Trump has a different leadership style David Rubenstein plays it by the book

Martin Pengelly


The billionaire philanthropist has published How to Lead, a selection of interviews with famous figures. Does he think the US needs a change of leader?

David Rubenstein’s first book of interviews featured leading historians and was called The American Story. Its sequel, focusing on business, politics, the military, the arts and sports, could easily have been called These American Stories. In fact it’s called How to Lead, but the billionaire investor and philanthropist has produced a collection of only-in-America tales.
His aim, he says, “is to kind of give the story about how certain people became leaders, and hopefully inspire younger people to maybe improve their own leadership skills”.


Presidents Bill Clinton and George W Bush are in there; the House speaker, Nancy Pelosi, is in there; so is Ruth Bader Ginsburg, supreme court justice and talisman to liberals everywhere. Jeff Bezos speaks, as do Bill Gates, Warren Buffett and Phil Knight, the man who founded Nike. Yo-Yo Ma shares his story, as do Jack Nicklaus and Mike “Coach K” Kryzyzewski, a giant of college basketball at Duke, Rubenstein’s alma mater.


One common thread is that like Rubenstein, who co-founded the Carlyle Group and is worth around $3bn, most of the interviewees did not come from money.


“As a general rule of thumb,” Rubenstein says, “certainly in western democracies over the last 100 years or maybe 200 years or so, [leaders] tend to rise up, to not come from extremely privileged backgrounds. There are some exceptions, obviously – President Kennedy, FDR – but generally you get more Harry Truman figures and the same is particularly true in the sciences, particularly true in the arts, and certainly true in the military and so forth.


“Growing up in a family with wealth has its benefits [but] you may not have to have all the qualities of a young person scrambling to kind of make a name for yourself.”


Rubenstein has signed the Giving Pledge, which means most of his wealth will not stay in his family. In his introduction to How to Lead, he sketches out how he won it: a career which began in the law, took in the Carter White House, then took off in private equity. But he’s evidently proud his father worked for the US Postal Service in Baltimore – as did he, in the summer while a student.


“My father didn’t graduate from high school, he went to world war two and never took advantage of the GI Bill or anything like that, so he had a blue-collar job … I didn’t feel terrible about it at the time. I recognised that I wasn’t from a wealthy family but in the end, the kids that I knew were from wealthy families, I can’t say they were necessarily happier than I was able to be.”
As it happens, Rubenstein shares a connection to the postal service with Robert F Smith, an investor who memorably paid the debts of a whole class at Howard University. In their interview, Smith tells Rubenstein his grandfather was postmaster for three post offices around Washington DC.


The USPS is in the news in Washington now. The postmaster general, Louis DeJoy, a Republican donor, seemingly mandated to damage the system before an election set to feature unprecedented voting by mail. How does Rubenstein feel about that?


“Well, I’m going to interview the postmaster general at the Economic Club of Washington in the next two or three weeks.”


Such are the circles he moves in – with care. DeJoy has justified the changes, among them ending overtime and removing sorting machines, as ways to improve cost efficiency. Rubenstein observes that the mail “is really a service not a business, so it’s hard to kind of compare the effects”. Otherwise, we’ll have to wait for the interview, most likely broadcast on Bloomberg or PBS.


How to Lead is not without its awkward questions. Colin Powell and Condoleezza Rice discuss the flawed case for war in Iraq. But George W Bush doesn’t and in other cases, such as that of David Petraeus, the general who resigned as CIA director over an affair with his biographer, the more painful parts of being a leader can remain untouched.
“I’m not a journalist,” Rubenstein says. “My job is not to ask questions that might embarrass somebody … people can judge whether that’s a good or bad thing.


“The people that I interview are people that I have known, generally, for a reasonably long time. So the appeal of it is they feel comfortable with me, and they might be willing to say some things they might not to a professional journalist. And here’s the cost of that: I won’t ask the embarrassing questions, because they won’t expect it from me.


“It’s not as if what you just cited [about Petraeus] is something that people don’t know about. But what I’m trying to focus on is, you know, David Petraeus who came from a relatively modest background. His father was in the Dutch merchant marine, he worked his way up and obviously had some good fortune but he came close to dying twice.


“Colin Powell. Think about what he saw growing up, the segregation in the south. You know, he can’t go get a hamburger in certain places and [he becomes] an American hero.”


It’s true that Rubenstein puts his subjects at ease – so much so that often, as in the case of the secretary of state, Mike Pompeo, and a remark that came to seem very telling after Donald Trump was impeached, they offer real insight.


‘History will judge’
Rubenstein asks Powell, a general and secretary of state, about his flirtation with running for president. He also asks Oprah Winfrey if she has thought about the White House, a question also pitched at Tim Cook of Apple, Bezos of Amazon and more.
Of course, non-politicians running for office is no longer an outlandish idea. Trump, a non-politician fighting for re-election, looms over Rubenstein’s book.


Billionaire interviewed billionaire before Trump set his sights on the Oval Office. Rubenstein was one of a stream of visitors to the president-elect during the transition four years ago. He says he’d like to talk again.


“I did ask him if he would let me interview him at the Economic Club of Washington DC, which is the format I used before. He said he would do it but then events overtook us and we never got it done. Between now and the election, probably not going to happen. But one way or the other, I wouldn’t rule it out. I’d like to do it.”


After four years of Trump, amid partisan divide, pandemic and a national reckoning on race, many who read How to Lead – a majority, if the polls are right – will think America needs a change of leader.


When we talked for The American Story, Rubenstein said it was too early to pass judgment on Trump, because “despite some of the flaws that have become evident”, the unpredictability of events meant “you can’t tell that he won’t be popular or that he won’t be successful”.


Since then, Trump has survived impeachment and presided over a chaotic response to the coronavirus pandemic in which more than 6 million have been infected and nearly 200,000 have died. His popularity remains stubbornly low.


“I think history will judge Trump better or worse depending on whether he gets re-elected,” Rubenstein says, informed by his experience working for Jimmy Carter, “who could not believe that he could possibly lose to Ronald Reagan” in 1980, then did.


“If [Trump] does get re-elected, despite all the challenges that he had, people will say, ‘Well, he actually managed to figure out how to be a leader of enough people to get elected.’ But if he loses the election …


“I suspect he may have a different view on it. He has a different leadership style than many people in the book, but he obviously has a leadership style that appeals to a number of people.”


Surely Trump’s response to Covid-19 could be called a failure to lead?


“It’s hard for me to know. Who has been a great leader in dealing with this situation? And I don’t think there are any easy answers. I wish we didn’t have as many people dying. No people dying. But it’s hard to know whether anybody [could have] prevented completely the loss of life. And probably it’s not possible.”
How to Lead does contain passages that resonate strongly as the election draws near. Speaking to Ginsburg, Rubenstein asks what she thinks “is the biggest threat to our democracy”.


“A public that doesn’t care about preserving the rights we have,” the justice says, in an interview from last September. “In a great speech on liberty, renowned judge Learned Hand said, ‘If the fire dies in the hearts of the people, no constitution and no judge can restore it.’ My faith is in the spirit of liberty.”


Rubenstein has used his billions to restore memorials to Washington, Jefferson and Lincoln, to preserve copies of the Declaration of Independence, the Magna Carta and more. Proceeds from How to Lead will go to the Johns Hopkins Children’s Center. You sense he shares Ginsburg’s faith.


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