How to Make a Few Billion Dollars

How to Make a Few Billion Dollars Plot Summary

Introduction

Have you ever looked at the world's most successful entrepreneurs and wondered what secret formula they possess that eludes the rest of us? It's easy to assume they were simply born different—blessed with supernatural vision, unwavering confidence, or perhaps just extraordinary luck. But what if the ability to create billions in value isn't mystical at all, but rather a set of learnable mindsets and methodologies? Across four decades as a serial entrepreneur, Brad Jacobs has founded and built seven different billion-dollar enterprises across entirely different industries—from oil brokerage to waste management, equipment rental to global logistics. His journey reveals something profound: entrepreneurial success at the highest level isn't about perfection or following a rigid playbook. Rather, it's about mastering certain fundamental principles: rearranging your brain to think differently, spotting major trends before others do, executing strategic acquisitions without imploding, building extraordinary teams, fostering productive communication, and creating unified cultures that outperform competitors. By understanding these principles and applying them with the entrepreneurial spirit that values both profit and excellence, you too can pursue audacious goals with greater confidence and clarity.

Chapter 1: Rearranging Your Brain: The Psychology of Success

When Brad Jacobs's oldest daughter Yasmina was planning her wedding in 2014, she asked him to officiate the ceremony. Though hesitant at first, Jacobs accepted and developed a unique approach. At the oceanfront ceremony in Mexico's Yucatan Peninsula, surrounded by family and friends, he guided everyone through a powerful thought experiment. "I asked everyone to try to imagine all the instances of love between two people that have occurred from the beginning of time until now," Jacobs recalls. During a minute of silence, guests' faces visibly transformed with this beautiful thought. He continued, "And now build on that, and get in touch with feeling all the love that exists on earth right at this moment." After another minute of reflection, he asked everyone to visualize all the love that could exist over billions of years to come. For the finale, they gathered all that love—past, present, and future—in their hands and pantomimed tossing it at the bride and groom. This "love vibe" exercise might seem removed from business, but Jacobs explains its profound relevance: "Fast-paced business environments swing between ups and downs, with many stressful interactions. Love is in an expansive emotional state that allows you to neutralize conflict and get everyone to a better place." He regularly applies this technique in tense business situations, such as difficult negotiations over acquisition terms. By mentally returning to that moment of intense love, he creates more constructive dialogue. This approach represents just one of many thought experiments Jacobs employs to "rearrange his brain"—deliberately transforming how he thinks to achieve massive success. Another powerful practice he shares is his approach to negative thoughts. "Stop beating yourself up mentally," he advises. "Successful people don't always think positive thoughts. Because of the way humans are programmed, most of us—especially people with dynamic personalities—find that negative thoughts surface automatically." Rather than being controlled by these thoughts, Jacobs employs a two-step process: first acknowledging negativity as natural self-critical psychology, then challenging its validity by recognizing it as an outdated survival mechanism. He reframes negative thoughts as merely one perspective rather than objective reality. This mental discipline has been instrumental in navigating business crises, like when XPO faced a devastating "short" report that caused their stock to plunge 26% in one day. Instead of panicking, Jacobs and his team analyzed the situation without judgment, radically accepted the circumstances, and made the bold decision to buy back $2 billion worth of their stock—an unprecedented move that ultimately generated $4 billion in profit. The psychology of success also requires humility. Jacobs shares a humbling conversation with his former music teacher Bill Dixon, who bluntly told him, "You're wasting your life. You could have been a good musician. You had talent. What are you chasing this silly money stuff for?" This perspective has kept Jacobs grounded throughout his success. "Making money is fun and it has its advantages," he reflects, "but it's not the only thing that's important in life."

