Larry Chiang’s 5th book, WTDTYASBS, launched at a Harvard Law School keynote, so he knows about grand openings (He even attends and promotes the ones he isn’t invited to also). As CEO of Duck9, he leads an army to help college student consumers get a FICO over 770. Post H.L.S. keynote, Harvard Business wrote: “What They Don’t Teach You at Stanford Business School” (his latest Harbus post: “Setting an intention for SXSWi”.
Chapter 11: How to Get Laid Out of the Loser’s Bracket
You are poor because you give up when you lose.
This chapter will show you how to win even when you think you lost.
Losing: to be deprived of or cease to have or retain (something).
The waitlist
Being placed on the waitlist happens. Someone decides that they will be the one to deprive you of something and you suddenly find yourself on the waitlist.
It looks like this:
- Your table at the busiest restaurant in town
- Your entry into the top club on new years eve
- Your admission into your college of choice
- You’re on the waitlist for a kidney. Organ receiving has high demand and you need a donation
- The job you really want when the position is not yet available
- The high demand condo in Miami with the view you want
What to do when you get placed into the loser’s bracket (a.k.a. the waitlist)
The funny thing about the waitlist is that many people actually decide to lose just because they get placed into the loser’s bracket.
Here’s how you win even when that happens:
- Dominate the waitlist: When you dominate the waitlist your presence is not forgotten. For many, the waitlist is the end. More on how to dominate the waitlist shortly.
- Don’t quit: Just because you are on the waitlist, does not mean you are done. For you, the waitlist is just the beginning.
- Never leave your wingman: You might at times find yourself in the waitlist along with someone else. Maybe it’s a friend or a business partner who is on the waitlist, and you just happen to be in it for the ride. Stay with them. The second you leave, things start to fall apart.
- Don’t take risks or throw hail marries: Take absolutely no risks when you are on the waitlist. The only exception is when you have built up social capital with someone and taking a risk can only make the situation better.
- Assume you are winning: When you assume you are winning, others do as well and this contagious thought eventually ends up in the person who will take you out of the waitlist.
Dominating the Waitlist
- Set up shoppe: As soon as you get placed on the waitlist, you need to set up shoppe. This is where you and your peers set up to win, and you make it visible to the everyone — especially the person who put you on the waitlist. Ideally there are 3–4 of you who set up and form a circle to talk about cool shit.
- Cold open from the waitlist: If you are on the waitlist, others will start to gather around you or nearby. Invite the cool ones to chat and make a connection. Imagine what the waitlist master is thinking when they see you making allies with their guests.
- Don’t let rando’s into your shoppe: When you are in your shoppe. You don’t let rando’s in. They have to deserve it. Think of your shoppe as a sacred temple. Everyone who is let into your shoppe is a reflection of you (as a person on the waitlist).
- Assume you are winning: When you assume you are winning, others do too, leading the waitlist master to wonder “Everyone seems to know this guy/gal. Did I just screw up by putting this person on the waitlist?”
- Be “Google-able”: Imagine their face when they find out who you really are.
- Stay off of your phone: You look like an idiot when you’re on your phone.
- Don’t look around: Similar to your phone, don’t you have better things to be doing?
- Don’t complain: Don’t complain about being on the waitlist. Don’t complain about being uncomfortable. Losers are uncomfortable and complain. If you’re uncomfortable do not complain. Don’t complain about anything. Remember — you’re about to win no matter what happens.
- Be the assistant: Help things work better. Could they really keep you on the waitlist when you’re appreciated by everyone that much?
- Work the friends: If the friends love you, they eventually won’t be able to help but love you too.
Don’t Take Risks
- When they say no, don’t try to sell them: When they put you on the waitlist, they expect you to try to sell them. Someone who belongs in the winner’s bracket is supposed to take the high road or not even be bothered by a no. Acknowledge it and move forward.
- You can’t fight stupid: Sometimes a stupid person puts you on the waitlist. Let others realize their stupidity so they can help you fix it.
