Billion Dollar Loser is Reeves Wiedeman’s account of a master manipulator of the easily manipulated who rose to fame and financial success due primarily—if not entirely—on the basis of garish self-promotion, intensive self-marketing and a seemingly unshakeable belief in his own genius despite all evidence pointing to something closer to an absolute absence of even above-average intelligence. No, it is not a biography of Donald J. Trump, but at the time of its publication it immediately became the definitive book about the Trump theory of the acquisition of wealth that was not actually about him.
The parallels run deep and paint a disturbing portrait of just how easily bamboozled people who should know better about handing over large sums of money really are. In fact, the primary lesson to be learned from Billion Dollar Loser is not really limited to just the nominal subject of the book himself—notorious co-founder of WeWork, Adam Neumann—but is about the system that allowed this particular narrative to track down the path it did. That track takes WeWork from head-spinning financial rise to death-defying economic collapse. The lesson that is to be gained for budding entrepreneurs is simple and inspiring while at the same complicated and depressing.
The manner by which Neumann rose to the dizzying heights of potentially great wealth is grounded in much of the same territory covered by a factual biography of Trump: make up stuff as needed, manipulate the system for borrowing money, and—most importantly—determine what any potential investor is actually seeking and convince them that is what you are planning, regardless of whether what they want has any relation whatever to what you are planning. All of this would be perfectly disposable insight if the book indicated that people like Neumann and Trump were the exception rather than the rule in the way that business works in America.
The message is, of course, exactly the opposite. The story that the author paints through a series of extensive and detailed interviews with a vast number of subjects with first-hand inside knowledge of the whole sordid story of WeWork’s rise and fall is relentlessly depressing not merely because it implicates the strategy of unending deception as the essential co-efficient in the calculus of enjoying wealth in America, but because that deception is perpetrated upon people who consistently position themselves as among the best and the brightest. Many of those who contributed to the rise of WeWork despite a significant lack of evidence that its business model could possibly be sustainable past the short term are also those representative of the idea that “Ivy League education” automatically translates into being smart.
What Billion Dollar Loser ultimately reveals—becoming just the latest in a long line of non-fiction books to do so—is the myth of American success. What does one learn about these widely-held ingrained myths of America by reading this story? Ivy League schools do not automatically confer a better education than other universities. There is no detectable correlation between becoming wealthy and intellectual superiority. Financial success in the business world is not determined entirely on the basis rational application of predictive modeling. The upper classes are in no way less susceptible to being ripped off by charlatans, grifters and con men than the lower classes they look down upon as genetically ignorant. The single most important asset when it comes to turning an idea into a successful business is not having a great idea, but having “connection to capital.”
By the last page, the image of achieving business success in America that one is left with after reading the parable of WeWork and Neumann brings to mind nothing more than a classic comedy routine by Steve Martin from the 1970’s. The routine offers advice on how anyone in America can become a millionaire and never pay a dime in taxes. The secret essential first step to making this desire a reality? “First, get a million dollars.”
