I knew the odds were approaching impossible if all bets were equal. @klye, @acidyo and I figured out the reason why the house got smoked:

https://www.steem-roller.com/# allows leveraged investing. You can leverage up to 99x your Steem investment. If I leverage 99x and there are few other investors, that means one winning bet at the maximum allowable bet (based on total amount invested and leveraged)can bankrupt me.

The gambler can easily add more funds, the investors are often AFK. Long story short, the leveraged investors get exploited very quickly as you can bankrupt them in 1 roll even at high odds of winning, bet 1 million Steem that you will roll under 98.99 and you can bankrupt a 100 Steem 99x leveraged investor in one easy to win roll. We found this out the hard way.

If you are AFK, I highly recommend you put your leverage to no more than 2x and this point since there are few investors. It's funny though, when someone is going full tilt, you can pull your investment and screw them over before they can attempt to Martingale or wait for the odds to turn.

EDIT: You win 10 Steem, in upvotes!