My $100,000 bet on Chris Rock

Ramit Sethi

Nobody on this site knows that 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 4 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 hand-written 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 ON 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 3 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 6 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 also have one more story about Chris Rock. It’s about taking risks, and it’s told by my friend Peter Sims, who just wrote the new book, Little Bets.

Peter — take it away.

* * *

Peter Sims: Chris Rock’s Little Bets

The following post is an exclusive excerpt from “Little Bets: How Breakthrough Ideas Emerge from Small Discoveries,” by bestselling author and former venture capitalist Peter Sims.

While there is no doubt Chris Rock has got great talent, his genius comes from his approach, that we can all learn from to do anything new well. The routines he rolls out on HBO and global tours are the result of what he has learned from thousands of little bets, nearly all of which fail.

In gearing up for his latest global tour, Rock made between forty and fifty appearances at small comedy clubs. His early performances can be painful to watch. Jokes will ramble, he’ll lose his train of thought and need to refer to his notes, and some audience members sit with their arms folded, noticeably unimpressed. The audience will laugh about his flops—laughing at him, not with him.

Developing an hour-long act takes even top comedians like Rock from six months to a year. If comedians are serious about success, they get on stage every night they can, especially when developing new material. They typically do so at least five nights per week, sometimes up to seven, and sweat over every element and word. And the cycle repeats, day in, day out. (Writers for the Onion suggest roughly six hundred possibilities for eighteen headlines each week, a 3 percent success rate.)

By the time Rock reaches a big show — say an HBO special or an appearance on Letterman — he’s flawless.

What we see on TV is not effortless genius. There’s a method to the madness. It’s the outgrowth of a brilliant approach, which includes:
Think about what you can afford to lose, rather than what you can expect to gain. Just as Chris Rock doesn’t plan or try to predict which jokes will work and which won’t before trying them.

Learn a lot from a little. Rock watches the audience body language closely, especially the die-hard regulars who typically sit in the center of the room. Seeking out a small group of these active users with little bets is a proven way to tap into unique insights and desires.

Learn a little bit from a lot of people. Comedians like Rock and Jerry Seinfeld constantly seek out new ideas and insights by carefully observing what’s going on in the world, whether it’s standing in line at Starbucks, talking with taxi cab drivers, or going to events. They get out of the office.

Improvise, test, iterate, and repeat. It takes comedians like Rock six months to a year to develop an hours worth of material. They must persevere and learn to develop what Stanford social psychologist Dr. Carol Dweck calls a “growth mindset,” to be able to overcome setbacks.

It all begins with one little bet. What will yours be?

# # #

Peter’s latest book, Little Bets, is available through all major booksellers. You can find more at his website, including a free excerpt.

Note from Ramit: The concept of “little bets” has changed many iwillteachyoutoberich readers’ lives by challenging their ideas of what risk is, and how they can use small tests to change their behavior. Most people think that top performers like Chris Rock are simply “geniuses” — an easy label that completely overlooks the thousands of little bets they make in their lifetime. By adopting their systematic processes, you can leapfrog your peers to dramatically higher performance. While natural talent matters, it’s not about being a genius — it’s about building a system to methodically test your assumptions and performance. This is a great book that’s worth your time.

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  1. Jim Mortensen

    I’m a visual artist that often does one-panel gags. I post them to Facebook, and try and gauge how well they work by the number of likes & comments.

    Would you consider that a decent “bar test”? I usually show people in person, but there’s only so many people I encounter during the day.

  2. Therese

    Love it. Everyone seems to think that successful people are just “natural geniuses,” but the fact is that success takes a lot of hard work and a “thousand little bets.” (this reminds me of the “shrug effect.”)

    The process of “a thousand little bets” might also be likened to Jim Collin’s (author of Built to Last) concept of “evolutionary progress”– i.e., “try a lot of stuff and keep what works.” Collins likens evolutionary progress to “branching & pruning”: if you add enough branches to a tree and intelligently prune the dead wood, then a twig that shows promise could eventually grow into a full-fledged tree.

    A good example of this is Google:

    “Google engineers are encouraged to spend 20% of their work time (one day per week) on projects that interest them (i.e., “trying a lot of stuff” or “a thousand little bets”)… Marissa Mayer, Google’s Vice President of Search Products and User Experience, stated that her analysis showed that half of the new product launches originated from the 20% time.” (including Gmail, Google News, Orkut, and AdSense.)

    Thanks Ramit and Peter! Will definitely take a look at “Little Bets.”

  3. Zachary


    I think that’s a great way to test your audience. Something to think about also, who your audience is. With facebook is that you can check the commentators profiles and develop a sense of your audience demographics.

    Talking to people one on one is awesome as well you can see their reaction right there without words.

    There is the method of viewing your material, facebook can be or not the medium preferred over a personal website, or an aggregate website. There you can test even further.

