Thinking Out Loud

I write about product management, team dynamics, technology trends, and the occasionally odd intersection of all three. The goal isn’t to convince you I have all the answers. It’s to share what I’m learning and figure out who I should be working with.

  • Part 6: Oracle Endgame: What Could Actually Happen

    Part 6: Oracle Endgame: What Could Actually Happen

    After six years at Oracle NetSuite and getting laid off in August 2025, I’ve been analyzing what’s happening at Oracle. What I’m seeing shares troubling patterns with the 1990 near-bankruptcy, though the mechanisms are fundamentally different.

    I’m not claiming to know which scenario is certain. What I can do is map the probable paths, show you the causal chains, and identify the warning signs to watch as this unfolds. The goal is to help current and former Oracle employees, investors, customers, and partners make decisions based on measurable signals rather than speculation or panic.

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  • Part 5: Oracle’s Credit Crisis Deepens?: When Bond Markets Flash “Danger”

    Part 5: Oracle’s Credit Crisis Deepens?: When Bond Markets Flash “Danger”

    Credit markets often see trouble before equity investors do. Oracle’s current credit metrics have deteriorated so rapidly that Morgan Stanley analysts now warn spreads could approach 2008 financial crisis levels. The numbers suggest we’re watching a high-stakes gamble that could reshape enterprise software.

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  • Part 4: The 10% Layoff Signal: Oracle’s most reliable crisis indicator across 35 years

    Part 4: The 10% Layoff Signal: Oracle’s most reliable crisis indicator across 35 years

    Oracle has executed significant workforce reductions at two critical junctures: during the 1990 near-bankruptcy and again in 2024-2025. In my view, this pattern isn’t coincidence. It may be Oracle’s most reliable leading indicator of strategic overextension.

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  • Part 3: Oracle’s RPO Shell Game – How $455 Billion Became a Red Flag

    Part 3: Oracle’s RPO Shell Game – How $455 Billion Became a Red Flag

    Oracle’s September 2025 announcement of $455 billion in Remaining Performance Obligations deserves careful scrutiny, especially when examined through the lens of ASC 606 revenue recognition requirements.

    The Headline That Moved Markets

    Oracle prominently featured its $455 billion RPO (up 359% year-over-year) at the very top of its Q1 earnings release, even above revenue and earnings per share.¹ CEO Safra Catz declared Oracle expects to sign additional multi-billion-dollar customers, projecting RPO would “likely exceed half a trillion dollars” soon.²

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  • Leadership In the First 30 Days: What I Learned Rebuilding a Collapsed Team

    Leadership In the First 30 Days: What I Learned Rebuilding a Collapsed Team

    May 2016. I stepped into a role knowing the entire development team had quit. Except one person and I couldn’t wait to start.

    This was a full-service digital marketing agency (a subsidiary of The Oklahoman, owned by a larger holding company). The environment was full of constant change, shifting priorities, and high expectations.

    We built and maintained client websites. For the clients who used us, we were a crucial part of their digital marketing presence. Our work directly powered SEO, paid media, social, and content campaigns. Had it not been for the team member that stayed, when the rest of the team walked out, organizational trust would have evaporated.

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  • Part 2: Inside Oracle’s OpenAI Deal – Why Wall Street Lost Faith

    Part 2: Inside Oracle’s OpenAI Deal – Why Wall Street Lost Faith

    This is Part 2 of a six-part investigative series analyzing Oracle’s $300 billion OpenAI partnership and the financial risks it creates. Each article examines a different dimension of what may be the most consequential bet in enterprise technology history.

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  • Part 1: Oracle’s $315 Billion Reality Check – When History Rhymes with 1990

    Part 1: Oracle’s $315 Billion Reality Check – When History Rhymes with 1990

    Series Note: This is Part 1 of a 6-part analysis examining Oracle’s financial risks through the lens of someone who spent six years inside the company.

    Having analyzed corporate risk patterns throughout my career in technology and product management, what’s unfolding with Oracle Corporation bears an unsettling resemblance to the company’s 1990 near-bankruptcy crisis. The numbers tell a story that should concern anyone invested in Oracle or considering its services.

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