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5 Steps to Winning Career Tournaments

There are tournaments everywhere–jobs, admissions, promotions, startup funding. Are you playing the game?

Tournaments are everywhere in life. And the sooner you can identify them, the better you can compete.

College admissions, getting into grad school, getting your first job, raising money, hiring a team, making partner at a law firm, getting promoted to executive, getting YouTube subscribers, getting tenure as a professor, you name it. All the things that people want are on the other side of a competitive process. The first part of the game is showing up.


In my career, I’ve won a few tournaments and I’ve lost a few. When I was at Stanford, there was a prestigious program called the Mayfield Fellows Program. People like Kevin Systrom from Instagram and Justin Rosenstein from Asana were selectees during their times at Stanford. I applied, but I was not selected.

For a moment, it was crushing to get rejected. Here were gatekeepers to my future and they said I did not pass. I was at Stanford and these professors, I thought, knew something I didn’t. In the moment I thought, “Shoot, what if I’m not cut out for being a startup founder?”

I’m glad I soldiered on though. It was just another tournament that I entered, but I didn’t win. Today in my career I know not to believe that the tournament gatekeepers have some special clairvoyant knowledge. They’re doing their best with incomplete information. And also the heuristic people apply may not be verifiably accurate over the long-term. When I got rejected from Mayfield in 2001, the program had only existed for about six years. It was probably too soon to know if the criteria they were using for the program was predictive or relevant.

Two really big lessons here.

  1. Don’t get mad at the gatekeepers. They are doing typically their best with imperfect information.
  2. Don’t get discouraged if you don’t get in. I knew I was a good engineer and I could ship any kind of user experience, and I love to do design. I knew my strengths. There were definitely people in that program who did get in, who had better resumes than me at that time, but they couldn’t have bought the skills that I had.

So, What Are the Rules?

These tournaments show up everywhere. They happen anytime there’s a finite resource: College admissions, grad school, job applications, incubators and accelerators, fellowships, academia, getting press for your business, raising money. These are all tournaments.

For all of them here are some generalizable rules that I think you should keep in mind, no matter where you are in the world and what stage of career you’re in.

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  1. Know You’re In One: Be aware of the tournament and lookout for competition. If you don’t know something is up for grabs, how can you even win? In high school, I was oblivious to the competition that was going on and luckily it didn’t hurt me too much since I was into computers, which was very fringe. Competitions are everywhere. At your job, like it or not, you and your peers are probably competing for the same bonus pool and/or who will be promoted. That’s just how it works. Be aware of the competition. Don’t be a dick about it, but know it’s happening.
  2. Learn the Criteria Early: People who are great at tournaments find out what the criteria is to win upfront. Get specifics. For instance, for college admissions, every college is looking for different things. Every incubator, too, every workforce, every boss. But you need to know the specifics. I realized getting into Stanford as an undergrad in 1999 was a function of being obsessive with consuming information from the Princeton Review online forums. My parents didn’t have money and my public school guidance counselors knew nothing about how to apply to the best universities. I went direct to the internet when lots of people didn’t have that advantage. I realized through that forum that I could learn how wealthy kids in prep schools got in to elite universities. And I learned by osmosis, through that forum. High SATs, check; extracurriculars, check; great essays, check. I improved my SAT score by over 400 points by studying the prep books and I learned this through the forum. The same internet advantage can be yours in whatever tournament you are entering. Every tournament has criteria. If you find out early, sometimes years in advance of the outcome, you will get a massive leg up.
  3. Up Your Odds: If there’s a tournament, know that there is randomness. Remember that nobody is clairvoyant. The selection committees are operating on limited information. So, in the face of randomness, increase the odds of you winning. If you had a 5% chance of getting into any given school or any given tournament, odds would dictate that you should apply to 20 schools or 20 such programs to stand a good shot of an accept. This goes for raising money, getting a job, or really any tournament in life. It’s usually a mistake to get too obsessed with one particular school, workplace, or investor. That being said, don’t run around saying that. It’s always a two-way street. Gatekeepers often use, “how much do you want us” specifically as a top criteria. This is just human nature. Remember that Princeton Review forum I was telling you about? That was one thing that forum taught me: Don’t get “oneitis”. This goes for many tournaments.
  4. Gather Advice: Tournaments have a repeating nature and that’s great because there are lots of people who have come before who can give you tips on that tournament. Whatever you are going through, preparing for that tournament will rarely be the first time, so find people who have done what you want to do and seek them out. People helped them along the way, so you will be surprised how often people will take time out of their day to help a stranger. I got a lot out of talking with YC alums when I was applying to YC. Even today, I try to help future YC alums. People want to help, all you have to do is ask. (Check out my “Nail Your YC application” video; likewise, my “Nail Your YC Interview” video here).
  5. Try the Window: When you receive a no, be thoughtful. I’m not saying never quit, but there are some tournaments you can’t win and that’s okay. It’s important to find the tournament’s where you can win, but also don’t let “no” turn into a no forever. It’s almost always a no for now. And then there are people who, when the door is locked, they find a window. I always think about the time I sent Instacart’s Apoorva Mehta an email saying, “No, it would be almost impossible to get you in [to YC] right now.” YC was over halfway done at that point. It was only a 10 week program and five weeks had passed. He took that know as a maybe. And he sent me a six-pack of beer with his new service that he had just brought online. We accepted him at Y Combinator the next day and Instacart’s now worth more than $17 billion. If you find the door is locked, always check the window.
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Okay, can we talk about one thing that has been bugging me? Some people have decided to opt out of all tournaments. They say the game is rigged. They’re not completely wrong. The system isn’t fair, hasn’t been fair, and sadly, probably won’t be fair anytime soon. And in the face of that you can still decide to play.

You’re not going to win every tournament, and not every tournament is worth playing. In fact a shocking few actually are, but that doesn’t have to define you. One thing I am thankful for about these tournaments is that they are the times for us as individuals to become our best.

The unhealthy way to look at tournaments is that there’s zero sum, when someone else wins, I have to lose, but there is a better way. The Latin root for competition is actually competere, which means strive together. That’s a powerful concept, and I think that underscores how these tournaments help us become the best we can be.

Here’s the coolest part. If you win enough, someday you will design a tournament for others. And trust me, that’s the real game. And when you do, you will be so excited that you got to be the one to push it in the right direction. But remember even when you’re the one creating it, it won’t be completely fair, but you can do your best. I know I’m trying.


Thanks for reading! To watch my full episodes that go into detail about these ideas — and more — head over to my YouTube channel.