The client was willing to gamble on furnishing for STR over LTR route and we were good for 3.5 years, then one day the man came and shut it down. 

I know people that are really good at their trade (plumbing, cleaning, electrician, etc) but they don't have financial discipline, they don't know how to market, they suck at customer service, they don't use tools to their advantage, etc.Cody Sanchez (lady in the video) buys different types of businesses and makes them profitable by applying basic business disciplines.

After 45 years investing across many asset classes, many investment types, and everything from lowest risk to outright gambles, I think I finally know the answer.The biggest divide is between investments in which operational control over that investment is with the investor, and investments in which control rests with another party.  

People mentioning that they put their life savings in something in hopes of a better future is gambling.

It’s just a gamble.  

I'm a high achiever, miniature boss-lady with a 140 IQ and an undergrad in mathematics.

All recent increases and near-term future increases are just gambling.

It's a gamble either way.

A gamble on gambles of volatility moving certain ways in certain time windows..... 

Wow you are a brave lady!