Brad Jacobs built 8 billion-dollar companies across oil, waste, equipment rental, and logistics—completing 500 acquisitions and raising $30 billion along the way. He built the world's largest equipment rental company in 13 months and turned a short-seller attack into a $4 billion profit. Learn his counterintuitive playbook in this How to Make a Few Billion Dollars book summary.
- Book: How to Make a Few Billion Dollars
- Author: Brad Jacobs
- Pages: 224
- Rating: 4.7 out of 5 Stars
- Recommended for: Serial entrepreneurs, M&A professionals, CEOs scaling companies, and anyone who wants to think differently about building wealth
The 30-Second Summary
Brad Jacobs built seven billion-dollar companies across completely unrelated industries—oil trading, waste management, equipment rental, logistics—completing 500 acquisitions and raising $30 billion over 44 years. What makes this unprecedented: he developed a repeatable playbook that works in any industry. His counterintuitive approach starts with meditation and "rearranging your brain" to see problems as assets, includes buying the software that powers your competitors to gain omnipresent market data, and requires overpaying for people so talented they'd cause panic if they quit. Most remarkably, he's done this while making "every possible mistake in business"—proving that the ability to transform failure into billions matters more than avoiding failure altogether.
In a nutshell: Business success isn't about being smarter or working harder—it's about thinking so differently that you find $4 billion opportunities where others see disasters.
About the Author
Brad Jacobs started his first company at 23 with a few thousand dollars and no experience, building it to $4.7 billion in annual volume within four years. Over 44 years as a CEO, he's created companies spanning oil trading, waste management, equipment rental, and logistics—including United Rentals (now $38 billion market cap) and XPO Logistics (the seventh-best performing Fortune 500 stock of its decade). He currently chairs three public companies and, at 68, shows no signs of slowing down.
The 3 Big Ideas
1. Rearrange Your Brain or Remain Mediocre
Most people think success comes from working harder within conventional frameworks. Jacobs argues you must literally rewire how you think. After becoming depressed when he couldn't find his next big thing in 2007, he spent months reading psychology books and meditating. His breakthrough: successful people don't avoid negative thoughts—they reframe them as "useful data rather than objective reality."
The core insight: Your internal monologue determines your external results. Master your mind first, then master the market.
When conventional wisdom told him not to buy back $2 billion in stock (26% of market cap) after a short-seller attack, Jacobs ignored the bankers. "Just because we were the first company to buy back such a high percentage of our stock didn't mean it was a bad idea." That contrarian move netted a $4 billion profit. The lesson isn't to be contrarian for its own sake—it's to think from first principles when everyone else relies on formulas.
Key takeaway: Spend 30 minutes daily on thought experiments and meditation. This isn't woo-woo—it's where Jacobs says his best decisions materialize.
2. Problems Are Assets in Disguise
At a lunch in his twenties, Jacobs unloaded his business problems on his mentor Ludwig Jesselson. The response changed his life: "If you want to make money in the business world, you need to get used to problems, because that's what business is. It's actually about finding problems, embracing and even enjoying them." This isn't feel-good nonsense—it's mathematical reality.
The core insight: Big gunky problems are where the best opportunities lie because most people run away from them.
When Congress allocated $600 billion for infrastructure through TEA-21, Jacobs immediately bought road rental companies. When only a third of the money materialized, he lost $500 million. His response? "Radical acceptance"—see the world for what it is, not what you wish it to be. He sold immediately, cut losses, and moved on to build United Rentals, now worth $38 billion. The failure taught him more than the success.
Key takeaway: When you hit a major problem, ask yourself: "Great! This is an opportunity for me to create a lot of value. How can I solve this?"
3. People Are Power Law—Pay Accordingly
Jacobs discovered what Steve Jobs knew: in most fields, the best person isn't twice as good—they're 50 to 100 times better. Yet most companies try to save $100,000 on salary while losing millions in opportunity cost. His rule: "An empty seat is less damaging than a poor fit."
The core insight: It's nearly impossible to overpay for talent. Apple paid $500 million to rehire Steve Jobs and got the deal of the century.
Jacobs uses a thought experiment to identify A-players: imagine them walking into your office and quitting. If your reaction is panic ("We're so screwed! There's no way we'll find someone this good!"), that's an A-player—overpay them immediately. His 174,000 employees don't work to make Brad Jacobs rich; they work for themselves and their families. "Money animates people everywhere."
Key takeaway: Never skimp on talent. Paying 30% above market for an A-player who delivers 100x value is the best ROI in business.
