In this episode of Yet Another Value Podcast Book Club, host Andrew Walker is joined by Byrne Hobart of The Diff to explore Softwar, the 2003 biography of Oracle co-founder Larry Ellison. Together, they dissect the contradictions of Ellison's public and private personas, Oracle's aggressive sales culture, and the book's surprisingly prescient predictions about tech's future. They reflect on ERP nightmares, Oracle's early brushes with collapse, and its surprisingly fertile alumni network. The conversation probes the blurred line between visionary leadership and red flags, while tracing Ellison’s uncanny resemblance to figures like Elon Musk. From petty footnotes to PR plays, it's a sharp look into one of tech’s most enduring empires.

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[00:00:00] Introduction to the podcast and book.

[00:01:48] Byrne joins the episode.

[00:01:49] Quick disclaimer on investment advice.

[00:02:37] Skipping the boating sections in book.

[00:03:30] Initial thoughts on Oracle in 2003.

[00:04:00] Larry Ellison's personality contradictions.

[00:05:45] Oracle's sales tactics and benchmark claims.

[00:07:00] Predictions on mobile and distributed systems.

[00:08:44] ERP transition challenges explained.

[00:10:03] Reasons to bet against Oracle.

[00:12:04] Oracle’s management style and red flags.

[00:14:23] Intelligence connections and conspiracies.

[00:15:54] Government ID advocacy post-9/11.

[00:17:24] Comparing Larry Ellison to Elon Musk.

[00:19:45] Book’s structure and humorous footnotes.

[00:22:55] Seibel rivalry and Oracle acquisitions.

[00:25:11] PR's role in Oracle’s strategy.

[00:26:40] Market perceptions and quarterly focus.

[00:30:03] Importance of sell-side analysts back then.

[00:31:29] Anecdotes about market cap drops.

[00:33:48] Oracle’s executive alumni shaping tech.

[00:36:23] Differences in tech executive pipelines.

[00:38:51] GE's internal business training system.

[00:41:09] Ellison’s hiring practices and red flags.

[00:44:05] PeopleSoft DOJ case and hypocrisy.

[00:46:43] Safra Katz’s rise at Oracle.

[00:49:19] Oracle’s leadership transition dynamics.

[00:51:54] Book's narrative style and structure.

[00:52:56] Author’s omission of Ellison’s childhood.

[00:55:13] Ellison’s charisma and software predictions.

[00:58:33] Ellison’s lasting influence and vision.

[00:59:45] Tease for next month’s book selection.

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