How I went from not knowing who painted the Mona Lisa to being a top 10% Learned League player in One Year (2023)

I knew it was one of those Ninja Turtles, but how was I to know if it was Leonardo, Michelangelo or Raphael?

I have always hated trivia. I don’t know things. Unlike chess, no amount of talent or creative brain power is going to help me figure out who was the king of England in 1200. So when friends of mine tried to convince me to join an elite trivia league called “LearnedLeague”, I was skeptical.

“It’s fun” they said. “There are levels for all different types of players, and even if you’re a total Trivia beginner, you’ll get matched with people your own level.”

The way that LearnedLeague works is that you are asked six trivia questions every day for five weeks. You are matched up against one opponent from your group. You both answer the questions, and also try to predict which questions will be most difficult for your opponent.

How I went from not knowing who painted the Mona Lisa to being a top 10% Learned League player in One Year (1)

Fun fact: In my second season, I infamously answered tyrannosaurus Rex to Question 5 at the last second, after having the correct answer down the entire day.

There are 5 levels, ranging from groups A-E. The top 10% or so of players are in Group A. The next 10% are in Group B, and 20% each are at levels C-E. I figured – it’s just six questions for five weeks; I enjoy competition even if it’s something I’m not great at, so it would be a fun little thing to do to pass the time.

My first season began in May 2021… and as I expected, I got my butt whooped. I got 44/150 answers correct in my rookie league, playing with all the other rookies, and got placed in the E group. Not only was I in the bottom group, but from looking around at other players, it was clear that I was one of the weaker ones, and approximately in the bottom 10% of all players leaguewide.

Where does one even begin if they want to succeed at something in which the entire breadth of human knowledge is the subject of study?

Because the league had such a cool competitive setup, it was kind of annoying to me that I’d never have any chance to promote to Group D. I just didn’t know enough things. Where is the Caspian Sea? What is the Caspian Sea? What’s an Opera? I think I’ve heard of Nutcracker! Like man, I just didn’t know a lot of things, and looking back, I feel like even 44/150 was a bit of an overperformance. But fortunately, they ask some pop culture stuff that if you just watch movies sometimes then maybe you can get them right. I was also lucky to get a question about a book they forced me to read in high school (Age of Innocence).

Aside from knowing some things about sports & games, I was pretty bad in all categories. Where does one even begin if they want to succeed at something in which the entire breadth of human knowledge is the subject of study?

My System

I decided I was not going to try to be competitive about it, but just for fun, I’d learn a few things. Because trivia is so varied, and there are so many things to learn about, I didn’t want to pick and choose what to learn at first, as I feared that would lead to me becoming too focused on just one specific area, and leave the rest lacking. So my strategy was:

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  • Go to JeopardyArchive, a cool site which has the questions and answers of every Jeopardy game ever played
  • Look at some of the recent Final Jeopardy questions
  • If I didn’t know the answer, study whatever the answer is

This way, I would get a pretty varied mix of topics, and keep learning something that was deemed important by the most famous quiz show in the world.

I amazingly got the first 15 Final Jeopardy questions wrong (I was really not good!), but it was fun learning about Leonardo da Vinci, Aaron Copland and whatever other random subjects came up at first.

I would make flashcards out of everything and store them in my Flashcards Deluxe app on my phone. At that stage, my philosophy was: it can’t hurt to learn a few things. Why not be a bit more cultured and worldly?

Then, I began to Google and make flashcards out of things like “ten most famous artists ever”, and “ten most famous paintings ever.”

Every time you learn a new fact, you are better at this game!

Sometimes, a famous book would be one of the answers, like Crime and Punishment by Dostoyevsky. I would do a deep dive into the book, starting at Wikipedia, then going to the book’s CourseHero page. I would watch videos about the book, find major quotes from the book, and get detailed summaries of all the key characters. By the time I finished these processes, I usually felt like I had a pretty good feel for everything that happened in the story. I’m sure that actually reading it could be an option, but I feel like I pick up most of the culture, messages, and vibe of the books by doing it this way. While I do enjoy reading for pleasure, I enjoy maybe dozens of other things more, so I don’t really want to spend my time focusing on one book for hours.