Key Frameworks
The Research Obsession Process
What it is: A systematic approach to understanding any industry before entering it—what Jacobs calls "getting the major trend right."
How to apply it:
- Read everything: journals, trade publications, employee reviews, social media
- Use paid services: Bloomberg, AlphaSense, SEC filings
- Attend conferences: meet management teams face-to-face
- Interview everyone: CEOs, bankers, VCs, journalists ("they're skeptical")
- Find the data bottleneck: identify valuable but hard-to-get information
When to use it: Before starting any new venture or making major strategic decisions. Jacobs spends months on this before each company.
The Problem-as-Opportunity Reframe
What it is: A mental model for converting setbacks into competitive advantages.
How to apply it:
- Initial reaction: excitement, not frustration ("This could create value")
- Analyze without judgment: spend hours understanding the real issue
- Find the hidden opportunity: what can you do that others won't?
- Act decisively: move while competitors are paralyzed
- Document lessons: turn this instance into a principle
When to use it: Whenever facing major setbacks, market crashes, or competitive attacks.
The A-Player Identification Test
What it is: A thought experiment to instantly identify your most valuable people.
How to apply it:
- Visualize the person quitting without warning
- Notice your immediate internal reaction
- If panicked: A-player (overpay them)
- If annoyed but manageable: B-player (develop or replace)
- If relieved: C-player (fire immediately)
When to use it: During performance reviews, compensation discussions, or organizational restructuring.
Notable Quotes
"During my 44 years as a CEO and serial entrepreneur, I've made every possible mistake in business. I've overpaid for acquisitions and botched integrations...And yet my teams and I have managed to create tens of billions of dollars of value."
Why this matters: Success isn't about avoiding failure—it's about failing productively and learning faster than competitors.
"All of them, to a person, have rearranged their brains to prevail at achieving big goals in turbulent environments where conventional thinking often fails."
Why this matters: The difference between average and exceptional isn't effort—it's literally thinking differently.
"Look, Brad, if you want to make money in the business world, you need to get used to problems, because that's what business is."
Why this matters: Redefines business from "avoiding problems" to "seeking problems"—a 180-degree mindset shift.
"Problems are an asset—not something to avoid but something to run toward."
Why this matters: While competitors flee from problems, you can monopolize the opportunities they create.
"Just because we were the first company to buy back such a high percentage of our stock didn't mean it was a bad idea."
Why this matters: First principles thinking beats conventional wisdom—especially when billions are at stake.
"I'm obsessive when learning about an industry."
Why this matters: Surface-level research produces surface-level returns. Obsession produces billions.
"An empty seat is less damaging than a poor fit."
Why this matters: Most companies fill seats quickly; winners wait for exceptional talent.
"It makes no financial sense to skimp on salary and incentives to save $100,000 a year when hiring a second-best candidate may cost you millions in lost profit."
Why this matters: Penny-pinching on talent is pound-foolish—the ROI on A-players dwarfs their cost.
"Money animates people everywhere."
Why this matters: Pretending money doesn't matter is naive. Top performers expect top compensation.
"Narrow your focus to your most important dreams and tune out everything else."
Why this matters: Radical focus beats scattered brilliance every time.
"Radical acceptance quiets the noise created by yesterday's decisions and today's wishful thinking."
Why this matters: See reality clearly or pay the price in lost time and capital.
"If you want to make a lot of money in almost any industry, plan to invest heavily in tech."
Why this matters: Technology is the universal force multiplier—ignore it at your peril.
"We could proactively adjust our pricing and asset management, while the rest of the industry was being reactive."
Why this matters: Information advantage creates pricing power and operational superiority.
"The deals I've avoided have contributed more to my success than the deals I've done."
Why this matters: Discipline in saying no preserves capital for exceptional opportunities.
"What's your single best idea to improve our company? What's the stupidest thing we're doing as a company?"
Why this matters: Two questions that surface more value than any consultant ever could.
"We have it in our own hands to either make life meaningful or just pass time until we die."
Why this matters: Intensity of focus determines quality of outcome—in business and life.
"If I put my whole heart and soul into a project, I had it in me to create really cool stuff."
Why this matters: Going all-in isn't just about effort—it's about unlocking capabilities you didn't know existed.
"Not a single one of them shows up to work because they want to make money for Brad Jacobs."
Why this matters: Alignment of incentives beats motivational speeches every time.
