The government claim to support startups but actually they barely do anything. There is a Entrepreneur Visa but you need a serious amount of funding, proof of intellectual property (even patents), backing of a VC or incubator, and credibility in the industry to get it. And even then the visa granted is dependent on your startup making hires of local citizens at a certain rate per year, in line with revenues. The actual visa itself is also relatively short term, it is basically issued on 12 month periods which isn't really enough to provide assurance and stability to a startup director.
The culture here is all wrong. The culture here is to go to Uni, attaining 2 degrees is not uncommon, then get a boring job in a mega corporate. And then spend the rest of your life twiddling your thumbs, stabbing and getting stabbed in the back, etc etc, where the gossip often revolves around bullshit job title acronyms like VP, ED etc. That is just the life here. If you ain't working in a mega corp then you are a nobody. And that's not my opinion, I have many many friends here that tell me straight that that is how life is here.
There is also an issue that working in "I.T." in Asia is stereotyped also. It is perceived as a somewhat low skilled office job. Even if you are a top level super senior software developer, try explaining that and most people will still just file you under "I.T." in their minds and maintain a superiority complex over you if they work in a dead-end mega corp job dealing in Excel Spreadsheets all day every day.
If you work in an actual startup in SG you are "different". You are seen as abnormal, risky and even stereotyped as "not being good enough" to work in a mega corp.
When I first came here I was introducing myself as "working on my startup". Most people assumed, seriously, I was just being shy about explaining I was unemployed at that moment, and they wanted to quickly change the subject. Even after clarifying that it is indeed profit making and growing well. So yes, saying your working on a startup here is actually almost as bad as saying you are unemployed. I learnt a better way of doing self introductions very quickly here.