Officially announcing On The Edge, my new book

Here's what it's about, and why you should consider buying it.

Feb 08, 2024

I’m incredibly excited to announce that the book I’ve been working on for the past three years, On The Edge, is officially on sale and will be published by Penguin Press on August 13. By the publishing industry’s standards, this is a lightning-fast turnaround. We think the book has a lot of news value and we’re trying to get it in your hands as fast as we can, while also giving it a rigorous copy-edit and fact-check and dodging some unfavorable dates this summer around the Olympics and the political conventions.

You can find the landing page for On The Edge here, with links to preorder from your favorite retailers. Some shop talk: preorders help a book reach bestseller lists — the inside-baseball reason is that they count toward the first week of its sales figures — which can in turn create a lot of forward momentum. If the book sounds like something you’d like — and if you’re a regular reader of this newsletter, I think you’ll like it a lot — I’d be deeply appreciative if you considered a preorder.

On The Edge is a big, weird, complicated book. The through-line is gambling and risk, but it interprets that mandate liberally. Over the past three years, I spoke with about 200 people for the project — some of the most interesting people I’ve ever met — and read roughly 100 books. I’ve really enjoyed the whole process, even the writing process. These are subjects that I was conversant in to begin with, a more natural fit than the elections beat. (I was a professional poker player in the mid-2000s before I ever built an election forecast; in fact, it was Congress’s attempt to ban online poker that sparked my interest in politics.) But there are cool things that happen when you devote this much bandwidth to a discrete project and connect different people and ideas. The book is sort of a hybrid: there’s a lot of proprietary reporting, but also deep-dive “explainers” into everything from game theory to how ChatGPT works. And there’s a participatory element: I found myself with a seat at the table for some epic poker hands, spent a year learning the ropes of becoming a serious sports bettor, and made two dozen reporting trips.

On The Edge does not yet have an official subtitle. The working version, “How successful gamblers and risk-takers think”, does reflect one main aim of the project. It’s about how practitioners think, with first-hand accounts from people who undertake risk for a living, rather than approaching the subject at arm’s-length. But the book turned out to be a little bit … darker than I’d expected going in, so we’re workshopping some new subtitles to reflect that. The universe of the book “blew up” as I was roughly in the middle of the project, particularly in late 2022 surrounding the “two Sams” that feature prominently in second half of the narrative: Sam Bankman-Fried, the former FTX CEO and now convicted felon, and Sam Altman, the CEO of OpenAI, which released GPT-3.5 — one of the most rapidly-adopted technologies of all-time — just two weeks before SBF was led off in handcuffs. I very much do not mean to imply that I consider SBF and Altman to be equivalent — the book expressly rejects the comparison. I’m just saying there was a lot happening, and I had a front-row seat for much of it.

I’m reluctant to reveal too much about the book’s thesis — but I can give you a map of the territory it covers. After a prologue and introduction, it contains eleven chapters between three parts.

Part I: Gambling

Chapter 1, Optimization, is about the evolution of poker, beginning with the late and legendary Texas roadhouse gambler Doyle Brunson, who I spoke with before his death, and carrying forward to the modern poker universe of game-theory-optimal (GTO) solvers, computer programs that literally calculate the Nash equilibrium for poker. Poker is increasingly a battle between man and machine, and the chapter is informed by interviews with many of the world’s best players. Both poker and game theory serve as lodestars throughout the book.
Chapter 2, Perception, is about the human side of poker: tells, cheating, the maddening variance of the game, and the broader question of human performance under pressure when we face high-stakes decisions. You’ll meet more world-class poker players here, from Maria Ho to Phil Hellmuth, to gain insights into topics such as how to spot when an opponent is bluffing and what it’s like to play a poker hand for hundreds of thousands of dollars. There’s also extensive reporting on the Robbi Jade Lew-Garrett Adelstein alleged cheating scandal, which blew up the poker world.
Chapter 3, Consumption, is about the commercial gambling industry. Americans are gambling at record rates, and Las Vegas grows both more spectacular and more debaucherous every year. Meanwhile, the United States is becoming increasingly divided between risk-loving people and risk-averse ones, with less middle ground in between, and with some alarming consequences such as stagnant American life expectancy. It covers the history of Vegas and gambling moguls from Steve Wynn to Donald Trump, how casinos use algorithms to manipulate the odds — as well as people who tried to beat the house. I’ll give you the real story of the MIT blackjack team, for instance, which isn’t very much like the admittedly fun movie version.
Chapter 4, Competition, is about sportsbetting, including the inside story of how brands like DraftKings and FanDuel came to be such a ubiquitous presence in the sports and media landscape. It covers the cat-and-mouse game between the world’s sharpest bettors and the sportsbooks. It also details my hands-on experience, including how I got limited by a half-dozen sites after less than a year into my sports-betting experiment despite turning only a modest profit.