- Be early: If you are late, they have way more reason to keep you on the waitlist. “If they were late did they really want it?” Plus, being early makes it way easier to avoid being waitlisted.
- Have impulse control: Sometimes the person who put you on the waitlist will attempt to taunt you in an effort to create more reason for you to stay on the waitlist. Caving to their actions does nothing to help you.
Assume You Are Winning
- Leave gifts: Having the clear goal that you will ABSOLUTELY get off of the waitlist makes it hard to keep you in the holding pattern for very long. Problem You’re in the losers circle outside of VIP. SOLUTION? GuaGuaGucamole #4: Crasher to VIP. Bringing the inner circle a gift catalyzes the assumption that you are part of the main event. Executing the gift of balloons makes you look like the VC and VIP, not a waitlister. A vc is a venture capitalist
- Improve the area: Make the loser’s bracket look like a good place to be. You might just turn it into the winner’s bracket by doing so.
- Turn the loser’s bracket into the winner’s bracket: When you assume you are winning, it inevitably spreads like wildfire. Send that assumption through the waitlist and people will start to think the loser’s bracket is actually with winner’s bracket.
There you have it. See how you can win even when they wanted you to lose? Use these strategies next time you get put on the waitlist, or the next time you’re in the loser’s bracket, and you’ll create your own success.
Tying It All Together
Failure is a necessary step in the path to success, but not everyone knows how to handle it. Many people give up at the first sign of failure, thinking that it’s a sign that they’re not cut out for success. But in reality, failure is a sign that you’re trying something new, and that you’re learning from your mistakes. In this chapter, we’re going to explore the concept of failing forward, and how it can help you become a successful entrepreneur and, of course, a pussy magnet.
Larry Chiang, the CEO of Duck9, encourages college student athletes at Stanford and the NFL to get a FICO over 810. But he also knows that success doesn’t come without failure. In fact, he advocates failing forward as a way to learn and grow. One of the keys to failing forward is to not let failure defeat you. Instead, use it as a learning opportunity.
Ryan Tedder, lead singer of One Republic, knows a thing or two about failing forward. He was dropped from Columbia and teased by two other labels before finding success. But he didn’t let those setbacks stop him. Instead, he kept pushing forward, using each failure as a chance to learn and improve. He built a base of support by getting a few hits and focusing on his fan base. He also put in the time and effort to practice, logging his 10,000 hours of songwriting just like an entrepreneur must put in their 10,000 hours.
Ryan Tedder’s concept of low-risk, no-risk practice is another example of failing forward. Instead of waiting for the perfect opportunity, he took every chance he could to perform and practice, even if it wasn’t a guaranteed success. This allowed him to hone his craft and build his skills, even when things didn’t go as planned.
Another key to failing forward is to learn from others. Larry Chiang is a big advocate of “paste copying,” which is basically taking the best practices of others and applying them to your own situation. Just like in football, where coaches use game film to analyze their own team and their opponents, entrepreneurs can learn a lot from studying the successes and failures of others. By emulating the best practices of successful entrepreneurs, you can avoid some of the common pitfalls that cause others to fail.
But failing forward isn’t just about learning from others. It’s also about taking risks and trying new things. Larry Chiang advises young entrepreneurs to try at least five pop-up internships, even if they’re not paid. This not only helps you build your skills and experience, but it also allows you to fail in a low-risk environment. If one internship doesn’t work out, you can move on to the next one without worrying about losing a job or failing publicly.
Failing forward is also about questioning authority and pushing boundaries. Larry Chiang’s mentor, Augie Garrido, was notorious for getting towed because he always parked where he wanted to, not where he was supposed to. He knew the rules, but he didn’t let them hold him back. This mindset can be applied to entrepreneurship as well. If you want to succeed, you have to be willing to take risks and challenge the status quo.
In conclusion, failing forward is an essential part of the path to success. It’s about not letting failure defeat you, but instead using it as a learning opportunity. It’s about learning from others and emulating the best practices of successful entrepreneurs. And it’s about taking risks, trying new things, and questioning authority. By failing forward, you can become a better entrepreneur, and of course, a pussy magnet.

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