If the assumption is that you're going to lose half your money up front, then my plan would be to make sure "my money" is as little as possible: learn based on

If the assumption is that you're going to lose half your money up front, then my plan would be to make sure "my money" is as little as possible: learn based on smaller bets. It sounds like Zillow built the Sea Dragon first, when they should have started with the Redstone and moved toward the Saturn V. If Zillow thought they had all the data they needed, there would have been little harm starting with $100 million in properties -- if the loss there ended up being $5 million, they would have known immediately something was up and that they had work to do.