Getting a Crypto Job

A year ago, I was ready for a change at work. A re-organization at my old company meant that I was spending about 6 hours per day in meetings, which drained me. In the wake of COVID, it was high time to heed my own advice:

Now is a great time to get a new job. With the labor market now untethered from your geographic locale, you can enjoy your current lifestyle while locking in the salary of a much higher cost-of-living city. The key is to do this soon – before companies start adjusting salaries for the cost of living where a given employee is located.

Work From Home

I drew up a list of what I’d like to accomplish in my next role:

  1. Have a large impact; solve important, complicated problems.
  2. Grow my technical skill set; spend time on heads-down execution, rather than in meetings and on process updates.
  3. Learn from incredibly smart coworkers. Specifically, learn how to scale a company from the seed stage (~$0 ARR) to $10M+ ARR and beyond, with the end goal of launching my own company 2-5 years down the line.

Let’s Talk Tactics

If I were to look for a job in the blockchain space today, I’d learn Solidity, launch a few dApps of my own, and join crypto project Discord servers as a way to dip my toes into the industry.

But last year I didn’t limit my job search to the crypto space. At the time, I didn’t even realize I could work in the crypto space! So here are a few tactics I used to find companies and jobs in the tech industry more broadly:

Ignore public job postings. Well, don’t actually ignore them. But they should be viewed as an indication that the company is hiring, rather than a comprehensive list of the roles it actually needs. Many early-stage companies find smart people and then write a job description for them, rather than publicly posting a job description for every open role. Similarly, you should view job requirements (particularly regarding work experience) as a mere suggestion. With 5 years of work experience, I could regularly get interviews for roles that “required” 7+ years.

Warm intros. I reached out to folks in my personal network for personal introductions to companies. Your university’s fellow alumni as well as first- and second-degree connections on LinkedIn are often happy to help.

Cold emails to founders. When the company is Series A or smaller (< ~25 people), the founders can be surprisingly responsive. To send a good cold email, you should:

  1. Find the right person. This is a decision-maker (i.e., someone who can actually hire you) in your area. At a company of this size, this will likely be the CTO for engineers and the CEO for everyone else.
  2. Keep it short. The person you’re emailing is busy. They don’t need your life story; a five-sentence email will suffice.
  3. Do your homework. Say something unique that draws you to the company. If you could send this email to several different companies, it’s not differentiated enough.
  4. Focus on the value that you’ll add. 90% of people who send these emails focus on themselves: their past experience, how much they’d learn at the company, etc. You want to highlight why the company needs you. In what ways are you uniquely qualified to help the company?

Early-stage startup boards. I found companies that were hiring on AngelList. Many startups don’t actively check their AngelList profiles, so it’s best to reach out directly once you find companies you’re interested in. Similarly, Work at a Startup, Y Combinator’s job board, is a great resource.

Through Work at a Startup, I ran across TRM Labs. On a whim, I shot off a note saying I’d be interested in a Data Science role. Here’s the exact message that I sent TRM to get an interview:1

Hey TRM Labs team! Reaching out because I’ve spent the past couple of years immersed in healthcare data – I’m drawn to working on a smaller team and getting closer to my academic roots in finance. Would love to chat!

Enter TRM Labs

Let’s take a step back. What is TRM Labs?

We are a blockchain intelligence company. We analyze blockchain data to help financial institutions and government entities detect financial crime and fight fraud in cryptocurrency transactions.

Our mission is to build a safer financial system for billions of people. We believe that:

  1. Crypto is poised for explosive growth.
  2. Risk management infrastructure is essential for that growth to occur.


I had played around with crypto on and off since 2013, but never thought that I could make it my career. So I was happy to hear that TRM attracts a motley crew:

  • Brilliant data scientists and engineers – with or without a crypto background. We work with huge, complex datasets, and our data is the lifeblood of our product.
  • Former law enforcement agents who specialize in investigating financial crimes.
  • Folks in the financial compliance space.
  • Cryptocurrency enthusiasts who have been in working on decentralized projects for years.
  • Anyone who is humble, smart, and driven, who wants to solve big problems and build the future of finance.

But when I reached out, I didn’t know any of this. At the time, all that I knew was that TRM was a small startup with some good investors (YC, PayPal, Initialized Capital, etc.) operating in the crypto space.

Interview Process

My process started with a standard 30 minute phone screen with our CEO, Esteban. He gave me an overview of TRM, dug into my background, and asked what types of problems I’d like to solve in my next role.

From there, he sent me an “AoR” (Areas of Responsibility) document. This was a list of all of the potential workflows that were open areas of need at TRM. I indicated my level of ability and interest for each workflow, then got on a follow-up call with Esteban to discuss. I respected how thoughtful Esteban was about building not only a great product, but a great company, as well as his emphasis on finding a good role for me, given my skills and interests.

We mutually agreed that TRM would be a potential fit, so I was given a take-home challenge involving SQL, writing, and project planning/project management. This was extremely open-ended. I then had a 3-hour virtual onsite to discuss the results of my take-home challenge, as well as some additional technical and cultural interviews.

It was tough to get a read on my performance during the virtual onsite. I think that this is a function of not being in the same room as others and being able to read non-verbal cues. Frankly, I thought that I had bombed the Python portion of the interview. I don’t have a degree in CS – I’m self-taught technically and don’t code well under pressure.

Being on the other side of interviews now, I realize that at TRM we intentionally hire for strengths, as opposed to lack of weaknesses. So the other facets of the interview may have made up for my relative weak performance on the Python portion. (E.g., I was able to send across some writing samples from this very blog.)

My final-round interview was on a Friday. Esteban called me and gave a verbal offer first thing on Monday morning. I was impressed by the quick turnaround; as a candidate, this made me a lot more excited about the company and the role. I also appreciated that they offered an Amazon gift card as a token of appreciation for completing the take-home challenge. These take-home challenges can be a substantial time investment for candidates, so the fact that TRM recognized this exemplified that this is a company that cares about its people.

