We have talked about analyzing investment opportunities by collecting data points about the people involved, the business being built, the market being transformed, and the potential payouts down the road. If you run a thorough due diligence process and you carefully weigh the risk and upside of a given investment, you are far more likely to make good investment decisions. However, there is one more key factor that you need to consider—you. As I look back on more than a decade of venture investments, there were certainly times when I passed on huge successes for good reasons—they didn’t fit into my investment thesis, or I was worried there would be too much dilution before they exited. Or perhaps ...

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