Gaining the Technology Leadership Edge

Success in tech doesn’t fail people—definitions of success do. In this episode, leadership and career coach Aylam Hoffstein shares how global living, personal loss, and fatherhood reshaped his approach to helping tech leaders find both fulfillment and performance. Having lived in ten cities across four countries, Aylam brings a perspective that resists rigid frameworks in favor of adaptable mindse...

Sales doesn’t have a talent problem—it has a professionalism problem. In this episode, Sean Shepard, a Silicon Valley entrepreneur, venture builder, and recognized sales influencer, explains why sales remains one of the most misunderstood yet essential functions in business. With over 30 years of experience, three exits, and leadership across venture funds and startup studios, Sean shares why sale...

Entrepreneurship isn’t always about chasing trends—it’s about noticing them early. In this episode, Dion Wilson shares how careful observation led him from national security contracting to the evolving world of comic books, independent media, and blockchain technology. While working on U.S. Department of Defense contracts in the mid-2000s, Dion noticed financial media shifting attention toward gam...

What if monitoring the planet didn’t rely on satellites alone? In this episode, Mathieu Johnson, CEO of Marble, explains how fast, small, and affordable drones could fundamentally change how we observe oceans, coastlines, and critical maritime activity. Growing up around aviation and skydiving, Mathieu developed an early passion for aerospace that later carried him through engineering studies, sid...

AI adoption isn’t failing because the technology doesn’t work—it’s failing because expectations, fear, and poor implementation get in the way. In this episode, AJ Malik, founder and CEO of PsychoMind, shares a grounded perspective on how businesses can actually succeed with AI. With roots in AI going back to a 1989 expert system project at IIT, AJ brings decades of experience from companies like G...

Why do so many AI initiatives fail—even when the technology seems impressive? In this episode, Dr. Michael Prok breaks down what it really takes to create value with AI in business. Drawing on decades of experience across academia, consulting, insurance, and enterprise transformation, Michael explains why AI success requires far more than strong technology or advanced analytics. He introduces a fi...

What happens when success collides with a life-altering crisis? In this episode, Daniel Gomez shares how a single phone call in 2017—his wife’s breast cancer diagnosis—upended his life and career. At the time, Daniel was running a multimillion-dollar organization, but faced a defining choice: outsource care for his wife or step away from the business entirely. He chose family, resigned from his ro...

Cybersecurity isn’t just about tools—it’s about priorities, culture, and understanding where real risk lives. In this episode, Brent Neal, Principal Advisor and vCISO at Vanguard Technology Group, breaks down how cybersecurity has evolved over the last two decades and why many organizations still struggle to get it right. From the early days of firewalls and antivirus software to today’s reality o...

In this episode of Gaining the Technology Leadership Edge, Mike sits down with Talila Millman, fractional CTO, executive advisor, and author of The TRIUMPH Framework: Seven Steps to Leading Organizational Transformation. Talila has led transformations across large enterprises, scale-ups, and early-stage startups. She explains why most change initiatives fail—not because teams can’t execute, but be...

In this episode of Gaining the Technology Leadership Edge, Mike speaks with Brian Galad, a technology mentor who has spent the last six years helping professionals—especially immigrants—navigate tech careers, interviews, and leadership growth. Brian shares the defining moment that changed his life. In May 2020, during a daily standup in a toxic organization, he shut his laptop mid-meeting and deci...

In this episode of Gaining the Technology Leadership Edge, Mike talks with Adam Livesay, founder of Elevate IoT, about what it really takes to modernize industrial and manufacturing companies with connected technology. Adam shares how IoT adoption began with smarter machines—but stalled because organizations weren’t ready to handle the data. Early customers didn’t have APIs, data governance, or se...

In this episode of Gaining the Technology Leadership Edge, Mike speaks with Matt Merritt, CEO of Snap Build, about building a fintech platform that removes friction from construction lending while operating inside a highly regulated environment. Matt shares his unconventional path from finance and accounting into ERP implementations, large-scale operations, and eventually fintech leadership. He ex...

In this episode of Gaining the Technology Leadership Edge, Mike sits down with Crystal L. Arch to explore leadership, product thinking, and what meaningful DEI looks like in practice—not just in policy statements. Crystal shares her unconventional path into tech, starting with early programming experience in COBOL, Fortran, and Pascal before shifting into product strategy to influence how technolo...