Due Diligence

After getting an offer from TRM, I had some follow-up questions to ensure that the company and role would be a good fit for me. I knew that joining as one of the first 15 employees of a seed-stage, remote startup meant that culture would be extremely important.

Esteban lined up some follow-up casual one-on-one meetings with various team members for me so that I could get a sense of what working at TRM would look like. He also got on the phone with me for about an hour to discuss all of the questions that I had.

Beyond that, two things in particular pushed me over the edge:

  1. The cocktail party test. If you were at a cocktail party, how excited would you be to discuss your current job? In my former role, if I was looking to get out of a conversation, I’d say that I was working for an “insurance company”, and if I wanted to continue the conversation, I’d say that I worked at a “healthcare startup”. With a job at TRM, I could tell people that I worked in crypto at a blockchain analytics company. That’s something that I’d be excited to talk about!
  2. Backchannel references. I reached out on LinkedIn to a few former employees of TRM, to chat about their experience at the company and why they left. I thought this would give me a more honest assessment of the company, compared to the point of view of current employees who were actively trying to recruit me. One of the people I reached out to was effusive in his praise of TRM. I’ll quote him directly:

    WOW this is an excellent strategy that I’m going to do for all my next jobs (reaching out to former employees). So, in short, TRM is a one in a million startup. The biggest names in crypto and fintech as clients, an incredible CEO, and a world class technical team. The primary reason I left was because I got an opportunity to more or less found a startup with a really good friend of mine that I’ve known for years. Even on my way out, everyone in the company wished me well and even got me a going away gift.

At that point, my decision was made. I negotiated my offer with Esteban and signed on to start working at TRM two weeks later.

One Year Later

Almost a year into my time at TRM, I can say that this was a great decision for me.

The crypto space is extremely exciting right now, and TRM is capitalizing on the trend of institutional adoption of crypto. We ship new product features extremely quickly and are growing our customer base.

I joined DoorDash as employee ~200 in 2016. The explosive growth that we’re experiencing at TRM is reminiscent of my time at DoorDash. Over the past year, we’ve gone from a dozen to over 40 employees. By this time next year, we’ll have over 100. Each new hire raises the bar for us as a company. In general, I rarely walk away from a conversation thinking “Wow, that person is really smart.” That happens to me regularly at TRM. I know that I need to bring my A-game every day at work.

We have employees all over the world and have embraced the remote work model. Long-term, we’ll likely have some offices in hub cities, with the opportunity to work from the office or remotely, depending on employee preference. We’ll also conduct off-sites a few times per year to get together in person and collaborate.

Because of this remote culture, we place a large emphasis on written communication. We document our thoughts and processes, and challenge each others’ thinking asynchronously, meaning I spend on average just 5 hours per week in meetings.

This remote environment has also given me a great deal of flexibility, given TRM is an early-stage startup. I largely set my own calendar and have been able to do things like go to the gym in the middle of the day. That’s not to say that we don’t work hard – the other side of the coin is that I’ve been on calls at 3 a.m. when we need to push out a new feature or report for our customers.

My day-to-day consists of varied tasks, as you’d expect at a startup. Some examples:

  • Analyzing illicit activity in the cryptocurrency ecosystem, then delivering the results of this analysis to regulatory agencies.
  • Building internal tools that help scale the work of Blockchain Intelligence Analysts and the Machine Learning team.
  • Defining the methodology for calculating the exposure to a given counterparty on UTXO blockchains.
  • Standing up or modifying an Airflow pipeline.
  • Meeting with clients; implementing custom reports for them based on datasets and on-chain data.
  • Extracting insights from our data to inform our product strategy.
  • Jumping into a sales meeting to highlight TRM’s analytic capabilities.
  • Designing a Data Science interview process to grow our team.
  • Writing this blog post.

Various Tasks

I’ve encountered a ton of autonomy at TRM. There is more than enough work to go around, so it is up to you to prioritize your work to make the maximum impact. We are a flat organization that places a lot of emphasis on being a “humble master of your craft”. We ship surprisingly quickly, communicate openly, and take full ownership of outcomes – whether a presentation to a regulatory agency or a last-minute client request.

I started this post by saying that one of my goals was to find a role where I could learn how to scale a company, before starting my own. I think I’ve found a great place to do that. I’m optimistic that TRM will be the last job that I ever have – but there’s a lot of work to do here first.

Interested in solving hard problems with us to make the financial system safer? Join us!


  1. I don’t follow all of my advice regarding cold emails here…this wasn’t the ideal message, but it got the job done. 

Stop Feeding the Dragon

If cars were invented today, they would be illegal.

We give 16-year-olds minimal training, then entrust them with the control of a 3,000 lb. weapon for the rest of their lives.1 You can be an awful driver, but even if you get into an accident, your license will rarely be taken away.

Over 100 people per day die in car crashes in the U.S. This is the leading cause of death for people aged 1-54. Each year, an additional 4.4 million people are injured badly enough to need medical attention, costing over $380 million in direct medical costs.

You are 750 times likelier to die in a car accident than on a commercial airline flight. Similarly, buses and trains are far safer than driving a car.

Car accident

If cars had not been invented, and we had designed 20th century cities around people, rather than the automobile, we’d have a robust public transportation network that would all but eliminate the need for cars, at least in cities and suburbs (see Japan). Even today, an auto-piloted Tesla is 9x safer than a human driver in a normal car. We should arguably drive cars the same way that pilots fly airplanes – with a bit of manual intervention when necessary, but otherwise letting a computer do the work.

So why do we still allow driving?

Defaults Define Us

Status quo bias is one of the most pernicious insensibilities that permeates our collective consciousness. In short, we have an emotional preference for the current state of affairs.

It is nearly impossible to contest the societal inertia around what already exists. But if you examine some of our cultural practices from first principles, they begin to appear more and more nonsensical. Some pertinent examples:

  1. Alcohol. Drinking is quite literally poisoning yourself. It is completely socially acceptable to have a few drinks after work, but this widespread usage leads to widespread abuse. Alcohol is one of the most dangerous drugs out there: it has high potential for addiction and long-term adverse health effects.

