Donald Trump Is Expertly Playing the CEO Card

January 26, 2016, 4:55 PM UTC
Donald Trump Attends The 16th Annual Outdoor Sportsman Awards
LAS VEGAS, NV - JANUARY 21: Republican presidential candidate Donald Trump speaks during the Outdoor Channel and Sportsman Channel's 16th annual Outdoor Sportsman Awards at The Venetian Las Vegas during the 2016 National Shooting Sports Foundation's Shooting, Hunting, Outdoor Trade (SHOT) Show on January 21, 2016 in Las Vegas, Nevada. The SHOT Show, the world's largest annual trade show for shooting, hunting and law enforcement professionals, runs through January 23 and features 1,600 exhibitors showing off their latest products and services to more than 62,000 attendees. (Photo by Ethan Miller/Getty Images)
Photograph by Ethan Miller—Getty Images

Elective politics may not exclusively be a rich person’s game. But most people who pursue politics are well-off, or aspire to be. And so they have to arrange their affairs so that they can pursue power while maintaining the type of lifestyle that well-educated executives and their children have come to expect. In this presidential campaign season, the dozen-odd serious candidates present an array of choices. Last week, a Fortune article detailed what might be called the “Wives of Wall Street” model, used by New Jersey Governor Chris Christie and Texas Senator Ted Cruz.

Here we analyze the “Megabucks CEO” model, used by billionaire developer Donald Trump and former Hewlett-Packard CEO Carly Fiorina. Despite their obvious disdain for each other — Fiorina recently called Trump the “Kim Kardashian of politics” — the two have much in common. Both have little or no experience in electoral politics but extensive resumes in highly public private-sector businesses. Their success in the business world has given them two key attributes: fame and fortune. The fame gives them vital name recognition in a crowded field. And the fortune gives them the capacity to be financially independent and fund their own campaigns.

Most significantly, their background allows them to make the argument that a company executive is best equipped to serve as the nation’s chief executive. For one of them, this model has worked brilliantly.


Key position: CEO of the Trump Organization, 1970s-Present

Private-sector accomplishments: A real estate developer, Trump turned his inherited fortune, based on middle-class housing, into gold-plated empire of high-end condominiums and office towers, casinos, and golf clubs. Branding genius amplified the value of his properties, and his brand, through best-selling books, a long-running prime time television show, The Apprentice, and merchandising.

Estimated net worth: $8.7 billion (according to Trump’s campaign); $4.5 billion (Forbes estimate).

How he uses it: Trump’s wealth, and his status as a one-man operation – he has no board of directors or public shareholders – has afforded him the freedom. It’s also given him an impressive plane (a Boeing 757 he bought from Microsoft co-founder Paul Allen) that he uses to barnstorm the country. He also deploys it as a sort of shock and awe – wowing middle-Americans with his phenomenal wealth and offering helicopter rides to kids in crucial caucus state Iowa. A self-professed self-funding candidate, Trump doesn’t spend any time attending fundraising with lobbyists and fellow fat cats. However, as of November, he had spent about $2 million of his own cash and received $4 million in contributions. This freedom has allowed him to take positions that are popular with segments of the electorate but anathema to the donor class – on free trade and immigration, for example.

Translating business into politics: Trump’s argument for the presidency is made in broad strokes, and it is explicitly linked to his experience in business. It’s the Art of the Deal writ large. He will “make America great again!” He will solve immigration and porous border by using his developers’ skills to build a “great, great wall” along the Mexico border, which, he insists, Mexico will pay for. “Nobody builds walls better than me,” he said. And he will deploy his superior negotiating expertise – honed over decades of real-estate wheeler-dealing, to get what America wants from Iran, from China and Japan, and from Congress. Politics and policy are no different than a high-end condo deal.

And it’s working for him. Polls now show the Republican rank-and-file regard him highly as a prospective boss. The latest CNN poll shows a whopping 41% of GOP voters regard him as their first choice, while 63% see him as the one most likely to win in November.

Achilles heel: In the polls, Donald Trump enjoys GOP frontrunner status. But not all of Trump’s endeavors have been equally huge or classy. And Trump’s long road to success has been filled with potholes. The man who wants to be the steward of the nation’s capital hasn’t always treated other people’s money with the respect it deserves. In the early 1990s, banks had to write down hundreds of millions of debt they had extended to Trump and his companies. Casino companies bearing his name have gone bankrupt several times.

Donald Trump
Trump in his office in Trump Tower, Fifth Avenue, New York, 1999.Photography by Michael Brennan Getty Images
Photography by Michael Brennan Getty Images


Key positions: president, Lucent Global Service Provider division (late 1990s), CEO of Hewlett-Packard (HPE) (1999-2005)

Private-sector accomplishments: Self-made telecommunications sales ace climbed the ladder at AT&T as the industry boomed. In 1995, she was tapped to lead spin-off of networking unit Lucent Technologies. Dubbed Fortune’s Most Powerful Woman in Business in 1998, she ultimately achieved the sort of mononym status in the 1990s held only by other icons: Madonna, Hillary, Beyonce. Shattered glass ceiling when named CEO of Hewlett-Packard in 1999, the first woman to run the Silicon Valley giant and a component of the Dow Jones industrial Average. At H-P, made unpopular decisions, doubling down on the PC by buying Compaq in controversial $25 billion in deal in 2001, the biggest tech merger at the time. In ensuing years, she cut 30,000 jobs in tough restructuring and was booted out amid boardroom brawl in early 2005.

Estimated net worth: $59 million

How she uses it: Liberated from having to seek full-time employment, she has continually dipped her foot into the political-media waters. A surrogate for John McCain in 2008, she then ran for Senate in California (unsuccessfully) in 2010, managing to outraise victor (and incumbent) Barbara Boxer, by $21.5 million to $18.9 million. Fiorina spent $5.5 million of her own money on that race. She continued to travel the country and speak as campaign surrogate before formally declaring her candidacy last May. For this campaign, she has pursued small-dollar donors. In the second and third quarters of 2015, she raised a combined $8.8 million.

Carly Fiorina, CEO and president of Hewlett-Packar
Carly Fiorina, as CEO and president of Hewlett-Packard, unveiling a new logo in 1999Photography by JEFF CHRISTENSEN AFP/Getty Images
Photography by JEFF CHRISTENSEN AFP/Getty Images

Translating business into politics: Fiorina combines social conservatism (not discussed with the media during her corporate career), with conventional Chamber of Commerce business policy. Her selling point isn’t simply that she’s a female in a field (and party) generally dominated by men, but that she has succeeded in the world’s most competitive arena: American business. “My story, from secretary to CEO, is only possible in this nation, and proves that every one of us has potential.”

Achilles heel: While running a huge company is a remarkable achievement for a person of any gender, Fiorina’s reign at H-P was controversial and not particularly successful. The stock fell in half during her tenure, a period in which the S&P 500 fell only 7 percent. The company shed thousands of jobs. As an anonymous tech CEO put it: “She was a value destruction machine with near zero cultural sensitivity.” And her failure to pay some 2010 campaign staff has further undermined her aura of competent management. After a brief surge in the polls, Carly Fiorina’s numbers have dropped. The most recent Fox News poll found her in sixth place among Republican candidates.

In the weeks to come, Fortune will explore the other models used by the presidential candidates.

Daniel Gross’ most recent book is Better, Stronger, Faster.