In the final episode of 2025 we welcome Lisa Morgan, writer for InformationWeek. Software is more essential than ever and the rules around using it keep getting messier. Lisa brings her expert insight to the software challenges business leaders are facing now. Craig and Lisa discuss how to deal with the friction that bubbles up during software audits and why misalignment between IT, procurement, legal, and business leaders turns small issues into larger crises. Lisa gives her prediction...

Fire code compliance, inspections, and safety operations is a niche yet vital industry that relies on processes that can become outdated and inefficient. When public safety is on the line, having a streamlined digital solution to simplify every step of the process is critical for companies who are responsible for managing this compliance. In this episode Craig interviews Drew Slocum, Chief Strategy Officer and co‑founder of Inspect Point, and host of The Fire Protection Podcast. Drew explains...

In this episode we welcome Martin Thompson, founder of ITAM Forum, a non-profit trade body run by ITAM professionals designed to educate companies on ITAM with a focus on business value. Martin and Craig explain how vendors use audits to force conversations, drive revenue, and steer customers toward shiny new cloud offerings. They discuss pain points companies are facing (like cloud spend, SaaS sprawl, and data quality), the EU vs US's secondary software markets and the differences in s...

On November 14, 2025 Fidelity Technology Group filed a lawsuit against Broadcom (owner of VMware), stating that Fidelity has a right to renew its subscription without price spikes. Broadcom is threatening to terminate Fidelity's software subscription, leaving Fidelity and its customers in the dark. In this episode we explain why Fidelity is suing Broadcom, what the challenges are in a lawsuit of this nature, and the potential outcomes of this case. We'll be covering this case in future ...

In this episode, we welcome Steven Dickens, founder of HyperFRAME Research and former IBM leader to unpack the rise of boutique analyst firms, the AI wave changing their playbooks, and the simple operating principles behind building a seven-figure practice in a year. We explore why budgets are shifting away from the "Big Four" toward independent analyst firms and how credibility compounds when you’re fast, available, and honest. Steven also shares pragmatic advice for early professionals, p...

The truth about audits is that many audit teams aren't deep experts any more. They're efficient machines that run on templates, throw jargon around, and rely on you to prove them wrong. In this episode we welcome back Matt Giuliano, Senior Delivery Director at Palisade Compliance, who has been on both sides of audits – previously building programs for vendors and now defending customers. Matt reveals how audits are conducted at large technology vendors. Craig and Matt discuss how vague polici...

In this episode we welcome Foster Awintiti Akugri, a Ghanian innovation strategist and fintech leader with over a decade of experience driving product development, market expansion, and strategic partnerships across Africa, the Caribbean, and North America. Foster brings insight into how Africa is shaping the future of technology: a young, fast-growing workforce and vast reserves of critical minerals are poised to shape chips, batteries, AI, and the global services economy. But enterpr...

In this episode, we sit down with serial founder and advisor Jim Ball to unpack how real companies grow: through teams, systems, and clear roles that compound over time. Entrepreneurship is a disciplined craft, not a daredevil act. We dig into the sell-build-run triangle that underpins resilient organizations. Jim explains when a CEO should jump on a sales call—and when they should stay out—and why the real goal is a system that closes deals while you’re working on the business. Jim als...

An ad in a Sunday paper, a faxed resume, and a week later Craig Guarente was on a plane to start at Oracle. That origin story sets the stage for a tour through three decades of deals, from paper contracts and fax machines to cloud subscriptions and the rise of generative AI. In this episode our usual host, Craig Guarente, is in the guest chair, interviewed by Marisa Gallicchio, Director of Marketing at Palisade Compliance. We talk about what has really changed in enterprise negotiations...

In this episode we sit down with Emmy‑winning executive and esports entrepreneur Anthony Gaud to map the real terrain of competitive gaming and the fractured media world we all inhabit now. The conversation widens to the media shift hiding in plain sight: Game Awards streams outdrawing the Oscars, streamers surpassing cable ratings, and a generation that knows MrBeast better than late‑night hosts. Anthony argues that rebuilding shared culture will require more live, scheduled moments - and l...