  2. Circumcision. We (rightfully) view female circumcision as barbaric. Even our language surrounding the practice – female genital mutilation – suggests this. Shouldn’t the same logic apply to males?

  3. Libraries. The government buys books, then lends them out for free to the public. If you proposed this idea today you’d be laughed out of the room and then sued to death by publishing companies.

  4. Football. Football is a brutal sport. I made my best friends playing football, gained confidence, learned countless life lessons…but I still wouldn’t let my future children play the game because of the risk of brain injury. A few months ago, I had a conversation with a former teammate where we wondered if there have been long-term negative cognitive effects.2 And I stopped playing at 19 – I can’t imagine the cumulative effects of years playing in the NFL. How many suicides from former football players are we willing to tolerate?

  5. Cheerleading. We sexualize pubescent girls by having them dance on the sidelines of high school sports games. In the most charitable interpretation, this is a bit…odd.3 See also: beauty pageants.

  6. Cigarettes. This is an interesting example, because the Overton window has shifted – we were able to overcome the societal inertia, and smoking is now a marginalized activity. This proves that overcoming status quo bias is difficult, but possible.

  7. Organized religion. Most people practice the religion they were born into: religious conversion rates are low, suggesting that the social switching costs from the religion of one’s birth are high. Many religious practices, while culturally significant, are not exactly logical.4

  8. Factory farming. The amount of suffering that we impose on sentient beings will make us seem barbaric in 200 years. I don’t have a strong rational defense of eating meat, much less factory farming.

  9. The U.S. Constitution. Our Constitution and the Founding Fathers are revered with religious zeal. The United States has the oldest continually operative written constitution in the world. But shouldn’t it have been updated more often in the past 234 years? We wouldn’t want our doctors using the oldest extant medical textbook, or our aerospace engineers using the oldest viable technology to build rockets.

Kant Betray Us

In confronting status quo bias, utilitarianism thrives compared to deontology. Utilitarianism claims that creating more happiness is just as good as preventing suffering.

The Room

Consider the trolley problem. A runaway trolley is hurtling down the tracks. Tied to the tracks in front of it are five people. If the trolley continues, it will undoubtedly run them over and kill them.

But wait! You’re standing next to a lever. If you pull the lever, you can divert the trolley to a different track, where only one person is tied to the tracks. What do you do?

If you do nothing, five people die. But if you pull the lever, one person dies. Utilitarians would pull the lever – the suffering of one person is less than the suffering of five. But deontologists would not, because they have an ethical duty to not kill people.

But not making a choice is itself a choice! Choosing inaction by default, rather than reason – tacitly endorsing the current state of affairs – demonstrates an incoherently fatalistic worldview.

Societally, we are faced with the trolley problem every day. And because we don’t make the difficult ethical decision to pull the lever, we default to the status quo and do nothing. Ex post facto, we all pat ourselves on the back for being good deontologists, while through our inaction we increase the amount of suffering in the world.

But what about Chesterton’s Fence? There must be some benefit for doing things the way that we do them.

I’m not so sure. Societal forces build up incrementally over time, as individual actors respond to the incentives present in their current circumstances. See Moloch.

Or, as Scott Alexander recently put it in a post regarding the effects of missing school in the wake of COVID:

Eliezer Yudkowsky tells a parable about a society where people hit themselves on the head with a baseball bat eight hours a day for some reason. Maybe they believe it drives out demons or something. Then they learn that it does not, in fact, drive out demons. But everyone has great reasons why they need to keep doing it.

“It’s a great way to increase your pain tolerance so that the little things in life don’t bother you as much.”

“It builds character!”

“Every hour you’re hitting yourself on the head with a bat is an hour you’re not out on the street, doing drugs and committing crime.”

“It increases the demand for bats, which stimulates the lumber industry, which means we’ll have surplus lumber available in case of a disaster.”

“It improves strength and hand-eye coordination.”

“It may not literally drive out demons, but it’s a powerful social reminder of our shared commitment for demons to be driven out.”

“It’s one of the few things that everyone, rich or poor, black or white, man or woman, all do together, which means it crosses boundaries and builds a shared identity.”

“It binds us to our forefathers, who hit their own heads with bats eight hours a day.”

“If we stopped forcing everyone to do it, better-informed rich people would probably be the first to abandon the practice. And then they would have fewer concussions than poor people, which would promote inequality.”

“It creates jobs for bat-makers, bat-sellers, and the overseers who watch us to make sure we bang for a full eight hours.”

“Sometimes people collapse of exhaustion after only six hours, and that’s the first sign that they have a serious disease, and then they’re able to get diagnosed and treated. If we didn’t make them bang bats into their heads for eight hours, it would take much longer to catch their condition.”

“Chesterton’s fence!”

None of these are false per se. Banging a bat against your head for eight hours a day does have lots of advantages. They’re just not advantages that would cause us to want to take up the practice if we weren’t already used to it.

With any of the examples above, I can build arguments that rationalize the behavior. Alcohol leads to social mingling that we wouldn’t have otherwise, football teaches teamwork, we need to circumcise our sons so that they aren’t embarrassed in the locker room. But that doesn’t mean that these we should engage in these activities. We should constantly be re-examining our assumptions from first principles.

For example, we are far too risk-averse when it comes to testing medicines. The Moderna COVID vaccine was ready in February 2020. It took another 10 months for it to get FDA emergency use authorization. This is just the most conspicuous example of a problem endemic in life sciences.

