"When you are asked if you can do a job, tell ’em, ‘Certainly I can!’ Then get busy and find out how to do it."
– Theodore Roosevelt

Mr. Roosevelt encouraged a $5000 loss.

TR liked to take chances, and it nearly killed him in South America and probably shortened his life.

I have a guess that these quotes by famous people encouraging risky behavior are disproportionately meant for the people who are more cautious than not, for the ones who indulge in careless risk-taking aren't usually in a stable enough position in life where they could do anything truly impactful. I know this is too presumptive and probably wrong, but just a guess that the risk-taking comes AFTER learning how to assess risk and step back when necessary.

@N00bPancakes IDK much about history but I can imagine something like this lol.

Someone: TR can you fight this war for me?
TR: Sure thing fam, on it!
*reading the art of war for 2 days*
TR: fck how did I lose that one lol?

@alcatraz627

Also survivorship bias. Had TR gotten killed in Cuba or something ... we probably wouldn't know that quote ;)

@alcatraz627 I can't find anything related to risk assessment in the quote so any follower will eventually doom him/her self if not cautious.

What's the $ 5000 reference about?

@asgs a loss to the company i was previously in