If You Had a Conversation With Someone Who Built a Trillion-Dollar Empire
What It Takes by Stephen A. Schwarzman, co-founder of Blackstone (Essential Reads 14)
What would it feel like to sit across from Stephen Schwarzman, the man who grew Blackstone from a $400,000 startup into a $500 billion powerhouse?
Not in a CNBC interview, not on a stage, but at a table — where the conversation turns less to market cycles and more to how you endure, how you negotiate with yourself, how you stretch ambition across decades without breaking.
Reading What It Takes isn’t like reading a business book. It’s like sitting in on that conversation, hearing someone tell you what they got wrong, what nearly broke them, and how they came to understand that success isn’t a clean line of smart moves but a pattern of tangled bets, small human insights, and sharp course corrections.
Here’s what I took away from sitting inside that mind for a few hundred pages.
Failures Are Gifts — If You Institutionalize the Learning
Schwarzman doesn’t hide his mistakes. He admits when emotions, loyalty, or sheer stubbornness clouded his judgment.
He talks about a deal that went wrong because he wanted to reward a partner whose ideas had been repeatedly shot down. The solution wasn’t to become colder or more detached; it was to build systems that forced rigor, skepticism, and structured analysis into every decision.
“Failures can be enormous gifts,” he writes, “catalysts that change the course of any organization and make it successful in the future.”
The deeper insight here is that success doesn’t come from having fewer failures. It comes from using those failures to build an institutional memory so the lessons don’t just live in your head but shape how the entire organization moves forward.
“Ask for More Than You Think” — The Ambition Muscle
There’s a funny moment when Schwarzman and his partner are on the phone with a Japanese investor discussing a potential $100 million fund commitment.
They hesitate, whispering back and forth: “Should we ask for $50?” “No, $100.”
The Japanese investor casually agrees — and Schwarzman later laughs, realizing they probably could have asked for $150.
“One of my unique qualities,” his partner says later, “is that my goals are so demanding and dynamic that sometimes it is even hard for me to accept yes for an answer.”
This anecdote isn’t just about money. It’s about the muscle of ambition — the instinct to stretch your ask, to believe the world will meet you at the level you set, and to get comfortable asking for more than feels safe.
Pattern Recognition Across Cycles
Schwarzman outlines how to recognize market tops: overconfidence, cheap debt, inflated forecasts.
But perhaps more interesting is his advice on timing market bottoms:
“It’s better to give up the first 10 to 15 percent of a market recovery to ensure that you are buying at the right time.”
Most investors jump too early, desperate to catch the bottom. Schwarzman’s discipline is to wait until momentum is real, even if it means leaving some returns on the table.
Strip Negotiations Down to the Essentials
In one vivid example, Schwarzman recalls working on a Tropicana deal. There were endless papers, stakeholders, deadlines, cross-pressures. But he realized that none of it mattered if you couldn’t focus the conversation on the few things that truly shaped the deal.
“Deals ultimately come down to a few key points that matter most to each side. If you can clear everything else away and focus on these points, you will be an effective negotiator.”
It’s a reminder that success, in negotiations or in life, often comes not from mastering every detail, but from knowing what matters most.
The Long Game Is Compounding Relationships
One of the most important segments perhaps is where Schwarzman reflects that the true power of his journey hasn’t just been financial scale, but the network effects of decades spent helping, listening, and building.
Schwarzman describes how, over time, the biggest challenges and best ideas find him — not because of luck, but because of the reputation he’s built as someone who knows how to untangle hard problems and get things done.
A lifetime of relationships, compounded carefully and with integrity, becomes a magnet for opportunity.
Solve Someone Else’s Problem to Solve Your Own
One fascinating theme in Schwarzman’s approach is that when you’re stuck, the best move is often to look outward.
In one example, during a tricky phase at Blackstone, a Japanese partner approached with a request that seemed tangential. Schwarzman realized that by helping solve their problem, he could unlock resources and momentum to address his own.
