Modern Meditations: Bryan Pellegrino

Bryan Pellegrino is one of the most interesting people I’ve ever met. Over a few days in March, I got to know the LayerZero CEO and hear his story. Though tech tends to be a magnet for the intelligent and eclectic, Pellegrino stands out all the same. 

Today, he is the co-founder and CEO of one of crypto’s most promising startups. LayerZero has raised more than $140 million in funding from Sequoia Capital, a16z, Multicoin Capital, FTX, and Tiger Global to build seamless connections between blockchains.

Bryan has a dazzling set of abilities and interests beyond LayerZero, though. For a time, he was one of the best heads-up poker players in the world, winning purses worth more than $500,000 and finishing second at a World Series of Poker event in 2012. After retiring from the game, he coded a machine learning model that helped better sequence baseball pitches, selling it to an MLB franchise. He then published with Noam Brown, a prolific AI researcher whose work was runner-up for Science magazine’s 2019 “Breakthrough of the Year.” Their collaboration led to the creation of Supremus, the world’s best one-versus-one poker AI.

On a lark, Bryan started buying trading cards in bulk before selling them to retailers at a mark-up. At its peak, that business did a few million in revenue a year, despite being little more than a side-hustle. He has, at various times, invested in startups, venture funds, sports franchises, and even a small Wyoming-based bank that he and a coalition hope to transform into a progressive, tech-forward institution. 

It’s not often you meet someone as singular as Bryan. When I do, I often ask myself the same thing: what is the most interesting question I can ask this person? How can we have the most unobvious conversation? 

Writer Martin Amis talks about the dangers of “herd words” in his book, The War Against Cliché. Amis argues that phrases like “She rummaged in her handbag” or “The heat was stifling” are empty, necrotic from overuse. Just as there are herd words, there are “herd questions,” too. Anytime we ask someone where they’re from or what they do, we inquire by rote. That is sometimes for the best – after all, we usually only feel comfortable speaking freely after some trust has been built. But, after exchanging niceties, how can we move beyond the herd? What do we need to say to get somewhere genuinely compelling? 

To answer these questions, The Generalist is kicking off a new series. “Modern Meditations” asks the most fascinating people in tech the most interesting, unobvious questions we can think of. In addition to giving you a look into the minds of the gigabrained, we explicitly hope to surface perspectives you have not considered and with which you may disagree. 

Given Bryan’s story, he is an ideal person with whom to begin. Here are his meditations.

1. What would you be doing if you didn’t work in tech?

I’ve been in love with computers since I was a kid, so it's hard to imagine not working with technology. I would probably try academia. In general, I like learning, and I’ve always been fascinated by math and physics. Those are fields with near-unlimited depth. Whenever I talk to a friend doing a math Ph.D., I feel a twinge of envy. 

I would also be interested in scaling a traditional business – real estate development, for example. How do you optimize and scale those systems? ‍

2. Which current or historical figure has most impacted your thinking?

I’ve never had a hero. That probably has something to do with the way I was raised. As the youngest brother in a competitive family, I had to scrap. Whether playing basketball against my dad and older brother or trying to win a board game, I was always at a disadvantage. Those experiences taught me to believe that I could get good at something, anything, as long as I put in the effort. The distance between ourselves and the people we worship – many who have achieved great things –  isn’t as vast as we think.

One person that has influenced my thinking recently is Albert Einstein. Reading Walter Isaacson’s book, I was surprised to learn that Einstein hated competition – he thought it was a waste of time. So much so that he wouldn’t even play a casual game of chess with friends. As someone that’s been so driven by competition, that’s made me pause and wonder: when is competition useful, and when can the scenario be adjusted to become purely collaborative or purely knowledge-seeking?

3. What is the most significant thing you’ve changed your mind about over the past decade?

The easy answer is religion. I was raised in a reasonably Christian household, but my belief and involvement have waned as I've matured. 

The more complicated one is how I spend my time and choose what to work on. It’s changed quite a lot over the years. 

