What to Read Next (No. 181): surprising startup protagonists

Happy Friday everyone! I hope your holiday weekend is relaxing and full of good reading. My family and I are on vacation in the Rocky Mountains—I brought with me Underland (which I’ve heard amazing things about) and The Count of Monte Cristo (which I’ve somehow never read, but everyone says I need to).

In this newsletter, I’m featuring a couple books that are still well within my current tech obsession, but with a fictional bent. Even more specifically, these two novels feature protagonists you don’t often find in startups.

Let’s jump right to it, and let me know what you’re reading this weekend!

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A Few Bookish Questions With Josh Ireland

I’m knee-deep into William Manchester’s big trilogy on Churchill, so I was thrilled be to able to ask Josh Ireland some questions about Churchillian books, among other things. Ireland’s Churchill & Son was recently published and provides a superb and unique portrait on Winston as son and father himself. The questions below are a fun window into Josh’s reading life and the books that have influenced him over the years.

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We Are Watching Eliza Bright by A. E. Osworth

How great is that cover?!

Published: 2021 | Pages: 402

Eliza Bright is a coder. She taught herself on YouTube and has a big-time dream of creating the next big game—the one that everyone is playing and that nobody can put down. Fancy Dog Games is the on the verge of a big release, but there’s a couple developers who aren’t happy about her involvement. Lewis and Jean-Paul insert a bit of a “prank” into her code—they consider it hazing; Eliza considers it harassment.

Things escalate. Quickly.

Eliza’s personal information—passwords, phone number, address—ends up online in the hacking community. Reddit. 4Chan. You recognize the names of the internet’s black holes. She’s been doxxed.

As can happen in our modern world, the ramifications of the stuff that happens in the digital ether translate into real harm for Eliza, for flabbergasted Fancy Dog Games CEO Preston Walker, for Eliza’s friend and coworkers, and even for the nameless internet mob whose rage simmers through on nearly every page.

The voice and narration of this novel are as unique as I’ve encountered. The unreliable narrator is, mostly, the collective angry male mob of the gaming world. Hence the “we” in the title. It’s utterly fascinating. There are times where the details of what has actually happened in the plot vs. what that collective mob makes up aren’t entirely clear, which makes reading it sort of a fun puzzle—the mob/narrator infers, for instance, a sexual relationship between Preston and Eliza; it’s obviously the only way she’d get a coding job, after all.

There are a few somewhat confusing sections that have a different narrator, but in these short chapters the author relies a bit much on Overzealous Capitalization, which is a Bit Distracting. It’s just about the only thing that takes this novel down from a 4.5 to a 4.

The real strength is how realistically Osworth portrays the rage of the internet mob and how quickly that rage gets fueled into an unquenchable, revenge-driven inferno. We’ve seen the stories in real life; in fiction, it’s even more powerful and visceral.

Read this book if: you want a thrilling, fast-paced read that paints a searing portrait of what it’s like to be a woman in tech and what it’s like to be a woman on the internet who’s become a target. It’s a little weird at times, and a little intense at times, but very satisfying at the end.

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Black Buck by Mateo Askaripour

Published: 2021 | Pages: 400

Darren is a barista in NYC. And he’s good at it. One day, on a normal-but-then-life-changing morning, Darren convinces a startup CEO to buy something other than his usual drink. Rhett is intrigued by Darren’s raw but incredibly sharp sales skills and recruits him to be Sumwun’s newest rep.

Askaripour’s sharp critiques about the white-dominated sales and tech world are both eye-opening and often funny (in a cringey way, to be sure). Darren, christened “Buck” on his first day, is told he looks like so-and-so Black celebrity on a daily basis. In mock phone calls, his white colleagues play act with stereotypical Black voices. He’s told not be so “aggressive” and Rhett is hoping that Buck can be the token symbol of Sumwun’s diversity for the media.

Frankly, it doesn’t even matter what Sumwun is (a therapy app, but “therapists” don’t need to be licensed; it gets messy). This is a culture that could be found—is found, really—in any variety of buildings in Silicon Valley, New York, Chicago, you name it.

Along the way, Askaripour—who comes from a real-life sales/startup background—throws in actual sales advice that’s addressed directly to the reader. It’s a really fun and playful format that gives the book the tone of one of those classic sales manual. There’s also some skewering of big-time entrepreneurs (Gary Vee, Jeffrey Gitomer, and more), which is quite funny if you’re familiar with those names.

Anyways, Buck eventually succeeds beyond his wildest dreams and turns his attention towards training the next generation of Black salespeople.

This is a book that’ll make you think not only about the Black experience in the business world, but will also genuinely inspire you at times. (Even with the surprising and slightly head-scratching thriller-like twists and turns near the end.)

Read this book if: you want an inside look at what startup culture is like, especially the sales department, from a new and exciting Black voice. Personally, I can’t wait to read what Askaripour comes up with next.

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-Jeremy