    Maybe there are some newspaper websites that would like your material. You could try selling to those sites and see how it goes. If you are looking to gain a larger audience or reader base. What is your goal, then test on metrics that you know are relevant to your goal.

  4. Jonathan Vaudreuil

    Isn’t entrepreneurship really a series of little bets? That is the closest description I’ve ever come up with, it’s a series of small bets with little bearing on the overall success of the company, but each takes the company in a different direction based on what works.

    It’s why I have a hard time discussing freelance/consulting work with many people in my parents’ generation. They view it as cutesy work, but a job with a company is oh so much better.

    The consulting work allows me the liberty of having multiple sources of income, and over time multiple ways of making money. A job is one source of income, and like a switch income is either “on” or “off.”

    I also loved the Chris Rock story – I’ve heard he does dozens of shows before every tour, and I believe it 100%. The best performers put in the hours to become the best performers, they’re not simply gifted at doing something. The book “Talent is Overrated” rips the notion of gifted apart and praises specific practice and never-ending learning as the truth behind every great success.

  5. Justin @ MoneyIsTheRoot

    Chris Rock is sheer comedic genius, I couldnt agree more. Like you said, his views are insightful and truthful, he just has a platform that is acceptable to raise these issues, whereas most of us can’t.

    The Little Bets article is interesting as well. I dont know that I can think of my own bet necessarily, but the overall theme seems to be risk/reward, much as the one you took in writing about Chris Rock as the make or break essay worth 100k….gutsy.

  6. Ryan

    That was a great story, which scholarship did you win Ramit?

    • Ryan

      is this story real?

  7. saro

    Don’t you think sincerity has alot to do with it too? I find it more believable that a 17 year old wants to meet Chris Rock.

    I wrote about wanting to meet Bob Marley on a college application and I got in. It was a long-shot college choice and I think my essay made a difference. I was sincere about it.

  8. Chris Fan

    Chris Rock has writers. The vast majority of what you see him perform on those HBO specials are jokes that he only had some involvement in creating. I don’t doubt that he rehearses – almost all well known comedians do.

    Watch him on a show like Real Time w/ Bill Maher. The last time he was on he had almost nothing to contribute because he clearly didn’t know anything about the events (current ones, as is the norm on Real Time) being discussed.

  9. Jodi

    That is such a cool story! I think you should write to chis rock and let him know

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    […] My $100,000 Bet on Chris Rock You’re almost always far better off being honest and shooting from the gut than saying the “correct” thing. (@ i will teach you to be rich) […]

  11. Jay

    What Ramit did with this Chris Rock essay is classic differentiation marketing. He knew that most people entering this contest would stick to the usual “safe” topics…and deliberately wrote about something that would make him stand out.

    How the hell could you possibly ignore an essay like that?

    A gutsy move, but in retrospect, it was also a wise one.

  12. Rowyn

    I remember writing that essay. My year, we had to sit out on the porch, because the mansion was undergoing some renovation. Of course, I can’t for the life of me remember who I wrote about. Wish I could read yours 🙂

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    […] My $100,000 Bet on Chris Rock You’re almost always far better off being honest and shooting from the gut than saying the “correct” thing. (@ i will teach you to be rich) […]

  14. Ben

    I did stand up for a while. It is a lot of testing down the to most minute detail at open mics. You have to be willing to fail 19 times and get laughs one out of 20. To put together an hour of stage comedy your options are:
    1) 6-12 months of doing what you describe above.
    2) Having a team of about 20 writers.
    For most big act touring comedians these days, #2 is way more common than you’d think.

  15. Marlee

    Hi Ramit,
    Although you down play the ingenious nature of your topic selection for this scholarship because you followed your instinct, it was a brilliant move. It took courage, and as you highlight here it required risk.

    I love this article because it highlights that fact that the best parts of our life experience live on the edge of taking risks. And for each little lost bet, you increase your chances of a big win.

    I found this inspiring and compelling. Plus, you’ve demonstrated a great way to make content compelling (throw in an unexpected analogy/make unusual connections).

    Thanks for this Ramit. I’ll be linking to it today. Hope you’ll be at BWNYC so I can shake your brilliant hand in person. 🙂

    Happy Friday!

  16. Justin

    I think this is a great example of focusing on one main thing, but trying it several different ways to find out what works.

    Rock knows he’s a comedian, but has to try a lot of different jokes/routines/deliveries to see what works. Its the same as any kind of business trying different marketing or manufacturing strategies to see what gets the best results.