Chapter 2: Spotting Major Trends: How to Ride the Wave of Change

Ludwig Jesselson, a mentor to Jacobs, once shared invaluable wisdom: "You can mess up a lot of things in business and still do well as long as you get the big trend right." This insight became a cornerstone of Jacobs' business philosophy, driving his obsessive approach to trend-spotting before entering any new industry. In 1989, a pivotal moment occurred when Jacobs was reading research reports in bed on a lazy Sunday morning in London. He came across analyst Bill Genco's report noting that the two largest waste management companies were each making about half a billion dollars annually in profit. "I thought, How hard can it be to have trucks pick up trash, deposit it in a safe place, and send out an invoice?" Jacobs recalls. His curiosity piqued, he began researching the industry deeply. Jacobs discovered two significant trends transforming waste management: decreasing landfill capacity due to tightening regulations, and increasing integration of hauling and disposal services. He founded United Waste Systems to capitalize on these trends, with a particular focus on leveraging technology for truck routing optimization. While most companies were routing trash collection "by the seat of their pants," Jacobs implemented computerized systems that dramatically improved efficiency. "Instead of sending, say, 50 trucks out over five days to pick up X tons of waste, 20 trucks could now perform the same service in three days by making more stops per hour," he explains. Their costs decreased, profit margins grew, and they gained a substantial advantage over competitors still using pencil and paper for route planning. Years later, when exploring the equipment rental industry, Jacobs again identified a massive market inefficiency: only 15% rental penetration, with 85% of equipment sitting idle and deteriorating on construction sites. The industry was growing organically, had minimal national competition, and offered thousands of potential acquisitions without widespread computerization or standardization. Recognizing this opportunity, Jacobs founded United Rentals and moved decisively on technology implementation by acquiring Wynne Systems, the industry's leading software provider. This gave United Rentals both a superior operational platform and access to aggregated data on industry-wide trends, enabling proactive adjustments to pricing and asset management while competitors remained reactive. Most recently with XPO Logistics, Jacobs spotted the emerging trend toward automation in freight brokerage. In 2011, most truck brokers were conducting business by phone rather than digitally. Anticipating the coming demand for digital service, Jacobs prioritized heavy tech investment from the start. He hired Mario Harik, who held a master's degree in machine learning and AI from MIT, as his third employee. Together they developed a vision for fully automating freight brokerage processes—revolutionary at the time. Ten years later, while zero percent of XPO's truck brokerage loads had been created digitally at the beginning, 96% now have a digital component, with many as touchless transactions through direct digital connections with customer systems. The accelerating pace of technological change makes trend-spotting more crucial than ever. Jacobs warns that artificial intelligence will be the central determining factor in whether businesses collapse or prosper in coming years. "AI is developing so rapidly no one knows what it will be capable of in even six months," he observes. "What's clear is that AI's impact will eventually exceed anything we can imagine."

Chapter 3: Mastering M&A: Building Empire Without Imploding

When Brad Jacobs set out to build United Waste Systems in the early 1990s, he pursued a clear acquisition strategy: avoid competing with industry giants in major markets and instead target overlooked tertiary markets like rural Mississippi and Michigan's Upper Peninsula. "Our M&A game plan from the start was to be a big fish in a small pond," Jacobs explains. The company rolled up landfills, then acquired collection companies hauling waste to those sites, quickly building geographic density and economies of scale. Eight years later, they sold the business for $2.5 billion. This success wasn't accidental. Jacobs follows a disciplined approach to acquisitions that begins with rigorous analysis. "We use ten years of earnings at zero growth as a baseline," he reveals. "From there, we make assumptions about what kind of organic revenue growth rate we can achieve over ten years, and what kind of margin we can realize." His team stress-tests every element of their projections, examining base-case scenarios, upside potential, and downside risks. Critically, Jacobs only pursues deals where "the downside scenario is still good for the company, the base case is excellent, and the upside case is off the charts." Speed becomes a competitive advantage in Jacobs' acquisition process. His team conducts extensive research before making initial contact with target businesses, allowing them to move quickly once discussions begin. "We can typically cut the due diligence and negotiation period from two or three months to a matter of weeks," he notes. A typical first meeting might include a statement like: "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 decisiveness gets attention, but Jacobs emphasizes it's backed by thorough preparation. Perhaps the most counterintuitive aspect of Jacobs' approach is his treatment of sellers. Early in his career, he wasted time playing hard-to-get during negotiations. "I sometimes went so far as to not return a seller's phone call to maintain an aloof posturing. Wrong!" he admits. He learned that most private sellers are deeply concerned about their legacies—whether employees will be retained and treated well, how customers and vendors will be handled, and how communities will be affected. Jacobs now prioritizes genuine communication: "If I admire what they've done with the business, I'll tell them that. If I'm eager to buy it, and not just on the fence, I'll tell them that, too." This approach was essential during XPO's aggressive growth phase in 2014-2015, when Jacobs signed agreements for three foundational acquisitions worth over $7 billion in just 13 months: Norbert Dentressangle in Europe, and New Breed and Con-way in North America. Rather than integrating these businesses sequentially, the team managed all three integrations simultaneously to avoid repeatedly doing and undoing shared services, IT systems, and branding. "I averaged 14-hour workdays during that period," Jacobs recalls, "and for the entirety of the process, my company knew we couldn't take our eyes off customer service, sales, IT, and all the day-to-day initiatives that create shareholder value." The results speak for themselves. New Breed became a cornerstone for XPO's successful GXO spin-off. Con-way's less-than-truckload business nearly tripled its EBITDA from 2015 to 2022 and generated about $4 billion in net cash. Norbert became XPO's European platform with doubled profit in three years. As Jacobs concludes: "If you plan to make a few billion dollars, you'll likely find that sleep is overrated—and that it's actually more fun to be awake."

