Bryan Cantrill: Sun's fatal flaw wasn't strategy — it was boredom with the business

Ahead of Oxide’s annual company meetup, the team made homage t-shirts riffing on logos of defunct computer makers, and the Sun Microsystems design provoked a wave of nostalgia. Cantrill, an ex-Sun engineer, uses the occasion to argue that reverence for Sun should be balanced against a clear-eyed accounting of its failures. His distilled verdict, refined over 15 years of reflection: Sun hadn’t lost on strategy so much as grown bored with the unglamorous mechanics of actually running a business.

He anchors the point in a 2005 episode that should have been a triumph for Sun’s decision to open-source Solaris. A fast-growing startup pioneering what became cloud computing was running OpenSolaris and wanted to buy a large amount of Sun hardware — proof the open-source model could drive sales. Instead, Sun couldn’t be bothered to return calls, and when it did, pitched the wrong product. Dell, by contrast, turned an overnight web form into a personal account rep who leased a full datacenter’s worth of servers within two weeks. The startup documented the contrast in a widely-read blog post, ‘The Sun Doesn’t Shine on Me.’

The lesson is that operational execution can nullify even a winning strategy: Sun folded a few years later despite getting many of the big technical bets right. The story has a coda that doubles as Oxide’s origin — Cantrill later joined that same startup, which also hired the Dell rep who’d won the deal, and the two of them went on to co-found Oxide. Studying dead companies, he argues, is about learning from what they got wrong as much as honoring what they got right.