    In a weird way, the fact that you wrote about Chris Rock (which made you stand out) reminds me of what Tim Ferris teaches. He’s always saying its easier to do something way above average (such as win a 100K scholarship) than to be average. To do that, just don’t do what’s average (like write a boring article about how you want to meet a famous scientists or whatever), but take the leap that most people aren’t willing to

  17. Therese

    One last comment to expand upon the one I previously posted: while making “little bets” is very important and a great way to “fail fast & fail small” while discovering what might work on a larger scale, it’s only one piece of a bigger puzzle and (probably) shouldn’t stand alone as your “one & only” main strategy.

    Far from being random and unfocused, every single “little bet” you take should be based upon your larger strategy and unrelentlessly focused upon what Jim Collins (author of “Built to Last” & “Good to Great”) calls your “core guiding principles”– the unchanging core beliefs upon which your business is based.

    Peter acknowledges this in his book excerpt:

    “These methods are decidedly not ways of just trying a lot
    of things to see what sticks, like throwing spaghetti against
    a wall. The most productive creative people and teams are
    rigorous, highly analytical, strategic, and pragmatic.”

    I haven’t read Peter’s entire book yet, but I assume that he delves deeper into this at some point.

    So again, “little bets” probably isn’t the most effective strategy if it is standing on its own. It’s only one piece of a larger strategy and works in unison with the bigger picture and the larger strategy. If used on its own in an unfocused way, it will scatter you, not strengthen you.

    If you’re interested in this idea I highly suggest you read Collins’ book “Built to Last.” It’s a little bit older, but I think it’s spot on… and it’s based on some great research, too.

  18. Kristia

    Love your post. I have a daughter who just completed her freshman year of college. Unfortunately, all of our efforts to receive scholarships were unsuccessful and very discouraging to retry. This post has really encourage me to try a different approach. Thanks for sharing!

  19. SoCalGirlSurfing

    Speaking of social commentary and elephants in the room, it is so very sad that you had to parenthesize the accomplishments of Watson and Crick.

  20. dan

    Ha, I was thinking about Chris Rock on Rich vs. Wealthy recently:

    “Shaq is rich. The white man who signs his check … is wealthy. ” 🙂

  21. Helen Neely

    Great piece Ramit, I once had an interview some years ago, and was asked to give a presentation to a panel of 3 interviews. I must say that was one of the hardest interviews of my life.

    Nice to see how smart you were at that age and still managed to secure the scholarship.

    Love your book BTW 🙂

  22. E

    I feel so much better because I had the same experience walking up that porch. I came early and was told to wait outside. They scared me from the get-go!

    I don’t remember who I wrote about though. Ramit, I hope you’re going to the summer gathering this year! I hope I get to hear another presentation by you!

  23. Andrew

    I remember being blown away by the off-the-cuff speech-making ability of Sidney Harman, founder of the electronics firm Harman International. A year or so later I saw him in a different context, speaking to a smaller group–nearly the exact same talk! That’s the first time it got me thinking people aren’t really winging it as much as it might seem–they’ve been practicing. You forget that the world really is a big place, and you can essentially be “practicing” all the time, and millions, billions of people will think it’s all new, every time–you don’t have to save it all for your big shot. I think what’s needed is the confidence to say “this one doesn’t really matter,” but that’s harder to do, especially for a perfectionist for the self-conscious–you kinda feel like a ham repeating the same stuff!

  24. Dee Kumar

    Interest choice of Mr Rock.

    But it is interesting that when you look a little deeper into someone’s motives, you can often find a cause or mission that drives them.

    You also have shown that thining outside the box makes you diffferent and thus stand out from the crowd. Good lessons.

  25. Alastair

    I really enjoyed reading this article. It just goes to show that if you’re not afraid to think outside of the box and gamble with expressing what you think, it can really prove fruitful.

  26. Leszek Cyfer

    I wonder whether you had some racist experiences that drawn you to the particular joke. Did anyone picked on you because of your ethnic belonging?

    Also I was baffled about the mentioned impossibility to discuss the racial issues intelectually. Is this a taboo in US?

    More to the theme – the missing out on things that are available is so common that it would be a good object for several articles.

    One facet of this is the mental attitude – to be aware and on lookout for such occasions, always ask for any new free things available.
    Second one is a strategy – to know what you want to achieve and then to methodically search for associated organisations and talk with people there for advice. The school financial advisors are obvious for the scholarschip example – other avenues can have their own advisors and a dolar spent on advisor can translate to hundreds or thousands of dolars gained from the advice.

    I would humbly ask you Ramit, if you could elaborate your experiences and thoughts on using advisors and on finding mentors (and other tangential sources of information I’m sure I’m not even aware of) – as a method of maximising effectiveness when pursuing your entrepreneurial path.

    Preferably as one of your brilliant, filled to the brim, lengthy articles 🙂
    (Not mentioning that it is a material for a bestselling book) (hint!)

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    […] and practice before taking their work to a public stage, look at Chris Rock. It takes him at least 6 months just to develop an HOUR-long stand up show. But by the time Rock arrives on stage, he’s […]

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