In this episode of Gaining the Technology Leadership Edge, Mike speaks with Eric Grafstrom, founder of ExitGuide, about startups, scale, and the quiet crisis facing small business owners who don’t know how—or if—they can ever exit their companies. Eric shares why he walked away from a senior role at Yahoo, realizing that large organizations removed the uncertainty and white space he needs to do hi...

In this episode of Gaining the Technology Leadership Edge, Mike sits down with Tracy Hill, founder and CEO of A Woman Up, to unpack the realities women still face in technology—and what actually helps move careers forward. Tracy draws on more than two decades in tech staffing, recruiting, and HR leadership to explain how bias has evolved but not disappeared. She shares candid stories from her earl...

In this episode of Gaining the Technology Leadership Edge, Mike sits down with community strategist Brie Lever to unpack what actually makes communities work—and why most fail. Brie shares her experience launching and scaling communities, from building a multimillion-dollar ambassador program for a fashion brand to helping Heartbeat relaunch its paid customer community during rapid growth. She exp...

In this episode of Gaining the Technology Leadership Edge, Mike speaks with Hutton Henry about what really determines success in technology-driven mergers, acquisitions, and scale-ups—and it’s not just the tech stack. Hutton shares how he began coding at age eight, joined Ford as a teenager, and spent ten years working on global systems serving hundreds of thousands of users. That experience shape...

Hospitals don’t lose equipment because people are careless—they lose it because saving lives comes first. In this episode of Gaining the Technology Leadership Edge, Mike sits down with Sam Yarua, founder and CEO of PI Cube, to unpack the hidden complexity of technology and asset management inside modern hospitals. Sam explains how hospitals operate more like living ecosystems than traditional orga...

Why do some SaaS companies lose—even when they’re first to market, well funded, and growing fast? In this episode of Gaining the Technology Leadership Edge, Mike sits down with Dan Spearing, founder of Aligned Software, to unpack a hard-earned lesson from Dan’s career: growth alone doesn’t win markets—focus does. Dan shares how he spent seven years helping scale an early-stage SaaS company by near...

Strong technical leaders don’t fail because they lack knowledge—they fail because their message doesn’t land. In this episode of Gaining the Technology Leadership Edge, Mike is joined by Brendan Gumarasami, founder of MasterTalk, to break down why communication is often the missing skill holding technology executives back. Brendan explains how many leaders rise through the ranks by being deeply te...

What if technology didn’t replace human interaction—but actually made it better? In this episode of Gaining the Technology Leadership Edge, Mike sits down with Nathaniel Smith, founder and CEO of Blue Nova Technology, to explore how seamless digital experiences can remove friction while keeping people at the center. Nathaniel shares how Blue Nova started with a simple idea: allowing customers to s...

AI is changing more than software—it’s reshaping how we work, create, and define value. In this episode of Gaining the Technology Leadership Edge, Mike speaks with Alexander DeRidder, founder of SmythOS, about the rise of AI agents and what they mean for the future of work. Alexander explains how agents differ from traditional AI by taking real action—collaborating with other agents, interacting w...

What happens when a technologist learns to slow down? In this episode of Gaining the Technology Leadership Edge, Mike speaks with Brad Messer about his journey from applied mathematics and data science into enterprise AI work—and eventually into entrepreneurship. Brad shares how his early exposure to big data and AI at Clarkson University led him to nearly a decade working in analytics and AI stra...

What does it really take to manage developers—and why does decentralization matter beyond crypto? In this episode of Gaining the Technology Leadership Edge, Mike sits down with Roberto Capodieci, a technologist and entrepreneur with decades of experience across software development, leadership, and decentralized systems. Roberto shares how he grew up coding from an early age, launched businesses a...

Most cybersecurity breaches don’t happen because of sophisticated hackers—they happen because of basic mistakes. In this episode of Gaining the Technology Leadership Edge, Mike sits down with cybersecurity consultant Mike Andrews of Yastis to break down why the majority of security incidents still rely on phishing, weak authentication, and poor access controls. Drawing from over 20 years in the De...