Mark: Imagine your company’s stock is in freefall. A vicious short-seller report just wiped out 26% of its value in a single day. Your advisors are panicking. The market is screaming "sell." What do you do? Well, if you're Brad Jacobs, you don't just weather the storm. You look at the chaos, see an opportunity nobody else does, and make a decision that nets your company a four-billion-dollar profit. Michelle: That’s not just a good business move, Mark; it’s a fundamentally different way of thinking. And that’s the heart of the book we’re diving into today, "How to Make a Few Billion Dollars" by serial entrepreneur Brad Jacobs. He’s started seven billion-dollar companies, and his core argument is that building something massive isn't about a secret formula you can copy, but about rewiring your own brain to operate on a different level. Mark: Exactly. And he’s refreshingly candid about it. He opens the book by saying, "I have made every possible mistake in business... and yet my teams and I have managed to create tens of billions of dollars of value." That "and yet" is what we're exploring. Today we'll dive deep into this from two perspectives. First, we'll explore that inner game: how to 'rearrange your brain' to turn crises into these massive opportunities. Michelle: Then, we'll shift to the outer game: the art of getting the 'big trend right.' It’s a fascinating idea he picked up from a mentor, that this single skill can forgive almost any other business mistake you make along the way. It’s a powerful one-two punch of mindset and market insight.

Michelle: So, Mark, let's go right back to that story because it’s so potent. A 26% stock drop in one day. Most CEOs would be in full-on damage control mode—press releases, frantic calls, a defensive crouch. What does Jacobs mean by 'rearranging your brain' in a moment like that? How does that actually manifest? Mark: It manifests as a complete rejection of conventional thinking. The book describes the scene: this short report comes out in 2018, he says it’s "packed with a lot of baloney," but the market doesn't care. It reacts first and analyzes later. The stock is in an absolute nosedive. His team's first move is fascinating. He says, "We concentrated on the situation at hand without judging what had happened to us." There was no time wasted on "this isn't fair" or "how could they do this?" Michelle: That’s a critical distinction. It’s not about suppressing emotion, but about preventing emotion from blurring judgment. He’s talking about a concept from psychology called Radical Acceptance. It doesn't mean you approve of what happened, but you accept the facts on the ground without resistance. The wish was for the stock not to have crashed. The reality was, it had. And fighting reality is always a losing battle. Mark: Precisely. So they accept the new reality. Then, they spend hours methodically going through the report, not for an emotional rebuttal, but to identify every distortion, every twisted piece of data. And in that process of calm, objective analysis, the rearranged brain spots the opportunity. He realizes the short-seller crisis has made his own company's stock absurdly cheap. He says they saw the new share price not as a disaster, but as "mana from heaven." Michelle: Mana from heaven! Most people would see it as poison from hell. That is a rearranged brain in action. It’s a complete cognitive reframe. Mark: And it leads to this audacious move. His team decides to buy back two billion dollars' worth of their own stock. His bankers and advisors are freaking out. They tell him, "No one's ever done this. It's too high a percentage of your market cap." And Jacobs's response is pure first-principles thinking. He basically says, "So what? Just because we're the first doesn't mean it's a bad idea." He saw it as a once-in-a-lifetime opportunity. Michelle: And the result of that thinking? Mark: The result is staggering. A couple of years later, those two billion dollars of shares they bought back were worth six billion dollars. A four-billion-dollar profit born directly from a crisis, all because they refused to react conventionally. Michelle: It’s like a martial artist using an opponent's momentum against them. The short-seller threw all this negative force at the company, and instead of trying to block it head-on, Jacobs just stepped aside, let the force create an imbalance—a cheap stock price—and then used that imbalance to his own massive advantage. Mark: And this mindset wasn't a one-off. It was trained. He tells another story about his most important mentor, a legendary commodity trader named Ludwig Jesselson. When Jacobs was in his twenties, he was having lunch with him, complaining about all his business problems. Jesselson stops him and says something that changed his life: "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." Michelle: That redefines the entire job description of an entrepreneur. You're not a manager who occasionally deals with problems. You are a professional problem-solver. The problems aren't an interruption of your work; they are your work. I've heard this echoed by other great founders. They get excited by waste and inefficiency because they see it as pure, untapped potential for improvement. Mark: Exactly. Jacobs says he learned in that moment that "problems are an asset, not something to avoid, but something to run towards." So when the short-seller attack happened decades later, his brain was already wired to see the problem—the crashed stock—as an asset. Michelle: So, 'rearranging your brain' isn't some fuzzy, feel-good mantra. It’s a pragmatic, offensive strategy. It’s about, one, practicing radical acceptance to see the world as it is. Two, reframing negative events and thoughts as useful data. And three, viewing problems not as roadblocks, but as the very raw material from which you create value. It’s the engine room of everything else he accomplishes.

