Mutual Fund Manager
Ever hear of "clearance?" That is, if you hear inside information, you"re supposed to go to a lawyer in your firm, confirm everything, and quickly freeze trading in the security. But you forgot. Oh well. Say hi to Bubba; you two are gonna get real tight.
You invest. You recommend. But you suck. You get fired. Luckily you passed the Shmoop Series 7 exam so you can get a job selling stocks to widows and orphans as a broker in a small office.
You survive. You invest about as well as Mr. Market. You remain at a modest-sized fund for 25 years, save your pennies, and eventually retire with lots of war stories and dreams of stocks gone by.
You're at a big fund house and you do really well. You end up running the place for $10 million a year and get offered amazing golf packages which you have to reimburse personally, but who cares—it's Augusta.
You start your own fund series. And it's successful. Results are so good, in fact, that you don't need much marketing: CNBC does it for you. Billionaire status with all the trimmings that come with being able to buy a city.