Though I agree with the sentiment, this is a lot easier to say when external to the problem. Much of it is about fixing or changing lifestyle and behaviour, and in such cases it may be easier to go for "safe" wins, such as a day job, with certain and known results (positives such as known income, and the negative such as web-app/startup opportunity cost) and building up and moving forward before re-exposing one self to risk (esp as it is similar as per his situation before).

The higher risk 'do another startup' could be the way to go, but in such an environment/situation, I fear this perhaps is only shying away from underlying problems and hence it is better to take safe route and fix them first.