By Ramit Sethi (Author, I Will Teach You To Be Rich)
Telling a story about Chris Rock helped me earn over $100,000 in scholarship money to attend college. During senior year of high school, my parents — immigrants who raised four kids and didn’t have money to send us to college — encouraged us to apply to every scholarship we could find.

Since I’m a big weirdo, I built a system that allowed me to apply to over 60 scholarships in a few weeks (I’ve detailed parts of the system I used to get so many college scholarships).

The largest scholarship I received had an extensive application process. First, you filled out an application with a handwritten essay, transcript, reference letter, and photo. Then, if you were selected as a finalist, you were invited to the foundation’s mansion. I had no idea about what I was going to encounter as I walked up the grand porch with my dad. As we got to the door, a very serious woman looked at my dad, frowned, said, “You can wait here,” and CLOSED THE DOOR IN MY DAD’S FACE. As she ushered me inside, I was too nervous to laugh at my dad standing outside, very confused.

Then she took me into a small room and handed me a piece of paper. “We’d like you to write an essay,” she said. “You have 30 minutes.”

I looked at the essay prompt. “If you could have dinner with anyone, living or dead, who would it be and why?”

Classic prompt. So I started thinking.

Nelson Mandela? Eh… it would be the “logical” choice, but honestly, dinner with Mandela wouldn’t be that exciting for a 17-year-old kid.

President Clinton? Would be cool to brag about… but what would we really talk about?

At this point, it’s about three minutes in to my writing time. I knew I could write some BS about Mandela or the President, but I would sound like every other candidate. Plus, I really didn’t want to meet them.

And then I got it: Chris Rock.

At 17, I was a huge fan of his, I’d watched all his specials, and I could recite his jokes in my sleep. But I thought that much of what people thought about him was superficial.

And so I started to write. I wrote about how he is perceived as simply a comedian, but is actually a highly astute social commentator. How his jokes reveal the things we want to say, but we can’t articulate — or we’re afraid to.

I decided to go all-in.

I described one of his jokes — a story about a black woman’s hands shaking as she buys groceries, hoping there’s enough money in the account — which sounds aggressive (and is) but is actually a deep, subtle commentary. In the essay, I deconstructed the joke. What could be offensive was actually examining racial attitudes that our society holds. And since we can’t discuss these attitudes intellectually, his comedy distills, simplifies, and reflects our attitudes, allowing us to have a shared experience around the elephants in the room.

I finished up the essay with a couple minutes to spare and handed it to the lady when she returned.

A few minutes later, I was shown into the interview room, where six interviewers faced me. The lady had taken my essay, made photocopies, and given copies to each of the interviewers, who had read it and were ready to discuss it with me.

“So,” one of them said gravely, “tell us why you chose Mr. Rock.”

And later, when I discovered that I had won over $100,000 in college scholarship money from this foundation, I thought back on that essay.

Choosing Chris Rock wasn’t the inspired choice of a future entrepreneur; it was a nervous kid in a room who really believed in something. I later heard that one of my friends wrote about Watson and Crick (who discovered the double-helix structure of DNA). Which essay would you rather read? Who would you believe is genuinely interested in the topic? Who took a bigger risk?

When it comes to risks, most people look at them as an “all or nothing” bet. But as I demonstrate in my example of testing responses in bars, you can use testing and other techniques to mitigate risk…and make little bets. I teach people how to use these little bets to make money on the side. And I still use little bets to grow my own business.

This post was originally posted at The Young Entrepreneur Council. The Young Entrepreneur Council (YEC) is an invite-only nonprofit organization comprised of the country’s most promising young entrepreneurs. The YEC promotes entrepreneurship as a solution to youth unemployment and underemployment and provides its members with access to tools, mentorship, and resources that support each stage of a business’s development and growth.

Photo credit: Aaron Patterson on Flickr.
About the guest blogger: Ramit Sethi runs a blog on personal finance help where he covers automation, psychology, and earning more. The New York Times best-selling author of I Will Teach You To Be Rich, shows regular people how to live a rich life by spending extravagantly on the things they love — and cutting costs mercilessly on the things they don’t. Formerly, Ramit co-founded PBwiki, a venture-backed startup. Follow him on Twitter at @ramit.