Shakespeare on Being Risk-Loving in the Loss Domain

In my school-days, when I had lost one shaft, 
I shot his fellow of the self-same flight 
The self-same way with more advised watch, 
To find the other forth, and by adventuring both 
I oft found both: I urge this childhood proof, 
Because what follows is pure innocence. 
I owe you much, and, like a wilful youth, 
That which I owe is lost; but if you please 
To shoot another arrow that self way 
Which you did shoot the first, I do not doubt, 
As I will watch the aim, or to find both 
Or bring your latter hazard back again 
And thankfully rest debtor for the first.

(The Merchant of Venice, Act 1, Scene 1, Lines 147-159)

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In As You Like It, Orlando, who has been thrust below his deserved state by his brother Oliver's neglect and enmity, chooses to risk a high probability of serious harm or death by taking on the Duke's mighty wrestler. When Celia and Rosalind try to persuade him against this decision, Orlando replies: 

...let your fair eyes and gentle wishes go with me to my trial; wherein if I be foil'd there is but one sham'd that was never gracious; if kill'd, but one dead that is willing to be so. I shall do my friends no wrong, for I have none to lament me; the world no injury, for in it I have nothing; only in the world I fill up a place, which may be better supplied when I have made it empty.

(As You Like It, Act 1, Scene 2, Lines 299-305)

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We all that are engaged to this loss

Knew that we ventured on such dangerous seas

That if we wrought out life 'twas ten to one;

And yet we ventur'd, for the gain propos'd

Chok'd the respect of likely peril fear'd;

And since we are o'erset, venture again.

Come, we will put forth, body and goods.

(King Henry IV, part 2, Act 1, Scene 1, Lines 238-244)