> I think of rolling the dice as taking a chance without any knowledge of the chance for it paying of. Rolling the dice just means relying on getting lucky (in

> I think of rolling the dice as taking a chance without any knowledge of the chance for it paying of. Rolling the dice just means relying on getting lucky (instead of being skillful or controlling the outcome), usually on an unlikely outcome. When you literally roll the dice the odds are completely transparent (1/6 chance of each d6 value). In this case (and in general with big rewrites), the thing you can never know about up-front - and therefore are relying on luck for - is whether you can build the new version within the time/resource budget that you allocate to it. If you get the estimation wrong, or hit unexpected problems/delays, then the rewrite can easily balloon from an ROI-positive project to a massively ROI-negative one. For a startup, this is particularly important because you could run out of runway before your rewrite pays off. This is why most people regard it to be a bad idea (or at least a risky one) to do a full rewrite of a product instead of incrementally evolving it. (Spolsky's essay on the subject I think is the canonical list of concerns with a rewrite: https://www.joelonsoftware.com/2000/04/06/things-you-should-never-do-part-i/ https://www.joelonsoftware.com/2000/04/06/things-you-should-...)