Not particularly. Most would interpret it here as "plucky". Small player tackling bigger players, having to work a bit harder and smarter, etc.

Interesting. I thought this word is often used by incumbents to look down at the newcomer. English is not my first language so it's good to learn these subtleties.

When I think "upstart", I think of my grade 9 English teacher who once described a fairly naughty student as "you young whipper-snapper!".

To me it does come off as vaguely negative - in context, perhaps hinting at skepticism of whether the company will succeed in overtaking Uber. But if so, only mildly; the word definitely has its positive connotations too.

When startups were "cool" and people weren't so keen to their puffery and PR hacks or vaporware smoke tests, it was positive.

However, these days you almost certainly want to be known as a "business" by anyone who matters, and one with good reviews.

Not really - rebel also has a slightly negative connotation.

How it sounds of depends if you are the empire, a Jedi or a sports fan.

In general I’ve seen ola fight tooth and nail against Uber by focusing on the vagaries and niches of the Indian market.

They took the fight to the a much stronger competitor. They couldn’t win on just funding advantages so kept carving out areas which Uber has not considered.

I’m betting Uber learnt a lot from that fight.

Let’s see how they fare in Australia. Wishing them Well.

I think it's negative, and describing them as "an Indian Upstart" sounds a bit racist to me.

Oxford dictionary definition #1: (derogatory) A person who has risen suddenly in rank or importance, especially one who behaves arrogantly.

In the same vein as "self taught" might have a negative connotation. Very class based. Severely dependant on context.