Related Ideas
Ludwig Jesselson on embracing problems: Jacobs's most important mentor ran the world's largest commodity trading company and taught him that business is fundamentally about finding and solving problems. This mirrors Danny Meyer's grandfather's wisdom that "the definition of business is problems" and that success lies "not in the elimination of problems, but in the art of creative, profitable problem solving."
Jeff Bezos on finding waste exciting: Bezos wrote to shareholders that discovering inefficiency is "incredibly energizing" because it represents "years and years of variable and fixed productivity gains." Like Jacobs, he saw problems as stored value waiting to be unlocked—the bigger the problem, the bigger the opportunity.
Henry Kaiser's work clothes philosophy: The legendary industrialist said "problems are just opportunities in work clothes"—the same reframe Jacobs learned in his twenties. Kaiser built an empire during World War II by running toward problems others avoided.
Steve Jobs on the dynamic range of humans: Jobs observed that while most things vary by 2x between average and best, in technology and business, the best person can be 50-100x better. This matches Jacobs's philosophy of overpaying for A-players because "it's nearly impossible to overpay for talent."
Charlie Munger's indifference to problems: When Jacobs references Munger's complete indifference to problems—seeing them as inevitable and something to "cope with"—it reinforces the pattern among all great capital allocators: emotional equanimity in the face of setbacks.
Peter Thiel on finding value in unexpected places: Thiel's observation that successful people find value by thinking from first principles rather than formulas perfectly describes Jacobs's $4 billion stock buyback win when conventional wisdom said it was impossible.
Andrew Carnegie on technology investment: Carnegie's 1800s insight that investing in technology compounds savings and creates competitive advantage proves Jacobs's point that technology has been the dominant megatrend for centuries, not just decades.
Sam Walton on frontline intelligence: Like Jacobs, Walton obsessively gathered data from frontline employees, knowing that executives filter reality. Both built empires by staying connected to ground truth rather than corporate abstractions.
Practical Applications
For Founders
- Strategic Planning: Get the major trend right—spend months researching before committing to an industry
- Problem-Solving: Create a "problem log" where you document every major issue and its hidden opportunity
- Capital Allocation: When others panic (like during short attacks), have the courage to deploy capital aggressively
- Mental Training: Dedicate 30 minutes daily to meditation and thought experiments—this isn't optional
For Investors
- Due Diligence: Look for founders who demonstrate "radical acceptance"—seeing the world as it is, not as they wish
- Pattern Recognition: The best investments often come after spectacular failures (Jacobs's $500M loss preceded his biggest wins)
- Talent Assessment: Evaluate whether founders overpay for talent or try to save pennies while losing dollars
- Trend Analysis: Focus on companies riding decade-long megatrends, especially technology adoption
Natural Next Reads
- Zero to One by Peter Thiel: Deeper exploration of thinking from first principles versus copying what works
- The Everything Store by Brad Stone: How Bezos applied similar principles to build Amazon
- Setting the Table by Danny Meyer: Another entrepreneur's take on problems as the essence of business
- Shoe Dog by Phil Knight: Building a global empire through constant problem-solving and near-death experiences
- The Outsiders by William Thorndike: Eight CEOs who, like Jacobs, generated exceptional returns by thinking differently. See my book summary →
Reflection Questions
- What problems in your business are you avoiding that could be $4 billion opportunities?
- Who on your team would cause panic if they quit tomorrow—and are you paying them accordingly?
- What "conventional wisdom" in your industry might be wrong because no one thinks from first principles?
- How much time do you spend managing your mental state versus managing your business?
- What's the stupidest thing your company is doing that no one will tell you about?
The Bottom Line
Brad Jacobs built eight billion-dollar companies not by avoiding mistakes but by maintaining mental equilibrium while making them. His secret isn't complex financial engineering—it's rearranging your brain to see problems as assets, overpaying for people who terrify you to lose, and having the courage to act when conventional wisdom says don't. The book's title promises to teach you how to make billions, but the real lesson is more valuable: how to think so differently that billions become the natural outcome. Start with his two questions: What's your single best idea to improve? What's the stupidest thing you're doing? The answers might be worth more than you imagine.
More Quotes
"A fellow CEO laid this out for me graphically once when we were talking about M&A deals. 'Think of M&A as having four quadrants defined by size and risk,' he said. 'Big, low-risk deals are the ones everyone wants, but they don't exist. Small, low-risk deals do exist, but you can't make much money from them because of their size. Small, hairy deals are the worst quadrant, because the reward is limited and the odds are stacked against you, so why bother? The bingo quadrant is the big, hairy deals. If you can find a big, hairy deal with solvable problems, that's where the real money is.'"
