Enterprising Minds

Hosted by Dave Dougherty, Ruthi Corcoran, Alex Pokorny

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Latest episode

Oct 2026

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EN-US

About the show

Welcome to Enterprising Minds , where industry veterans, and friends, Alex Pokorny, Ruthi Corcoran, and Dave Dougherty delve into the evolving world of digital marketing, merging insights with innovation. Each episode explores the intricacies of marketing technology, AI-driven strategies, and key trends—from SEO tactics to data-driven decision-making. Beyond just discussing current trends, our hosts examine the interplay between technology, leadership, and organizational culture, providing practical advice on how creativity and personal development can revolutionize marketing and business strategies, keeping you at the cutting edge of innovation. Join the conversation by subscribing to Enterprising Minds on Apple, Spotify, YouTube, or your favorite podcast player. Don’t miss out on our bi-weekly episodes that bridge the gap between technology and creativity in digital marketing, and like, comment, and share to stay at the forefront of innovation with insights that can transform your business strategy and personal growth.

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60 recent

October 21, 2026Episode 8741 min

Ep 87: AI as a Coworker - Agents, Automation, and the Frustrations of Working with AI

What happens when AI starts behaving less like a tool and more like a coworker? And why do we expect perfection from AI when we'd tolerate the same mistakes from a human colleague? In this episode of *Enterprising Minds*, Alex and Dave share their experiences building AI workflows, experimenting with Claude Cowork, and navigating the frustrations of AI memory, inconsistent outputs, and automation. They also explore what's coming next, from autonomous agents and AI swarms to entirely new ways of working. Plus, they discuss practical AI wins, including automating corporate paperwork, analyzing public data, and planning home renovations. It's a conversation about moving beyond AI as an answer engine and discovering what these tools can actually help us accomplish. What have you built or automated with AI recently? Let us know in the comments! Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

October 6, 2026Episode 8651 min

Ep 86: Laser Cats and Compliance - Designing Websites for the AI Search Era

If customers discover your content through an AI chatbot, what should your website do when they finally arrive? Alex Pokorny and Dave Dougherty explore whether AI search creates room for more distinctive website design, while keeping accessibility, technical information, and discoverability in place. The conversation connects website strategy with public relations, customer service, and the relationships behind a brand’s reputation. From nostalgic internet design and Liquid Death’s personality to a frustrating retail chatbot experience and a B2B purchasing example, Alex and Dave discuss where efficiency helps, where automation creates friction, and why understanding your customers still matters. Explore more from Enterprising Minds at https://enterprising-minds.com, and share how AI search is changing your approach to websites and customer relationships. Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

September 22, 2026Episode 8545 min

Ep 85: The Three-Week Funnel That Keeps a Job Search Moving

Alex opens with a side project he cannot put down: a statistical model that answers which small business a town can actually support, and where it should go. He built it from free U.S. Census APIs, Overture business data, and a federal dataset on underserved healthcare areas, stitched together with Python in a free Google Colab notebook. The finding underneath the project is the part worth keeping. Population-dependent businesses hold a fairly tight ratio to the people around them, and when a town grows or shrinks, the businesses lag that change by years. The gap between the two is the opportunity. The conversation then turns to what happens after the research is done, which is where most side projects die. Dave walks through the planning system he actually keeps: a free Asana project built for the year, chunked into quarters, with the podcast cadence, basketball season, and family time loaded in as real constraints. The system is built to push back, asking how many hours a week he can honestly give something before it goes on a list. Alex makes the harder argument. Most AI-generated to-do lists are noise, and the better question is what actually breaks if you skip the task. The second half is for anyone watching layoffs land near them. Alex shares the job search framework he built after his own layoff and later ran with roughly 15 people. Name your salary floor before you need it. Apply only to your top tier for the first three weeks, then widen one tier at a time. Treat applications as a funnel where a cohort goes dead by week four. Take two days a week off from searching on purpose, because endless scrolling is neither pleasant nor effective. Dave adds the layer the framework predates, including using voice capture and a transcript to turn a career into case studies you can use in interviews and on a site. Both hosts land in the same place. The tools got radically cheaper, the data got radically more available, and the constraint moved. What is scarce now is judgment about what deserves your time. Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

