2024 Book List For the Startup Leader

Table of Contents

A sci-fi thriller, a memoir doubling as a history of AI, two how-tos to build gen AI apps, a leadership memoir, two business manuals that double as self-help books, and a repeat entrant. This year’s list is as wide as it is deep. It is about jumping feetfirst into the details of AI, sci-fi (is there a difference?), the brains of babies, scaling a business, and building one that lasts. There are memoirs by a Black woman and an Asian American immigrant woman: one who helped give us BET, and the other who is considered the godmother of AI. We have Jim Collins show up twice (thanks to my rules), and a re-read of a reprint. I hope they pique your interest and you enjoy reading them as much as I did.

Sidebar: All My Book Lists

Rules for Book Selection

If this is your first time reading my recommendations or if you just need a refresher, I have two simple rules—one for me and one for you.

The No-FOMO Rule: I don’t read a book the year it comes out. This prevents me from using the Amazon 1-click button every time a new book is published. Rare exceptions are when the work, the topic, or the times make the book required reading.
The Respect-the-Audience Rule: This public list is for the time-crunched startup leader. They have a lot on their plate, and asking them to read something long form is a big ask.

The Scientist in the Crib: Minds, Brains, and How Children Learn—Alison Gopnik, Andrew N. Meltzoff, Patricia K. Kuhl

I first read this book in 2020 to better understand my newborn. I re-read it in 2024 to better understand AI. If algorithms constantly need data to fine-tune their models, babies do the same—always building new neural connections and pruning old ones. In fact, by age two, a child’s brain is the largest it will ever be as a percentage of body mass. To understand how neural networks work, it’s essential to first understand how humans learn. They say our days begin and end as stories, and this book reveals how our brains create those stories.

Generative AI on AWS—Chris Fregly, Antje Barth & Shelbee Eigenbrode

If you scroll through social media, it seems like everyone knows exactly what to do with generative AI. Everyone. Yet, as accessible as LLMs have made building new applications, it’s critical to pause and understand the nuances of creating such solutions. While this is a technical book, I recommend it to everyone. Not because it will make you an expert developer overnight (it won’t) but because it reveals the massive number of detailed decisions required to build complex, scalable AI systems.

Fair warning: This book is a beast to finish. It took me two and a half months, and I have software engineer training. Still, it’s worth it. Tap into your founder mode and read it even if you’re not technical. Remember, Mark Cuban was a management grad, but that didn’t stop him from pulling all-nighters reading networking tech manuals to become the best salesman in his company.

Project Hail Mary—Andy Weir

Everybody needs a break, and for those obsessed with solving problems, this tale of space travel offers a deep dive into problem solving through the scientific method. Andy Weir—who wrote The Martian—takes you on a journey that keeps you engrossed like a Netflix Drive to Survive episode. I re-read pages just to be sure that I had read what I had just read.

A reader should give a writer the benefit of a long start; a writer should not expect one. Andy wastes no time pulling you into his world and keeps you jumping from one scene to the next. But I don’t want to say more for fear of spoiling the suspense. Take it from a non-sci-fi reader: Dive into this book this holiday season.

Walk Through Fire—Sheila Johnson

While Valley techies joke about going “founder mode on a burrito,” Sheila Johnson’s version of founder mode was about being in service to a larger cause at great personal cost. She was the supportive, subservient wife, mother, and co-founder of BET. Her memoir tells the story of her role in the creation of BET, including how she wasn’t allowed to attend its IPO listing. It is also the story of a failed marriage, a lost pregnancy, and a philandering spouse. For most of her adult life, she fit the archetype of the long-suffering wife.

Yet it is also a story of reinvention and redemption. As the founder of Salamander Resorts, she overcame racism and sexism—despite her billionaire status—to build one of the most exclusive five-star resorts in the world. Walk Through Fire is a reminder of the superhuman perseverance that underpins all great accomplishments.

The Worlds I See—Fei-Fei Li

If I had to pick a favorite, Fei-Fei Li’s part memoir, part history of generative AI would be it. Once you read it, you’ll not only see how far the field has come but also appreciate her incredible personal journey. As I mentioned when I wrote about it this summer, I found many parallels between her story and mine. No, I’m not saying I have much in common with a Princeton-educated, CalTech PhD, ACM fellow, and Stanford professor. But I can relate to the journey of a teenager arriving in the US on the coattails of immigrant parents who uprooted themselves to give their only child the best chance at success.

