Review: The Hard Thing About Hard Things — Ben Horowitz
7/10 Leadership Training · 7/10 Enjoyable
2014 HarperCollins
Overview
Before he became one of the most powerful VCs in Silicon Valley, Ben Horowitz was a tortured CEO trying to keep his startup afloat during the dot-com crash.
You might recognize his name from Andreessen Horowitz (a16z), which — despite sounding like a 19th-century law office — is a relatively new venture firm that has skyrocketed in prestige and influence. Its unique founder-focused culture is captured in the motto: “some experience required.”
Marc Andreessen earned that experience by building the first popular web browser and spinning it into a billion-dollar company: Netscape. Horowitz joined a few years later, rose quickly through the ranks, and after Netscape was sold, co-founded a cloud startup called LoudCloud with Andreessen. As CEO, Horowitz piloted LoudCloud through the chaos of the dot-com crash, eventually stabilizing and cruising for a few years before a billion-dollar buyout by HP.
His experience as CEO was harrowing, and the books Horowitz turned to for guidance — notably Built to Last by Jim Collins — offered little help. This book is his response to that brand of secondhand academic wisdom. It’s part trauma journal, part CEO bootcamp: an ode to the man in the arena, tightly focused on Horowitz’s personal struggle. At times, his “how-to” framing leaves you craving the story behind the bullet points — but even so, these pages clearly convey the weight of leadership.
This isn’t the book you read before dropping out of college to found the next Snapchat — it’s the one you should’ve read that might have kept you in school.
He Can Write
Amidst a sea of business-book blowhards, Horowitz stands out as a surprisingly good writer. Maybe it’s from years of blogging. Maybe it’s his obsession with rap music. Or maybe he just follows his own advice: “CEOs should tell it like it is.”
His voice is wry, clear, and — by tech founder standards — very cool. He opens chapters with lyrics from Nas or DMX, talks about his failures with a sardonic grin, then hammers home a dead-serious lesson.
Of course, we’re talking about a white, nerdy, likely-billionaire VC, so “cool” is relative. But grading on a curve? He pulls it off.
He isn’t afraid to get personal, either. Horowitz writes about crying on his first day of kindergarten, battling depression when his startup seemed doomed, and getting a wake-up call from his dad to fix his marriage. After a short biographical section filled with moments like these, the book jumps into lessons — starting with struggle, honesty, and layoffs, then moving on to demotions, delusions, and “Nobody Cares.”
It’s around here that we start to wonder if our careers would benefit from simply having more panic attacks.
Still, something’s missing. His personal story fades, and the chapters start to feel like disjointed essays.
Almost All Blog
Maybe the downside of being the man in the arena is that you’re too busy to write a book from scratch.
Uncharitably, this is a short but compelling autobiography sandwiched around a thick filling of reused blog posts. It feels a little rich to bill the book as the backstory behind the blog when it’s almost 90% blog. I’m sorry, Mr. Horowitz — I’m telling it like it is.
To be fair, these are great blog posts. We’re talking about the guy who wrote the ultimate PM post: “Good Product Manager / Bad Product Manager.” But by their nature, blog posts don’t add up to a cohesive argument. Some even contradict each other — one claims CEOs are partly born, partly made, while the next insists they’re as synthetic as Jolly Ranchers.
Each post is focused and structured, but taken together they form a kind of hopscotch through loosely related topics. They have firepower, but it’s buckshot, not a sniper bullet.
What’s more, these posts weren’t written for general readers. They’re aimed at a very specific audience: startup CEOs living through what Horowitz experienced.
For CEOs Only?
If you’re not a CEO — and specifically a CEO whose company has grown big enough to suffer from organizational headaches — then much of Horowitz’s advice takes some imagination to apply.
That’s not to say it isn’t valuable. It can make you a better manager, a wise advisor to founders, or simply a very savvy employee. Still, we should add “becoming the CEO” and “scaling to 20+ people” to the list of hard things not in this book.
The posts often read like Horowitz is talking to his past self, processing old wounds by sending instructions back in time. Witnessing that conversation is fascinating — but digesting these generic how-tos, clearly drawn from specific circumstances, can feel like watching a movie with the sound off. “Don’t poach employees from your friend’s company.” “Don’t split a role between two people.” “Concessions to political maneuvering are dangerous.” It’s obvious there are great stories behind each of these; we just don’t get to hear most of them.
