That's the problem.. A few vivid examples shouldn't influence a view on this. Data should. A little finance 101: The longer you hold an investment, the higher

That's the problem.. A few vivid examples shouldn't influence a view on this. Data should. A little finance 101: The longer you hold an investment, the higher the return demanded. The riskier the investment, the higher the return demanded. To judge the wisdom of an investment strategy, one needs to weigh these against the potential return. A successful small early investment (for example, Peter Thiel investing in Facebook in 2004) will return much more on a percentage basis than a successful large late investment (for example, Yuri Milner investing 200M in Facebook for 2% of the company in 2009), but they are also much risker and take longer to see a return. Even though Thiel made a billion dollars and Milner only made a few hundred million while investing 400x more money, based on these numbers alone it's hard to say which was a better investment on a risk-adjusted basis. We don't know what the expected value of each investment was (probability weighted terminal value of Facebook). We don't know what their cost of capital was (what else they could have been doing with the money). All of these matter. My point is that it's hard to figure this stuff out. Real academics have a tough time coming up with definitive answers to these questions. Furthermore, the answer can change over time. The fact that chili tastes better when it's cooked slowly is of no consequence to this question.