The inventor of ImageNet, you also see why Fei-Fei is considered the godmother of AI. She and her lab furthered the careers of many current leaders including Timnit Gebru and Andrej Karpathy. This book is about entrepreneurship at the edge of the wave and the emotional and intellectual fortitude it takes when you’re the only one working in the lab for years on end. Today, the biggest constraints to progress are access to data and compute power. When Fei-Fei and her team were solving the challenges of image recognition, they had to scrounge for funding and navigate ethical dilemmas, including using Amazon Turk workers to train their models. Now, working on transforming photos into 3D worlds, Fei-Fei closes the book with her concerns about the breakneck pace of generative AI deployments and the ethical challenges developers still face.

OpenAI API—Henry Habib

At first glance, it may be hard to see the difference between ChatGPT and the OpenAI API. If you’re a prompt engineer or building an app, I think you should at least consider getting an API key and experimenting with the company’s API. It helps you appreciate the pre- and post-processing that a product like ChatGPT handles. It could also give you insights into what you need to do to make your job or product more effective.

Good to Great—Jim Collins / Built to Last—Jim Collins and Jerry Porras (needs quote)

“YOU haven’t read Good to Great?” my wife asked incredulously. It wasn’t an endorsement of the book’s fabled status in corporate America (it was required reading for the management track at one of her previous jobs) but a reflection of her surprise that, knowing me, I hadn’t read it yet. This is where my FOMO rule both put me behind and, in a profound way, helped me.

Unintentionally, I read Good to Great before Built to Last, the order Jim Collins now recommends. A lot has been said about the companies he praises for their Good-to-Great or Built-to-Last virtues that are no longer either. However, the real lesson is how fleeting success can be. If you take your eye off putting the right people in the right roles for the right mission, it can disappear quickly.

Jim is a great writer, following in the tradition of his hero, Peter Drucker. Like The Effective Executive, these two books have stood the test of time as leadership manuals, not just for business but for life.

Poor Charlie’s Almanack—Charlie Munger

I first read this book over fifteen years ago and recently revisited it through the Stripe Press re-release. What sets Charlie apart is his ability not just to speak simply but to distill complex issues into clear, actionable challenges. For that reason, this book deserves a spot on every leader’s bookshelf. Each time you read it, you’ll discover something new.

The Billionaire Who Wasn’t—Conor O’Clery

Chuck Feeney made his billions as a founder of Duty Free Shopping (DFS). He intentionally gave it all away during his lifetime, dying as he intended—in a rented apartment in San Francisco, with “his last check bouncing.” That last part is likely just for effect. Long before The Giving Pledge, there was Chuck Feeney, quietly donating hundreds of millions to causes under strict confidentiality, with no need for buildings, endowments, or awards bearing his name. This book tells the story of how he built his fortune and how he gave it all away.

The narrative is raw in its exposition of his humanity and the flaws of the institutions he built. You see the challenges he faced when trying to institutionalize his wealth, only to encounter the institutional imperative to perpetuate itself. This led to a long, ugly fight to maintain control over how his money was spent and to ensure it went toward the causes he believed in.

If there’s a leadership lesson here, it’s that Feeney was entrepreneurial to his core. He found a deep, personal connection to solving problems—first with international commerce and the spend-happy global tourist. He solved that problem, got paid well for it, and when the challenge lost its luster, he sought new problems his money could solve.

Situational Awareness—Leopold Aschenbrenner

OpenAI SuperAlignment guy Leopold Aschenbrenner wrote a series of essays on generative AI and released them as a 135-page PDF. It’s dense. What Situational Awareness gives you, though, is a framework to cut through the generative AI hype. While the framework is expansive, some critics on X have called it flawed or incomplete. But I think those criticisms miss the point.

The goal of a thought framework is to provide a starting point for discussion, exploration, and judgment. It isn’t to predict the future with precision but to help readers build antifragile mental models. In that context, this work delivers. Every leader building generative AI solutions should read Leopold’s essays.

The Friction Project—Robert L. Sutton, Huggy Rao

This is a repeat because I first read an early version last year and re-read it this year. More people need to understand the critical role friction plays in our social lives—not just in physics. Bob and Huggy have crafted a timeless manual on becoming a friction-fixer. For more, check out last year’s review or my interview this year with Huggy Rao.

Finally

These are the books I’d recommend if we were catching up over coffee or a drink—personal picks based on wherever the conversation led. Some great reads, like Adam Grant’s Think Again, didn’t quite make the list. Not because they’re not worth reading—they absolutely are—but you’ve probably already seen them on Instagram. You’re here for something fresh, and I hope these selections give you just that.