The only time I was an employee was in college. I worked at the University of New Hampshire’s networking lab building VoIP (Voice over IP) technologies. In my first six months working there, I built a new system from scratch and signed customers like Vonage worth an additional $600,000 per year. I vividly remembered my review. The team told me my work was amazing and that they could increase my salary by the maximum allowable amount of $0.50. I went from earning $10.25 an hour to $10.75. At that moment, it became obvious that I wasn’t built for that environment. Even if you shot the lights out, your earning potential barely moved. 

I decided that the next thing I did had to be meritocratic and provide a lot of freedom. I wanted to earn what my output deserved and work on my schedule. 

Online poker fit both of those criteria. If I played well, I made money. If I didn’t, well…I didn’t. I could work from around the world, as much or as little as I wanted. For a while, I felt like I’d found the perfect optimization. But after a few years, I realized it was effectively the same as being a high-paid consultant. I got paid for my time. But I wasn’t building anything of lasting value, and there was no leverage on my work. 

I realized I needed to update my framework. Today, when I think about optimizing my work, I focus on whether my time is being put towards building something enduring and whether it has the potential to reward me optimally. There are many jobs where your earnings are relatively low even if you hit the right tail, becoming one of the best in the world. For example, even if you become the seventh best chess player on earth, you’re likely to need another job or source of income.

Ultimately, this personal journey has given me a broader framework I’ve found useful.

1. Do I want to become world-class at something? Everyone has different priorities. That leads to different optimizations. You might decide you want to optimize for proximity to family, financial stability, the ability to work remotely, or becoming world-class in a certain industry. Knowing this helps direct your energy. If you do want to become great at something, you have to answer the next question. 
2. Will you put in the effort to become world-class? My time in poker helped me understand what it takes to become truly great at something. Once you get high up in any field, there are extremely talented people competing hard to win. To be one of the very best, you must make significant sacrifices. These usually come at the expense of things like family time and outside hobbies. 
3. Is the thing I want to become world-class at worth it? If you do manage to hit the right tail in your field, will it have been worth your time? From a financial perspective, at least, many industries don’t reward even their greatest practitioners. Given our finite time, you want to make sure there is asymmetry at the bounds. 

Thinking through these three questions honestly has helped me better direct my time towards pursuits that make me happy. 

4. What craft are you spending a lifetime honing?

Probabilistic evaluation. It’s played a role in everything I’ve done, from poker to investing to building LayerZero. 

Here’s an example of how it manifests in my current day-to-day. Right now, we’re weighing up LayerZero’s roadmap as it relates to ecosystem expansion. We have a strong foothold in the EVM (Ethereum Virtual Machine) space and are close to deploying on Solana. But over the last few months, new ecosystems like Aptos and Sui have emerged and gathered momentum. Aptos even poached Solana’s Head of Marketing recently. 

What should we do? Is it worth reordering our roadmap to prioritize Aptos or Sui? Or should we focus on shipping our Solana deployment? Decisions like this are probabilistic. What is the payoff function? What are you giving up? 

5. What is your most contrarian, high-conviction opinion?

I’ve realized that I don’t spend much time wondering what other people are thinking. One of the hardest questions for me to answer is something like, “What do other people think about you?” The truth is, I have no idea. That makes it tricky for me to know whether an opinion is genuinely contrarian or not. 

Something I believe very strongly that I don’t think is common is that the world is constantly improving and that technology can solve almost all of our problems. That might not be true in every dimension, in every instance. But from a high level, I think it’s right. I will always bet on progress and technology. 

6. What piece of art can you not stop thinking about?

A seven-foot triceratops skull. The amount of time I have spent thinking about it is crazy, but I find it fascinating. When it first came up for auction a few years ago, I didn’t move quickly enough. Now, it’s coming up again. 

My son is obsessed with dinosaurs, and I love the idea of him getting to grow up in a world where that kind of magic exists in his home. There’s also a ten-foot Mosasaurus skeleton I’ve been eyeing. They’re both just amazing, incredible artifacts. 