Extend this to any technological improvement that can prevent human suffering. Nick Bostrom tells The Fable of the Dragon-Tyrant:

There was once a dragon that terrorized the planet. It was so powerful that humans could not hope to defeat it. So humanity reached a state of dreadful detente – they would send 10,000 human beings to be eaten by the dragon each day. This went on for as long as anyone could remember, so that a mythology arose around it:

Spiritual men sought to comfort those who were afraid of being eaten by the dragon (which included almost everyone, although many denied it in public) by promising another life after death, a life that would be free from the dragon-scourge. Other orators argued that the dragon has its place in the natural order and a moral right to be fed. They said that it was part of the very meaning of being human to end up in the dragon’s stomach. Others still maintained that the dragon was good for the human species because it kept the population size down. To what extent these arguments convinced the worried souls is not known. Most people tried to cope by not thinking about the grim end that awaited them.


Over time, the dragon’s appetite grew and grew. Entire industries and professions sprung up around the dragon: dragonologists to study it, operations experts focused on feeding it most efficiently, finance professionals to set the dragon-administration budget. The dragon became an accepted fact of life; bureaucrats focused on managing the existence of it, rather than slaying it.

A group of scientists who studied the dragon argued that he could be defeated. It would take time, money, and a lot of hard work, but it could be done. At first, the people wrote them off as crazies. Everyone knew that the dragon was simply a fact of life to be accepted. In fact, it was being eaten by the dragon that gave life meaning – to be human meant living a finite life to the fullest, before ending up in the belly of the beast.

In the end, despite this philosophical reprehension, the dragon was defeated. But not before he caused immeasurable suffering.

This parable is used as an argument for allocating resources to life-extending technologies. But beyond that, we continue to feed large and small dragons each day: all of the suffering that we allow simply because that’s the way things are.

Each day that we don’t act, we continue to feed these dragons. Time is of the essence.


  1. Cars are often used in terrorist attacks

  2. With a N of 1, I’m not sure if I’ll ever know the magnitude of the effects on my brain. But I don’t think anyone can say that nine years of tackling people and seeing stars during games helped my brain development. 

  3. Cheerleading has very high participation prices, because the industry is a monopoly. Additionally, I originally wanted to include a point about the large number of injuries in cheerleading, but that may be a misleading narrative

  4. A religion is just a cult that has gathered mainstream acceptance over time. 

You're Not Too Late

When you’re a very online person, it’s easy to think that you’ve missed the bus.

I often think that the blog post I want to write has already been written. That I can’t make money investing in a company – the stock has already gone up 10x and I didn’t get in early enough. That I missed out on gigantic crypto gains.

So on a daily basis, I try to remind myself: You’re still early.

Didn't miss the bus

Hiding in Plain Sight

In the 1994 movie Forrest Gump, Forrest finds out that his business partner “invested in some sort of fruit company” and that they “didn’t have to worry about money anymore”. That company was, of course, Apple.

The implication is that Apple was a great investment prior to 1994. However, if you put money into Apple stock the day that the movie was released, you would have returned 640x on your investment (27% per year).1 Apple has tripled in market cap in the past three years alone! And this is a stock tip found in one of the most iconic movies of the past 30 years, one that won the Best Picture Oscar.

Zoom out on an exponential curve and it still has the same shape. But your y-values (i.e., what you care about) will have changed dramatically.

The Bus Is Parked

Working within crypto over the past year, I’ve been exposed to tons of new, exciting concepts:

  • Decentralized exchanges
  • Zero-knowledge proofs
  • NFTs
  • DAOs
  • Yield farming
  • Perpetual swaps
  • Etc.

If you recognize (recognize – you don’t even need to be able to define) one of those words, you’re early to crypto.2 It’s easy to think that the innovation has already taken place, but the space is just 12 years old. Even the current king of crypto (or, if you prefer, the “Prince of Risk”), Sam Bankman-Fried, only began working in crypto in 2017.3

Recently, I’ve been following the explosion in the NFT space, wondering if it’s too late for me to get involved. Let’s take a look at some numbers:

And some comparables for market sizing:

We’re still really early on! There is a ton of growth potential for NFTs across a few axes:

  1. Existing crypto users
  2. Art collectors
  3. Asset traders
  4. Gamers

You don’t need to be first to see a trend to capitalize on it. Facebook wasn’t the first social network. Google wasn’t the first search engine. Coinbase and FTX weren’t the first crypto exchanges.

So no, the bus hasn’t left the station. Hell, the bus isn’t even in the station yet – it’s in the parking lot waiting for the driver to start his shift.


This blog post is NOT investment advice. Do your own due diligence.

  1. $148.60 close price on August 27, 2021 compared to pre-split share price of $.233 on July 6, 1994. 

  2. Relevant thread, and some of the inspiration for this post, found here

  3. I’m sure he was trading on the side before this, but we’ll use him founding Alameda Research as the official start date. 

  4. I’d argue that the NFT market has much larger potential, given lower barriers to entry and the potential size of the metaverse compared to tracked art sales, but this is still a relevant number. 

Up in the Air

Most people hate flying. And they’re right – air travel largely sucks. You’re jammed into a tiny space, treated like a head of cattle, essentially just riding a bus in the sky.

That may all be true. But it’s also true that planes are my happy place. Up in the air, I’m free.1


I spent several years taking 50+ flights per year, both for work and pleasure. Leaving is always crazy: do laundry, then pack my clothes, make sure I haven’t forgotten anything.2 But once I get to the airport, all of that changes.

Little perks make flying alone as stress-free as possible. Airline status. TSA PreCheck. Lounge access. You can play the credit card game to get these benefits for free.

Walk to the gate just before they close the door to the flight. (Of course you want to maximize lounge time.) And you don’t want to be trapped in that metal tube with the masses for any longer than necessary.

The real magic occurs once we’re airborne, though. I have no WiFi, no communication with the outside world. I’m untouchable.

I get my best work done on airplanes. I can actually focus on writing.3 I have the willpower to sit down and read a book without checking Twitter. I’ll become engrossed in a movie.

Over the past decade or so, I’ve felt my attention span drastically shortening. The inside of an airplane is one of the last refuges from distracting interconnectivity. Much of modern-day knowledge work is simply being a human router. But our best work requires deep focus and solitude; flights provide that environment, allowing us to execute.

