How to Make a Few Billion Dollars

“Problems are an asset—not something to avoid but something to run toward.”

“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. It’s actually about finding problems, embracing and even enjoying them—because each problem is an opportunity to remove an obstacle and get closer to success”

“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.”

“When using this technique, it’s important to refrain from projecting bias onto the subject of your concentration. If you choose to focus your attention on a person, don’t rush to judge that person as being good or bad. In many ways, the concepts of good and bad are just tools that our self-centered minds use to sort through sensory data. For example, a controlled fire at a comfortable distance feels warm, so your brain thinks that’s good. An uncontrolled fire that’s burning your hand hurts, so that’s bad. It’s the effect the fire has on you that makes your brain think it’s good or bad, not the simple fact that it’s a fire. Non-judgmental concentration trains your brain to realize that the people and things in your life don’t exist relative to you; they simply exist. If you can take yourself out of the equation, you’ll have a much clearer view. Uncluttered by judgmentalism, you can work more efficiently, because you won’t be as distracted, and you can think more objectively, too.”

“Problems are an asset—not something to avoid but something to run toward. Big ambitions often beget even bigger problems. If your initial reaction to a major setback is overwhelming frustration, that’s understandable, but it’s also counterproductive. Once you’re over that moment, pivot toward success: “Great! This is an opportunity for me to create a lot of value. If I can just figure out how to solve this problem, I’ll be much closer to my goal.”

“When I have negative automatic thoughts, I use a two-step process to achieve a calmer, more rational state of mind and make better business decisions. First, I acknowledge the negativity as my natural, self-critical psychology kicking in. Then I challenge the validity of that perspective because, millions of years ago, our human psyche was programmed to default to anxiety and fear as a survival mechanism. We’ve been slow to evolve. Automatic negative thoughts are a knee-jerk mental reaction to a situation that almost always can be reframed in a positive light.”

“If you stare at your hands for a few minutes, the strong brain-hand connection can trigger dissociative, trancelike experiences. My feeling-the-brain technique is similar, but instead of directing my awareness to my hands, I put it on my brain. I close my eyes and gently allow my mind to merge with its physical counterpart, the brain, to “feel” it like a tactile sensation. The effect is a spontaneous explosion of rich and unusual experiences. Often, the boundaries of my senses get mixed up and I slip into synesthesia. I might see sounds, or hear colors, or smell emotions. If I’m tired or just not in the zone, I can close my eyes and feel my brain and be instantly energized. Feeling the brain is a powerful technique that can help you rejuvenate and be more creative. I encourage you to try it and see for yourself.”

“Finally, I’ll share something that might spare you some time in rearranging your own brain. “Not beating myself up” has been a hard-learned lesson for me and those around me. I became much happier in my middle age when I stopped expecting unrealistic levels of perfection from myself and my family, my friends, and my co-workers, not to mention customers, vendors, and shareholders. The reality is that when you’re trying to make a few billion dollars, your team is likely running in multiple directions at a fast pace. Accept that some goof-ups are inevitable, and you’ll find that it’s much easier to maintain your mental equilibrium as you pursue big goals.”

“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.”

“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.”

“The question, “What was the happiest part of your day?” has a more uplifting effect than “How was your day?”

“fact that it’s a fire. Non-judgmental concentration trains your brain to realize that the people and things in your life don’t exist relative to you; they simply exist. If you can take yourself out of the equation, you’ll have a much clearer view.”

“I created XPO with a private investment in public equity (a “PIPE”) that gave me control of a logistics company with about $175 million in revenue. Its main focus was freight transportation: matching truckers with shippers, forwarding freight, and expediting urgent shipments. I felt confident we could create a business model with a major upside to earnings by applying scale and technological innovation, and we did that, building XPO into an integrated, global logistics leader.”

“Intentional daydreaming (or gedankenexperiment, mental synthesis, or whatever you want to call it) can change how we see our world, but thought experiments are not limited to genius scientists. Gifted artists, composers, and mathematicians use them for creative work or problem-solving, sometimes without realizing it. Hypnotherapists evoke vivid imaginings during trances. Yogis do it while practicing their inner exploration, and some religious orders access gedankenexperiments through contemplative prayer. Meditation has been my main hobby since I was a teenager. It’s helped me stay calm and think creatively in challenging circumstances.”

“If you resist embracing an imperfect situation today, you might lose the opportunity to capitalize on it tomorrow.”

“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.”

“Structurally, is it an industry where companies have advantages of size and economies of scale? 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. Improving the actual profitability of the business is the second-biggest lever.”

“At some point in the integration process, I tell new team members, “I’m only going to make one promise to you, and I promise this 100 percent: Despite trying my best, I’m going to mess up some things. So, give me a break, please, and give me some time to get it right. Also, feel free to tell me when I’m messing stuff up, and I’ll listen to you. We’re all on the same team now. And if we work together constructively on the basis of mutual trust, we can create something magnificent.”

“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 of dollars in lost profit.”

“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.”

“Homebuilding, for one, will benefit from AI in terms of design and marketing, but an actual physical home won’t go away anytime soon. Even if we start spending a lot of time in the metaverse, as long as we have physical bodies, we’re still going to sleep in a real bed, brush our teeth over a real sink, take a real shower, and use a real toilet. At the moment, AI appears to be more of a friend than foe to the homebuilding industry, along with staple sectors of the economy, such as clothing and food.”

“When I notice I’m feeling anxious about something, I ask myself a basic CBT question: “What’s the worst that can happen, and how would I cope with that?” Or, “If a friend had a similar worry, how would I advise them to handle it?” By putting distance between myself personally and the source of the anxiety, I can think more objectively about positive outcomes.”

“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 will be the path to do that, and how fast can we move along that path? Is the industry growing much faster than GDP so that we’ll probably generate top-line growth each year just by showing up and can build from there? 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?”