How to Make a Few Billion Dollars

When Brad Jacobs attended his daughter's destination wedding in Mexico, he never imagined that officiating the ceremony would teach him something profound about making billions. As family and friends gathered on the pristine coastline, Jacobs asked everyone to visualize all the love that had ever existed throughout human history, then imagine channeling that energy into the wedding rings. The transformation was immediate. What seemed like an unconventional approach actually created the perfect atmosphere for collaboration and success.

This moment captures the essence of what separates ordinary business leaders from those who create extraordinary wealth. Making a few billion dollars isn't just about having the right strategy or being in the right place at the right time. It requires a fundamental rewiring of how you think, how you build teams, and how you approach the inevitable chaos of high-stakes business. Through his journey from a 23-year-old with just a few thousand dollars to building seven billion-dollar companies, Jacobs discovered that success comes from mastering three critical elements: anticipating major trends before they become obvious, assembling teams of exceptionally talented people who genuinely enjoy working together, and maintaining the mental flexibility to turn every setback into an opportunity. This book reveals the specific techniques and mindset shifts that have generated tens of billions in shareholder value across multiple industries.

The phone call came on a December morning in 2018 that would have sent most CEOs into panic mode. A notorious short-seller had just published a scathing report about XPO Logistics, packed with misleading data and twisted facts designed to crater the stock price. Within hours, XPO's share value plummeted 26 percent as trading bots picked up the negative coverage and amplified it across financial media. The short-seller was already counting their profits from the coordinated attack.

Most companies facing such an assault either go silent or lash out defensively, often making the situation worse. Jacobs chose a radically different path. That evening, he was hosting a dinner for fund managers at his Connecticut home, including Matt Fassler, XPO's new chief strategy officer who had joined just one week earlier. Rather than cancel or deflect, Jacobs and his team spent five hours methodically dismantling every false claim in the report. By dessert, the investors who had arrived with concerns left as believers in XPO's long-term prospects.

The real breakthrough came when Jacobs applied what he calls "radical acceptance" to reframe the crisis. Instead of viewing the stock collapse as devastating, he saw it as an unprecedented opportunity to buy back shares at bargain prices. When his bankers balked at the proposed $2 billion buyback, calling it too aggressive, Jacobs pushed forward anyway. The board approved the bold move, and those shares eventually became worth $6 billion, generating a $4 billion profit.

This story illustrates the power of what Jacobs calls "rearranging your brain." Success at the billion-dollar level requires training yourself to see problems as opportunities, to embrace imperfection rather than demand it, and to maintain emotional equilibrium when others are losing theirs. The key is developing what cognitive behavioral therapy calls "dialectical thinking" - the ability to hold multiple perspectives simultaneously and find truth in apparent contradictions. When you can genuinely accept that setbacks are inevitable while maintaining unwavering optimism about outcomes, you unlock a level of mental flexibility that transforms how you navigate high-stakes situations.

In 1979, a 23-year-old Brad Jacobs was half-watching the CBS Evening News when a report about the Iran hostage crisis caught his attention. Oil prices were soaring, and for the first time ever, an American company - Exxon - had reported quarterly earnings exceeding $1 billion. The words "obscene profits" flashed on screen, and Jacobs remembers thinking, "That sounds pretty good! Maybe I ought to check out the oil sector." This casual moment would launch his first company and teach him the most valuable lesson of his career.

Starting Amerex Oil Associates with just a few thousand dollars, Jacobs discovered something remarkable about the oil markets. Crude oil futures traded in New York and Chicago, while cash markets operated in Houston and London, but these markets seemed largely oblivious to each other. The same barrel of oil often had different prices across markets, creating perfect arbitrage opportunities. While other brokers relied on tribal knowledge and waited days for information to travel by telex, Jacobs invested in building a crude internet-like system using appliance-sized computers and green screens. This allowed Amerex to share pricing data globally within hours instead of days, giving them an enormous competitive advantage.

The lesson became clear: getting the major trend right can compensate for numerous other mistakes. As his mentor Ludwig Jesselson later told him, "You can mess up a lot of things in business and still do well as long as you get the big trend right." Today, that major trend is artificial intelligence, which Jacobs believes will be more transformative than e-commerce, social media, or mobile technology combined. He's witnessed AI eliminate the need for human intervention in 96 percent of truck brokerage transactions at his companies, turning what once required armies of phone calls into seamless machine-to-machine operations.

Successful trend-spotting requires systematic research and genuine intellectual curiosity. Spend time with industry experts, attend conferences where real practitioners gather, and most importantly, listen to what your customers dream about having, regardless of cost or feasibility. The entrepreneurs who capture "obscene profits" are those who identify major shifts before they become obvious to everyone else. In our current era, that means understanding how AI will reshape entire industries within the next decade, not just improve existing processes around the edges.

When Brad Jacobs decided to enter the construction equipment rental industry in 1997, he discovered a market that made no commercial sense. Only 15 percent of construction equipment was rented, meaning 85 percent of machines sat idle on jobsites, getting rusty and dusty while contractors paid depreciation costs. Within 13 months of founding United Rentals, Jacobs had acquired enough companies to become the world's largest equipment rental provider, proving that Adam Smith's invisible hand of capitalism was indeed at work.

The key to United Rentals' M&A success wasn't just identifying opportunities - it was executing deals without imploding. Jacobs developed a systematic approach that began long before making contact with sellers. His team would research potential acquisitions for weeks, understanding their operations, culture, and hidden challenges. When they finally approached a seller, the conversation often went like this: "This is what we're prepared to pay for your business, on these terms. If this is acceptable, we can be signing a definitive agreement in two weeks." This speed and preparation gave them a massive advantage in competitive situations.

