As a startup founder I found many facets of the venture capital system frustrating: the lack of accessibility of investors, the difficulty of knowing which ones my company was a strategic fit for, and the general unwillingness to invest in the unfamiliar. Of the three, that last bothered me the most. Investors disproportionately placed their bets on people with more experience, who knew the right buzzwords to say at the right time. Perhaps even more frustratingly, they were far more likely to invest in founders who had gone through the startup journey before. I understood that experience is a way to mitigate risk, but why should I be punished just because I was young and hadn’t started a company before? That didn’t detract at all from the quality of my company.

I wouldn’t go so far as to call my founder self naive, but my perspective has certainly shifted as I’ve settled into the venture capitalist role. I still believe many of the things I did as a founder: many VC’s really do make themselves too hard to access for entrepreneurs and are too scared of getting outside of their comfort zone. However, on the matter of first-time vs. repeat founders — at least — I have a much better understanding of the investor bias.

I spent a fair amount of time on Quora this weekend answering questions. Here are some of them from seemingly prospective or new startup founders:

These are all reasonable questions on some level. But none of them instill a whole lot of confidence in an investor. They’re just not the types of questions that an experience founder would ask, because that founder has learned the answers to them the hard way: by knowing that $100K will barely buy you ramen in Silicon Valley, that getting anything done in the business world takes money, and that your own faith in your startup is nowhere near all it takes to convince investors to place their bets.

My founder self didn’t fully appreciate how scary a first time founder can be to an investor. The first time founder is an unknown quantity… sure, they can be the next Zuckerberg; but they’re far more likely to burn through every dime they’re given with nothing to show for it.

So how much does being a repeat founder matter? I could point you to some of the good data hiring around the internet on that advantage: it’s stark. But you can certainly argue that’s a self-fulfilling prophecy: investors like repeat founders and give them money, which makes them more likely to be successful.

So instead, let me tell you what it looks like from a VC’s perspective in three different scenarios:

That last case might be a little hyperbolic, but it’s not far from the mark. Venture capitalists really like experienced founders with previous successful exits under their belts. They have their reasons, some of which are good and others of which might not be. At the end of the day, those reasons don’t matter to you as a founder. You just have to be aware of what’s happening on the other side of the closed door so that you can make the most of your situation.

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