The Investor's Dilemma

I am slightly troubled with the idea that technology investing is nothing but a crude, self-fulfilling way for previously successful founders to fund the next versions of themselves. I’m not expressing my issues with investors looking for patterns when they invest – pattern recognition is necessary to be a good investor. However, I feel like this obsession for patterns can let a margin of founders slip past the cracks. I appreciate the quality of intellectual honesty – I wonder if you truly can align your investment style with pure intellectual honesty, e.g., can part of your investment process avoid sucking up to conventionally great founders/companies? I cannot stand that.

In this vein, I also wonder if the founders who slip through the cracks are the types, when at least moderately successful, to be the ones who generate positive FCF businesses as opposed to failed venture-backable-type companies. I am increasingly getting excited about the prospect of a small, healthy, and operable business that I can grow on my own accords. This is probably where I will align my efforts for the next few months.

A tertiary note I have is that every time I fail at X, I only want to win at X +a*n (n = the number of times I have failed). In other words, if I mess up on a Calc 1 exam, I then set my sights on a Calc 2 exam. Not trying to be cryptic, but this is how I believe company builders should be positioning themselves for conflict-resolution.