One thing that Adam Grant writes about in his book, "Originals", is how it's a bit of a fallacy that founders often dive head first and risk it all when starting their companies. Could be somewhat of a confirmation bias but he gives some great examples of how risk averse many founders actually are when starting their companies (Warby Parker was the main example if I remember correctly).

http://www.adamgrant.net/originals

I came to say just this! He goes on to say that the great startup risk takers are confused with great "risk mitigators" who often hedge these risky bets. One example he gave was Woz who was working with HP when focusing with the creation of Apple.

It's rather inspiring. It shows you can swing for the fences without sacrificing much.

"[Swinging] for the fences" literally means to swing a baseball bat as hard as you can at where you think a baseball will be thrown[1]. You're far less likely to connect with the ball, but you will propel the ball much farther if you do manage to.

Swinging for the fences is more apt for companies like Magic Leap, Groupon, Gilt, Pebble, etc.

I'd characterize this guy's approach as being more like "Moneyball." [2]

[1] https://en.wiktionary.org/wiki/swing_for_the_fences

[2] https://en.wikipedia.org/wiki/Moneyball

"Swing for the fences" is basically the same as "go big or go home." You are going to either strike out or hit a home run.

I'm not sure "Moneyball" fits here, the premise of Moneyball was using advanced analytics to take advantage of market inefficiencies.

I would say the baseball idiom that fits here is "cover (one's) bases"

https://idioms.thefreedictionary.com/cover+(one%27s)+bases

>cover (one's) bases To ensure one's safety or success by dealing with every potentially problematic aspect of a situation or activity. A reference to baseball, in which the defensive players must make sure all bases (and baserunners who may occupy them) are accounted for.

(I am fascinated about how many English (American?) idioms are derived from baseball and how I never really thought about it until a couple years ago)

To me, being able to play again is vital if you're going to play a high-risk game.

Eg. making 101 100:1 bets makes way more sense than risking everything on a single victory-or-bust gamble.

This is play for play the 4 hour work week strategy. I keep meaning to test out something with it, just got no ideas :(

This is how I built mark II of my startup. As long as you are willing to work hard for a few years it is the best way. Three years of doing nothing but working and sleeping and I was able to resign from my job and still owned 100% of my startup.