Dear Fortune 500 CIO. Is Oracle still a software company?
Why Oracle's pivot to AI infrastructure should change how you think about Oracle spend.
Influence
Influence.
Open letters, reports, and playbooks for the CIOs and procurement leaders sitting across from Oracle. Long-form below as PDFs on request. Shorter takes on LinkedIn.
Reports
Recent reports.
The Oracle Q4 Playbook
Eight rules from three decades of negotiating against Oracle. The traps to watch and how to walk away with a better deal.
Mythos and Oracle Mythology
Why Oracle's AI security narrative does not survive contact with the routine quarterly patch cycle.
LinkedIn
Posts & commentary.
Shorter takes on what's moving in the Oracle commercial landscape and what's showing up in client deals this quarter.
An AI dot-bomb could raise your Oracle bill 5 to 10 times.
If the AI boom breaks Oracle's balance sheet, expect the Broadcom-VMware playbook: kill perpetual licenses and force customers onto subscription bundles. Oracle milks the few thousand accounts that cannot leave. Optimize before today's spend becomes tomorrow's baseline.
Oracle priced its AI bet for a scarcity that won't last.
Think twice before buying the ORCL dip. Open-weight models like Kimi K3 and a flood of cheaper chips are the headwinds. In the 1990s, telecoms went bankrupt laying fiber priced for a five-year scarcity; Oracle's may last 12 to 18 months.
Even the government can't escape the Oracle concrete.
The Pentagon's $7B Oracle deal claims $441M in savings, but most comes from cutting resellers, not Oracle, and the real discount is just 6 to 11 percent. Its Microsoft consolidation saved ten times as much on four times the spend.
Threats turn to begging.
The assumption is that a distressed Oracle squeezes its base harder. After hundreds of negotiations, I find the opposite. The typical customer is already over-licensed, so there is nothing left to audit, only something left to cancel and replace.
Oracle reports a sharp increase in audit rhetoric.
A satirical dispatch: Oracle's audit teams are quietly deprioritized, yet the marketing of audit defense keeps its predatory reputation alive. The point underneath: no number of audits can fill the hole Oracle's debt-fueled OpenAI bet opened in its balance sheet.
A distracted vendor is a negotiable vendor.
S&P just cut Oracle to one notch above junk, blaming OpenAI, half of its $638B backlog, with the stock down nearly 60% from its peak. It is now a leveraged data center builder focused on one tenant, not you. The best time in decades to negotiate.
For in-house counsel: the Oracle barrier is not technical.
Misplaced fear of Oracle as litigious perpetuates millions in waste. The barrier is the misunderstood mix of Oracle's business practices, contractual terms, and public policies. Software costing tens of millions might run for a fraction with informed legal counsel as the backstop.
Oracle's core competency is collections, not software.
The $20B customers pay for on-premise support is the anchor Oracle defends to fund its AI data centers. With new license sales falling, it force-feeds the cash cow: the annual uplift doubled from 4% to 8% with no reset.
Can Oracle's anchor tenant pay the rent?
OpenAI, the anchor tenant of Oracle's $638B backlog, lost $21B on $13B of revenue in 2025, with the deepest losses in the very years it owes Oracle most. Your support renewals are the high-margin money backstopping that bet, which makes you the collateral.
The new Oracle reads like a utility.
To grasp the new Oracle is to understand utilities, REITs, and defense contractors. Ratings agencies stopped grading it as software. Nearly half its $638B backlog rests on OpenAI, and FY26 interest nearly matched new license revenue.
Oracle is no longer a software company.
A definitive, and tongue-in-cheek, declaration ahead of the June 10 earnings call. Most companies use Oracle software, but that no more makes Oracle a software company than owning a fire extinguisher makes you a fireman.
The Pope, Anthropic, and Oracle's bet.
The Vatican's new AI encyclical, with Anthropic's Chris Olah at the presentation. Oracle's debt-fueled AI data center buildout now sits at the center of a grand cultural experiment, and its bet is not on its own software.
Oracle is downstream.
SpaceX's pre-IPO filing informs Oracle's debt-fueled bet on OpenAI. The S-1 exposes a profitable Starlink monopoly funding a $6.4B AI operating loss.
Postgres is not the answer to Oracle.
Oracle's deep discounts on high list prices forfeit as licenses are removed. You could spend years migrating, but until you sweep the floor, you will not reduce OpEx.
The Hotel California.
To understand Oracle is to understand its database-in-a-box Exadata product. The Hotel California.
CoreWeave vs Oracle.
I've already covered how Oracle stacks up against Microsoft, AWS, and Google in the AI buildout. Bottom-up — operating from debt — requires studying CoreWeave's financials.
Oracle's FY26 Earnings.
Oracle's FY26 earnings report will only be meaningful if it announces a major new customer that expands its $553B RPO — ideally a sovereign such as Saudi Arabia, the UAE, or Japan.
Independent Oracle Cost Recovery.
My new website for Advizant. I think in all fairness, I should explain to you exactly what it is that I do. I was trained by Oracle to be a technical presales engineer in the late 90s.
Oracle vs the other AI hyperscalers.
$2T in AI backlog among Oracle, AWS, Microsoft, Google. Oracle is dwarfed by the others' cash position, betting on one customer (OpenAI), and pivoting rather than extending.
