How Richard Branson decides what and who to bet on — and why he believes we all need autobiographies

Known worldwide for his daring escapades and zest for life, Richard Branson is not your average entrepreneur. He’s predisposed to take risks and has had more than his share of ups and downs launching new business ventures. But his gut-based approach to business and life has always helped him land on his feet — except when it comes to the occasional rough landing, like the time his hot air balloon caught fire and crashed in the Arctic, or when he jumped off of the Palms Casino Resort in Las Vegas in high winds. His many adventures and business endeavors — and his philosophy driving both — are now documented in a new documentary on HBO and his recently released updated autobiography, Finding My Virginity. 

I had the opportunity to catch up with Sir Richard during his recent visit to New York. Branson is a repeat guest on This is Working — as a stunt, we once did a live video interview sitting side-by-side on a Virgin America flight (he wanted to show off what he said was the fastest inflight internet) — and it’s never a dull conversation. This time we invited him to help launch LinkedIn Audio Events, a decidedly less risky proposition than bungee jumping off Victoria Falls. In true Branson form, he took the leap.

Branson has said, “If your dreams don’t scare you, they are too small.” I wanted to know what he’s learned from having the courage to pursue big dreams. In the latest This is Working, I asked him to share why he thinks everyone has a story to tell, why he relies on instinct over data, and his perspective on the difficult task of handling mass layoffs.

You can download the podcast on Apple, Spotify, or wherever else you listen to your podcasts. Or just click here:

Some people, myself included, hate watching themselves on screen and I was curious whether Branson had screened the documentary. His answers surprised me a bit. Here is what he had to say along with some edited highlights of our conversation:

“I was lucky enough to watch it with my children and grandchildren and they discovered a lot of footage going back many years that I didn't even know existed. And so I think it's good at some stage in your life to either write a book or do documentaries to share one's wonderful experiences with other people. I think everybody has an interesting life and I think we all have children and grandchildren and we should all one day sit down and try to write a book about our lives, and that's something I encourage anyone to do.”

In the documentary you say, “Your life is not wasted if you've learned a lot and you've shared it. If you have learned a lot and you haven't shared it, your life is somewhat wasted.” Can you elaborate on that?

“Yeah. I think it would just be very, very sad if one goes through life and learns incredible things and have incredible experiences and you don't try to help other people learn from your experiences. I've published a number of books, my new book Finding My Virginity is sort of an updated version of my second half of my autobiography. Hopefully there'll be a third one day. It's quite therapeutic writing a book and being able to look back at those experiences and learn from them oneself as well. And the same applies to the making of the HBO documentary.”

 Most of us aren’t going up in hot air balloons and breaking world records, or going into space. What would you say to people about the need to tell their own stories even if they don’t think their life is extraordinary?

“I'd honestly think that everybody's story is fascinating. I would encourage anybody to keep a diary. Every day just in conversations with people you're going to learn something. You're going to learn something from your children when they're young, the wonderful quotes that you get from kids and grandkids. For instance, just before I went up to space, my granddaughter, who was six, just pulled me down to her to whisper something to me. Now I need to put it in context. She knows that I was a pirate, and I was dumped on an island in the Caribbean by bad pirates, and that I developed Necker Island myself. And she and the other grandkids are all sworn to secrecy. So, when she pulls me down before I go to space, she says, ‘Papa Papa, do you realize you are going to be the first pirate ever to go into space?’

“It's just little moments like that. If you write down these magical moments that your kids say, even if you don't turn it into a book when they're 21 or when they're getting married, these sorts of stories are magical to be able to tell. But I think for most people nowadays, you can publish a book quite easily. You don't have to go to Penguin to publish a book and it's just lovely to write a book for your children or your grandchildren about your experiences.”

I noticed that you have a piece of paper in front of you with notes on it. Are you always taking notes?

“I have a notebook almost everywhere I go. I flew over the ocean on Virgin Atlantic. I went around and talked to our staff, talked to our customers. Any little comments I would write down and then follow up on when I arrived at the other end. I think if you don't take a note, you're going to forget something that somebody who maybe works for you, has told you that that is important to them and it's very important that you get back to them. Conversations are wasted again if you don't take notes of those conversations because you're only going to remember one or two things that somebody says and if you've got a list of things that need to be done from a conversation, you owe it to the person who's sitting telling you those things to take notes.”

In your book, you say that there is no more important job than being an entrepreneur. Can you explain why you feel that way?

 “Well, look, obviously I'm slightly biased, but almost everything in this world has come about through entrepreneurs. I mean, an entrepreneur's job is to try to improve people's lives and the only way they're going to be successful is if they do improve people's lives. So I think every entrepreneur has created something which is making a positive difference in other people's lives and collectively the world is a much better place as a result of all the entrepreneurs that have set up in my lifetime than it would've been without them all.”