"One of the first things I look for in an industry is scalability. I want to be able to envision how I'll take a business from a few million dollars to tens of billions of dollars."
"What's the base price/volume combination we need to be profitable, and how realistic is it to significantly increase our profit margin over time? What could prevent us from doing that?"
"Are there ways to grow the business organically or through M&A? What multiples will I likely have to pay for companies I acquire, and is that number a large enough discount from the multiple I'd expect my company to trade at? This is important because the arbitrage between our cost of capital and what multiple we're able to buy companies at is the biggest value-creation lever in a roll-up."
"Be a futurist and figure out the bullish and bearish trends driving your industry. If you get the major trends right, you can make mistakes and still succeed."
"So much of success in business comes from keeping your head in a good place."
"I don't take it for granted that I'm going to be successful. Unexpected stuff can happen at any time. A healthy fear of failure has kept me sharp."
"Life can be uncomfortable, but you can accomplish a lot if you can figure out how to reframe the uncomfortable things in ways that allow you to utilize them."
"Embrace everything that comes your way, the good and especially the bad. And don't just accept adversity—figure out how to capitalize on it."
"Being dialectical means looking at something from different perspectives and interpreting it in multiple ways that are all valid."
"If I had tried to do everything I wanted to, I never would have accomplished anything big. Narrow your focus to your most important dreams and tune out everything else."
"Our species is moving along a new evolutionary path toward using technology to augment our senses and outsource our memory and cognitive functions."
"I like big industries because even a small chunk of a huge, growing industry is still big."
"The easiest way I know to create tremendous shareholder value is to buy businesses at profit multiples lower than the multiple our stock trades at, and then significantly improve those businesses."
"Bigger is better in business most of the time, but not always. Understand the pros and cons of size. Some service industries are better off local."
"I wasted a lot of time early in my M&A career because I thought I could pay less by playing hard to get. I learned it's better to let sellers know how excited I am to do a deal and the price and terms that work for me."
"It's better to be slightly understaffed, but not badly understaffed. A team that's appropriately lean has a more concentrated focus and gets more done."
"An organization is like a party. You only want to invite people who bring the vibe up."
"If you hire a B player, they'll probably hire C players. Then you'll have C players led by B players. Yikes."
"Give the person you're with your entire attention while listening to them non-judgmentally. This is the greatest gift you can give anybody."
"A customer relationship is like any other relationship—for it to succeed, you have to be clear about how much you value it, and continually work on improving it."
"In some businesses, there's a perceived conflict between quality and speed. A world-class organization figures out how to achieve both."
Introduction from the Book
During my 44 years as a career CEO and serial entrepreneur, I think I've made every possible mistake in business. I've overpaid for acquisitions and botched integrations. I've run operations for cash when I should have invested for growth. I've delegated tasks I should have done myself. Sometimes I've hired the wrong people, or made strategic bets that didn't pay off.
And yet, my teams and I have managed to create tens of billions of dollars of value for our shareholders. This book is about what I've learned from my blunders, and how you can replicate our successes.
In corporate America, I'm what's called a moneymaker. I've started five companies from scratch—seven if you include two spin-offs—and turned them all into billion-dollar or multibillion-dollar enterprises. My teams and I have completed approximately 500 acquisitions and opened more than 250 greenfield locations. In total, these ventures have created hundreds of thousands of jobs and raised about $30 billion in outside capital.
These experiences have allowed me to share thought experiments that can help you learn to think differently—an essential prerequisite to accomplishing big things. I also share how I spot big trends and capitalize on them through M&A, and I give you my thoughts on what I consider to be the biggest trend of all: the rapid evolution of technology and what it could mean for humankind. I lay out my approach for finding superhuman talent, "overpaying" them, and creating a love-vibe culture that nourishes them. And I confess my deep-seated aversion to boring meetings and share the techniques I use to make them electric.
This book is a guide for anyone who wants to achieve wealth creation through free markets or pursue their personal version of the American Dream. If you have a burning passion to make enormous amounts of money in business, or want to turbocharge your chances of success in sports, the arts, politics, philanthropy, or any other part of your life, read on.
— Brad Jacobs
Who is Brad Jacobs?
Brad Jacobs is a career CEO and serial entrepreneur with a unique track record as a Wall Street moneymaker. To date, he has founded and led seven billion-dollar or multibillion-dollar companies, creating tens of billions of dollars of value for shareholders.
