Taking advantage of one-sided bets

Last week, I got to work nearly 2 hours late. As I sat in gridlock, it dawned on me how powerful the principle of asymmetry is, the same principle that disrupted my morning, is perhaps the most underrated principle in investing. I live in Manly NSW and our offices are in Sydney CBD – which means I must run the Military Rd gauntlet - a stretch of road that is very sensitive to slight changes in the number of road users. An equation inspired by Nassim Taleb, does a good job of explaining my morning: 15% increase of cars on the road (due to 5mm of rain) = 300% increase in total travel time. As we can see, the increase in travel time was highly asymmetric to the increase in road users. As I learned the hard way, the trick is to have asymmetry working for you - not against you; where the potential gains are greater than the downside risk. So how can one incorporate positive asymmetry within their portfolios? (VIEW LINK)