Self-made billionaire Richard Branson founded the Virgin Group back in the early 1970s, and has been able to grow his net worth to more than $5 billion. The billionaire is one of the most endearing CEOs out there, and those that have worked for one of his 400 companies generally approve of his leadership. Not everyone is a fan, however, and there’s another billionaire that’s had a long-standing rivalry with Branson, and that’s Donald Trump.


While the two have exchanged jabs since the early 2000s, Branson says that their problems actually go back to the 1990s when they met only once. It was then that one of Trump’s businesses had gone bankrupt and invited Branson to a meeting for advice “He invited me to lunch or dinner at his house,” Branson said. “I thought we would have an interesting conversation about a whole range of issues, and he just spent the whole lunch talking about five people he rung up to try to get help from…and how these people had refused to help him and how his life’s mission was going to be to destroy these people.”


Branson didn’t specify when the lunch was held, but it’s clear that it was during the early to mid part of the 1990s. This led to unease between the two billionaires, and the heat between them rekindled in 2004 when Branson’s show, “The Rebel Billionaire”, didn’t achieve success. This prompted Trump to write a personal letter to Branson.

In the letter, Trump writes that “At least your dismal ratings can now allow you to concentrate on your airline which, I am sure, needs every ounce of your energy. Like television, you should try to get out (of) the airline business too, as soon as possible! Actually, I wonder out loud how you can be anywhere close to a billionaire and be in that business. Perhaps the title of your show, The Rebel Billionaire, is misleading?”


Branson was also asked about that letter when recalling his first meeting with Trump, telling reporters that “I think (Trump) went bankrupt on four different occasions. I’m not sure I would necessarily want to do business with someone that just on and on kept going bankrupt. I don’t think he was a particularly successful business person…But look, he’s done all right and obviously he’s proved us all wrong.”

At the time, Trump had responded that “I have watched your show. I wish you came to me and asked my advice – I would have told you not to bother. You have no television persona and, as I found out with others a long time ago, if it’s not there there’s not a thing in the world you can do about it.” Trump also noted that Branson would go “down in flames” like another billionaire, Mark Cuban, supposedly did (according to Trump) after his reality series “The Benefactor” was cancelled.


Asked about the difference between “The Rebel Billionaire” and Trump’s reality series “The Apprentice”, Branson said “I think that people will find that the two things are completely and utterly different. (Trump had) a very different approach to the way we run our business. I mean, I think Donald is very much the suited man, who, you know, has his boardrooms and I think a sort of fairly 1980s approach to business. I’d like to think that we have a 21st century approach to business. I’m out and about. Never sit behind a desk.”


After “The Rebel Billionaire” had been cancelled, Trump was asked about the show and said that he never met or knew Branson, but said “I think he’s got zero personality.” However, the two had been photographed together in 2002, while Branson has the vivid story of meeting him in the 1990s. Branson decided not to attack hard on Trump, responding by saying “I have enjoyed our time we have spent together and would not denigrate you personally…Perhaps you could re-read what I have said to date and decide whether it’s worth us remaining as friends – or alternatively, you adding me to your list of enemies. It’s your call.”

During Donald Trump’s presidency, Branson hasn’t been shy about his criticism of Trump. In a blog post that he titled “I want an entrepreneur to become President one day – just not Donald Trump”, Branson said “Great entrepreneurs build business with purpose at their heart and always treat people with respect. These are not characteristics I see in Mr. Trump – neither in his previous business dealings, not in his campaign.” Needless to say, their vast differences in the way they go about their business will likely make these two life-long rivals, no matter what position they’re in.