Enterprising Minds

Hosted by Dave Dougherty, Ruthi Corcoran, Alex Pokorny

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Latest episode

Jul 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.

Listen to episodes

60 recent

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

May 12, 2026Episode 7757 min

Ep 77: AI Tutors, College, and the Future of Education in 15 Years

What will education look like 15 years from now — and will college still matter? In this episode of Enterprising Minds, Alex, Dave, and Ruthi explore the future of education through a first-principles lens: What is school actually for? Is it about job skills, critical thinking, confidence, community, or learning how to learn? The conversation covers how AI tutors and personalized learning could reshape classrooms, why great teachers and mentors still matter, and whether college will continue to serve as a safe place to explore, fail, and figure out who you are. The crew also debates the role of humanities, technical skills, Socratic learning, outdated curricula, and how AI could help teachers focus less on managing at scale and more on facilitating meaningful learning. If you’re interested in AI in education, the future of college, personalized learning, critical thinking, or how technology may change the way the next generation learns, this episode is for you. 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

April 28, 2026Episode 7645 min

Ep 76: AI That Actually Helps - Home Agents, Coaching Assistants, and a 4-Hour Audit

In EP 76 of Enterprise Minds, Alex and Dave get tactical about the AI workflows they’re actually using right now. Alex shares how he built personal agents for lawn care, plant watering, groceries, and even work-from-home fitness reminders—while also unpacking the real tradeoffs of giving AI access to browsers, calendars, and notifications. Dave explains why personalized AI use cases are what finally make the value click for most people, using examples like a custom coaching assistant for youth basketball and Special Olympics planning. They also dig into one of the biggest “oh crap” moments yet: Dave used AI to complete what used to be a $15,000–$20,000 agency project in just four hours, including brand standards, SEO audits, a content roadmap, and formatted Asana task uploads. From there, the conversation gets bigger: how AI may change how we judge quality, credibility, and even people themselves. It’s a practical, thoughtful episode on where AI is already helping—and where it’s starting to get strange. 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

April 14, 2026Episode 7544 min

Ep 75: Claude, Cowork, and the New AI Oh Crap Moment

In this episode of Enterprising Minds , Dave, Alex, and Ruthi dig into their latest experiences with Claude and Claude Code, and why these tools sparked a genuine “oh crap” moment about how quickly AI is changing work. Dave shares how Claude compressed months of startup research into a polished report and slide deck in under half an hour, while Alex explores how AI is becoming less of a novelty and more of a practical task agent for coding, analytics, and personal workflows. Ruthi brings the counterbalance, asking the most important question of all: faster work toward what end? The conversation moves beyond hype into something more useful: where AI actually adds value, where it still falls short, how enterprise environments lag behind consumer tools, and why change management may be the real bottleneck. From side hustles and coaching youth basketball to lawn care agents and enterprise analytics, this is a grounded discussion about what happens when AI starts removing the parts of work people least enjoy. 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

March 24, 2026Episode 7434 min

Ep 74: AI Wrote the Report and Missed the Biggest Problems

In this episode of Enterprising Minds, the team digs into where AI still falls short in real-world work. Alex shares how Claude and ChatGPT produced polished SEO and paid search reports that completely missed critical issues hiding in the source data, while also struggling badly with logic and humor in a fiction-writing experiment. Ruthi and Dave unpack why AI often excels at summarizing known best practices but stumbles when real judgment, application, and iterative thinking are required, leading to a practical conversation about better prompting, better workflows, and why human oversight still matters. 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