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...

Oracle’s Java licensing changes bring a unique challenge to universities – students also count as employees under the latest license metric. If a university has 2000 employees and 30,000 students, what was a $300,000/year Java bill now costs millions. In this episode Craig and Dan DeVenio, CCO of Palisade Compliance, discuss the challenges that universities face when licensing Oracle Java and what they can do to mitigate risk. Craig and Dan also discuss how Palisade Compliance helped the Univ...

Successful procurement strategies are often built on factors such as cost, innovation, and quality. While these solutions create lasting change that lead to decreasing costs and increasing profit, one element that is often overlooked is arguably the most vital: investing in people and their success. In this episode we welcome Rafael Vendramini, a long-time procurement professional and thought leader in the area of technology and humanity and culture, and how these things fit together and help...

Organizations face mounting pressure to digitally transform while simultaneously managing tightening budgets and aging infrastructure. The solution for many has become third-party support — not merely as a cost-cutting measure, but as a strategic tool that returns control to the customer. In this episode, we welcome Lee McArthur who runs strategy and business development at CDS. Craig and Lee discuss navigating support beyond Oracle and how businesses are redefining their technology relations...

Generative AI tools, like ChatGPT, are frequently used to quickly find information and advice for any topic. People who are looking for software asset management (SAM) or licensing advice might not realize that these AI-generated responses are not always helpful. In fact, much of this advice can wind up costing you millions of dollars. In this episode Craig welcomes two fellow Palisaders, Adi Ahuja and Max Shlopak, where they interview ChatGPT about SAM and licensing. Tune in to hear what our...

Keystone Negotiation is the global leader in Microsoft negotiation advisory services. In this episode, Craig welcomes Keystone Negotiation's Founder and Negotiation Advisor, Mark Kenny. Craig and Mark discuss Microsoft Azure licensing, common mistakes when negotiating, and what customers should do when renewal time is around the corner. To learn more about Mark and Keystone Negotiation, visit: https://keystonenegotiation.com

In this episode we welcome Ward Classen, General Counsel at Sparta Systems (a Honeywell company) and author of The Practical Guide to Software Licensing and Cloud Computing - now in its eight edition and widely recognized as the definitive treatise on the subject. Ward and Craig discuss vendor approaches to contracts, your licensing rights as a customer and how to exercise them, pitfalls and traps to look out for, and more. To learn more about and purchase The Practical Guide to Software Lice...

In this episode our host Craig Guarente welcome Ryan Triplette, Executive Director of the Coalition for Fair Software Licensing. Craig and Ryan discuss the Coalition and it's mission to highlight the importance of fair and transparent software licensing terms for both public and government sectors. They also share their experience with software licensing across industries, the challenges that different companies face while licensing software for critical business functions, and what organizat...