September 1, 2026Episode 8445 min

Ep 84: Handing Out AI Licenses Is Not a Rollout

Buying AI seats is not the same as rolling out AI. The gap between the two is training, and it's where most enterprise deployments quietly stall. This episode covers what actually drives adoption: culture, access setup, and hands-on demos that give people a reason to care before you hand them a tool. AI doesn't behave like a normal software rollout. The capabilities keep shifting from chat to reasoning to more autonomous work, so training built for one stage goes stale fast. The hosts also draw a line worth drawing: a lot of products marketed as agents are pre-trained chatbots wearing a better name. People adopt differently. Experimenters figure it out by breaking things. Everyone else wants a walkthrough. Designing for only one of those groups is how enthusiasm dies in month two. That same gap shapes the anxious conversations about capacity and job security, most of which trace back to a fuzzy understanding of what AI genuinely replaces. Reliability is where the standards diverge. Trust but verify is a reasonable posture for drafting. In finance, legal, and technical support, the tolerance for a confident wrong answer drops to roughly zero. The episode ends on craft, and the case that AI nudges creative work toward the internet's average, stripping out the personal bias and narrative that make it distinct. Good enough tasks, yes. Differentiated work, not yet. Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

August 18, 2026Episode 8350 min

Ep 83: The ROI of AI - Productivity, Creativity, and the Work That Actually Matters

What is the real ROI of AI—and how do you prove it without reducing every benefit to hours saved or headcount eliminated? Alex and Dave dig into the increasingly complicated business case for enterprise AI, from software licenses and token costs to agentic workflows, human oversight, and the danger of measuring productivity by output alone. They examine why an AI-generated presentation, report, marketing campaign, or analysis isn’t automatically valuable just because it was created faster. The conversation expands into organizational change, leadership, marketing and sales alignment, AI-generated content, creativity, and what Formula 1 can teach businesses about feedback loops and performance. The central question: Are we using AI to produce more work—or to produce better outcomes? Plus, the episode takes a detour through K-pop Demon Hunters, guided journals, C-3PO, laundry-folding robots, Roombas, and the future of physical AI. Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

July 29, 2026Episode 8249 min

Ep 82: AI Turned a Phase 10 Question Into 7.5 Million Simulations

A casual question about the card game Phase 10 turned into 7.5 million Monte Carlo simulations, a research paper, a DOI, an ORCID-linked researcher profile, and a submission for publication. In this episode of Enterprising Minds, Alex explains how an AI-assisted probability question became an unexpected research project—and why the experience felt fundamentally different from ordinary chatbot use. The conversation expands into a practical and philosophical discussion about the new AI workflow: How do Claude, ChatGPT, Gemini, and Copilot differ as research tools, thought partners, and everyday assistants? When should AI push back instead of immediately producing an answer? How do we prevent personalized AI systems from trapping us inside information bubbles? And when AI helps create a paper, presentation, email, image, or story, who deserves credit—and who remains accountable? The hosts also explore: -Using AI for research, simulations, DIY projects, and creative work -Why some AI-generated material feels generic -The difference between delegating work and abandoning responsibility -Why sending unedited AI output shifts the burden to the recipient -Whether sharing prompts or interactive conversations is more useful than sharing giant AI-generated documents -Building custom creative-writing systems with craft guides and character cards -AI licensing, artist compensation, and music-industry royalties -The rise of agents, Cowork-style tools, and computer-controlling assistants -Whether increased AI productivity could intensify workplace burnout The real question is no longer whether people are using AI. It is whether they are using it thoughtfully—and whether they are willing to take responsibility for the results. Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

July 14, 2026Episode 8137 min

Ep 81: The Real AI Divide - Enterprise Restrictions vs. Personal Innovation

Microsoft Copilot promises deep integration with the tools businesses already use—but licensing restrictions, limited access, and inconsistent capabilities can make the experience frustrating. In Episode 81 of Enterprising Minds , the team explores the gap between enterprise AI platforms and more flexible tools like ChatGPT, Claude, and Gemini. They discuss why Copilot can feel limited, how AI agents differ from traditional chatbots, and what changes when AI can complete tasks instead of simply generating text. The conversation also covers practical automation examples, including updating dozens of YouTube descriptions, reformatting spreadsheets, tracking open tasks, and turning one information-gathering meeting into multiple finished business documents. Beyond workplace productivity, the hosts examine how AI can support citizen science, historical document preservation, creative writing, cooking, personal projects, and everyday experimentation. They also discuss security, trust, human oversight, and why some forms of friction are still necessary for developing real skill and judgment. Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