Mark: And that ability to see problems as opportunities is completely useless if you're pointed in the wrong direction. This brings us to his second huge idea, which came from that same mentor, Mr. Jesselson. He 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." Michelle: I love that idea because it implies a hierarchy of importance in business. Not all decisions are created equal. Getting the big picture right provides a tailwind so strong it can cover for a multitude of smaller operational sins. This is about separating the signal from the noise. Jacobs is obsessive about this. He's not just looking at what's hot; he's looking for fundamental, structural shifts in how an industry works. Mark: His process for this is insane. Before entering an industry, he reads everything: trade journals, financial reports, employee reviews. He attends conferences, talks to CEOs, investment bankers, venture capitalists, journalists—anyone who lives and breathes that world. He's trying to build a 360-degree map of the territory before he takes a single step. Michelle: It’s about knowing more than anyone else. The good ones just do more research. They put in the work. Mark: And his first company, Amerex Oil, is a perfect example of this in a pre-digital world. He starts this oil brokerage in 1979. To understand how brilliant this was, you have to picture the era. There’s no internet, no email, no Bloomberg terminal on every desk. He says the main source of information on the price of oil was a newsletter that came in the mail. Michelle: In the mail! For an industry doing deals worth tens of millions of dollars over the phone. That’s an almost comical level of information lag. Mark: It's completely wild. He describes making handshake deals for $75 million with clients in Europe and Asia with nothing on paper for days. He saw the core problem immediately: there were, in his words, "isolated pockets of valuable oil pricing data trapped all over the globe." The big, underlying trend wasn't "computers" or "software." The trend was the fundamental need to capture and share information more quickly. Michelle: The technology is just the tool to ride the trend. The trend itself is the human or business need. That's a key insight. Mark: So what does he do? There's no off-the-shelf solution. He builds his own. He sets up a proprietary IT system with these giant, appliance-sized computers and green-screen terminals in his offices in New York, London, and Houston. Every time a broker learned something—a price, a buyer's interest, a seller's activity—they entered it into the database. This allowed them to share information across the globe in hours, not days. Michelle: In that environment, hours versus days is the difference between seeing the future and reading about the past. He essentially created a private, real-time information market while his competitors were waiting for the postman. Mark: He created an information arbitrage. And it made them a fortune. He applies this same pattern recognition over and over. In the 1980s, he gets into waste management. What's the trend? Not just trash. It's two things: landfill capacity is becoming precious due to new regulations, and mom-and-pop haulers are running their routes by the seat of their pants. So he capitalizes on it with tech-based truck routing. He says they could do the same work with 20 trucks in three days that used to take 50 trucks five days. The profit margins exploded. Michelle: Again, the trend isn't the software itself. The trend is the opportunity created by inefficiency. He's a master at spotting these structural weaknesses. Mark: But my favorite example is from United Rentals in the 90s. He's rolling up the equipment rental industry, which was slow to computerize. He discovers that almost all of the larger regional players are running their businesses on software from one company, a company called Wynne Systems. So what does he do? Michelle: Let me guess. He doesn't compete with them. He buys the software company. Mark: He buys the software company! It's a genius move. He says it accomplished two things. First, they got an industry-best platform for their own use. But second, and this is the god-mode part, the acquisition gave them access to aggregated, anonymized data on macro trends across the entire industry. He could see equipment gluts or shortages forming before anyone else. Michelle: He bought the industry's dashboard. He wasn't just playing the game; he was watching everyone else's cards. Mark: And here’s the killer quote from the book: "We could now proactively adjust our pricing and asset management while the rest of the industry was being reactive." And this is where the two core ideas of the book merge so beautifully. Michelle: Exactly. You need the rearranged brain—the courage, the non-conventional thinking, the willingness to make a move that seems strange, like buying a software company instead of more rental yards—to actually act on the trend you've identified. Anyone could have looked at the oil industry and said, "Wow, this is slow." But it took a certain mindset to build a solution from scratch and bet the farm on it. The mindset gives you the clarity to spot the trend and the courage to capitalize on it.

Mark: So when you boil it all down, you have these two powerful, interconnected engines driving his success. There's the internal one—your mindset—that allows you to stay calm, see opportunities in what others view as chaos, and actively run towards problems. Michelle: And then there's the external one—your obsessive research and analysis—that helps you identify the big wave, the mega-trend, that you need to be riding. One without the other is incomplete. Mark: It's true. You can have the most resilient, positive mindset in the world, but if you're passionately selling horse-drawn buggies in 1920, that tailwind of history is going to be a headwind, and it will crush you. Michelle: And conversely, you can be a brilliant analyst who sees the future with perfect clarity, but if you're paralyzed by fear or conventional thinking, you're just a spectator. You'll be the person in 20 years saying, "I knew that was going to be big," while someone else is reaping the rewards. It’s the combination of seeing and doing that creates the magic. Mark: It really leaves you with a powerful question from the book. As part of his feedback loop, Jacobs asks his team, "What's the stupidest thing we're doing as a company?" It's a fantastic question, designed to cut through politeness and expose flawed assumptions. Michelle: And it’s a great question to ask ourselves, not just in business, but in our own lives. What's the "stupidest" assumption we're holding onto? What's the one problem we keep avoiding, that if we just turned and ran towards it, might actually hold our biggest opportunity for growth? Mark: That’s the challenge. It’s not about finding a secret formula, but about having the courage to rearrange your own thinking and then relentlessly seeking the truth about the world around you. And if you can do that, as Brad Jacobs has shown, the results can be extraordinary.