The best laugh I’ve ever had in a meeting came courtesy of my buddy Gordon Ritter. For those who don’t know Gordon, he’s got this awesome and disarming zany earnestness that would probably make him the perfect guy with whom to watch Russian Dash Cam videos: “Did you see those cows tumble out of the truck when it tipped over?!? AND WALK AWAY LIKE NOTHING HAPPENED?!?!?!”

But I digress . . . it was the spring of 2003 and I was meeting with Gordon and his partners as they were raising Emergence’s first fund.   As the meeting was wrapping up, Gordon slid a piece of paper across the conference table: “our reference list,” he said. I had been in the LP biz for a couple of years at that point and was feeling pretty clever. “Well, I like to do off-list references,” I quipped. Looking serious, Gordon started to rummage around in his bag. After a few moments, he said, “I’ve got an off-list list in here somewhere . . . “ I must have looked completely bewildered as I stammered, “but then the ‘off-list’ would be ‘on list’ and I’d have to go off-off-list . . .” At that point, Gordon couldn’t bear it anymore and broke into a wide grin that gave us all permission to crack up in hysterics at the absurdity of what I’d said . . .

I thought of this story the other day while hanging out with my buddy David Katzman. Over dinner, we mused that it’s possible to do too much due diligence. David reminded me that Fred Wilson wrote a great blog post on this subject a couple of years back. Fred is famous for his gut and has an amazing hit rate on his intuition. Kaztman and I observed that, in contrast, it seems that some outsource their thinking to others by doing endless research. Indeed, having sat in front of a thick diligence binder, I’ve often thought that there are a lot of heuristics that are the enemy of good decisions. Confirmation bias is probably the most insidious of these, but overgeneralization is also pretty sinister, too. Sometimes it can be easy to forget that data is not the plural of anecdote.

I’ve learned by watching some of the best investors around that having a well-formed thesis simplifies investing: if you don’t have a good sense for what you’re seeking, how will you ever find it without boiling the ocean? Pasteur famously said, “in fields of observation, chance favors the prepared mind.” And very practice of developing a thesis helps you figure out what questions to ask and where the data sources, especially the orthogonal ones, lie. Classically practiced diligence mainly helps one manage conventional risks as seen through the prism of other people’s biases.

In having a prepared mind, investors should strive to develop opinions, a scarce resource in a hurried, reactive business. Oftentimes, the more diligence you do under the guise of “getting smart,” the more your mosaic of facts will resemble everyone else’s. But I guess that’s ok when for people who think it’s better to fail conventionally than it is to succeed unconventionally.

Of course, some people are ok with being copycats and there are folks that distill diligence to one call: to their favorite bell cow. At Old Ivy, we had a few folks who simply tried to index our portfolio. The problem with that approach is that they often couldn’t access the things we were most excited about, not to mention the fact that we were pursuing a strategy specifically tailored to our needs. Specifically, we were exploiting some unfair advantages that we had, especially low liquidity needs and long, long, long time horizon. Confounding matters further, when people called me to find out what we at Princeton were doing, I only shared my second-best ideas. Should I feel guilty?

Probably not. Too many people are intoxicated by opiate-like embrace of the crowd.  Indeed, taking the time to develop an opinion and resist FOMO takes courage and an investigators eye while the easy path relies on unfocused and reactive probing that captures more noise than signal because of poorly tuned antennae.  Robust non-conformists with the courage of their convictions tread through the thickets of embarrassment and career risk that come from being wrong and alone in search of fortune and glory. We make the road by walking it. Which path will you take?