In venture capital, I suspect that hatred of losing may be a disadvantage. No matter how successful you may be, most of your individual investments will lose money and hatred of losing may make you too risk-averse. It might be better to have the ability to simply forget your losses and put them behind you.
I discovered in high school playing poker with friends that I hated losing, but I didn’t enjoy winning very much in that context. So I stopped playing poker. Decades later, I hated “angel investing,” perhaps for the same reason, and I stopped doing that.
Romance is probably another area in which you probably take a different approach if you love winning more than you hate losing, or vice-versa. Think of it as a game in which your self-esteem is at stake.
But I wonder if the relative strength of your feelings about winning or losing is generic or instead is specific to context. As Tyler points out, there are some activities where losses are relatively costly, and in that context I would say that it makes sense to be averse to losing.
My advice to people is to take chances that have high upside and low downside, while avoiding the reverse. It is relatively simple, obvious advice, and in some sense it is neutral with respect to winning and losing per se.
1. Start with objective probability distribution. Eg 50/50 coin flip
2. Overlay your emotional cost function. Eg losing $1 causes you $1.1 of distress and winning $1 gives you $0.8 of pleasure. Most diminishing marginal utility curves would mean that $0.9 (the average of $1.1 and $0.8) is less than $1.
So your hurdle rate for getting involved is 11%. Or more complicated, depending on the tail probabilities and your utility response to those.
But there is also
3. Emotional cost function of the marginal player. Your should still avoid games (businesses) with the expected payoff above your hurdle rate if the marginal players’ hurdle rate is lower.
The same as the door-to-door brush salesman experience. Nine times you get rejected, the tenth you sell a brush. Only necessity makes you to take the beating and go on. Or faith, if you sell Bibles. Angels must believe in miracles, and miraculously, sometimes they happen.
“My advice to people is to take chances that have high upside and low downside, while avoiding the reverse.”
The hard part is recognizing which is which.