Gaining the Technology Leadership Edge

Entrepreneurship isn't just about achieving financial milestones; it's also about navigating the mental, emotional, and spiritual challenges that arise. Join Mike as he chats with Mohamed Ahmed, author of "The Inside Out Entrepreneur," who shares insights from his five-year journey of building and selling a startup. Explore how mindset influences business growth, the dangers of hustle culture, and...

Join Mike as he delves into the 30-year journey of Jeff Barrella, CEO of Andromeda Technology Solutions. Discover how Jeff and his co-founders grew their business from a small startup to a 50-person team with repeated recognition as a best place to work. Explore insights on intentional company culture-building, leadership evolution, and navigating industry shifts like moving from break-fix to mana...

Mike and Ted Santos delve into the transformative journey of CEOs, emphasizing the often-overlooked necessity of personal change to drive business transformation. They explore common pitfalls, such as shifting blame to others, and the significance of leadership style in breaking stagnation. As Ted outlines his approach to producing business "miracles" by fostering disruptive strategies and redefin...

Join Mike as he delves into the world of legacy systems with Juan Lucas Barbier, the renowned COBOL Whisperer and founder of Cobb COBOL Agency. Discover why COBOL remains vital in today's tech landscape, powering critical sectors like banking and healthcare. Juan Lucas shares insights on modernizing COBOL systems using AI and human expertise, emphasizing the importance of documentation and domain-...

Mike engages with Frank Carone, former chief of staff to New York City Mayor Eric Adams, exploring the art of negotiation, leadership, and building a "culture of yes." Frank shares insights from his diverse career spanning law, business, and government, reflecting on pivotal projects like Willets Point and his tenure as commissioner for New York City’s Taxi and Limousine Commission. Listen in to d...

Explore the strategies behind Daniel Friker's impressive growth of a $300 million portfolio with nearly 50% profit increase. Mike and Daniel delve into the three fundamental tenets of business success: planning, executive sponsorship, and execution. Learn how utilizing data visualization tools like Power BI can drive incremental changes and improve operations. The discussion also touches on AI's r...

Sharissa Sebastian Depen joins Mike to unpack a leadership problem that hides in plain sight: why high achievers can have the title, salary, and influence—and still feel stressed, stuck, or unfulfilled. Drawing from her coaching work and her own career turning point, Sharissa argues that workplace happiness starts with alignment: knowing who you are, what you value, and why the next step actually...

What separates great individual performers from great leaders? In this episode of Gaining the Technology Leadership Edge, Mike sits down with David Kitchen (Coach Kitch) to break down the mindset shift leaders must make when moving from doing the work themselves to winning through others. Drawing from his experience coaching elite athletes and executives, Coach Kitch explains why leaders are “beho...

What if the biggest barrier to your leadership success isn’t strategy, talent, or execution—but communication? In this episode of Gaining the Technology Leadership Edge, Mike sits down with Tissa Richards, repeat software founder, CEO, award-winning author, and global leadership expert, to unpack why most leaders think they’re communicating clearly—and why they’re often wrong. Tissa explains how f...

AI is no longer a future concept in customer experience—it’s already reshaping how companies engage, sell, and support at scale. In this episode of Gaining the Technology Leadership Edge, Mike sits down with Alex Levin, founder of Regal.io and former growth leader at Handy, to explore how AI-powered contact centers are transforming entire industries. Alex shares lessons from scaling businesses thr...

Every leader faces curveballs. The difference between those who break and those who build something stronger is how they respond. In this episode of Gaining the Technology Leadership Edge, Mike sits down with Joelle Kaufman, a 25-year B2B SaaS executive, go-to-market leadership coach, and generational cancer survivor, to unpack her Curveball Method for leading through adversity. Drawing from her e...

What if one of the most painful moments in your life became the catalyst for your greatest professional breakthrough? In this episode of Gaining the Technology Leadership Edge, Mike sits down with Brian Strong, CEO of 10Hats, to explore a leadership journey shaped by sales, startups, setbacks, and perspective. From selling railroad materials to telecom, founding and exiting a GovTech software comp...

