Sean, I think that this is what life is all about, and you are 100% correct about being all in. But if you read through Gladwell’s book Outliers (sic), you will find that often luck, the time frame, the place where you were at in life are major factors which contribute or not contribute to your success. Most of these ventures you mention sound like they were doomed to fail before they started, and if by chance one had happened to be Snapchat or Facebook, things would be different. That said, you could do a statistical study and probably find that yes multiple ventures going on is a major negative in the chances of success at entrepreneurship, but so are having a family, a major hobby or calling, even mental illness or a personal illness. In the book Y-Combinator Graham mentions that he was negative on women and older people in tech entrepreneurship as well as people with a family or distractions, because he wanted to reduce the chances of failure. Some of these things we can control, but some why should we control. You should just be proud that you took those chances, whether good or bad, learned and you are better for it. One entrepreneur I know says you can fail 30 times but you really only have to be bigly successful once!

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