Cal Newport describes this phenomenon in his book, Deep Work:

As a popular speaker, Shankman spends much of his time flying. He eventually realized that thirty thousand feet was an ideal environment for him to focus. As he explained in a blog post, “Locked in a seat with nothing in front of me, nothing to distract me, nothing to set off my ‘Ooh! Shiny!’ DNA, I have nothing to do but be at one with my thoughts.” It was sometime after this realization that Shankman signed a book contract that gave him only two weeks to finish the entire manuscript. Meeting this deadline would require incredible concentration. To achieve this state, Shankman did something unconventional. He booked a round-trip business-class ticket to Tokyo. He wrote during the whole flight to Japan, drank an espresso in the business class lounge once he arrived in Japan, then turned around and flew back, once again writing the whole way—arriving back in the States only thirty hours after he first left with a completed manuscript now in hand. “The trip cost $4,000 and was worth every penny,” he explained.

I’m missing those long solo flights. I’ll use my miles for a round-trip to Japan once I get a book deal. 😛


  1. Obvious reference to the movie Up in the Air. I’m not sure why it was so celebrated by frequent fliers, though. It’s a good movie, but it doesn’t extol travel so much as abase it. 

  2. Back when I lived in New York, before departure I’d also clean my apartment to prepare it for Airbnb guests. I’m still mad at that guy who stole my shoes. 

  3. Coding can be tough without the internet, though. 

Book Review – Barbarian Days

I am an obsessive person. Throughout life, I’ve had various passions – chess, boxing, travel, options trading – some more serious than others.

I’ve long wondered: “What if I were to pursue one of these passions to the absolute limits of my abilities…even if it meant the utter and deliberate neglect of every other area of my life?”

William Finnegan’s Barbarian Days: A Surfing Life is a 447-page meditation on this sort of devotion: a life designed around chasing the evanescent moment just before the crash of a wave.



William Finnegan grew up in the post-World War II boom of Southern California. He lived a typical suburban Los Angeles life, with the exception of a couple of short stints in Hawaii, where his dad worked on site as a film producer.

The stories from Hawaii were by far the most interesting part of his adolescence. His childhood, like the childhoods of many Baby Boomers, seemed to be defined by violence. Upon arriving at the rough-and-tumble Kaimuki Intermediate School, Finnegan is regularly whacked over the head with a two-by-four during shop class. He becomes acquainted with festive Hawaiian celebrations such as “Kill a Haole Day”, in which any white person was fair game to be beaten up.

My orientation program at school included a series of fistfights, some of them formally scheduled. There was a cemetery next to the campus, with a well-hidden patch of grass down in one corner where kids went to settle their differences. I found myself facing off there with a number of boys named Freitas—none of them, again, apparently related to my hairy tormentor from wood shop. My first opponent was so small and young that I doubted he was even at our school. The Freitas clan’s method for training its members in battle, it seemed, was to find some fool without allies or the brains to avoid a challenge, then send their youngest fighter with any chance at all into the ring. If he lost, the next biggest Freitas would be sent in. This went on until the nonkinsman was defeated. It was all quite dispassionate, the bouts arranged and refereed by older Freitases, and more or less fairly conducted.

With this backdrop of violence in an antediluvian Hawaiian paradise and post-modern Southern California suburbia, surfing is both a respite from – and a part of – the pressures of adolescence.

But surfing always had this horizon, this fear line, that made it different from other things, certainly from other sports I knew. You could do it with friends, but when the waves got big, or you got into trouble, there never seemed to be anyone around.

Everything out there was disturbingly interlaced with everything else. Waves were the playing field. They were the goal. They were the object of your deepest desire and adoration. At the same time, they were your adversary, your nemesis, even your mortal enemy. The surf was your refuge, your happy hiding place, but it was also a hostile wilderness—a dynamic, indifferent world. At thirteen, I had mostly stopped believing in God, but that was a new development, and it had left a hole in my world, a feeling that I’d been abandoned. The ocean was like an uncaring God, endlessly dangerous, power beyond measure.

And yet you were expected, even as a kid, to take its measure every day. You were required—this was essential, a matter of survival—to know your limits, both physical and emotional. But how could you know your limits unless you tested them?

Surfing Hawaii

The opening of this book dragged a little, but served to establish Finnegan’s origin story:

My father liked to tell a story about a day when I got discouraged. From the warmth of the car, he had been watching me flounder—I imagine him smoking his pipe, wearing a big fluffy fisherman’s sweater. I came in, my feet and knees bleeding, stumbling across the rocks, dropping my board, humiliated and exhausted. He told me to go back out and catch three more waves. I refused. He insisted. I could ride them on my knees if necessary, he said. I was furious. But I went back out and caught the waves, and in his version of the story, that was when I became a surfer. If he hadn’t made me go back out that day, I would have quit. He was sure of that.

From a young age, Finnegan is independent and stubborn. As he becomes a teenager, he also becomes more withdrawn. He regards himself as somewhat of a reclusive romantic, using surfing as a vehicle to reach a higher spiritual plane.

What could rightly have worried my dad about me and surfing was the special brand of monomania, antisocial and ill-balanced, that a serious commitment to surfing nearly always brought with it. Surfing was still something that one did—that I did—with friends, but the club thing, the organized-sports part, was fading fast. I no longer dreamed about winning contests, as I had dreamed about pitching for the Dodgers. The newly emerging ideal was solitude, purity, perfect waves far from civilization. Robinson Crusoe, Endless Summer. This was a track that led away from citizenship, in the ancient sense of the word, toward a scratched-out frontier where we would live as latter-day barbarians. This was not the daydream of the happy idler. It went deeper than that. Chasing waves in a dedicated way was both profoundly egocentric and selfless, dynamic and ascetic, radical in its rejection of the values of duty and conventional achievement.