This is a profound shift in mindset: rather than zeroing in on your own roadblocks, ask: Whose problem can I help solve right now?
That ripple effect often circles back in ways you can’t predict.
The Mind Always Moves the Goalpost
One of the quietest but most powerful observations in the book is how ambition works.
Schwarzman points out, almost offhandedly, that “what was once your dream eventually becomes your inconvenience.”
It’s a line that lands softly, but if you sit with it, it reshapes how you look at achievement. We dream of the big win, the promotion, the deal, the opportunity. We fight for it, sometimes for years. And then, almost without noticing, we’re complaining about it: the workload, the responsibility, the grind.
Schwarzman doesn’t mock ambition. He honors it. But he’s clear-eyed about the nature of the mind: the goalpost moves. What thrilled you yesterday burdens you today. That’s not a sign you’ve failed; it’s a sign you’re wired to stretch, again & again.
Tougher the Problem, Fewer the Competitors
One of the most practical but profound lessons in the book is about where you position yourself in the landscape of challenges.
“If something’s easy,” Schwarzman writes, “there will always be plenty of people willing to help solve it. But find a real mess, and there is no one around. If you can clean it up, you will find yourself in rare company.”
He’s not romanticizing suffering. He’s pointing to a sharp insight about value creation: the hardest problems — the ones everyone avoids — are the places where differentiation and rare value creation happens.
Listening Is More Valuable Than Selling
Early in his banking career, Schwarzman discovered something that runs against most “alpha” business stereotypes: the most powerful people in the room don’t talk the most.
“I didn’t just try selling whatever it was I had to sell. I listened. I waited to hear what people wanted, what was on their mind, then set about making it happen.”
In negotiations, in deal rooms, in strategy sessions — he understood that people care most about their own problems. If you tune yourself to listen closely, not just to their words but to their anxieties, their hesitations, their hopes, you gain access to the most valuable currency in business: trust.
Hire 10s, Not Nines
At Blackstone, Schwarzman wasn’t content to hire strong performers. He wanted 10s out of 10 — people who didn’t just execute brilliantly, but who thought for themselves, saw new opportunities, and moved the business forward without being told.
“Nines are great at executing and developing good strategies,” he writes. “But people who are 10s sense problems, design solutions, and take the business in new directions without being told to do so. Tens always make it rain.”
This wasn’t just about recruitment. It was about building a culture where entrepreneurial people had room to invent, to push, to disrupt from within.
Selling Your Vision Is a Repetitive Art
One of Schwarzman’s sharpest, most applicable lessons is about persistence in communication.
“As a salesman, I’d learned you can’t just pitch once and be done. Just because you believe in something doesn’t guarantee anyone else will. You’ve got to sell your vision over and over again. Most people don’t like change, and you have to overwhelm them with your argument, and some charm.”
The Power of Showing Up in Person
In multiple anecdotes, Schwarzman emphasizes that the most consequential moves often happen not over email, not through intermediaries, but face-to-face.
There’s something about physical presence — the nuance, the unspoken dynamics, the human connection — that can’t be replaced.
This comes through in his relentless travel during fundraises, his instinct to get on a plane when negotiations hit a snag, his habit of sitting with people rather than sending messages.
In an era obsessed with efficiency, Schwarzman reminds us that some forms of influence still require physical proximity.
Ending…
By the time I reached the end of What It Takes, I didn’t feel like I’d just read another business book.
I felt like I’d been sitting across from someone who’s been through decades of battles, wins, near-misses, and reinventions — someone who knows that success is never permanent, and that the real game is how far you’re willing to keep stretching.
What stayed with me wasn’t the empire Schwarzman built, but the way he thinks: the habit of asking bigger questions, of listening harder, of never confusing arrival with the end.
This isn’t a book of neat lessons. It’s a reminder that the work, the ambition, the stretch — that’s where the meaning is. And for people wired like that, the game is never really over.