Chapter 4: Building the Dream Team: Talent That Creates Billions

When Brad Jacobs interviews potential executives for his companies, he's looking beyond their resumes and skills. "I'm actively monitoring my thoughts and feelings: Do I feel relaxed and strong in this person's presence? Am I inspired by them?" Jacobs explains. This personal assessment is just one layer in his comprehensive hiring process, where senior candidates typically undergo seven or eight interviews before joining the team. Jacobs points to three remarkable leaders—Mario Harik, Malcolm Wilson, and Drew Wilkerson—who currently run XPO, GXO, and RXO respectively, as examples of his hiring philosophy in action. Though completely different in background and style, all three share four essential qualities Jacobs seeks in every hire: intelligence, hunger, integrity, and collegiality. "Intelligence is a must-have for me," Jacobs emphasizes, noting that screening for superior intelligence eliminates 90 percent of all candidates. He references a Spencer Stuart study confirming that CEO intelligence is most closely correlated with organizational success. However, Jacobs distinguishes between intelligence and pedigree. Drew Wilkerson, for instance, attended a college ranked below the top 100 but demonstrates extraordinary business mastery. "If I'd only looked for Ivy League graduates, I would have missed out on him—and RXO would have a less capable CEO," Jacobs reflects. Equally important is hunger—the drive to work relentlessly toward big goals. "Hungry people have tenacity and want to work hard," Jacobs explains. "They get motivated by big projects and work nights and weekends, whatever it takes to succeed." He only hires people motivated to make substantial money, believing compensation is the most effective motivational tool. This ties directly to his strategy of building slightly understaffed teams, which he finds more focused and productive than overstaffed ones. Integrity forms the third pillar of Jacobs' hiring criteria. "The success of any company depends on its people fulfilling their obligations," he states. Through experience, Jacobs has learned three crucial lessons: people who lie about small things will lie about big things; dishonest people eventually get caught; and truly honest people demonstrate integrity through actions rather than words. Even one person lacking integrity can disrupt an entire workplace by forcing colleagues to waste time looking over their shoulders. Finally, collegiality completes Jacobs' framework. "I don't think cutthroat people help an organization in the long run," he observes. "Collegial teammates are usually more successful than nasty ones." This preference isn't purely strategic—it's also personal. After a life insurance assessment suggested he might have about 5,000 good days left, Jacobs concluded, "I don't want to spend even one hour with people who are unkind." Once hired, Jacobs categorizes employees as A, B, or C players. He uses a simple thought experiment: imagining how he'd feel if they resigned unexpectedly. If his reaction is panic—"We're so screwed! How did we get into this situation? There's no way we're going to find somebody as fantastic as this person!"—that's an A player. For B players, he might think, "I don't like this, but I can live with it." C players prompt relief: "I was going to fire this person sooner or later anyway." Jacobs maintains a policy of being "a C-free zone," counseling managers to graciously but promptly exit underperforming employees. To retain top talent, Jacobs "overpays" his teams, ensuring compensation aligns with company goals. "Many of my people have made tens of millions of dollars—in one case, over a hundred million dollars—and I was delighted to pay them," he states. "The business received a large return on capital from those investments: tens of billions of dollars of value created for our shareholders."