At that point, it started to become obvious to me that I wanted to spend more time on this. It felt like a great hobby for the following reasons:

  1. It’s a fun competitive environment that has been created by someone who has been very diligent in making the competition as engaging as possible.
  2. It is extremely rewarding to actually know things. After knowing very little for 43 years (aside from a few areas I specialized in such as chess, poker, CrossFit, etc), it’s cool to suddenly be able to have conversations about history, art, literature and opera.
  3. It is very clear when you are improving. Every time you learn a new fact, you are better at this game. If you do the hard work, your performance in competitions goes up very clearly.
  4. The accomplishment of learning new things, and having the knowledge pay off, provided a huge dopamine hit.

My Stats

Let’s take a look at how my performance changed season by season. Keep in mind that each season you have to answer 150 total questions:

Season 1: (May 2021 – Rookie Group) 44/150 29%. In your first season they put you in a “Rookie Rundle”, which places you with other players who are competing for the first time. After that you get moved to a group between B-E, depending on your placing. My rookie performance of 44 correct answers put me in the bottom 5-10% of all players in Learned League, and off to Group E I went.

Season 2: (August 2021 – Group E) 60/150 40%: This was my first season in Group E. I finished somewhere in the middle of the pack, but my 40% performance was a major increase on my rookie season. On the plus side, 40% in Group E is typically well above average, so it was a good omen of things to come. While the improvement was great, I was still in the bottom 25% of players in the league.

Season 3: (November 2021- Group E) 82/150: 55%: This was my breakout season. Getting over 50% correct answers in Group E is a massive score, and I easily qualified for Group D the next season. My score would have even put me in the upper echelon of players in Group D, so with two months to prepare, I expected to be pretty competitive there too. Also this result put me in approximately the top 35% of all players in the league, which is a huge turnaround from bottom 25%.

(Video) Painting Famous Art on Keycaps (harder than expected)

Season 4: (February 2022 – Group D) 93/150: 62%: My percentage here was enough to handily win my Group D. I clinched first place with 1-2 matches left in the season. My performance also would have been one of the top performances in Group C. My performance this season put me in the top 20% in the league.

Season 5: (May 2022 – Group C) 103/150: 69%: I had by far the most correct answers in my Group C, and clinched first place with one match to go. This was my most recent season, and like the past seasons, my performance would also have been strong one level up (My total correct answers would have tied for second place in the Group B division). Another cool thing is that the 6 day Jeopardy champion at the time of this writing, is in the same Group B that I’m moving into (she has since lost). With this result, my performance was just about top 10% in the league.

Since there are over 30,000 players playing in the league, I figured that people would be interested in a step by step guide to how to get a lot better in just one year. I have yet to find any other player on Learned League with such a stark progression as mine (basically going from one of the worst players in the league to top 10% in a year), and the very large majority seem to stay at the same level throughout time. Here is my stat page:

How did I improve so fast? Slowly but surely I turned into a trivia machine. I started out being very bad at Jeopardy. I would try and solve an entire board, untimed, and get about 25-28 questions correct out of 60. After a few months I got that number up to 40+. Then in February 2022 I started watching the games live and tracking something called the CORYAT score. That number started around 23,000, but it’s now June 2022 and it’s around 27,000, but it’s slowly creeping more and more towards 30,000+ (I got 30k+ in 4 of the last 5 games since writing this). It’s not a mind blowing number, I believe that lots of players with Jeopardy aspirations get 30,000+, but it’s high enough that if I was on the show, I could easily win a few games. It also helps that my Final Jeopardy and Double Jeopardy correct rates are well above the show averages.

I have studied every question on every Jeopardy board since the beginning of 2020, and every Final Jeopardy answer since 2012. I literally mean that I know the answer to every single question in the last 3 years, not that I have just casually glanced at them.

