Software has always been their Achiles heel.
Their laptop where cool but running widows with super custom drivers. Their music players were cool but running weird formats with proprietary interfaces. Anything that needs software intercompatibility has been basically doomed under Sony.
In contrast Apple has decent software and overcomes the strategy tax by canibilizing itself restlessly and letting third parties eat their lunch where they’re not good enough (to a point. Apple still clings at default apps on iOS for instance)
I'd point more towards the competitiveness of the digital music market making their aggressive attempts to lock customers into their own narrowly focused music platform much less appealing. In game consoles, proprietary content is the point; not so much in audio gear.
In that respect their MD player was also running decent software, it just didn’t talk to anything not Sony produced.
Anecdotally, they also have a joint venture with Docomo that worked on NFC payment solutions that was super successful with genuinely strong software.
On the music market, I think the lockin wasn’t so much an issue (iPods also locked you in to some extent) than Sony’s desktop software being utter garbage.
I actually bought a Net Walkman at that time because I liked the hardware more, and it was hell: I’m not even sure there was any mac support, I might have run a VM for that, and even in a proper windows environment it was still buggy, extremely time consumming to move tacks to the player, yet limited and low quality. I personally think Sony lost to itself, more than the competition coming for Sony.
So far, they have 3 generations of those (over the past 5 years iirc). You know what the naming scheme for each generation is?
MDR-1000X (that’s the gen i have and love; heard that the 3rd has some great improvements over the first two as well) -> WH-1000XM2 -> WH-1000XM3
To add an insult to injury, it is literally just one character away from just as poorly named “sony airpods”, which is WF-1000XM3.
I had a Sony MP3 player in 2000. It only played atrac files and I had to specially rip and encode my cds to be able to play. The hardware was neat, it was like a thick pencil. But the software was purposely horrible because Sony wanted to not allow mp3s or songs bought outside their ecosystem.
At roughly the same time I got an iPod, and an Apple-hating housemate bought a Sony MP3 player with a name only a barcode scanner could love. Also it couldn’t play MP3s, instead a weird proprietary format that didn’t work anywhere else. Songs had to be converted using their crappy software.
He swapped it for an iPod within weeks.
Even now, the conversation is ‘what are those?’, ‘oh, they’re AirPods’. Compared to ‘what are those?’, ‘oh, they’re Sony WC-31... err, Sony headphone things.
Good work guys.