Chapter 5: Running Electric Meetings: Turning Dialogue into Gold

Brad Jacobs's approach to meetings was profoundly shaped by his experience at Bennington College in Vermont. With classes averaging just nine students, the 90-minute sessions were intensely interactive. "It wasn't an option to sit and observe," Jacobs recalls. "The sessions were fast-paced, challenging discussions. There wasn't even time to raise a hand to be called on—if we wanted to survive, we had to engage." This dynamic contrasted sharply with his later experience at Brown University, where he found himself in vast lecture halls, passively absorbing information from professors who didn't know him. The lesson stayed with him: learning style matters, and lively discussion produces better outcomes than one-way communication. Throughout his business career, Jacobs has strived to recreate that Bennington classroom feeling in corporate meetings. At XPO, Jacobs revolutionized the traditional monthly and quarterly operating reviews (MORs and QORs) that form the backbone of business management. Instead of presentations that waste meeting time, his team distributes comprehensive slide decks in advance. "In 30 minutes of advance reading, most people are able to review what would take a couple of hours if it was being presented live to a bored audience," he explains. Each attendee must submit their top takeaways and questions before the meeting, which are then compiled into a digital survey where participants rank items by importance. When the meeting begins, discussion jumps immediately to the highest-ranked questions and observations. A designated moderator—sometimes the unit leader, sometimes an unexpected choice—guides the conversation. "I'll do everything I can to avoid a situation where an attendee comes with a script they've crafted, determined to present a curated narrative," Jacobs says. "Everyone at the meeting needs to know the real deal on the unit's performance." Jacobs particularly values conflicting opinions, viewing them as the very purpose of the meeting. "I get nervous when I'm in a meeting where everyone is in unanimous agreement that things are copacetic," he admits. The moderator ensures everyone speaks up, often going around the room multiple times to pose the same question to every participant. By the meeting's end, all attendees should have a clear understanding of performance relative to plan, opportunities for improvement, and tactical steps to achieve targets. The same philosophy extends to board meetings, where directors have standing invitations to all operating reviews. "Some corporations have rubber-stamp boards that don't know much about what's going on within the organization—they show up four times a year for choreographed meetings and then disappear," Jacobs observes. "I view this as a missed opportunity." For external communications, Jacobs applies similar principles. At industry conferences and fireside chats, he typically speaks briefly before moving to unscripted Q&A. "I'd rather be rough around the edges than polished," he explains. "My actions are communicating to the audience, 'You've honored me with your time, so I want to honor you by talking about what interests you.'" Despite the spontaneous nature of these meetings, Jacobs enforces four simple rules: turn off all devices; only one person talks at a time with no side conversations; give the speaker full attention with an open mind; and disagree respectfully. These guidelines aren't merely suggestions—Jacobs once banned a chief customer officer from all operating reviews for a full year after repeated side conversations. "It was a tough hammer to bring down on a member of the C-suite," Jacobs recalls, "but he accepted it with his characteristic charm and the rest of the team got the message: Follow the rules!" Jacobs frequently ends meetings with morale-boosting exercises. One favorite technique involves going around the room and asking each person, "Whose star went up in your eyes during the meeting, and why?" These moments of recognition create a positive atmosphere that strengthens team bonds and ensures people leave feeling energized rather than drained.

Chapter 6: Creating a Unified Culture: How to Outperform Competition

Inside Brad Jacobs's home in Connecticut sits a bronze sculpture called Large, Sad Sphere—a humanoid figure slouched over in apparent sadness with a small cube sitting atop its perfectly spherical head. Jacobs interprets it as a kid who's sad because he's thinking inside a box, illustrating how limited thinking restricts possibilities. This visual metaphor captures a fundamental truth about organizational culture: companies that think differently outperform those that follow conventional wisdom. At XPO, Jacobs fostered a culture where over 100,000 employees worked together under the banner #WeAreXPO. This unified approach contributed to XPO becoming the seventh best-performing stock in the Fortune 500 over a decade, and being named one of America's Best Large Employers by Forbes. "I can't think of anything more gratifying than creating an environment where people can't wait to spend the day with their team," Jacobs reflects. The power of collaborative culture is illustrated by Jacobs's reference to The Superorganism by Bert Hölldobler and Edward O. Wilson, which describes how social insects function in highly developed team structures. Ant colonies, for example, operate as a single, coherent entity more powerful than the sum of its members. These superorganisms demonstrate extraordinary communication, with ants interacting through multiple channels including pheromones, movement, touch, and sound. This enables sophisticated division of labor that elevates each member's performance. Jacobs applies this superorganism concept to corporate culture while recognizing a crucial difference: "The idea of a company unified like an ant superorganism is a cool concept—but, at the same time, people are unique, and a culture that unifies a group must also make space for individualism." Communication forms the foundation of this balanced culture. "I'm a big advocate of communication in all its forms," Jacobs states. "It makes it possible for me to convey my vision to employees in ways that can inspire them, like a rallying cry." During his CEO tenure, Jacobs maintained multiple channels of engagement: emails, social media, site visits, town halls, phone calls, and video chats. He regularly held onscreen meetings with frontline employees like truck drivers, maintaining a consistent cadence to reinforce openness. The board of directors receives the same transparent treatment. "The boards of each of my companies performed their duties well, and continue to do so under my successor CEOs, in part because information is shared so freely with them," Jacobs explains. Unlike many companies that restrict board-executive interaction, Jacobs gives directors full access to the organization: "If a director wants to speak to someone, they pick up the phone and call them." Equally important is listening—the more challenging dimension of communication. Jacobs creates direct listening channels for employees to contact him, sharing his phone number and email address. "Opening up a listening channel at the top of the company can be a powerful way to signal that leadership values the free flow of ideas and information," he notes. He recounts how an employee once emailed about a facility roof that had been leaking for two months due to bureaucratic delays. The quick resolution validated that employee feedback wasn't falling into a black hole. XPO's all-employee survey exemplifies this feedback approach, asking straightforward questions: Are employees happy in their jobs? How can we fix the situation for those who aren't? What's your single best idea to improve our company? What's the stupidest thing we're doing as a company? Senior management reads every response—tens of thousands—within ten days, and shares summaries of both favorable and unfavorable results with all employees. "Most companies wouldn't dream of making internal survey results available to the full workforce," Jacobs acknowledges. "But our attitude is that criticism from employees isn't dirty laundry—it's gold." This culture of open communication extends to customers through collaborative feedback loops. At United Rentals, these loops enabled the company to conduct free equipment utilization audits for customers, sometimes even advising them to buy rather than rent certain machines based on their usage patterns. "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," Jacobs concludes.