Some people have a strategy to focus only on the most commonly asked topics on Jeopardy. I feel like that’s a good idea if you are rushed for time and cramming for something, but I have all the time in the world, and because my Flashcard system makes it possible to retain information easily, I want to know everything. If its on any kind of quiz competition and I get it wrong, into the Flashcards it goes. This also prevents there from being too much of a ceiling in my potential. At some point, you’re going to be facing people who also know all of the basic and most common topics on Jeopardy, so to only focus on that stuff is a good short term solution, but long term it’s less ideal.

I have also memorized every single LearnedLeague question since Season 50 (that’s about 10 years of seasons, and about 6000+ total questions). The league tends to repeat questions every now and then, so it is really helpful and I include every question, correct or wrong, in my flashcards. Although I have to shamefully admit that I got a question wrong about “Ontology” in this most reason season, despite having already made a flash card about what Ontology from a previous Learned League season. To be honest I still don’t really know what it is. It’s something about the philosophy of the nature of being, whatever that means. But it’s okay, I have come to grips with the idea that occasionally I’m just going to forget things, however I try to put myself in the best position not to…..

My FlashCard Factory

How does my flashcard system work? I have manually created about 38,000 flashcards in the last year. I use spaced repetition, which basically means that when I get a flashcard correct, I will see it less frequently, and when I get one wrong, or if it’s a newer card, I will see it more frequently.

I use a very aggressive formula for the spaced repetition. I think that it’s very important not to be a perfectionist and to accept that I am going to forget lots of things. Perfectionism will kill you when you need to gain such a wide breadth of knowledge. The main thing is to keep adding new information and remembering as much of it as possible. It’s much better to know 85% of 38,000 flashcards than to know 100% of 2000 flash cards. Some things I get wrong over and over and I’m fine with it, it’s just one thing. Instead of spending too much time trying to fix that one issue, I’d rather be absorbing lots of new information.

If it takes me two years to learn a fact, that’s totally fine, as in the meantime I’m filling my brain with lots of other facts as well.


When I add a card for the first time, and I am first tested on it and I get it correct, I either mark it as correct (in which case the next time I see it will be in 8 days), or I mark it as super correct (in which the next time I see it will be 20 days).

Perfectionism will kill you when you need to gain such a wide breadth of knowledge. It’s much better to know 85% of 38,000 flashcards than to know 100% of 2000 flash cards.

I start each day by reviewing all the cards that are “due”, which means that the countdown to when they are supposed to be studied has been completed. I then count them as either “wrong”, “correct” or “super correct”. Correct means the multiplier of its current interval will triple. So if I haven’t seen it in 10 days, and I mark it as correct, I’ll see it again in 30 days. If I mark it as Super Correct, it will increase the interval by 6.7 times. I have a 5 second timer on each card, and if I easily get the card before the timer goes up, I mark it as super correct. The maximum interval is set to 730 days, and anytime I get an answer wrong, it cuts the interval in half, and it quizzes me on the question again immediately the very next day, forcing me to repair the connection in my brain.

Since I began this process about one year ago, I have been making just over 100 flash cards per day. I also strongly prefer entering cards myself, because I want to check for quality control, and because I find that you learn a lot through the flash card creation process.

When I add a card, if I don’t understand the reason for why something is correct, I do my own research and write all the reasoning down on the answer side. I’ll never just write an answer with no explanation, unless no explanation is required for full understanding.

I Never Play Anything “Just for Fun”

I tend not to watch or do any trivia related activity for fun. What I mean by that is whenever I get something wrong, I will make a flashcard out of it. Playing and studying without working to correct my mistakes would help me about 20% as much as focusing on what I got wrong.

For me, this is an important part of studying for any endeavor, whether it’s chess, poker, trivia or even something physical like CrossFit.In chess it can be tempting to play blitz game after blitz game without learning from your mistakes. It’s okay to have fun sometimes, but I know that I have massive amounts to improve, and if I don’t do this process, I won’t get there.