In his late teens, Finnegan takes a break from surfing to become a bit of a hippie. Channeling his inner Kerouac, he embarks on a cross-country road trip with his friend Domenic. They have teenage adventures – drinking in bars, dropping acid in New York City, ironically choosing not to make the trip to Woodstock:

It was 1969, the summer of Woodstock, but the flyers for the festival plastered around Greenwich Village mentioned an admission charge. That sounded lame to us—some kind of artsy-craftsy weekend for old people—so we skipped it. (My newsman’s intuition, never great, was then unborn.)

He also backpacked around Europe with his first serious girlfriend, Caryn, who is portrayed as his “true love” throughout the book. In his travels and relationship with Caryn, Finnegan’s restlessness and selfishness is apparent.

We had started to quarrel, Caryn and I, and we didn’t fight well. On the road, moreover, I turned into a tyrant, setting a merciless pace as we bummed around Western Europe, living on crackers and fresh air, sleeping under the stars. There was always someplace new, someplace better, we had to be. I dragged her on grueling pilgrimages to rock festivals (Bath) and surf towns (Biarritz) and the old haunts (and graves) of my favorite writers. Caryn, less callow, did not see the reason for all the hurry. She pressed dried flowers in her journal, went to museums, and, already fluent in French and German, undertook to learn each language we encountered. She finally dug in her heels on the western Greek island of Corfu after I announced that I had a burning desire to see more “Turkish influence.” I could go hunt for Ottoman minarets on my own, she said. And so I up and left her on the remote, mountain-backed beach where we were camping au naturel. Neither of us, I suppose, believed I would really do it, but I had become adept at, if nothing else, moving quickly through strange territory at low cost, and within a week I was in Turkey itself, newly intent on traveling overland to India. Motion, new companions, new lands were my drugs in those days—I found they did wonders for the adolescent nerves. Turkish influence fascinated me for about half an hour. Then only Tamil influence would do.

Holy shit. Finnegan abandons his 17-year-old girlfriend on a Greek island because he wants to see Turkey. Eventually, a few weeks later, he goes back for Caryn and finds her in a campground south of Munich. When he reunites with Caryn, he writes only, “She seemed fine”, and the two resume their travels.

Later, as a college dropout, he convinces Caryn to move with him to Hawaii so that he can chase waves. Here, Bill’s manipulative charm is in full force:

Caryn did have one motive that was her own for agreeing to come to Maui. Her father was reportedly there. Sam had been an aerospace engineer before LSD came into his life. He had left his job and family and, with no explanation beyond his own spiritual search, stopped calling or writing. But the word on the coconut wireless was that he was dividing his time between a Zen Buddhist monastery on the north coast of Maui and a state mental hospital nearby. I was not above mentioning the possibility that Caryn might find him if we moved to the island.

Eventually, Caryn puts her food down and they break up. Good for her.

By the age of 25, Finnegan has lived many lives. After his travels and his time living in Hawaii, he returns to California and graduates from college. He then gets a job as a brakeman on the railroad. This part of his life he glosses over in his memoir – I would have loved to see a lot more written about this.

The story picks up with him and his friend Bryan embarking on a round-the-world trip in pursuit of waves.

I had five thousand dollars in the bank, by far the most I had ever saved. I was twenty-five, and I had never been to the South Seas. It was time for a serious surf trip, an open-ended wave chase. Such a trip felt strangely mandatory. I would go west forever, like Magellan or Francis Drake—that was how I thought of it. In truth, difficult as it was, pulling up stakes was in many ways easier than staying. It gave me an excellent excuse to postpone mundane but frightening decisions about where and how to live. I would disappear from the overdetermined, underwhelming world of disco-dulled, energy-crisis America. I might even become another person—someone more to my liking—in the Antipodes.

A good memoir makes you reflect not only on the life of the person who wrote the book, but on your own life. I saw a lot of myself in this section of the book. A scary amount. Or at least, the part of me from my early 20s that thought traveling the world would provide a sense of meaning in my life.

Like Finnegan, I spent half a decade flying around the world in search of novelty, looking in hostels in South America or Southeast Asia for the answer to a question that I had never defined.

What was different for Bill, however, was the surf-centricity of his trip. As a surfer, he has a higher calling (cue eye roll from the rest of us) than the other backpackers he encounters.

Surfing, under the circumstances, was a godsend. It was our project, why we got up in the morning. After we ran across a group of Western backpackers in Apia, I grumbled, according to Bryan, that they “were nothing but goddam sightseers.” I didn’t remember saying that, but it was in fact how I felt. We did plenty of palagi looking-looking-looking ourselves, and there was something obscene about that, but at least we had a purpose, an objective, however fleeting, pointless, idle, and silly it might seem to anyone else.

Throughout this time, he and Bryan are reading and writing, which becomes apparent in reading the multi-page descriptions of a wave that Finnegan surfed 40 years ago. He captivates you with the romantic natures of becoming one with the ocean: the moment of encountering the divine in the barrel of the wave. He talks about finding the perfect wave on a desolate island – Tavarua, Fiji. He and Bryan camp there for a week, avoiding the snakes that blanket the island, surfing the perfect wave day after day. At the time, perhaps 10 people in the world knew about that wave.



I first read this book having never surfed, yet I was spellbound. It is clear how much Finnegan is devoted to the pursuit.

Finnegan prioritizes surfing and his own ego above all else. He shows flashes of self-awareness, but throughout the book his narcissism is unparalleled. He leaves behind a string of girlfriends that he either abandons to travel – or worse, takes with him to live in squalor on remote, inhospitable islands, all in the pursuit of waves.

Was “surfing” even what I was doing? I chased waves instinctively, got appropriately stoked when it was good, got thoroughly immersed in working out the puzzle of a new spot. Still, peak moments were, by definition, few and far between. Most sessions were unremarkable. What was consistent was a certain serenity that followed a rigorous session. It was physical, this postsurf mood, but it had a distinct emotionality too. Sometimes it was mild elation. Often it was a pleasant melancholy. After particularly intense tubes or wipeouts, I felt a charged and wild inclination to weep, which could last for hours. It was like the gamut of powerful feelings that can follow heartfelt sex.

