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Not On Your Side

This is completely anecdotal.

One of the most exciting seats to be in is someone who previously could have been in a traditional, institutional venture capital seat. Not only is having the privilege of participating in a job like that rare, but forces you to quickly learn about one of the most difficult-to-understand industries imaginable.

I come from a family of finance parents. I can assure you, not finance in the way that someone would learn how to stiff cut-throat deals, but the type of finance that uses actual data, numbers, and the most dirty of all words: rules. Rules, specifically, is something that venture capitalists, although subjected to many of them, they encourage others to ignore for the sake of catching the cool breeze of a potential “big break.”

And to clarify, I love venture. Even in some of the few months in between jobs, in between funds — more specifically, I’m still excited in the idea of finding people who take on that risk individually before they even have the 1) money or 2) opportunity and definitely not 3) the exposure to highlight what a risky, smart, and talent individual they are. That’s something that is wonderful and borderline beautiful.

And sure, there are a lot of venture capitalists that position themselves are “contrarian” to some mystical and air-ed out status quo. But, to most of my founder friends, I will always encourage them to ask exactly what (and who) the VC is contrarian to? Could it be the “greater industry?” Could it be their parents? Could it be the industry they were in before they were in proper tech or proper finance?

There’s one thing that, in this grey area of my career, personal life and somehow in the most honest and confident I have been, assure you is that: just because someone is “contrarian,” it doesn’t mean that they are on your side.

You can be contrarian. They can be contrarian. But this doesn’t assure shared values, intelligence, risk appetite, or that you two would even be friends.

There’s a 30% chance that you’ve been on this blog long enough to learn that there was a few years where I was very uncertain and concerning-ly determined to figure out and succeed to make a name for myself within the venture capital industry. And I have.