Not to brag, but I could have predicted the rise of those examples given. Had I been able to invest, I would have done so. Evernote, on the other hand, I would have stayed away from..
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How is that not just bragging?
It's not bragging because he hasn't actually done it and just talking about in on HN in retrospect. You and I could say the same thing too for example, and that wouldn't make us a bragger. It would however make us braggers if we actually did invest and made tons of money out of it.
It sounded like he was bragging that he could have done it.
If I were a VC investing in consumer internet technology, I would be looking for market dominance, a clean user experience, a unique angle that differentiates it from similar services, scalability, high profitability, relatively low costs, and broad appeal. Investing in Facebook in 2007 would have been easy, seeing that the site was already gaining a lot of traction and had high profit potential. Most social networks fizzle out pretty quickly. The hardest part is probably getting the opportunity to invest, not choosing the company.
I def. know a lot about this area, and myself predicted the rise of valuations of major web 2.0 companies like Facebook, Snapchat, and Uber.
But I don't think it's that hard of a skill picking the winners from the losers. But he problem is if everyone followed this strategy you would have a lot of unfunded companies.
It's survivorship bias. Sure, it's easy to point out how obvious the winners were, but there are probably 10 others that looked like winners but ended up failing.