[Intermission]

Chapter 4.5, Inspiration, more explicitly enumerates the personality traits of risk-takers and what makes the difference between successful ones and failures. This chapter serves as an “intermission” of sorts between Parts I and II, breaking slightly from the main narrative to explore risk-taking outside of the otherwise largely quantitative terrain of the book. I spoke with astronauts, explorers, former professional athletes and even Nobel Prize-winning inventors and they have some incredible stories to tell.

Part II: Risk

Chapter 5, Acceleration, is about venture capital and Silicon Valley, beginning with the miraculously lucky outcome of a car crash involving Elon Musk and Peter Thiel. It’s informed by exceptionally candid interviews with many leading VCs and founders, as well as some of their harshest critics. It explores Silicon Valley’s Techno-Optimism, why founders like Musk remain so highly-regarded there, and the contours of the clash between Silicon Valley elites and a rival group of elites in politics, academia and media. I think Silver Bulletin readers will particularly like this chapter; On The Edge is not a “politics book”, but it has lots of politics in it, and it’s influenced my thought process on how political coalitions are evolving in the US.
Chapter 6, Illusion, immerses us in the crypto boom and Meme Stock Bubble of 2021-22, including wild yacht parties in Miami and trips to the Bahamas to meet with SBF. The chapter is not anti-crypto, but it takes its subject seriously, describing how the idealistic aims of Bitcoin and Ethereum were hijacked by scammers and schemers at a vulnerable moment for the world in the shadow of the COVID-19 pandemic. It features conversations with people from all corners of the landscape — who were sometimes more honest with me than they probably ought to have been. It’s a fun chapter, such as in exploring the game theory of memestocks and shitcoins.
Chapter 7, Quantification, is about the effective altruism (EA) and adjacent rationalism movements. These are incredibly influential movements with ties to some of the most powerful people in the world — and ties to nearly everything in the book, from SBF to AI to venture capital and even poker. But the book argues that EA and rationalism aren’t actually all that much alike. Although they share a tendency to “quantify the unquantifiable” and common interests in subjects like prediction markets and existential risk, they also have a lot of clashing personalities and ideas. This is one chapter where I’d rather not tip my hand too much. I have a lot to say about EA, based on interviews with both the leaders of the movement and many external critics.
Chapter 8, Miscalculation, returns to SBF and explores what happened in detail at FTX and how he was enabled by many people in his broader orbit. I spoke with Bankman-Fried both before, during and after the bankruptcy. I know there are some other very good books on SBF, but I have the advantage of fortuitous timing — since his criminal trial happened right as I was writing the chapter, I contrast what he told me against court transcripts as well as conversations with people who were close to him. Although SBF is an outlier in some ways, his “type” — i.e. the overconfident Boy Genius quant with an insatiable appetite for risk — is a familiar typology in the universe of the book and I think that gives the reporting some additional texture.

Part III: The End

Chapter ∞, Termination, is a deep look into the question of existential risk surrounding AI and nuclear weapons. Here, I won’t be so coy: I think AI is a potentially transformative technology but also a potentially dangerous one and that we are plausibly at a pivot point in world history analogous to the Manhattan Project and the Industrial Revolution. I spoke with accelerationists and doomers and everyone in between, including Altman — as well as people who are familiar with the technical inner workings of ChatGPT and other large language models. After many interviews with experts and sleepless nights pondering these questions, I think I have some worthwhile insights — the chapter is not overly proscriptive, but it takes some novel approaches to help you interrogate the debate.
Finally, Foundation, a short concluding chapter, reframes these questions in the broader context of the history of technological and economic progress — a context that is often ignored despite its profound implications for our future. The chapter articulates some foundational principles that I hope will be helpful in navigating the pivotal moment that the world finds itself in and preserving humanity’s ability to make good choices for itself.

So … yeah. I recognize that the relationships between these subjects might not seem obvious. But as you’ll see in the book, they have deep connective tissue: the same personality types and the same reference points kept coming up over and over, more so than I would ever have imagined when I embarked on the project. On The Edge is a big, weird, complicated book — but also a fun, informative, provocative, and sometimes deeply personal one. I think you’ll really like On The Edge, and I hope you’ll consider buying it.