7. What are you obsessed with that others rarely talk about?

Work. I can talk about work indefinitely. And it doesn’t have to be my work – I’m just as happy to hear about what someone else does for a living, even if it has nothing to do with my interests. If I’m sitting next to someone at a meal that runs a lumber company, I want to spend as much time as possible hearing about how that business functions. Thinking through how it can be optimized or scaled and learning what the strongest levers and competitive edges are is fascinating to me. Each business is a new problem to solve. 

It might not be the most balanced approach. My wife is French and Swiss, and I’ve found that Europeans, in particular, prefer to have a more conversational separation between the office and leisure. But I am just endlessly fascinated by different businesses. 

8. What contemporary practice will our descendants judge us for most?

Exposing children to manipulative, algorithmically curated content. If your kid is active online, they face a constant barrage of advertisements and feeds designed to discover which extreme they lean toward most and inundate them with the most polarizing opinions available. The goal is maximum engagement in both directions. It seems obvious that this cannot be good for brains still in development. I think we’ll be judged for how few protections we’ve put in place and our broad lack of concern. 

9. What risk are we radically underestimating as a species?

Artificial intelligence. Experts in the field tend to overestimate this risk, but society radically underestimates it. If you asked the average person how significant a threat AI poses, they would weigh it at effectively zero.

While I think the risks are low, the tail risk is so extreme that it requires attention. The concern isn’t the creation of the Terminator but the emergence of an optimization function that we rely on too heavily and is misaligned with humanity’s goals. The canonical example is Nick Bostrom’s “Paperclip Maximizer.” If we created an AGI (Artificial General Intelligence) whose sole purpose was to collect paperclips, as its competence and power expanded, it would rationally reorganize the world to meet its goals. This might sound silly, but it’s a good illustration of how misdirected intelligences can cause havoc. Our descendants will certainly judge us if we're cavalier about this danger, just as we criticize previous generations’ handling of nuclear weapons. 

The good news is that the tail lives in both directions. We should be alert to the worst-case scenario, but I think it's much more likely that we have a positive skewed outcome. AI can have a meaningful impact on almost every sector. 

10. What job that doesn’t exist today will be vital in fifty years?

I try not to think that far ahead. The world changes too rapidly to predict what it will look like half a century from now. Often, people who sculpt a more definitive vision of the far future start to act as if it will come true. They shape their path to fit this imagined eventuality, and the more they do so, the more they internalize perceived sunk costs. They don’t want to revise their opinion since doing so would mean their effort went to waste. The result is a kind of vision blindness, where a person ignores disconfirming evidence for fear of what it would mean for their invented future. I’m not sure that’s productive. 

11. If you had the power to assign a book for everyone on earth to read and understand, which book would you choose?

I’m skeptical of received wisdom. I seldom learn how to do something by studying how people have done it before me. If I’m playing a board game for the first time, I don’t want to know the established strategies. I want to read the rulebook and find my own optimization. 

Because of that, I’ve always disliked books that try to teach you something explicitly. I don’t think the best way to learn how to negotiate is from a book on negotiation, for example. 

Because of that, I’m picking Ender’s Game by Orson Scott Card. It’s a story I loved and would enjoy having as a shared global text for the conversations it would spark. It’s a brilliant and thought-provoking story. 

In particular, I enjoyed its commentary on authority. In pursuit of its goals, a military manipulates an amazingly bright kid into becoming a weapon. The protagonist is deceived at every step to carry out what he would have considered deeply unethical tasks had he understood what he was doing. It’s a fascinating dissection of game theory on multiple sides and an illustration of how authority functions. 

12. How will future historians describe our current era?

Despite its problems, historians will remember our era as one of the most special in human history. There has never been a better moment for bright, motivated people to impact the world. That’s not true everywhere, but on a relative basis, opportunity is more abundant than ever. Much of the world has enjoyed geopolitical stability in recent years, too.

Technology and the rise of globalization have played a vital role in that. We have access to the world’s accumulated knowledge, computers in our pockets, and a reach we’ve never had before. I hope it only gets better.