> Also, what is "success"? Taking $350MM in investment and not showing profitability

That's an odd thing to say. Most companies that take investment aren't profitable- that's kind of the point of taking VC: you want the cash in order to greatly grow the business more than if you were sitting within profitability the entire time. There's a difference between "unprofitable" and "choosing not to be profitable".

What's more, GitHub wasn't profitable the last ~5 years or so, from the day they took VC. But they sold for $7.5B, so it doesn't seem that Microsoft has a problem with their "unprofitability". That's how many solid, foundational companies are created.