Over some random discussion with friends, it was mentioned that Singapore rarely produces really good startups. This probably due to a generally well-structured life we have here and Singaporeans are generally considered as 'rule-followers' rather than 'ground-breakers'.
If we were to list homegrown recognisable startups or unicorns that is noteworthy internationally, Grab and Garena (now known as Sea) comes to mind (though some might argue that neither of them are really founded by local bred Singaporeans). Of course, there are some more regionally known such as Ninja Van, Carousell and Propertyguru.
Hopefully, we can start to change that stereotype and hope that some of these startups can make it onto the international stage eventually.