For instance, when I watch the Chase each week, I make flashcards out of every single question I don’t know. It’s a bit more time consuming because there is no website where I can just copy and paste the questions, but the idea of getting something wrong and not putting myself in the best position to get it right next time is too painful for me. It feels like nearly a waste of time to watch the show without going through this process.

Beyond LearnedLeague

I have recently joined two other trivia leagues:

BPTrivia and SchoolofTrivia

What I like about playing in all 3 of these leagues is that they all have different scoring systems and styles. Also you will learn things that will help you in all of the other leagues, and in Jeopardy. So you are not only competing but also training!

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SchoolofTrivia is particularly fun because I am constantly going head to head against well known Jeopardy contestants (and sometimes holding my own!). I was just in a group with 4-5 tournament of champions qualifiers for the current 2021-2022 Jeopardy season. This league has four divisions from Senior to Freshman, along with an elite division of the top 10 players. I was shocked at how competitive I was here, as I made it past the Freshman and Sophomore divisions in my first two seasons. I was particularly proud to win clear first place in the Freshman in my first season, going head to head with a 7 day Jeopardy winner and only passing her on the final few days. (Although she kicked my butt this last season!). This league is run by a former Jeopardy Tournament of Champions winner (and a poker player!) Alex Jacob.

BPTrivia has the hardest questions of the three, and has the strongest opposition. They also have a lot of other mini quizzes throughout the week. For the first 6-8 months of my Trivia life I sort of shied away from taking it seriously, but I’m finally at the point where I feel I can compete reasonably here too, and most importantly, I can learn more things.

I have also started getting into CrossWord puzzles. I noticed that a lot of top trivia players are good at them, and I felt it might help all to make sure everything is connected and improve my ability at wordplay related clues (didn’t pay off in yesterday’s Jeopardy game in which I went 0/5 in a wordplay category). I started doing them back in January 2022 and have gotten a ton better and have started to become slightly addicted to them. Have only recently gotten to the point where I can complete the Thursday, Friday and Sunday puzzles without any help.

I am also on a 128 day streak on DuoLingo. At the moment, I’m studying Spanish, French, German, Japanese and Italian all at once. I don’t expect to get fluent, but it’s a fun little game to play, and I feel like it’s also good for the brain. Also knowing that “Inu” means “Dog” in Japanese got me an $800 question in a recent Jeopardy game.

One major takeaway from this, and anything you may want to put your mind to, is the extreme benefit you get when you really enjoy the process. Right now I enjoy almost nothing as much as cramming new information into my head and testing myself on it. Whenever I have down time, it’s a chance for me to learn one more thing, to look at one more jeopardy board, and to make Flashcards for every answer I don’t get right.

The next level up is always daunting. However at every step of the way, the next level up has seemed so far away, and then I’d reach it in a few months.

I’m curious to see where I will plateau, and whether it will come due to lack of the sustained effort that I’ve been putting in, or because my method is no longer sufficient to substantially improve. The fewer questions that I get wrong each season, the less likely it is that any studying will target those few topics.

The next level up is always daunting. I can barely imagine getting to 110 correct questions in the 150 question LearnedLeague season, yet alone 120, which is what I’d probably need to be a serious competitor in Group A. However at every step of the way, the next level up has seemed so far away, and then I’d reach it in a few months.

To conclude, I’m pretty proud of what I’ve accomplished in a year. I know I’m competing against people who may have over a decade of trivia experience. Many of them have done Quiz Bowl, many have been on and studied for Jeopardy. It’s nice to start a new thing, decide to take it really seriously and then see proof that the work you do, and the methods you use are good ones. I honestly didn’t expect in my wildest dreams that I would improve this much in just a year.

Oh, and not to leave you hanging – it was painted by Leonardo Da Vinci in the early 1500s, and has been on display in Louvre since 1767, save for four years in Napoleon’s bedroom, a couple brief exhibitions in NYC, Tokyo and Moscow, and a scandalous theft in 1911.

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