This week as Donald Trump was crowned the Republican presidential nominee, a ghost from his past also emerged into the spotlight. In a profile for the New Yorker, Tony Schwartz, the ghostwriter for his 1987 book The Art of the Deal, expressed regret over co-creating a mythical Donald Trump. The depiction spawned a reality TV show, The Apprentice, which made Trump a household name and painted him as an embodiment of the American Dream. Both the book and TV show were incidental, pivotal events that helped the real estate tycoon secure the nomination.
“Trump’s self-portrayal as a Horatio Alger figure buttressed his populist appeal in 2016,” wrote the New Yorker’s Jane Mayer. “But his origins were hardly humble.” (Trump’s father played a significant role in his success, but gets little credence in the book.)
The Art of the Deal fits a specific genre of business and self-help books—the ones that gloss over the role of privilege in success. Circumstances involving privilege are too-often treated as minor details instead of the critical factors that they are.
In his autobiography Losing My Virginity, Virgin founder Richard Branson, who was born into a distinguished British family, recounted how he was once warned by a teacher that he would either go to jail or become a millionaire. Both happened: when he went to jail for tax evasion after opening up his record store, his mother remortgaged the family home to bail young Branson out and pay the government a very expensive fine that saved him from re-arrest, trial, and more jail time.
To that end, one reader posted this review of Branson’s book on Amazon, citing Nassim Taleb’s Fooled by Randomness:
“There are several points in Branson’s story where I can’t help but think that if one of the many possible alternatives were to have taken place, he would have been wiped out in a manner that would have been difficult to recover from. Whether in reference to his ballooning adventures, or how some Virgin companies were saddled with very heavy debt, one can’t help but wonder how much his success (and current good health) are owed to luck.”
Had Branson’s genetic traits also been different (like Trump, Branson is fair-skinned and blond), it’s hard to know where he would be today.
Luck played a similar role for American multimillionaire Ryan Blair, whose book is titled Nothing to Lose, Everything to Gain. A former gang member, he would likely have spent his life in and out of jail if not for his mother’s eventual relationship with a real estate entrepreneur. Instead, Blair found success and admiration.
Quartz’s Gideon Lichfield captured the sort of randomness described by Taleb in his analysis of two wunderkinds: Martin Shkreli, the biotech entrepreneur indicted for securities fraud, and George Hotz, who was the first to jailbreak Apple’s iPhone. “It might not have taken much—a slight difference in character, a chance encounter with right or wrong person—to switch their roles of hero and villain,” wrote Lichfield.
Accounting for such randomness, it’s surprising how many business and self-help books are taken at face value. Many entrepreneur autobiographies are more an aggrandizement of the sort of lifestyle that privilege affords than how-to guides for the masses. Literary agent Ted Weinstein put it well when he commented that the pinnacle of Silicon Valley’s Maslow hierarchy of needs (above “Quit job, travel the world” and “Medium blog post with life advice for others”) is a book deal.
Many profiles are premature; more accurately the books are marketing vehicles veiled as autobiography. For example, when the Gilt Groupe co-founders Alexis Maybank and Alexandra Wilkis Wilson published By Invitation Only in 2012, their luxury flash sales site was valued at more than $1 billion; the company sold for a fraction of the amount this year. In their book, the young Gilt co-founders recount how attending Harvard (the birth place of many startups) played an integral role in founding their company, which is now deemed a cautionary unicorn tale.
Miki Agrawal, also an Ivy League graduate who is best known for her underwear line THINX, wrote about her entrepreneurial journey in Do Cool Sh*t. Copies of her book lined the window sills of her new gluten-free pizza restaurant in downtown Las Vegas when it opened in 2013, coinciding with her book release. In his foreward to her book, investor Zappos CEO Tony Hsieh highlighted the restaurant as an integral part of his downtown revitalization efforts. A few months later and with little fanfare, the restaurant quietly closed.
One Amazon reviewer described Agrawal’s book as misleading but informative:
“It should also be noted that this book is similar to others of its kind, in that it is written by an Ivy League graduate in NYC who likely has more access to wealthy connections that the average person. Much of what I have read in this book simply did not apply to my situation. I have to imagine this sentiment will resound with many who read this book and don’t have the access to capital that she does.”
As with politics, the publishing industry is not a meritocracy. Bestselling author Tim Ferriss of 4-Hour Workweek fame—and also an Ivy League graduate—has shared that he knows many CEOs who have bought their way onto the bestseller lists. Among those is Hsieh, who hired marketing consultancy ResultSource to ensure the success of his 2010 autobiography Delivering Happiness. He also is known to place large orders for books published by entrepreneurs who contribute to his Downtown Project (one example is digital strategist Amy Jo Martin’s Renegades Write The Rules; her startup Digital Royalty shut down last year).
In the marketplace of ideas, those with the most exposure win. That’s why, in spring 2009, Hsieh appeared on The Apprentice with Trump. The Wall Street Journal described the collaboration this way:
“Donald Trump is known for many things: his cotton-candy hairdo, his ostentatious lifestyle and an ego the size of New York City. But in the business world he’s also known for his eccentricity, unconventional management style and bold marketing practices, qualities that have made him one of the richest men in the world. So it perhaps makes sense that Trump recently made Zappos.com Inc. the subject of a business competition on his reality television show, The Celebrity Apprentice.”
Delivering Happiness includes an excerpt Hsieh wrote about networking for Ivanka Trump’s 2010 book, The Trump Card. With that book title, at least she owned her privilege.