The software asset management industry has long suffered from a fundamental misunderstanding: that technology alone can solve compliance challenges. In this episode, we welcome Rory Canavan, founder and CEO of SAM Charter. Rory and Craig discuss why so many organizations continue to face painful audits despite investing in expensive SAM suites. Drawing from his decade-plus experience developing SAM frameworks for organizations worldwide, Rory shares how process-driven approaches have deliver...

The contract world is broken, and Ken Adams, Head of Adams Contracts - a division of LegalSifter, has spent over two decades trying to fix it. In this episode, the world's foremost authority on contract language reveals why most business agreements are dysfunctional and how to break free from the "copy-paste machine" that perpetuates bad drafting practices. Ken highlights his highly customizable, automated templates that force users to make deliberate decisions through a dynamic questionnaire...

In this episode we welcome Ashley Cruz, a highly accomplished marketing technologist and IT leader with over 13 years of experience driving digital transformation and operational excellence at Televerde, a global sales and marketing solutions provider. Ashley and Craig discuss her journey at Televerde from calling agent to IT leader and the challenges and opportunities she has faced in her role as Head of Information Technology. Ashley and Craig also discuss the Televerde Foundation, a nonpro...

Migrating to the cloud is something many companies will do in the near future, if they haven’t already. These migrations can be costly, complex, and slow – and with so many cloud providers out there, the task of adopting new technology can be a confusing and daunting process. In this episode we welcome Raj Joshi, Founder of CloudifyAI, a company dedicated to revolutionizing the way businesses leverage data and AI to drive innovation, create value, and solve complex challenges. Raj and Craig d...

CIO Dive is a leading publication that provides in-depth journalism and insights into the most impactful news and trends shaping IT. In this episode we welcome Matt Ashare, Senior Reporter at CIO Dive. Matt and Craig discuss current IT trends and influences, how CTOs and other technology executives are forging paths to adopt new technologies, and customer sentiments around IT vendors. Visit CIOdive.com to get the latest IT news.

In this episode Craig welcomes Brian Luper, Director of IT Procurement at Rutgers, The State University of New Jersey. Brian focuses on overseeing a team that deals with endpoint management, remote support, managing physical and virtual computer labs on campus, as well as coordinating central software licensing for the institution. Craig and Brian discuss the Rutgers IT organization’s challenge of developing and offering services to the entire university community of of 2,000 employees...

In this episode Craig welcomes Sally Guyer, CEO of World Commerce & Contracting, formerly IACCM, a non-profit association and the only global body promoting standards and raising capabilities in commercial practice. Craig and Sally discuss WCC’s mission to transform contract management and the contracting process within global trade while encouraging commercial innovation. Learn more about how Sally and WCC are transforming contract management at worldcc.com.

In this episode Craig is joined by Shawn Helms, Partner at McDermott Will & Emery to discuss AI Law and Business, a new legal treatise co-authored by Helms and published by ALM Law.com. Craig and Shawn highlight the rapid shift in artificial intelligence, the evolution of contracting and other business functions in response, and the legal implications of this technology. To learn more about the treatise, visit AILawCenter.com. -------- Shawn and Palisade Compliance would also like to brin...

In this episode Craig welcomes Adi Ahuja, Palisade Compliance's resident Oracle negotiations expert. Craig and Adi walk through Oracle's negotiation playbook. They discuss common scenarios and tactics that a company might encounter when negotiating with Oracle, the best time to begin these conversations, and the inside scoop into how negotiations are handled.

Like Oracle, most technology vendors audit their customers. These compliance audits aren't random; there is a methodology that's followed before the audit letters are sent out. While the process of determining who to audit may vary between vendors, the end goal is the same: generate revenue. In this episode Craig welcomes Matt Giuliano, Senior Delivery Director at Palisade Compliance and former Oracle LMS program manager and audit team manager. Craig and Matt discuss the audit playbook that m...