Ep 50: Navigating the World of Freelancing - Essential Tips and Advice

How do you balance innovation and caution in the age of enterprise AI? In this lively and thought-provoking episode of Enterprising Minds, hosts Dave Dougherty, Ruthi Corcoran, and Alex Pokorny dive into the complexities of AI in HR—from data privacy dilemmas to tool adoption challenges. Should you feed proprietary or personal data into AI tools? What happens when employees bypass official channels? And how do performance reviews and enterprise culture evolve with AI assistance? Tune in to hear debates, frustrations, and surprising insights that will resonate with every professional navigating AI in the workplace.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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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

In this episode of Enterprise Minds, hosts Dave Dougherty, Alex Pokorny, and Ruthi Corcoran explore the evolving discussion around agentic AI and its current state. They dissect the difference between longstanding automated workflows and the emerging (yet often overstated) promise of agentic AI—technology that can reason, act, and learn independently. Through personal anecdotes, analogies, and real-world examples, they explore the current capabilities and limitations of AI tools, highlighting the critical gap between today’s practical tools and tomorrow’s intelligent agents. Packed with insights, humor (including Darth Vader ducks), and grounded analysis, this episode is a must for tech professionals, marketers, and AI enthusiasts looking to make sense of the hype and the reality.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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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

In this episode of the Enterprising Minds podcast, co-hosts Ruthi Corcoran and Alex Pokorny dive deep into the evolving world of AI tools. From personal applications, such as sunscreen research and interior design experiments, to professional use cases that revolutionize marketing workflows, they explore the real-world implications of integrating AI into daily life. Alex shares how he builds automated systems using ChatGPT, Google Ads Scripts, and Screaming Frog, while Ruthi reflects on prompt engineering and the limitations of current AI models. Together, they discuss the pitfalls of modern search engines, the erosion of trust in e-commerce due to AI-generated content, and the value of having intelligent agents assist in troubleshooting and creativity.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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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

Welcome to the latest episode of Enterprising Minds! In this episode, the entire crew dives deep into the current state of AI adoption and its impact on work and productivity. Alex kicks things off by asking whether we're near the 'critical mass' point where the widespread access to AI tools like ChatGPT is leading to meaningful output. The team explores their experiences with AI, discussing the shift from staying current with developments to effectively applying the tools in their daily lives. Topics include the impact of AI on productivity, the shift in use cases from idea generation to personal development, and the future of managing AI-driven systems. We also touch upon the importance of finding balance, strategic thinking, and continuous learning in an increasingly AI-driven world. Join us for a thought-provoking discussion about the future of AI and how it affects our work and lives.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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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

In Episode 53 of Enterprising Minds, hosts Dave Dougherty and Alex Pokorny take us into the AI Playground — a space where creativity meets strategy. From text-based RPGs and WWII battle simulations to public speaking and marketing strategy, this episode dives into surprising, fun, and impactful ways AI is being used beyond the typical productivity narratives. Hear personal stories, experiments, and expert insights on how AI can augment creativity, leadership, and business innovation. Whether you're just starting your AI journey or looking to deepen your engagement, this episode offers inspiration and practical examples in equal measure.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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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

In this episode of Enterprising Minds, Dave, Alex, and Ruthi dive deep into the realities of freelancing—from initial struggles and business development to pricing strategies and the art of building lasting client relationships. Alex shares hard-earned lessons from years in digital marketing and SEO freelancing, revealing how he navigated subcontracting, agency collaborations, and the elusive retainer model. Ruthi brings an outside perspective, raising key questions about overhead, pricing psychology, and the emerging impact of AI on freelance work. Whether you're starting out or looking to grow your freelance business, this episode is packed with insights you won't want to miss.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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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

In Episode 51 of Enterprise Minds, Dave Dougherty, Alex Pokorny, and Ruthi Corcoran dive deep into what it really takes to navigate and complete corporate projects successfully. From building smart alliances to managing egos and creating compelling visions, they offer tactical strategies for surviving and thriving in complex corporate environments. Whether you're spearheading a small initiative or leading a large enterprise project, this conversation offers essential advice on making real progress.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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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

Welcome to our milestone 50th episode! In this special episode, we delve into the world of freelancing, inspired by a listener's request. Join hosts Alex, Ruthi, and Dave as they share their personal experiences and expertise in freelancing, from the basics of setting up an LLC, managing finances, and understanding insurance, to practical advice on finding clients and projects. Whether you're considering freelancing or looking to improve your freelance business, this episode is packed with valuable insights and actionable tips to help you succeed. Don't miss out on this comprehensive guide to starting and thriving in the freelancing industry!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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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

In Episode 49 of Enterprise Lines, we explore the complex and often misunderstood balance between AI-driven automation and the irreplaceable value of human expertise in today’s business landscape. As AI tools become more sophisticated, businesses face new challenges in delivering truly personalized experiences, especially in the world of B2B commerce.The conversation begins with reflections on upcoming speaking engagements before diving into a candid discussion about AI’s current limitations. Alex shares how AI often struggles to provide meaningful context—like understanding personal budgets or intent—and how human interactions still outperform machines in these nuanced scenarios. Ruthi offers a compelling analogy using different types of travel experiences to illustrate the gap between generic AI personalization and authentic, human-centric connections.As the episode unfolds, Dave and Ruthi highlight the shifting role of sales in B2B, emphasizing that simply repeating website content no longer adds value. Instead, salespeople must become knowledgeable advisors. The team also reflects on how websites are becoming critical sources of truth in a world where misinformation and counterfeit content are on the rise.From the threat AI poses to entry-level roles, to the rise of AI agents capable of executing tasks previously reserved for humans, the episode unpacks how businesses must evolve. The conversation closes with a vision for the future—one where websites feed intelligent chatbots, SEO becomes a strategic backbone, and companies must still rely on creativity, critical thinking, and human agency to succeed.Whether you're a marketer, strategist, or tech leader, this episode will challenge your assumptions and spark new ideas about the future of work and technology.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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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

In Episode 48 of Enterprising Minds, we tackle a pressing workplace challenge: effectively onboarding and engaging entry-level employees in an increasingly remote corporate environment. As we approach our 50th episode milestone, we share insights and tips in a coffee talk-style discussion featuring hosts Ruthi Corcoran, Alex Pokorny, and Dave Dougherty. Key topics include the shift toward remote work since 2020, strategies for fostering a welcoming culture, and practical advice for new hires and managers. Join us as we explore ways to build connections, handle communication, and set new employees up for success in today's dynamic work landscapes.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/453sNKx Do you have ideas or suggestions? Get in touch at [email protected] Connect with Dave Website: http://bit.ly/3Z5L3Pn 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