One tell-tale sign is endpoint security and using his own device. It's the kind of permissive cultural thing that does not scale because of compliance issues and developer productivity overhead. But it's very hard to wrench these long-time devs away from their preferred Linux distribution which requires conditional build stuff everywhere to support. Use a work computer for work, let them monitor the updates and stuff, as long as they're not using the webcam to record you who cares?
The database backup story - my guy you were on the database team. Backing up the databases is job 1. You can't just passive-voice away "oh there were no backups". But of course he's more interested in fighting about sharding architecture than actually keeping the site running day-to-day.
His big takeaway is that Gitlab didn't spend enough time on performance for their hosted offering which was a huge money loser. Just because he thinks performance stuff is fun to do, if the hosted offering is a money pit of course they're not throwing more resources at it. You have to make an actual business case for why your thing is more important and makes money more than another project. You don't just engineer in a vacuum for the fun of it.