Later in the book, when he and Bryan recollect their travels, Bryan seems bothered by how they, as two relatively rich Westerners, took advantage of their hosts in the South Pacific. Bill isn’t nearly as troubled:

He [Bryan] once wrote that he had just realized that the hospitality we received back in 1978 from Sina Savaiinaea and her family in Samoa had cost them a lot of money, relative to their wealth, and that we had repaid them with trinkets rather than the cash that they desperately needed and were expecting but were too polite to mention. He was so horrified he couldn’t sleep. And I wasn’t at all sure he was wrong.

Many of us have a small voice inside calling to us to abandon any pretense of a normal life and live like a drifter. And isn’t life fleeting? Why not choose to live as a latter-day barbarian, surfing in tropical locales?

So this section of the book was alluringly romantic. It calls to us, reminiscent of the Choose Life monologue from Trainspotting, which argues there is no real difference between the hedonistic pursuit of pleasure through drugs and the rat race of chasing job promotions and the materialistic trappings of everyday life.

I get it! Bill isn’t hurting anyone. But don’t we have a greater responsibility to the world than this? Even Bill was full of self-doubt:

But I did wonder what I was doing with my life. We had been gone so long now that I felt unmoored from all possible explanations for this trip. It was certainly no longer a vacation. What was I vacationing from? I had wangled a one-year leave of absence from the railroad, which had run out while we were in Kirra. Officially resigning my job as a trainman, and my precious seniority date—June 8, 1974—had been unexpectedly difficult emotionally. I still believed I would never find another job so satisfying and well paid. But it was done. I panicked sometimes, convinced I was wasting my youth, aimlessly wandering on the dark side of the moon while old friends, classmates, my peers, were building lives, careers, becoming adults back in America. I had wanted to be useful, somehow, to work, to write, to teach, to accomplish great things—what had happened to that? Yes, I had felt compelled, almost required, to take a big surf trip. But did it really need to last this long?

As my partner put it: “This book was about his relationship with surfing. His wife, his daughter, friendships – they were only mentioned in relation to the ways that they interfered with his surfing. He’s obviously a smart guy – if he had spent half of his effort on something worthwhile rather than surfing, he could have cured cancer.”

After several years of travel, Finnegan eventually settles in apartheid South Africa and becomes a schoolteacher. Here, I think he first grows a conscience and realizes that the world is bigger than himself.

I had no right to judge how South Africans, black or white, dealt individually with their extraordinary situation, but working on the Cape Flats, seeing the workings of institutionalized injustice and state terror up relatively close, was deeply affecting me—was making me impatient with, among other things, myself. There was simply no escaping politics, and I found no common political ground with any of the surfers I met. So I chased waves alone.

Finnegan, ever the rebel, ignores orders to teach a curriculum that complies with the government regime. He does what he can to help his black students. While his efforts come from the right place, as an outsider they are noticeably ham-handed. One example: he begins a career-counseling project for his students, trying to get them permits to attend formerly all-white colleges. In doing so, he wades into a morass of politics, not knowing that applying for a permit was extremely controversial as it served to perpetuate the system of inequality.

In the end, I came to see my careers program as an enormous American folly, even in some cases quite destructive, where it encouraged false hopes or encouraged kids to defy boycotts that I knew nothing about.

Yet at least Finnegan is thinking of people other than himself. He beings to take his career as a writer much more seriously:

At the end of the school year, I found myself vowing to take no more day jobs. I would write for a living, period. I started writing essays, short features, for American magazines. I wrote nothing about South Africa—though I had a pile of overflowing notebooks. I yearned to go home—wherever exactly that might be. I clung to a line in one of Bryan’s letters. He had moved back to Missoula. There was a spot on the softball team for me, he wrote. A spot on the softball team.

Big Waves, Big Egos

From South Africa, Finnegan moves to San Francisco to pursue a career in journalism in earnest.

San Francisco is not particularly known for its surfing. In fact, most people don’t realize that people surf in the city. Most can’t. But if you’re willing to brave 40 degree water and 20 foot waves, you can shred some serious gnar in the shadow of the Golden Gate Bridge.

I once read an interview of a war reporter who said that the military is one of the only places where men can express love 1 for one another. That society has so stunted men emotionally that they need the trials of war to tell their friends that they care about them.

I think that you can extend this – at least for those of us who have not been on the battlefield – to sports. For what are sports if not men playacting war? In the case of surfing, you risk death by drowning every time you’re out there. In this chapter of the book, surfing is the vehicle in which male friendships and emotions are explored.

Surfing San Francisco

In the big waves of San Francisco, big personalities come out. In particular this chapter highlighted two larger-than-life characters.

  1. Doc (Mark Renneker), a brash doctor who broke every rule of surfing etiquette and was the most polarizing surfer in San Francisco, either loved or reviled by every other surfer in the city.
  2. Peewee (Bill Bergerson), a local carpenter who was extraordinarily reserved, down-to-earth, and best introduced by the following story:

    Once, on a crowded day at VFW’s during my first winter in San Francisco, a local surfer was behaving badly—stealing waves, jumping the queue, and threatening anyone who objected. Peewee warned him once, quietly. When the guy kept it up, then nearly decapitated another surfer with a clumsy pullout, Peewee invited him to leave the water. The miscreant snarled. Peewee knocked him off his board, turned his board over, and, with small, sharp blows with the heel of his hand, broke off each of his three fins. The guy paddled in. Years later, Ocean Beach regulars who hadn’t seen this incident were still asking those who had to tell it again.

Doc was famously committed to surfing big waves. While he lived with his long-term girlfriend, he refused to get married, because once you get married (and especially after you have kids), you become too risk-intolerant for massive swells.

“The rule about guys getting married: their readiness to ride big waves goes down one notch immediately,” he liked to say. “And it goes down another big notch with each kid. Most guys with three kids won’t go out in waves over four feet!”

Mark had a commitment to surfing that makes Finnegan look positively listless.