Your competition is evolving—but are you? In this episode of Gaining the Technology Leadership Edge, Mike welcomes Christopher Larsen, a technology executive, coach, and founder of KnowledgeGain, to explore a powerful intersection most leaders overlook: cutting-edge technology and ancient holistic practices. With a background in engineering, executive leadership, and mindfulness-based coaching, Ch...

What if the leadership style you were taught is the very thing pushing your best people away? In this episode of Gaining the Technology Leadership Edge, Mike sits down with Haley Anthony, combat veteran, leadership coach, and founder of Rise Executive Coaching, to unpack why fear-based leadership is not just outdated—but actively harmful to performance, culture, and retention. Drawing from her mil...

What if the key to stronger teams isn’t fixing weaknesses—but fully understanding and leveraging what people naturally do best? In this episode of Gaining the Technology Leadership Edge, Mike welcomes Jennifer Pasquale, a dual-certified Gallup CliftonStrengths coach, to explore how strengths-based development transforms individuals, teams, and entire organizations. Drawing from her work with corpo...

As AI models consume massive amounts of data, a critical question is emerging: who actually owns the content that trains them? In this episode of Gaining the Technology Leadership Edge, Mike sits down with Sharon Boulding, former CTO and CISO, AI cybersecurity expert, and founder of Parsifer, to explore the hidden risks AI poses to content creators, publishers, and the broader digital ecosystem. S...

Broadcasting live from HumanX in Las Vegas, one of the world’s leading AI conferences, Mike Mahoney takes listeners inside the conversations tech leaders can’t afford to ignore. In this episode of Gaining the Technology Leadership Edge, Mike breaks down how AI is reshaping industries—from enterprise operations and cybersecurity to healthcare, marketing, and autonomous systems—while raising critica...

From yacht chef to underwater filmmaker to award-winning creative director, Shelby Ring’s path into video production is anything but conventional—and that’s exactly what fuels her success. In this episode of Gaining the Technology Leadership Edge, Mike sits down with Shelby, founder of Ruby Riot Creatives, to explore how rebellious thinking, adaptability, and storytelling instincts translate into...

Reaching 100 episodes is more than a milestone—it’s a moment to reflect on what truly separates good leaders from exceptional ones. In this special episode of Gaining the Technology Leadership Edge, Mike Mahoney distills insights from 100 conversations with founders, executives, technologists, and leadership experts into 10 practical leadership lessons you can apply immediately. Rather than revisi...

Tech leaders obsess over productivity, innovation, and growth—but too often overlook the one factor that makes all three sustainable: mental health. In this episode of Gaining the Technology Leadership Edge, Mike is joined by Sarah Harris, a licensed clinical social worker with over 20 years of experience, to unpack what it really means to build a well-being culture inside high-pressure tech organ...

What if the key to better leadership, clearer communication, and sustained performance isn’t another framework—but your own body? In this episode of Gaining the Technology Leadership Edge, Mike sits down with Ruth Cummings, a body–mind coach with over 50,000 hours of experience working with CEOs, professional athletes, and high-performing teams. Ruth explains how stress, pressure, and unresolved e...

Joshua Santabria, founder of GO Architect and creator of the community engagement platform Engage, joins the show to unpack how large-scale planning decisions can be made without sidelining the people most affected by them. In this conversation, Joshua explains how traditional approaches to community engagement—static PDFs, in-person meetings, and limited access—often fail to produce meaningful in...

Kevin Dean, founder of Manobyte, joins Gaining the Technology Leadership Edge to explain what most companies get wrong about AI and automation—and how technical leaders should actually think about implementing it. AI isn’t new. What’s changed is the scale, accessibility, and speed. But as Kevin explains, dropping AI into an organization without clear processes and strategy doesn’t create leverage—...

Nick Coniglio and Marni Stockman join Gaining the Technology Leadership Edge to unpack what Ted Lasso gets right about leadership—and why those lessons matter for technical leaders today. As former founders of a SaaS company that scaled during the same years Ted Lasso aired, Nick and Marni didn’t model their business after a TV show. Instead, they noticed striking parallels: leading with empathy,...

John Driscoll, CEO of Naked Development, joins Gaining the Technology Leadership Edge to break down what actually separates successful startups from those that quietly run out of runway. After helping launch more than 500 apps, John has seen a consistent pattern: startups don’t fail because of bad technology—they fail because they move too slowly, misunderstand the problem they’re solving, or burn...