June 23, 2026Episode 8032 min

Ep 80: Separating AI Discovery From Execution

In Episode 80 of Enterprising Minds, Dave breaks down one of the most useful shifts he has made in working with AI: separating discovery from execution. Instead of jumping straight to “create this thing,” Dave walks through how to use AI to build better context first. He shares how he created an AI project manager for work, used voice memos to capture project details, developed personal brand standards, and applied lessons from creative writing to make AI outputs more aligned with personal taste, voice, and intent. This episode is especially useful for anyone who feels overwhelmed by AI tools or frustrated that the outputs sound too generic. The key takeaway: better AI results come from better setup, clearer context, and more deliberate prompting. Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

June 9, 2026Episode 7942 min

Ep 79: Why AI Won’t Replace Taste, Strategy, or Human Judgment

In Episode 79 of Enterprising Minds, Alex and Dave dig into the current state of AI in marketing, business, and everyday workflows — from the shift away from prompt engineering toward AI agents, to the growing reality check around costs, token limits, subscriptions, and automation fatigue. The conversation explores whether AI agents still deliver enough value to justify the time spent building and managing them, how model improvements are changing workflows, and why more powerful AI does not automatically mean better results. They also unpack the widening gap between AI hype and practical use, including Google I/O announcements, AI IPO speculation, data center realities, and the CFO-level questions emerging around AI budgets. From using voice memos as a project management tool to the risks of generic AI-generated campaigns, this episode makes the case that AI is useful — but not magic. The real differentiator is still human taste, strategic thinking, experience, and knowing when not to automate. Watch as Alex and Dave discuss why AI may not be a moat on its own, how marketers should think about automation more realistically, and why the best use of AI might be freeing up more time for actual human connection. Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

May 26, 2026Episode 7854 min

Ep 78: AI Agents, Creative Workflows, and the Hidden Cost of Limitless Productivity

In this episode of Enterprising Minds, Dave and Alex explore how AI is moving beyond simple chat tools and into more complex workflows, from Microsoft Copilot Studio agents to personal AI project management systems. Alex shares what it is like to build agents inside Copilot Studio, including the surprising complexity of creating tightly governed enterprise tools, the difference between personal AI experimentation and corporate AI rollout, and why organizational change management may be one of the hardest parts of AI adoption. Dave brings the conversation into personal productivity and creative work, explaining how he uses Claude, Asana, voice memos, and brand standards to build a “co-CEO” system for his personal brand, podcast, and writing goals. The hosts also discuss the psychological side of AI-assisted productivity: tracking wins, avoiding the trap of split attention, and recognizing the early signs of AI burnout. The episode closes with a deep dive into creative writing. Alex explains how he is using Claude as an editor and structural partner as he writes a comedic novel, while Dave shares how AI is helping him return to poetry, evaluate literary journals, and manage submissions. Along the way, they unpack why AI can support writers without replacing the craft, why humor is still hard for large language models, and why editing remains the real work. Subscribe to Enterprising Minds on Apple , Spotify , YouTube , or your favorite podcast player. Subscribe to the Pathways Newsletter where we're exploring AI, marketing, and marketing careers together every week! You'll get unique case studies, deeper dives into some of the podcast topics, and more: https://bit.ly/em-pathways-pod Do you have ideas or suggestions? Get in touch at enterprisingmindspodcast@gmail.com Connect with Dave Website: https://bit.ly/em-dave-website-pod YouTube: http://bit.ly/41zuOfc Instagram: https://bit.ly/41zCPjZ LinkedIn: https://bit.ly/40J3867 Connect with Ruthi LinkedIn: https://bit.ly/3ZvZH1v Connect with Alex Website: http://bit.ly/3Z5MwVT LinkedIn: http://bit.ly/3KPDmIy

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