TLDR; 1. Start-ups love OSS. OSS loves NIX. 2. Mac's just work (mostly). 3. Cult of Apple. 1. OSS is generally free. Windows software, esp. on the server side

TLDR; 1. Start-ups love OSS. OSS loves NIX. 2. Mac's just work (mostly). 3. Cult of Apple. 1. OSS is generally free. Windows software, esp. on the server side, tends not to be. For a start-up it means you might need to invest some sweat but you can spend your cash elsewhere (typically on hires or feeding yourself). OS X being a NIX allows easier porting of OSS than Windows. 2. Apple tech has a reputation for "just working" and continuing to work. Windows is still perceived to need a spring cleaning to reinstall it every year or so to keep it purring. Apple being a closed ecosystem from end-to-end doesn't have to support as much random stuff as MS. It keeps the problem space narrow and presumably that results in higher reliability. 3. The cult of Apple. Apple has a brand that is perceived as creative, fun, enlightened, whatever. MS is viewed as big enterprise. , which is often the Goliath that start-ups are looking to slay. -- Anecdotally one company I was an early "many hats" hire I standardised on Macs because it meant less effort for support and licensing was easier. If someones Mac was acting up/it fell down the stairs we could swap the drive to another machine and not faff with driver setup. If someone left the company, we could easily transfer the licenses which isn't always as straight forward between Windows and OS X. One drawback is that we had one developer who preferred Windows. He was probably less productive than he could've been as a result. I would generally advocate to allow developers to pick their hardware when they start and take it when they leave. Once the company was big enough for a full-time IT support staff we diversified but it's a tradeoff either way.