We’re looking at a potential recession in the US, energy concerns in Europe, covid concerns in China. Is this a time for people to back off from entrepreneurial dreams? Or do you lean into moments like this? Is there a right time?

“I think that you should only go into a venture if you've come up with an idea that you feel you're going to be proud of doing, that it's going to be worthwhile your time to do it, and that other people are going to benefit from. If you've got an idea like that, I don't think it matters really when you start it. 

You should only go into a venture if you've come up with an idea that you feel you're going to be proud of doing, that it's going to be worthwhile your time to do it, and that other people are going to benefit from. If you've got an idea like that, I don't think it matters really when you start it.

 “I started out in business when interest rates were, believe it or not, at 22%. Never really thought about that because I didn't have any money anyway, and we just had to try to sell our products in advance in order to get the cash flow to survive. I think it is possible to look at difficult times like today and still start businesses. The only drawback is if you want to raise money, today's going to be slightly more difficult than it would've been a year ago, or that it may be, would be in two years time.” 

The fact that money is easier to raise — that’s so different than when you started. Do you think that’s a good thing or is there benefit in self-funding?

“I didn't have any money. I literally had the £200 that my mother got from finding a necklace and selling it, and therefore I had to pre-sell advertising before I could bring out a magazine, or I had to hand out leaflets outside the Royal Albert Hall for when I was selling music and get the money in advance before I sent people their records. So it was forced upon me. As a result, the Virgin Group, we still own 100% of. And that has given me the flexibility to take the group into space, or airlines, or a whole raft of different ventures that I most likely couldn't have done if I'd had outside shareholders. 

“That said, there weren't such things as venture capitalists around when I started, there are today. For your first business, if you can get properly funded by a venture capitalist, or by a family member that may well help you and you can learn the ropes with that first business. Then maybe your second business, you try to own 100% yourself.”

How do you think about internal mobility in your companies? And what do you look for when you're hiring people?

“So first of all, we're very fortunate at Virgin that we've got people who have been with us a long time. So when we start a new company, [there are people we] we can draw on. For instance, Virgin Atlantic has the best upper class, the best lounge really in the world at Heathrow. It was built 15 years ago by a wonderful lady. And when we decided to launch a cruise company, rather than bringing in cruise experts, we brought in her and a bunch of people who would never go on a cruise line to create Virgin Voyages and the end result was a cruise company that myself, my wife and our friends all love to go on, are completely different from Carnival or any of the other cruise companies. Much more fun. It just feels very, very Virgin, and so that's something we're able to do. We start a train company, we know how to make sure that train company is the best in the world, that we're able to draw on different companies for new ventures. 

We try to promote from within as much as we can because you know somebody's weaknesses and strengths when you promote from within.

"We try to promote from within as much as we can because you know somebody's weaknesses and strengths when you promote from within. Obviously on occasions we bring people in from outside. It's not always easy to get that right. We'll get people to send a five minute video just to get a flavor of their personality through the video. We found that's very effective."

What traits are you looking for when you do hire from the outside?

I'll tell you a fun story. Many, many years ago I had a TV program called a pretty horrible name, The Rebel Billionaire of all things. And I asked people to send in five minute videos. And one girl sent in this video and she'd just come up with this idea and she was in her basement. And she flashed her butt at the end of the video and said, ‘You've got to take me on.’ Well, if somebody flashes their butt at me, how can I say no? Her idea had been to make women's butts look better. And it turns out that it turns into Sara Blakely and Spanx, and the rest is history. She just managed to get that little fun bit of flavor across in a five minute video. And I think you can see a lot more in a five minute video than you can in a CV.”

“I think it helps if they've got the personality before they actually come to us. I mean, it's difficult to create personality. It is absolutely critical to us that they are decent people, that they're good with people. The kind of leaders that praise, don't criticize is something I've said all my life, but that really is the kind of person we want. If you get the wrong person in, particularly at a senior position, you can destroy a company really quickly. And you've got to be really, really careful to make sure that the people that you bring in genuinely care about people and don't ruin a wonderful atmosphere that maybe has been spent years being built.  

If you get the wrong person in, particularly at a senior position, you can destroy a company really quickly. And you've got to be really, really careful to make sure that the people that you bring in genuinely care about people and don't ruin a wonderful atmosphere that maybe has been spent years being built.

“I think one of the worst things that have been done for business is programs like You're Fired [Ed note: I think maybe Richard was taking a jab at The Apprentice…] or with people who are sort of relishing firing people. I think it's a horrible example of just how business shouldn't behave. It should be something that is an incredibly painful thing for managers to have to do, to ask people to leave. and they should feel it. and they should not seem to be relishing in it.”