Over the course of his career, Jacobs has raised $30 billion of debt and equity capital, including three IPOs, and led approximately 500 M&A transactions across multiple industries.
In the supply chain industry, he grew XPO into a top ten global logistics provider, and then executed a strategic plan for a $7 billion spin-off of GXO Logistics and a $5 billion spinoff of RXO, creating two new public companies in about 15 months. XPO was the seventh best-performing stock of the last decade in the Fortune 500 and became a "32-bagger"—initial investors in XPO made more than 32 times their money.
Prior to XPO, Jacobs founded United Rentals and United Waste Systems. He built United Rentals into the largest construction equipment rental company in the world in 13 months. United Rentals was the sixth best-performing Fortune 500 stock of the last decade and became more than a "100-bagger"—the share price at inception was $3.50, and its stock now trades at more than 100 times that price. United Waste's stock outperformed the S&P 500 by 5.6 times from the time Jacobs took the company public to its sale for $2.5 billion.
Jacobs is managing partner of Jacobs Private Equity, and serves as chairman of the board of XPO (NYSE: XPO), GXO Logistics (NYSE: GXO), and RXO (NYSE: RXO).
Buy the Book
For more, I highly encourage you to order How to Make a Few Billion Dollars by Brad Jacobs and read the entire book yourself.
History of Technology Timeline
To understand the most important trends in business, start by looking at the most important trend of all: the evolution of technology over the last two million years. Two things stand out. First, the frequency of technological development is accelerating. Second, humans are in the process of merging with the technologies we create.
More than 2 million years ago
Early humans in Africa make the first stone tools from split pebbles
1 million years ago
Humans begin to use fire as a tool
500,000 years ago
Humans build the first shelters
350,000 years ago
Humans begin to hunt with spears
100,000 years ago
Humans begin to trade using beads made of shells
60,000 years ago
Humans begin to use spears for hunting, protection, aggression
1000 BC
Early accountants in Asia create the abacus
635 ВС
The Chinese produce the first coins
600 BC
The Romans build the first public sewer system
200 BC
The Chinese invent the compass
AD
725
Buddhist monk Yi Xing creates the first mechanical clock
900
The Chinese first use gunpowder in war
1182
The Chinese invent the magnetic compass
1284
The Italians invent eyeglasses
1328
The Europeans invent the sawmill
1440
Johannes Gutenberg invents the printing press
1530
Europeans invent the spinning wheel
1609
Galileo Galilei invents the telescope
1662
Blaise Pascal invents the public bus
1698
Thomas Savery invents the basic steam engine
1769
A French military tractor becomes the first self-propelled road vehicle
1793
Eli Whitney invents the cotton gin
1795
Nicholas-Jacques Conté invents the modern pencil
1838
A British steamship makes the first transatlantic crossing
1839
Charles Goodyear develops a way to make rubber strong, durable, and elastic
1850
Isaac Singer introduces the sewing machine
1857
William Kelly invents the blast furnace
1865
Giovanni Caselli introduces the first commercial facsimile system
1869
John Wesley Hyatt invents synthetic plastic
1874
Remington Company introduces the mechanical typewriter
1876
Alexander Graham Bell invents the telephone
1877
Thomas Edison invents the phonograph
1880
Thomas Edison invents the incandescent light bulb
1882
America opens the first hydroelectric power plant
1883
England constructs the first electric railway
1885
Gottlieb Daimler builds the first four-wheeled automobile using an internal combustion gas engine
1886
Josephine Cochran invents the first practical dishwasher
1892
Rudolf Diesel invents the diesel engine
1894
Nikola Tesla invents radio signal coils
1896
Gottlieb Daimler builds the first truck
1901
Henry Booth invents the vacuum cleaner
Thomas Edison invents the alkaline storage battery
1902
Marie and Pierre Curie discover the existence of the elements radium and polonium
1903
Willis Carrier introduces the first electric air conditioner
1908
Henry Ford uses the assembly line to introduce the Model T
Thomas Edison develops a moving picture with sound
1910
A plane transports commercial freight for the first time
1913
England manufactures the first stainless steel
1914
Electric traffic lights are invented in the United States
1920
James Smathers invents the electric typewriter
1921
Karel Capek invents the robot
Western Union introduces the telegram
1923
Clarence Birdseye invents frozen food
1927
Erik Rotheim invents the aerosol can
Philo Farnsworth invents the all-electric television
1933
Eric Fawcett and Reginald Gibson invent polyethylene
1935
Robert Watson-Watt pioneers the development of radar
