2025 Book List for the Startup Leader

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I read to make sense of the moment we’re in. Some years the themes show up early. This year, it took longer. The pace of AI made everything feel unsettled. The questions felt weighty and the answers not forthcoming. What is AI really? How much of this is hype and how much is a hinge moment? Does leadership still matter? Do we matter?

Those questions drove this year’s reading. They led me to Jensen Huang’s origin story, Jeff Bezos’s operating playbooks, and Jim Collins’s timeless clarity. 

This year, Melanie Mitchell was my personal teacher on AI, taking over from Fei-Fei Li. Mustafa Suleyman made some big-picture predictions, but none at the scale of Max Tegmark.

The year had me rereading Anthony Bourdain, because nothing speaks of operational pressure like a professional kitchen; it reveals more about leadership than any management slide. And I found comfort in the contradictions of Will Durant’s reflections.

Now in its fifth year, I don’t make these recommendations lightly. Long-form reading is a time commitment, especially when online life flashes something new every five seconds. Asking you to spend fifteen minutes a day with any of these books is a big ask, and one I make without reservation.

If you’re wrestling with the same questions I am, read on. It will be worth your time.

Sidebar: 48 Books, Two Simple Rules

The No-FOMO Rule
I don’t read books the year they come out. It keeps me honest, keeps my reading queue sane, and keeps this list focused on what lasts. When I break this rule, it’s deliberate.

The Respect-the-Audience Rule
These recommendations are for the time-crunched leader. Every book across these forty-eight picks has earned its place. 

All My Book Lists

BE 2.0 — Jim Collins and William Lazier

Reed Hastings said to read the first 86 pages of Beyond Entrepreneurship. BE 2.0 is in part a response to a new life the book got thanks to Reed’s recommendation. Ten pages in, you can see why. It’s blunt, broad, and bedrock in its advice. If entrepreneurial thinking is a cornerstone of leadership, this book is for any leader. 

BE 2.0 builds on the original text that he co-wrote with his mentor Bill Lazier, but also what Jim thinks now (circa 2020). He makes my list two years in a row because having read his books years after their release, his advice is nontransient. 

So much of what Jim and Bill say makes sense, not because it feeds into my confirmation bias but because of the hard things they ask leaders to do.

Working Backwards — Colin Bryar and Bill Carr

If BE 2.0 explains what great companies are made of, Working Backwards shows how they operate. Colin Bryar, Jeff Bezos’s Technical Advisor, and Bill Carr spent more than a decade on Amazon’s vaunted S-team. They helped build many of Amazon’s signature operational processes including the 6-page memo, the PRFAQ, and the cultural shift that allowed the company to get rid of PowerPoint.

The idea for the memo itself grew out of a discussion between Colin and Jeff about Edward Tufte’s essay on the problems with PowerPoint.

Bryar and Carr focus on mechanisms rather than mythology. They are honest about what worked, what didn’t, and why.

Amazon Unbound — Brad Stone

Where Working Backwards explains Amazon’s internal architecture, Amazon Unbound shows you what happens when that architecture is pushed to its limits. Stone follows Amazon’s transformation through the 2010s to date and the pressure test of COVID. It is a case study in ambition and scale, the history of Amazon under siege, and a reminder that even the most refined companies are still human systems.

The book is also a chronicle of Amazon’s scale and strategic freedom. Amazon could choose to become UPS if that’s what serving the customer requires. Twilio, by comparison, cannot become AT&T just to get rid of pass-through fees.

Artificial Intelligence — Melanie Mitchell

This book demands and rewards patience. A professor at the Santa Fe Institute, Melanie Mitchell takes a measured view of what AI is and is not. The early chapters read like a refresher course, but once she begins challenging the futurism that dominates the discourse, the book becomes essential.

The Amazon six-page memo has a FAQ section at the end of it. Douglas Hofstadter did the same in his 1979 book Godel, Escher, Bach. Melanie adopts that structure and answers many of the burning questions that every AI influencer seems to have answers to, but she does so with the rigor of a scientist. You could jump to that section if you want, but take the time to read the preceding chapters to fully understand the answers. If you’re trying to stay level-headed about AI, this is essential baseline reading. 

