"Given how you can “game” your pitches - from the VCs perspective isn’t this bad? Wouldn’t that mean potentially bad companies could “con” you into funding them?"

It's pretty similar to gaming job interviews. But in my experience, VCs are very good at reading between the lines, to the point that they sometimes understand the pitch better than the person making it. I don't see anything here as gaming it though. Some VCs even recommend you do something similar.

"I wonder what the downside is of being strictly objective is (if possible)."

The best investments often have a lot of strengths and a lot of weaknesses. Being strictly objective usually emphasizes the weaknesses more. A lot of VCs look for strengths, but these are often unique and poorly defined.

To a large extent investing is about pattern-matching. You are basically looking at the same situations day-in, day-out for years. You see what works, try to fit it in a box, etc.

This is kind of a doubled-edged sword situation though. After a certain point, you just start blocking situations out mentally. You try to take shortcuts by just looking for X. You don't react when the world starts changing. If you are in an environment where your sample is very tainted (which happens in VC), it is also very easy to actually get reinforced on situations that aren't optimal (this is why most VC funding goes to people who know each other).

I would characterise myself as someone unusually able to switch my thinking when required and I still have a long list of rules that seem basically arbitrary to an outsider (for example, if the CEO has a knighthood, the company will likely do very poorly)...and no pattern is foolproof (the obvious example is Tesla, I don't tend to invest in companies where the CEO is a habitual bullshitter...most of the time that rule works, in that case it didn't work so well).

But investing is about pattern-matching, it can be extremely arbitrary. If you are looking to raise money, I would consult with someone who understands the market you are trying to raise in (i.e. so you can pitch to that pattern...I don't think it will improve your odds of success but it will mean that the funder understands what the situation is), and remember not to take it personally.

Tesla is exactly what I mean -- they wouldn't pass most checklists. Elon has plenty of weaknesses but he has proven to be able to build good companies again and again.

I wouldn't say it's pattern matching. That works great for stocks and established companies, but with "moonshots", you're looking for things that have not existed before. Everyone looks for the next Zuckerberg, Bezos, Gates, Musk, whatever, but the pattern is there is little pattern.

Certainly, it's possible to sell certain VCs on borderline-fraudulent visions of the future, the so-called Investor Storytime pitch. I'm think of Juicero, YikYak, WeWork, etc.

However, that doesn't mean that to be a fraud-resistant VC you shouldn't be looking for a story, or that as a founder you're pulling a fast one by having a narrative in your pitch.

To understand something, you need to make connections. To convince someone to invest, you need to get the investors to understand what your business is and why it's going to grow and make money. Connecting a series of facts and ideas from a starting point to an end IS the definition of a narrative.

That's just how humans interact, disseminate information, and learn. Even technical work (and pure math!) does this.

Honestly, it’s crazy. We back incredible women who end up spending at least four times fundraising than similarly qualified men, consistently get offered lower valuations, and end up raising less capital. It’s fucked up — the three solo female founders we backed are some of the best performers in our fund I so that makes me wonder how many incredible women aren’t getting funded at all who would also crush if they had the resources.

Yes, they do all the time. And it's likely still easier for men to do so than for women.