I think about this big question a lot: "What separates us from them?"

I'm talking about the difference between smart, talented, driven people like you and me, who still have to struggle with life's day-to-day challenges--and them. Meaning, the fortunate, super-successful among us--people who sometimes (but not always) have made enough money never to have to be concerned about it again. Self-made billionaires, for example.

The answer I've come up with is: not much. Not much separates us at all. And while that can be highly frustrating at times, I think it's also inspiring.

So as part of an ongoing series, here are five very quick but inspiring stories about the lives of self-made American billionaires. If they can do it, I hope the thing you can take away from their stories is that you can potentially do it, too.

(There are many other inspiring stories to tell, and I'd like to ask for your help. Whose stories should I focus on next in this series? I hope you'll contact me here and help me choose.)

Blakely graduated from Florida State in 1993, intending to go to law school--but then she did poorly on the LSATs, twice. She took a job at Disney World, hated it, and wound up in sales, cold-calling prospects and trying to sell fax machines to businesses.

She was an excellent salesperson, but it was the challenge of dressing professionally in the Florida heat that led to her true success. She kept her day job, but spent nights and weekends working on the product that would become Spanx. The cold-calling experience came in handy, as just about every adviser, supplier, and retailer she reached out to told her it wouldn't work--but she didn't listen. Her company is now an apparel juggernaut; she owns the whole thing, and her net worth is estimated at $1.1 billion.

Graves graduated from college, landed a position as a database administrator, and quickly decided it was a dead-end job that really wasn't for him. So in 2010, he started networking and applying for jobs at cooler internet startups, such as Foursquare. But he got turned down.

Rather than let this dissuade him, Graves started doing business development for Foursquare anyway--traveling around Chicago during his off hours and convincing businesses to sign on. His hustle led to an internship--and ultimately an opportunity to become the first employee of Uber. His net worth is approximately $1.5 billion, after only five years.

Plank got kicked out of one high school and played football at another before going to prep school in hopes of a Division I college athletic scholarship. That didn't happen, so he enrolled at the University of Maryland, where he walked onto the team--and ultimately came up with the idea for his company Under Armour, after growing frustrated by how his uniform became sopped with sweat.

Plank maxed out his credit cards and worked from his grandmother's basement. Finally, in 1999, he bought a $25,000 ad in ESPN magazine that led to $1 million in sales. Now, Wall Street values Under Armour at almost $20 billion, and Plank himself is worth about $3.7 billion.

Woodman failed with his first two startups--EmpowerAll.com and Funbag. To fund his next idea, he and his wife bought 600 seashell belts in Bali at $1.90 each, then drove up and down the California coast selling them for $60 a head. (In fairness, Woodman is the son of a venture capitalist, and he was able to get a $260,000 investment from his parents as well.)

 Nevertheless, you probably know his company: GoPro. Woodman's net worth is now approximately $1.6 billion.

DeJoria was homeless at one point and lived in his car. He grew up in foster care, served two years in the U.S. Navy, and had odd jobs including working as a janitor and--no joke--"a door-to-door encyclopedia salesman," before getting a job at Redken Laboratories, which sold hair products to salons.


With a few years of experience and a $750 loan, DeJoria cofounded John Paul Mitchell Systems in 1980, which, although it "should have gone bankrupt perhaps 50 times in the first year," according to DeJoria, grew into a $1 billion-a-year business. As a hobby, DeJoria also co-founded Patron Spirits. His net worth now: about $4 billion.