Recalling his L.A. youth, he told me, “Among my friends, there was a strong belief in the surfer’s path. Most people swerved from it sooner or later.” For his models for aging well, he looked to older surfers—he called them “elders.” Doc Ball, a lifelong surfer and retired dentist in Northern California, then in his eighties, was a favorite. “He’s still stoked,” Mark said. “He still skateboards!”

Peewee, on the other hand, struck me as preternaturally wise, at least if I were grading on curve for surfers.

“It’s such a great sport it corrupts people,” he said. “It’s like drug addiction. You just don’t want to do anything else. You don’t want to go to work. If you do, it’s always ‘You really missed it’ when you get off.” As a carpenter, Peewee said, he had some job flexibility, and he tried to take a month off each year to go surfing someplace else, like Hawaii or Indonesia. But there was no way that he could surf as avidly as he had surfed while growing up—not without risking dereliction…

He was equally closemouthed on the subject of big waves. He preferred them to small waves, he said, because they were uncrowded. “Crowds can get tense,” he said. “In big waves, it’s just you and the ocean.” Peewee was known around Ocean Beach for his iron nerves in big surf, but it took him a number of years, he said, to build up to facing very big waves. “Each new wipeout makes you realize, though, that you’re actually safer than you thought. It’s just water. It’s just holding your breath. The wave will pass.” Did he never panic? “Sure. But all you have to do, really, is relax. You’ll always come up.” In retrospect, he said, the times when he had thought he was drowning were not in fact such close calls.

How the World Goes On

After San Francisco, Bill moves to New York where he becomes a staff writer for The New Yorker. Still, he manages to surf nonstop. He makes annual pilgrimages to Madeira, in Portugal, where he encounters harrowing waves.

There was another one [wave]. It was bigger than the others. But the important thing about it was that it sucked all the water off the shelf. Boulders started surfacing in front of me, and then I was standing in a field of rocks in rushing, waist-deep water. I did not understand where I was—a field of rocks had risen out of the ocean, quite far from shore, at a break I thought I knew. In a lifetime of surfing, I had never seen anything like this. The wave mutated into a hideous, boiling, two-story wall of whitewater almost without breaking—it had run out of water to draw from. I had a moment in which to decide what to do before it hit me. I picked a fissure in the wall and threw myself up and into it. The vague hope was that if I wriggled in deep enough, the whitewater might swallow me rather than simply smash me to pieces on the rocks. Something like that occurred, apparently. My feet were sliced up from the leap, but I did not hit the bottom as I rag-dolled shoreward in the bowels of the wave. And when I next surfaced I was in deep water, in the channel east of Pequena, safe…

That night, back in Jardim, I lay in the dark on a lumpy cot thinking about quitting surfing. The southeast wind groaned in the eaves of the old house where I was staying. Various parts of me hurt. My left eye was weeping from too much sun and saltwater. One hand throbbed from a gash received trying to get ashore at Madonna. The other hand throbbed with urchin spines picked up in a collision with the reef at Shadowlands the week before. Both feet ached with infected cuts. My lower back felt like I had spent the month digging a ditch. I truly was too old for this. I was losing my quickness, my strength, my nerve. Why didn’t I just leave it to guys in their physical prime, like André? Even the guys my age who still tried to ride serious waves—guys in their forties, even fifties—managed to get in the water two hundred, three hundred days a year. Who was I kidding, trying to skate by on a small fraction of that? Why not walk away while I could? Would quitting really leave such a big psychic hole?

For the rest of the book, Finnegan makes the excuses of an addict. Well into middle age, he constantly takes the risks you’d expect from an 18-year-old. He has a wife and child, yet goes out in waves alone that all other surfers are content to watch from shore.

I found myself getting more reckless, even before my parents died. In Dubai, chasing a story about human trafficking, I stepped on the toes of Uzbek slavers and their local protectors and had to leave the emirate in a hurry. Reporting on organized crime in Mexico, I edged further into the lion’s den than I should have. This was the sort of work I had sworn off when Mollie was born. The same impulses were showing up in my surfing. I went to Oaxaca to ride Puerto Escondido, which is generally considered the heaviest beachbreak in the world. I snapped two boards and came home with a perforated eardrum. I wasn’t turning into a big-wave surfer—I would never have the nerves for that—but I was pushing into places where I did not belong. On the bigger days at Puerto, I was the oldest guy in the water by decades. What did I think I was doing? I liked the idea of growing old gracefully. The alternative was, after all, mortifying. But I rarely gave my age a conscious thought. I just couldn’t seem to pass up even a slim chance of getting a great wave. Was this some backward, death-scorning way to grieve? I didn’t think so. A few weeks after my sixtieth birthday, I pulled into two barrels, back-to-back, at Pua‘ena Point, on the North Shore of Oahu. They were as deep and long as any tube I had ridden since Kirra, more than thirty years before. Both waves let me out untouched. Being adjacent to that much beauty—more than adjacent; immersed in, pierced by it—was the point. The physical risks were footnotes.

He’s condemned by self-love. He’s entirely full of himself. But at least he is self-aware enough to recognize all of this.

Despite how hard I’ve been on Bill throughout this review, I absolutely loved this book. I read it for the first time in the summer of 2019, in a surf-themed bar on the Lower East Side. I re-read it in San Diego, where quotes from the book bounced around my head while I paddled out into waves. The writing in this book is beautiful – I hope that my liberal sampling of quotes does it justice.

While William Finnegan is not exactly a sympathetic character, that is in part because he has lived a life that induces envy, one that most of us could only dream of. He ends his memoir recounting a surf session in Tavarua, which has been turned into a luxury surf resort:

The waves kept pouring through, shining and mysterious, filling the air with an austere exaltation. Inia was on fire, as a surfer, as a preacher. Did I still doubt? “We will not fear, though the earth give way and the mountains fall into the heart of the sea, though its waters roar and foam.” I continued to doubt. But I was not afraid. I just didn’t want this to end.

That’s exactly how I felt reading this book.


  1. Philios, to be precise.