Mythos and Oracle Mythology.
Separating fact from sales rhetoric on how AI should affect patching strategy. Especially relevant for self-supported customers and those on Rimini Street or Spinnaker.
Oracle Fusion: green path vs Custom AI.
Where Fusion ERP / HCM / SCM Cloud subscribers can pick up productivity for free, and where partner-built marketplace agents flip you to a paid Custom AI Subscription.
Safra Catz, Uber, and the OCI elasticity narrative.
Dara Khosrowshahi credited OCI elasticity at CloudWorld 2023. The actual Uber margin story was charging riders more, paying drivers less, and building an ads business.
Dear Fortune 500 CIO. Is Oracle still a software company?
$124B in debt. $248B in AI data center leases. Up to 30K layoffs to service it. How to respond within your organization, IT budget, and vendor relationship.
Death, taxes, and Oracle software support.
Two of those are inevitable. Oracle's fiscal year ends May 31. If a quote is on your desk, search for "Total Support Stream" and the first-renewal-year language. That's the roll-in clause to watch.
Oracle's $20B support business: not done cutting.
A carousel digging deeper into the prior post. Oracle's most valuable asset is its $20B annual software support collections business — and the math of debt vs free cash flow forces what comes next.
Mythos gives Oracle a defensible narrative for support uplifts.
Oracle increased its "inflationary adjustment" from 3-4% to 8% in 2022 using the Covid spike. AI's bug-finding powers may give them the next reason. The direction of travel is one-way.
Oracle's Q4 ends May 31.
If you have a deal or renewal on the table, the next six weeks could shape your cost structure for a decade. The Q4 Playbook in three pages — eight sections, starting with the biggest mistake Oracle customers make.
ORCL, Bloom, and the warrant.
$553B in RPO Oracle can't deliver without electricity. Bloom Energy is the only quick gigawatt-scale answer. Oracle negotiated a warrant at the October 2025 price before announcing the 2.8 GW expansion.
CIOs wondering when AI will replace their Oracle stack.
You'll be waiting a long, long time. Decades-old codebases have institutional inertia organizations rarely overcome. Pair that with punitive support policy lock-in: using less Oracle doesn't incrementally cost less.
License orders are perpetual. Forever.
Quick Q4 reminder: a license order initiates a perpetual financial obligation. Especially important when the order rolls preexisting software support into the new deal.
Java. A four-letter word.
1,000+ companies consulted since Oracle started charging for Java in 2018. The egregious Employee metric has made sense for exactly one organization. Unsuspecting customers keep paying — which is why Oracle keeps pushing.
Oracle is not done cutting.
The math is painfully clear. Debt and free cash flow from FY2016 to FY2028. Before AI, debt was serviceable. Then Cerner. Now the AI capex era.
Oracle's layoffs: there is no account team relationship.
The only built-in memory in your relationship with Oracle is the volume-based discounts you have already negotiated. Loyalty to your sales rep is misplaced.
Oracle's AI moat isn't what you think.
Not its superior software (old-timers will tell you Sybase was better in its day). Not its 26ai features (1 in 10 shops at best will adopt). Not vertical integration. The real moat is somewhere else.
Prediction: Oracle adds "Database Singularity" in June.
Oracle will package its AI database features as an extra-cost option on top of EnterpriseDatabase for on-premise installations. Watch for the announcement in June.
Testing Oracle's 26ai agentic AI features.
Oracle dropped a new EnterpriseDatabase 26ai feature set. Spawned a team of Claude Code agents to plan tests and write a pros / cons summary of Oracle's PL/SQL implementation of AgenticAI.
Larry Ellison's neuroplasticity.
Tens of billions into AI infrastructure and into Paramount. Cerner was Larry's last foray into his lifelong core competency of dominating database and apps. ChatGPT released five months later may have struck him as the end of profitable IP-centric software.
Why AI doomers and euphorics aren't using the tools.
Advizant has been building production systems for weeks. Not prototypes, not demos. Full applications. The shift since February's Opus 4.6 release has been an event horizon.
Most Oracle customers aren't getting full value.
The technology is excellent. The gap is between legacy commercial terms and what enterprises need in the AI era. Same pattern across thirty years in the ecosystem.
Forget what you think you know about AI.
A 25-page report produced in 5 hours using Claude Code, pulling data from spreadsheets, PDFs, and a RAG-enabled Oracle 26ai database. The shift is in how the work gets organized, not in the hype.
Larry Ellison: the celebrity of my career.
Paramount's acquisition of Warner Bros. Discovery sits at the collision of legacy tech, AI, politics, entertainment, and news. A reflection on Ellison's bluster.
The Mendelsohn slide I mocked at CloudWorld 2024.
Vibecoding via Cursor and Claude Opus 4.6 makes everything before January 2026 feel archaic. More working code in a week than in years prior — including a RAG pipeline in 26ai.
If Oracle is across from you right now.
Thirty minutes. No sales pitch. A direct read on the deal on the table.
Book a 30-minute consultEric Guyer. Founder, Advizant LLC
eric.guyer@advizant.ai · +1 (630) 881-5085
linkedin.com/in/ericguyer