The most critical insight Jacobs learned was that sellers are often temporarily insane during the sale process, overwhelmed by stress about their legacy and employees' futures. Instead of playing hard to get, which he admits wasting time on early in his career, he learned to be genuinely enthusiastic and transparent. He would tell sellers exactly how excited he was to do the deal and share his honest assessment of the business. This authenticity built trust and prevented deals from falling apart during the emotional period between handshake and signing.

Cultural integration proved to be the make-or-break factor in M&A success. Jacobs realized you can't force-fit incompatible cultures - you must buy companies where the cultural differences are manageable. At United Rentals, this meant finding entrepreneurial owners who shared similar values around customer service and operational excellence. The integration playbook included hundreds of specific tasks assigned to individuals, not committees, with regular progress monitoring. Most importantly, they respected what made acquired companies successful in the first place, rather than imposing wholesale changes that could destroy the value they had just purchased.

The three CEOs currently running Jacobs' companies - Mario Harik at XPO, Malcolm Wilson at GXO, and Drew Wilkerson at RXO - couldn't appear more different on the surface. Mario grew up in Beirut and conveys technological brilliance with a distinct Lebanese accent. Malcolm is a patient, measured Englishman with decades of logistics experience. Drew is a Southerner with a Carolina drawl who gets straight to the point. Yet all three possess identical qualities that Jacobs considers non-negotiable: intelligence, hunger, integrity, and collegiality.

The intelligence requirement eliminates 90 percent of candidates immediately, but Jacobs learned not to confuse pedigree with ability. Drew Wilkerson attended a college ranked below the top 100, yet his mastery of the brokerage business is extraordinary. When Jacobs interviews candidates, he asks about GPA and IQ scores, but more importantly, he assesses whether they can think dialectically - holding multiple perspectives simultaneously and changing their opinions when presented with new evidence. True intelligence reveals itself through humility and curiosity, not arrogance or rigid thinking.

Hunger manifests as genuine enjoyment of intense, results-oriented work environments. Jacobs only hires people motivated to make serious money, believing that if someone claims they're not motivated by money, they either lack honesty or the drive necessary for success. The hunger test involves assessing whether candidates would thrive in slightly understaffed teams, where focused effort replaces redundant busywork. This approach requires vigilance about burnout - occasionally Jacobs has to tell his heaviest hitters to rest and recharge rather than risk mental exhaustion.

Integrity and collegiality work together to create what Jacobs calls a "love vibe" culture. Someone willing to lie about small things will lie about big things, and dishonest employees blind management to operational realities. Collegiality matters because, as Jacobs puts it, he probably has only 5,000 good days left in his life and doesn't want to spend even one hour with unkind people. The combination creates teams where everyone genuinely likes working together, making the intense work not just bearable but genuinely enjoyable.

At age 16, Brad Jacobs left traditional high school to attend Bennington College, where classes averaged nine students and every session was 90 minutes of fast-paced discussion. There wasn't time to raise hands - survival required immediate engagement. The practitioner-teachers knew every student's name, and students addressed professors by their first names, creating an atmosphere of peer-level intellectual combat. When Jacobs later transferred to Brown University, sitting passively in lecture halls with 150+ anonymous students felt suffocating after the electric energy of Bennington's collaborative learning environment.

This contrast shaped Jacobs' approach to corporate meetings for the next four decades. He refuses to tolerate the "big company-itis" that turns capable executives into passive observers watching rehearsed presentations. Instead, he creates what he calls "electric meetings" with three essential ingredients: the right people, a crowdsourced agenda, and an atmosphere where everyone feels safe to respectfully disagree. Monthly operating reviews become intellectual battlegrounds where the smartest people in the company tackle the thorniest problems together.

The process begins weeks before the meeting when financial teams distribute slide decks that attendees must read in advance. As each person finishes reading, they submit their top takeaways and most important questions. These submissions get compiled into a digital survey where attendees rank each item from one to ten in importance. By the time everyone walks into the room, they've absorbed the information, formulated their thoughts, and prioritized the group's collective agenda. No time gets wasted on slide presentations that could be read faster individually.

The magic happens when conflicting opinions emerge and get explored constructively. Jacobs learned that validation must precede correction - saying "I see your point, but I think the projections might be off" rather than simply contradicting someone. The goal is productive dialectical thinking, not winning arguments. When meetings work properly, attendees leave energized rather than drained, clear about next steps, and confident they contributed meaningfully to solving important challenges. The investment in creating electric meetings pays dividends in faster decision-making, better solutions, and teams that genuinely enjoy the intellectual combat of high-stakes business.

The path to creating billions in value isn't about perfecting every detail - it's about mastering the fundamental drivers of exponential success. Rearrange your brain to see problems as opportunities, identify major trends before they become obvious to competitors, and build teams of exceptionally talented people who genuinely enjoy working together toward ambitious goals.

Start by implementing systematic trend research in your industry, dedicating time each week to understanding where technology and customer needs are heading over the next five to ten years. Build feedback loops with customers, employees, and industry experts to stay ahead of changes that could make or break your business. When hiring, never compromise on the four essential qualities: intelligence, hunger, integrity, and collegiality. Create meeting cultures that prioritize genuine dialogue over corporate theater, and maintain the mental flexibility to turn every setback into an opportunity for value creation. Remember that building something great requires accepting imperfection while maintaining unwavering optimism about outcomes - this paradox unlocks the kind of thinking that transforms industries and generates extraordinary wealth.