Need a Reframe (https://digitalcowboystudio.com/#56cd3c51-fd5d-42db-b308-b56e3496e701)
Get my eBook The Pivotal Tech Leader's Guide to the Untraveled Road (https://www.amazon.com/dp/B0FTSGCLQL?ref_=cm_sw_r_ffobk_cp_ud_dp_MJR2M9GP67PKPTX0YZTG_1&bestFormat=true) on Amazon
Follow me on LinkedIn (https://www.linkedin.com/in/iamthedigitalcowboy)
Get full access to Digital Cowboy Roundup at digitalcowboystudio.substack.com/subscribe (https://digitalcowboystudio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
26 Nov 2025
S1 EP6 - Human & AI Collaboration Around The Next Corner
In this episode, we look around the corner at true Human & AI Collaboration aka Collaborative AI, and ask the question:
"How do we move closer to achieving Collaborative AI?"
I introduce a 3-part reframing that is needed in order to adjust our vision so we can make it around the corner and not just adopt the next wave of AI, but adapt to is successfully.
As I discuss in the episode, this is a pretty meaty topic, so I'll be following up with a lot more detail in articles and posts.
Be sure to Subscribe (https://digitalcowboystudio.com/#1951ce92-e8c3-4cf2-be56-6e9b45c5d353) to keep up to date on posts, podcasts, promotions, publications, and any other newness!
The LinkedIn article for the 10 Collaborative AI Enterprise Use Cases (https://www.linkedin.com/feed/update/urn:li:activity:7399420617982345216)
The website post for the 10 Collaborative AI Enterprise Use Cases (https://digitalcowboystudio.com/f/human-ai-collaboration-it%E2%80%99s-time#56cd3c51-fd5d-42db-b308-b56e3496e701)
You can get my eBook The Pivotal Tech Leader's Guide to the Untraveled Road (https://www.amazon.com/dp/B0FTSGCLQL?ref_=cm_sw_r_ffobk_cp_ud_dp_MJR2M9GP67PKPTX0YZTG_1&bestFormat=true), on Amazon
Get full access to Digital Cowboy Roundup at digitalcowboystudio.substack.com/subscribe (https://digitalcowboystudio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
19 Nov 2025
S1 EP5 - Tech Leaders and Innovation Pt2
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.
Christopher is the CEO of Twelve33 Solutions and an expert in Innovation tools, techniques, and training.
You can reach Christopher via contact@twelve33solutions.com (mailto:contact@twelve33solutions.com) and his website (https://twelve33solutions.com).
I inteviewed Christopher for my book, "The Pivotal Tech Leader's Guide to the Untraveled Road" but in this part of the interview I ask him the question:
"Can anyone be taught to innovate or is it just those in the 'Ivory Tower'?"
You can get my eBook The Pivotal Tech Leader's Guide to the Untraveled Road (https://www.amazon.com/dp/B0FTSGCLQL?ref_=cm_sw_r_ffobk_cp_ud_dp_MJR2M9GP67PKPTX0YZTG_1&bestFormat=true), on Amazon
Be sure to Subscribe (https://digitalcowboystudio.com/#1951ce92-e8c3-4cf2-be56-6e9b45c5d353) to keep up to date on posts, podcasts, promotions, publications, and any other newness!
Get full access to Digital Cowboy Roundup at digitalcowboystudio.substack.com/subscribe (https://digitalcowboystudio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
12 Nov 2025
S1 EP4 - Tech Leaders & Innovation Pt1
In this episode, I invite Christopher McCune to the Roundup! This is part 1 of the discussion.
Christopher is the CEO of Twelve33 Solutions and an expert in Innovation tools, techniques, and training.
You can reach Christopher via contact@twelve33solutions.com (mailto:contact@twelve33solutions.com) and his website (https://twelve33solutions.com).
I inteviewed Christopher for my book, "The Pivotal Tech Leader's Guide to the Untraveled Road" but this gives us the opportunity to dig into more detail as I ask him the question:
"What is Innovation and why should it matter to Tech Leaders?"
You can get my eBook The Pivotal Tech Leader's Guide to the Untraveled Road (https://www.amazon.com/dp/B0FTSGCLQL?ref_=cm_sw_r_ffobk_cp_ud_dp_MJR2M9GP67PKPTX0YZTG_1&bestFormat=true), on Amazon
Be sure to Subscribe (https://digitalcowboystudio.com/#1951ce92-e8c3-4cf2-be56-6e9b45c5d353) to keep up to date on posts, podcasts, promotions, publications, and any other newness!
