In this episode, host Jason Cohen reconnects with longtime colleague Andy Roach, Founder and CEO of Triple Orbits Technology. Andy brings nearly three decades of experience building technology for knowledge workers across professional services and the automotive industry. 

The conversation covers what responsible AI adoption actually looks like inside an organization: governance, data protection, and why people and process have to come before any technology decision. Andy also shares his take on the AI hype worth ignoring, why creativity can never truly be replaced, and what the next decade might hold for the generation growing up as AI natives. 

In this episode of On the Right Stack, host Jason Cohen sits down with Joshua Brown, a seasoned CISO and cybersecurity leader with more than 25 years of technology experience.

The conversation debunks the "dark art" of technical security, reframing cyber risk as a critical business problem rather than just an IT issue. Joshua cuts through the current AI hype, breaks down why compliance programs are failing to produce better security outcomes, and highlights why the best defense is mastering unsexy basics like patch management. He also shares firsthand leadership lessons on managing a crisis, earning credibility at the board table, and avoiding the trap of becoming the "department of no."

Host Jason Cohen sits down with Jeff Stamps, a pharmacist and healthcare leader with decades of experience in long-term care pharmacy, who guided a company through rapid growth, a global pandemic, and a successful acquisition.

They get candid about what makes technology leadership actually work: the four traits of a great CIO, why cybersecurity has to be a top priority before disaster strikes, where AI is genuinely useful in healthcare, and how to earn a real seat at the executive table. A practical, jargon-free look at how leadership and technology come together to drive results.

Not every technology decision gets made in Silicon Valley, and that is exactly the gap this podcast was built to close. Host Jason Cohen sits down with Craig Walker, founder and CEO of Dialpad, bringing a veteran operator’s perspective to a conversation about unified communications, early AI adoption, and what it takes to lead technology transformation at any scale. Real experience. Real insight. No hype.