I asked this question to Alan recently, and here were my takeaways:
One important thing is to have a pretty full picture of the ongoing trends in CS software and hardware. They had this at PARC because their team included hardware and software specialists. All together they were up on all the literature. If you can pretty accurately predict the trends, it's usually not to hard to buy it today. However it may not be processing power or storage that's the key. For example Dynamicland buys very expensive projectors to "buy" the future of AR and VR