Get full access to Digital Cowboy Roundup at digitalcowboystudio.substack.com/subscribe (https://digitalcowboystudio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
29 Oct 2025
S1 EP2 - AI. Yeah. What is it Good For?
Still no red carpet at the Digital Cowboy Studio, but another red-hot topic.
In this episode, we turn up the lights and ask
"Are we getting what we want – and NEED – from the current generation of AI?"
I've lassoed a couple AI tools to help with this one.
If you are curious about the state of AI, this episode is for you!
Website blog post AI. Yeah! What is it Good For. Huh?! Absolutely Nuthin' (file:///C:/share/per/brian/DCS/biz/Marketing/podcast/ep2/TBD)
Linked in article AI. Yeah! What is it Good For. Huh?! Absolutely Nuthin' (file:///C:/share/per/brian/DCS/biz/Marketing/podcast/ep2/TBD)
You can get my eBook The Pivotal Tech Leader's Guide to the Untraveled Road (https://www.amazon.com/dp/B0FTSGCLQL?ref_=cm_sw_r_ffobk_cp_ud_dp_MJR2M9GP67PKPTX0YZTG_1&bestFormat=true) on Amazon
Be sure to Subscribe (https://digitalcowboystudio.com/#1951ce92-e8c3-4cf2-be56-6e9b45c5d353) to keep up to date on posts, podcasts, promotions, publications and any other newness!
Get full access to Digital Cowboy Roundup at digitalcowboystudio.substack.com/subscribe (https://digitalcowboystudio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
22 Oct 2025
S1 EP1-No Red Carpet but a Red-Hot Topic
No red carpet at the barn door of the Digital Cowboy Studio for this premier episode.
And that's just fine 'cause we're talking about function over form right now.
In this episode we put the hot iron on and ask,
"What if everything you thought you knew about Technology Leadership was not only out of date— but completely wrong?!"
I pull out some guidance from my book, "The Pivotal Tech Leader's Guide to the Untraveled Road".
If you're an aspiring, stalled or struggling Tech Leader, or just passionate about technology's impact on business, this episode is for you!
You can get my eBook The Pivotal Tech Leader's Guide to the Untraveled Road (https://www.amazon.com/dp/B0FTSGCLQL?ref_=cm_sw_r_ffobk_cp_ud_dp_MJR2M9GP67PKPTX0YZTG_1&bestFormat=true) on Amazon
Be sure to Subscribe (https://digitalcowboystudio.com/#1951ce92-e8c3-4cf2-be56-6e9b45c5d353) to keep up to date on posts, podcasts, promotions, publications and any other newness!
Website blog posts:
This isn't 'Leadership is Hard', It's Mission Impossible (https://digitalcowboystudio.com/f/5-sources-in-2025-agree-there-is-a-tech-leadership-crisis)
3 Key Aspects of Pivotal Tech Leaders (https://digitalcowboystudio.com/f/3-aspects-of-pivotal-tech-leaders)
5 Common Maladies That Are Crushing Tech Leaders (https://digitalcowboystudio.com/f/5-common-maladies-that-are-crushing-tech-leaders#56cd3c51-fd5d-42db-b308-b56e3496e701)
Linked in article:
This isn't 'Leadershp is Hard', it's Mission Impossible (https://www.linkedin.com/posts/digitalcowboystudio_this-installment-of-my-5-in-2025-series-pulls-activity-7381674829906833411-p10y?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAChDPkB8Zm59XJWOvu0MUsGRLhHOpBR9Lw)
5 Common Maladies That Are Crushing Tech Leaders (https://www.linkedin.com/posts/digitalcowboystudio_as-part-of-my-5-in-2025-series-here-are-activity-7381312433161822210-qDJV?utm_source=share&utm_medium=member_desktop&rcm=ACoAAF-E-_8Bh0u9Pd1ELKpnPetFAZ7FTVPMHm8)
SN.AFU and the 3 Factors Driving the Living Nightmare (https://www.linkedin.com/posts/digitalcowboystudio_the-global-leadership-crisis-has-been-cutting-activity-7380240317649903616-5Pux?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAChDPkB8Zm59XJWOvu0MUsGRLhHOpBR9Lw)
Get full access to Digital Cowboy Roundup at digitalcowboystudio.substack.com/subscribe (https://digitalcowboystudio.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4)
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