Wins & Updates

• Reaching Universities: Recently gave a lecture on asymmetric bets at McGill University. I’ll be joining a panel at Wharton in March and giving a short talk on prompt engineering at Oxford in April. I’ll share all of that content with you over the next few months.

• Podcast: A podcast hosted by McGill University, sharing my advice for college students. Recording here.

• Ask: If you find the content interesting, I would love it if you could share the newsletter with your friends.

Taking asymmetric bets means punching above your weight class. You’re playing at the border between possible and impossible given your resources, network, and experience.

These improbable but non-zero opportunities tends to come with positive side effects: you will probably be the least qualified person in the room. Or at least, that has been the case for me. The generous interpretation is that you have the greatest opportunity to learn than anyone else in that room. As the adage goes:

This has been the story of my entire career.

“Barely” Making It to Y-Combinator

In my Medium article, I wrote about how I “barely” made it into Y-Combinator, the most prestigious startup accelerator in the world. I was a first-time founder with no product, and I applied to YC less than a month after incorporating the company.

Most YC founders have a 10-minute interview for a yes or no to a coveted spot in the accelerator. For me, it took 4x the time. After the interview, I received an email that all founders dread - acceptance is communicated via phone call. I ignored the email, thinking I had enough rejections for the day.

But in my bathroom break, as I was browsing emails, I accidentally clicked on it to see the message below (I’ll paraphrase for confidentiality):

I was up for it.

My co-founder and I received the phone call to confirm joining Y-Combinator. But knowing that I “barely” made it gave me more gratitude and motivation to work harder. Here’s a more recent one.

Creating a Spot at TEDxStanford

In my last post, I shared that I became a TEDxStanford speaker. And yes, it’s TEDx and not TED, so for some, it may not sound impressive. But to me, the extent of my speaking has been corporate presentations and university lectures, not production-grade talks, so this was a great opportunity to stretch myself.

Anticipation of an interview on “speaking” was already stressful, but when I logged into the Zoom meeting - inevitably always staring a few minutes late to add more stress - I saw an army of people looking into the camera. It was intimidating to see 20 eyeballs staring at me. And honestly, I bombed it. If my memory serves me well, one of the questions was: “put simply, what are you trying to say?”

Assuming the worst, I worked all weekend to cope. To my surprise, I received an email confirming my spot as a speaker, and they matched me with a speaking coach. In the first meeting with my speaking coach, I learned about what happened behind the scenes:

There were 15 people shortlisted for 8 speaking spots. I was shortlisted but not in the final eight. But the selection committee - including my speaking coach who I’ve never met - had such a large contention about a few speakers that they added two extra slots for the event. I was one of them. It turns out my speaking coach listened to my application video and ranked my idea as number one. And because she championed my idea, I was able to squeeze into a spot that didn’t exist.

I didn’t know her. She didn’t know me. But it happened.

Live Your Life On the Edge of Possibilities

These are two of many examples. Joining SoftBank was one of those experiences. When I helping hire to replace my role before moving from the Bay Area to London, I reviewed CVs of other candidates. Their CVs blew mine out of the water, but my boss who hired me took a chance on me based on my interview. Again, didn’t know him before the interview. And how do you think I felt when I joined the board of a billion-dollar company with the former board member of Volkswagen and Lufthansa sitting across from me?

I’m not suggesting that everyone should go do this, but for those of you who want to give it a try, how do you know if you are living on the edge?

How Do You Know You’re Living on the Edge?

Generally, I take a mix of two approaches:

1. Is it technically possible?

Technical possibility is an important one. I try to see opportunities in its purest form without artificial barriers. This means that unless there are laws of physics or structural limitations stopping it, then it’s technically possible. Let’s take job applications as an example (though they may not always be asymmetric bets).

I would not apply to a law firm to be a practicing legal professional because I’m not licensed to practice law - though parenthetically in intellectual property law, no JDs are required. The same applies if a job requires a specific skill I don’t have and can’t reasonably gain in a short amount of time (fluency in German, for example). In contrast, I’d ignore proxies or artificial requirements such as “x number of years.”

Starting new projects also works in the same way. Writing online to grow a large audience and eventually write a book was technically possible, so it was a matter of understanding what it takes for that to occur - a Need-to-Believe analysis.

2. What’s the hit rate?

While Asymmetric bets (few wins outsize all other outcomes by several magnitudes) are expected to fail most of the time, it shouldn’t be so much to demoralize you. There were times where 100% of my shots would fail in a year. That probably means I’ve reached too far out into the realm of impossibility. And then there were years my hit rate would be really high, but the “wins” weren’t quite spectacular, and I’d adjust accordingly.

When you start applying Asymmetric Principles, you will find yourself pushing the edge of what’s possible - often to your surprise. More often than not, I don’t make it. But because I make many asymmetric bets, I find myself in a room where I am the least qualified. But I come out a little smarter and stronger every time.

The book launch is March 25th! Pre-orders are out in every major book retailer!