The Coming Wave — Mustafa Suleyman with Michael Bhaskar

If Melanie Mitchell explains how things are, Mustafa Suleyman explains where things could go. The DeepMind co-founder (and current CEO of Microsoft AI) takes a strategist’s view, attempting to answer the heavy questions about the future trajectory of this technology.

Am I allowed to be disappointed by a book and still recommend it? I think so. I wanted more DeepMind founding stories, and there are very few. There are also surprisingly few references to his Nobel Laureate co-founder, Demis Hassabis. (Melanie cites Demis liberally; Mustafa barely mentions him. One can read between the lines.)

But while you may want more startup war stories, the technology framing stands on its own. Mustafa gives you the vocabulary to discuss power, disruption, governance, and the consequences of progress that outpaces oversight. If Melanie is the scientist in the lab, Mustafa is the diplomat at the negotiating table.

The Thinking Machine — Stephen Witt

This book breaks my No FOMO rule. If Melanie Mitchell spoke about the fundamentals of AI and Mustafa Suleyman wrote about its future, The Thinking Machine is about the man and the company at the center of the “Cambrian explosion” of technology, apps, and startups that now call themselves “.ai”. Like those other AI reads, it’s the story of the complex stack that is AI—but this time told through the rise of NVIDIA and Jensen Huang. 

There are plenty of five-second clips of Jensen saying he doesn’t like to fire people and would rather “torture them to greatness.” That can create the illusion of utopian job security, but as the book shows (and as Stephen Witt experiences himself), that “torture” can mean a public, two-hour dress-down at an all-hands for screwing up. The point isn’t softness; it’s that Jensen believes the greatest risk in business is the death of risk-taking. If failure gets you fired, people stop making big bets—and NVIDIA never becomes the bedrock of today’s AI ecosystem.

Along the way, the book reveals Jensen as a textbook Level 5 leader: personally humble, fiercely professionally driven, ambitious for NVIDIA more than for himself, and disciplined about taking blame while giving credit. And yet, it’s equally clear there is no obvious public successor. He has built the world’s most valuable, decentralized startup, but there’s no visible number two. Maybe there can’t be. The combination of hardcore engineer, consummate CEO, and savvy statesman is too much to reasonably expect from anyone—anyone but Jensen.

Kitchen Confidential — Anthony Bourdain (reread) 

I recommend this book every year to my UCLA B-school capstone teams. Not because every cohort inevitably has a food startup trying to be the next Cava or Chipotle, but because hidden in this gem of a book are universal business truths. It keeps you honest about the work. Bourdain writes about craft, pressure, hierarchy, and the human cost of excellence with unmatched clarity.

In an age obsessed with efficiency, it reminds you that behind every great experience is a system held together by people giving their best under pressure.

Fallen Leaves — Will Durant

Imagine your 95-year-old grandpa wrote candidly about what he thought of life, war, love, government, and God. Now imagine he was also a world-famous philosopher and historian. Will Durant published his first book in 1917 when he was still in his early thirties. Later, with his wife and writing partner, Ariel, he went on to produce an eleven-volume, ten-thousand-page work, The Story of Civilization. Along the way, they won both the Pulitzer Prize and the Presidential Medal of Freedom.

That framing matters because Fallen Leaves is unapologetically candid. Some turns of phrase and judgments will make modern readers wince. It has the spiciness of a grandpa who has seen everything and is not compelled to soften his views. And yet, once you absorb who the author is and the life behind the words, it’s hard not to marvel at the precision of the language, the brilliance of thought, even when it feels dated.

The book is a short treatise on the ideas that mattered most to Will. He completed it as a manuscript, intending for Ariel to read and review it. That never happened. He died roughly a year later, within two weeks of his wife’s passing.

Fallen Leaves might have been lost altogether had it not been rediscovered decades later in his granddaughter’s attic. It is blunt, personal, and precise. In a time when many leaders feel pressure to prove relevance through output alone, Durant’s reflections feel grounding.

He writes about ambition, mortality, and meaning with the clarity of someone who has lived the full arc of a human life. This book reminds you that wisdom, like ambition, is a private quest.

Finally

These books shaped how I thought about this year. They helped me understand AI without losing perspective. They gave me better models for leadership and structure. And they reminded me that judgment, character, and humanity matter more than inference or compute.

If you’ve read any of them already, I’d love to hear what stayed with you. And if you think something else should make the 2026 list, let me know.

Happy Holidays!

TJ