Chapter 7: The Entrepreneurial Spirit: Taking Pride in Value Creation

Steve, the HVAC technician who services Brad Jacobs's Connecticut home, once showed up on a Sunday during a heat wave when the air conditioning failed. As Steve worked, he shared how he had left a large HVAC company after it was sold to private equity and its service quality deteriorated. "There's no pride in their service," Steve explained. "They're giving the industry a bad name around here." This conversation revealed what Jacobs considers the essence of entrepreneurial spirit. Steve embodies the qualities that drive business success: he takes pride in his work, prioritizes customer satisfaction, and isn't embarrassed about making money to support his family. "He's a hardworking, take-pride-in-your-work entrepreneur who puts his customers first," Jacobs observes. "He cares a great deal about doing his job the way it should be done." This spirit has been the common thread through all of Jacobs's ventures. At United Waste Systems, his team pursued profit in a fragmented industry disrupted by regulatory changes. They improved America's cleanliness while giving hundreds of small business owners lucrative exit options. With United Rentals, they created efficiencies in construction logistics, improved worker safety with well-maintained equipment, and reduced environmental impact by optimizing equipment utilization. XPO and its spin-offs invested heavily in technology that made trucks more efficient and improved supply chain management—essential services that enhance quality of life. Jacobs recalls an email from a hedge fund owner who had liquidated his XPO position with a $500 million profit. The fund manager pointed out that most of that extraordinary return went to ordinary people participating in pension plans and endowment programs. "Reading his letter, I was extremely proud that our company could be counted on to create that value," Jacobs writes. "This is only possible because we operate in free markets where creating prosperity is a virtue." The entrepreneurial mindset involves both ambition and execution. Jacobs shares a formative experience from his youth at the Rhode Island Governor's School for the Gifted in Art and Music. On the first night, a program leader challenged the students: "This is an opportunity to go deep on a project and do the best work you've ever done—but you have to decide if you want it." This speech gave Jacobs a powerful insight: "We have it in our own hands to either make life meaningful or just pass time until we die." This philosophy has guided Jacobs throughout his career. He prioritizes his family, his understanding of life, and his work, dedicating most of his time to these pursuits. While his business success creates positive societal impacts like job creation and charitable partnerships, he ranks family and life experience slightly higher in importance. For Jacobs, entrepreneurship isn't just about wealth accumulation—it's about the satisfaction of materializing big concepts and creating value that benefits many. "I love being a CEO," he reflects. "For me, the motivation is less about the accumulation of wealth and more about the satisfaction of materializing a big concept. There's a joy in creating value, and an even greater joy in knowing that so many people beyond our organization are benefitting from our accomplishments."

Summary

The true secret to building billion-dollar enterprises isn't found in perfect execution or supernatural talent, but in mastering fundamental principles while maintaining an entrepreneurial mindset that values both excellence and profit. At its core, extraordinary success requires rearranging your brain to think expansively, spotting trends before others, executing strategic acquisitions, building superstar teams, fostering electric communication, and creating unified cultures where people thrive together. Begin by practicing thought experiments that expand your perspective beyond immediate concerns. Train yourself to reject automatic negative thoughts and replace them with radical acceptance of reality as it is. When evaluating opportunities, invest the time to become deeply knowledgeable about industry trends—particularly how technology might transform the landscape. Build your organization with people who possess not just skills but intelligence, hunger, integrity, and collegiality. Create environments where open communication flourishes and meetings generate real solutions rather than boredom. Above all, remember that the entrepreneurial spirit is about taking pride in both the value you create and the journey itself—finding meaning in building something that benefits not just yourself, but countless others whose lives are touched by your enterprise.

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Brad Jacobs

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