The biggest mistake entrepreneurs make when pitching VCs is to argue that their startup is likely to succeed. Instead, they should argue that there is a small probability their startup could be a billion dollar or greater exit. There is a big difference between these arguments – the mean of the return distributions might be the same but what VCs care about is right side tail of the distribution.
Investor sentiment, the old saying goes, is a horse race between fear and greed. The fear and greed in venture capital is all about investing in or missing out on the next Google. No VC stays up at night worrying about missing the next startup that’s flipped to Google. The way you get VCs interested is to convince them there’s a small but non-negligible chance you’ll create a billion dollar (valuation) business.
I’ve learned this lesson first hand on both sides of the table. One example: A good friend of mine was starting a company a few years ago. I was excited about the idea and tried to help him raise venture money. After the entrepreneur pitched some VC friends of mine, I was surprised when the they came back to me to say they are passing because “it seems like a smallish, ‘lifestyle’ business.”
The entrepreneur had made a very good pitch for why his product was valuable, why he could create a profitable business, that he was very smart and well prepared, and so on. What he needed but failed to do was leave the VC with the nagging thought that this could be the “the next big thing.” Part of this was because of the entrepreneur’s natural modesty. Some people don’t have the chutzpah to aggressively assert that their idea is the next big thing, even when, deep down, they truly believe it. In everyday life, this kind of modesty is a virtue. When pitching VC’s, it is the single worst thing you can do. (If deep down, you don’t believe your idea will be the next big thing – don’t raise VC money. Once you raise VC you are committed to going for the billion dollar exit whether you like it or not.)
I don’t know if this obsession with the upside outlier case is a good strategy from the VC’s perspective or not. Granular VC return data is hard to come by. I tend to think it is a good strategy – one Google or Facebook (and a lot of other billion dollar exits that aren’t nearly as famous) can make up for a ton of misfires. And the anecdotal return numbers I’ve heard from VCs suggests it works. But I don’t really know.