1. Shove it through while public market sentiments are still positive and accepting or riskier bets.
2. The numbers can only look worse in the future.
The fact that the company is in the red, in itself, is not a reason to stop going public. Companies like FireEye are in the red but have multiplied in market cap since going public.
FireEye debuted at $20. It hit a peak of ~$85 shortly after the IPO. Its closing price today is $28.76.
As of September, 40% of the companies that went public in the past year with market caps above $1 billion were below their offering prices[1]. The market for IPOs has become even tougher since September. Just look at Pure Storage[2] and CytomX[3].
In my opinion Square is getting out to market while they can.
[1] http://www.bloomberg.com/news/articles/2015-09-14/many-of-th...
[2] http://www.wsj.com/articles/pure-storage-trades-below-ipo-pr...
[3] http://www.bizjournals.com/sanfrancisco/blog/biotech/2015/10...