Still, there’s a lot of wisdom here. One of the book’s biggest strengths is offering a better definition of the CEO role — something more useful than “the number-one salesperson.” To Horowitz, the CEO must tell the company story, churn out good decisions, give constant feedback, hire and direct great people, and set realistic objectives.
Other pearls follow: blame yourself when you lay people off. Don’t hire big-company execs until you truly need them. Invest more in training than you think you should. Hire people who care about team success, not personal glory. And communication will be your biggest challenge as you grow.
These are great lessons. But Horowitz wasn’t kidding when he said they were “hard.”
This Sounds Awful
Horowitz’s picture of a CEO is unabashedly miserable. Cold sweats, sleepless nights, boiling guts — these are all de rigueur. CEOs are expected to know what to do “in all matters all the time,” and anything that goes wrong is their fault. CEOs are lonely: unable to confide in employees for fear of causing panic, and unable to talk to outsiders who don’t understand. Psychological meltdowns are normal, just not discussed. One CEO friend calls it “the torture.”
If you work for a CEO who isn’t visibly destroying themselves for the company, Horowitz might even make you a little resentful.
Is this really the best model of leadership we have? Horowitz doesn’t describe a bad leader — he depicts an incredible one — but the people powering our economy and reinventing society shouldn’t be so miserable. No wonder they sometimes do crazy things.
Horowitz’s description begs us to search for a better way. Could more vulnerability and a supercharged support system work better? Or should we start training AI agents to be startup CEOs?
Horowitz doesn’t ask these questions, but he makes it hard not to.
Why Even Do It?
So, why would anyone actually want to be a startup CEO?
Given compensation often in the tens of millions, money is the easy answer. But Horowitz tells us to “take care of the people, the product, and the profits — in that order.” He says his primary reason for getting out of bed as CEO was to make his company a good place to work.
Could wanting your employees to be happy really be enough to make the torture worth it? In the same breath he mentions that his employees worked 12- to 16-hour days. Did he forget to include a chapter on how to get teams to happily work 16-hour days?
Spending every waking hour building cloud infrastructure software and “happiness” don’t seem like natural bedfellows. But paired with Horowitz’s emphasis on hiring brilliant people, it starts to conjure an image of elite engineers whose greatest joy is writing cutting-edge code.
Sending such engineers home to see their families might be the real gift. Still, in that rarified world, maybe making employees happy really could be a CEO’s raison d’être. It tracks, too, that many of Horowitz’s former team members later joined him at a16z.
It’s an uplifting thought. But we should probably add “how to hire a team of savants” to the list of hard things this book doesn’t explain.
Courage Is the Job
Though Horowitz’s message is scattered across blog posts, one theme connects the work: courage. Most of his stories and lessons are about pushing past fear to do the hard things.
From meeting his best friend, to meeting his wife, to bouncing back from a 35-cent stock price, courage was the catalyst.
At its core Horowitz’s wisdom is gritty, hands-on experience with the many and endlessly challenging forms courage can take. He says it best: “It’s the moments where you feel most like hiding or dying that you can make the biggest difference as CEO.”
If you can handle the heartburn, the sleeplessness, the torture, the reward is greatness. That’s all it takes — no special gene, no insider connection — just the will to keep going.
It’s ultimately an uplifting message, one that encourages us to rely on our uniqueness.
Conclusion
It would be nice if Horowitz told us the full stories behind his lessons, instead of just the takeaways. That’s what he promised in the introduction — and when he delivers, it’s excellent. His blunt, sardonic personality shines through, and his narrative is a joy to read.
We don’t know if he was too busy, too private, or too kind to dish dirt on former colleagues, but more often than not, he holds out on us. The result is less a cohesive book than a well-curated blog anthology. Thankfully, the posts are still well worth reading, or rereading. Together, they suggest a style of leadership that is both highly admirable and punishingly difficult.
Still, sometimes just admitting that things are hard gives us the clarity to do something, instead of looking for an escape hatch or a secret weapon. Horowitz reminds us there are no silver bullets — only lead bullets: face things head-on, tell it like it is, and, in his words, “embrace the struggle.”
Quinn Mitchell is a product manager in Brooklyn, NY writing about business strategy, product theory, and technology. More at LinkedIn.