But companies have to do it sometimes, right?

“Well, if there's a danger that you're going to lose the company if you don't make tough decisions, then obviously there sometimes has to be justification for it. And we at Virgin, during Covid, the teams had to make tough decisions, but they were painful decisions. They were agonized over. Fortunately, most of those people have got their jobs back at Virgin a couple of years later, but [layoffs] should be agonized over.

“I sat in a car once, many years ago, actually in 2008. It was a banker in the back of the car and he'd been given a list of people to sack. And he was giving them about 30 seconds each just picking up the phone, ringing them, sacking them, putting the phone down, ringing up, sacking them. No words of sympathy or understanding. And I found it thoroughly unpleasant. And at Virgin, I'd like to think that if people go to a pub that they'll be proud of the fact that they work for the company. Now, if you're the kind of company that relishes sacking, people are not going to be proud of working for your company. So you've got to be humane and human about it.” 

In the HBO documentary you say, "Almost everything in my life has been instinctual and not premeditated.” In our data-intensive world, that’s a tough call: do you trust the data or your gut?

“It slightly depends what reason you're doing what you're doing. Are you’re doing it solely because you want to make a lot of money or are you doing it because you want to create something that you're really proud of? If you're doing it because you want to create something that you're really proud of, I mean, if I go back 38 years to the start of Virgin Atlantic, I'd flown on a lot of other people's airlines. I hated the experience and I felt that we could create the kind of airline that myself and my friends would like to fly on. I did not get any accountants in to give me any figures because I knew that they would either tell me I was mad and I shouldn't even dream of going to the airline business, or if they were trying to be nice to me, they might do the figures to make it look like we could make some money, but it had to be my own instinct that the world needed a better airline. And so we literally just started with the one plane.

And 38 years — through lots of ups and downs — we are still going strong. I never made a lot of money out of the airline business. Most likely we've net lost money, I suspect, in those 38 years, but it's been something I've been immensely proud of. And it really helped put the Virgin brand on the map on a global basis. So it's helped with other ventures that we've done since. 

Don't worry too much about the bottom line, and I suspect you'll be able to pay the bills because it's the best in its field.

So I think one's instinct to create something you can be proud of. If you create the best, by and large, the best will survive. I've just been to the new Virgin Hotel in New York, just off Times Square. It will be the best hotel. It opens in a couple months time. It will be the best hotel in New York. If it's the best you know that it will survive many, many, many years. If you cut corners and it's mediocre, then it doesn't necessarily deserve to survive. And so create the best. Don't worry too much about the bottom line, and I suspect you'll be able to pay the bills because it's the best in its field.”

When people come to you within the company with ideas, what do you expect from an internal pitch? Do you want to see all the data or are you willing to trust the instincts of your team?

“More the latter. I mean, obviously it depends on the individual. I mean, the guy, Jamie [Siminoff], who started Ring, came to me with an idea the other day. And without really listening to the idea, I just felt, ‘Well, if it's Jamie, he created something extraordinary. We should seriously look at it.’ And so the individual that comes to you can play a large part in it, then give them their head and see what they can create. And sometimes it'll work out, sometimes it won't.”

This past summer, Patagonia’s founder announced that he would put almost all of the company shares into a nonprofit that supports environmental causes. Are you thinking about what comes next for the Virgin Group and how, or if, you want to pass it on?

“We are thinking very hard about this, and my kids are also thinking very hard about it. I think as a family, we know that there's a limited amount of money that we as a family need. It helps to have money for education, or for health emergencies, or for a roof over the head and so on. But the kinds of vast fortunes that are being made in Silicon Valley and other places should ultimately be put to dealing with some of the major problems of this world. And I don't think our family would be any different in that thinking. All I can say is watch this space, but it'd be a different kind of space on this discussion.”

“It is interesting, I think with that Patagonian announcement, they ended up getting criticized. And one thing I talk about in the HBO documentary Branson is how when people do something for the right reasons, that is the time they get criticized. When people do things just to make money for themselves, they never get criticized. And it's a sad, I think, reflection on the press the way that happens. And I think Patagonia had, if I remember right, they had some knocks from it. And the press have a job to do to keep people honest, but they should be consistent, I think.”

How do you deal with it when the criticism comes your way?

“I think the only thing you can do is just to prove the critics wrong and just put your head down and prove them wrong. If it's very inaccurate, I might drop a line to the journalist and just say, ‘This is why I think you got it wrong.’ And then finally, I think you have to have thick skin. If you're a high profile global known around the world, you just have to accept that you're going to get your knocks and you're going to get good comments as well. And take the rough with the smooth.”Don't worry too much about the bottom line, and I suspect you'll be able to pay the bills because it's the best in its field.”