12 Jul 2019

A Life Less Ordinary: Jason Stockwood

Jason Stockwood, vice chairman of online insurance broker Simply Business, describes himself as “an accidental businessman”. From tough, single-parent, council estate origins, the autodidact followed his passions and earned a philosophy degree before going on to management roles at the likes of lastminute.com, Travelocity, Match.com and, ultimately, Simply Business, winner of The Sunday Times 100 Best Companies To Work For 2016.

Stockwood favours a four-day work week, believes technology needs to be a force for good, and says we’ll look back on our relationship with mobile phones in the same way we currently think about smoking. His book, Reboot: A Blueprint for Happy, Human Business in the Digital Age, sets out his vision. That new technology can empower teams, fuel creativity and make people happier.

 

He speaks to us about his background, about giving employers more freedom through tech, and why he ends his lectures with the words: “Remember, you die.”

 

One of the perverse benefits of having the childhood I had was that there was no expectation to be successful. We were skint, and I don’t know who my dad is to this day. But I had a great childhood: three brothers I love and a really weird confidence – an inverse relation between confidence versus ability a lot of time, but I’d rather have it that way round.

 

I wanted to get away and see the world. After getting a scholarship to go to school in America, and living on a kibbutz in Israel, I worked at Disney World for a year in Epcot. While I was there, I started to read and educate myself. I was reading the beat poets – Jack Kerouac and Lawrence Ferlinghetti and all those guys – and followed what they were talking about. It was always philosophy.

 

I think people born today with my type of background have a bigger uphill struggle than I had in the ’70s, when there was the welfare state, free school meals, benefits, free university and grants. Student loans were just coming in, so I was better off than I’d ever been. I had one A level. It was the last year you could get a mature student grant as well.

 

“You need to fulfil your career and intellectual ambitions. But it all pales in comparison if you’re away from the ones you love and care about.”

 

I was the first in my family to go to university – mum still has no idea what I studied – but I was just curious. I remember thinking I didn’t have the intellectual chops, because although I had lots of questions, I couldn’t frame them properly. I didn’t have the language, which is why I went to study philosophy. It was about trying to find the right questions rather than the right answers. But it’s the thing I believe has stood me in the best stead in everything I’ve done. Having a degree forced me to think more expansively. It informed my development as a leader, but I didn’t study philosophy with the end goal of becoming a leader.

 

Grayson Perry has informed some of my thinking. In The Descent of Man, he looks at post-industrial areas in the north-east, where men had to be ‘hard’. When those industries went, those residual ideas of toughness went as well. I was born in a town where you were supposed to act tough, but it was because those industries required that. When they went away, you didn’t need to be tough anymore, but there was a generation caught in the middle. They respected where they were from but tried to redefine their values off the back of that.

 

In the ’90s, there was an optimism about a version of socialism that was going to be more caring and inclusive. I was never motivated by making money. It was about being around interesting people, and lastminute.com was ideal. Nobody had any idea that the internet would stick around for any length of time, but it did feel like a once-in-a-couple-hundred-of-years change in technology and way of working. It was an amazing culture – hugely ambitious but very informal and relaxed. It was a weird balance of massive ambition and a desire to change the world.

 

I’d done travel, I’d done dating, but thought insurance was boring, and customers hated it. My wife said: “Well, don’t you think that would be a good reason to try to do something about that?” I thought: “OK, I could try to build a business that actually paid claims and was transparent about pricing.” So I took on Simply Business and said: “I’ll give it two years.” It was a shell of a business, in debt, and the tech was terrible. But I knew there was some fairly interesting open-source software out there. So we changed 53% of the people in the first year and rewrote the platform. We had a massive stroke of good fortune a couple of years in when fintech became a thing.

 

At the end of my book lecture, I finish with the line: “Remember, you die.” It’s the most depressing way to finish a presentation. But I’m not religious – I’ve got a good 20, 30 working years left if I’m lucky, and so if you’re doing things you don’t enjoy with people you don’t care about, and you’re not spending time with your family, then do something else, because you’ll be dead at some point.

 

A coach once said something amazing to me. I was overwhelmed, spinning plates all over the place, and I said: “I’m saying yes to too much.” And he said: “Rather than trying to find a way to say ‘no’ to stuff, why don’t you get the resources to say ‘yes’ to more stuff.” It’s so simple: get people around you to support you so you can say yes to all the things you want to do, to fill your life.

 

I resigned as CEO of Simply Business last year, and it was the easiest rational decision, but the hardest emotionally. The house we bought in London was 14 minutes by Vespa to my office, so it meant I could still have my breakfast with my family and be in the office early, and if I left at half-six, I could say it was a full day. And all of a sudden, I found myself on planes more and more. So I said to my wife: “There’s only one of two responses to this. We either move to New York or Boston, or it’s time to resign.” She had no interest in moving to the States. And I didn’t want to be away from my family – it’s that simple, really. You need to fulfil your career and intellectual ambitions. But it all pales in comparison if you’re away from the ones you love and care about.

 

When I drop my kids off at school, the last thing I say to them is: “Ask good questions today.” I say it every day, and it annoys the hell out of them. They’re super-smart, but asking questions sets you apart, particularly in an age where anything logic-based will be done infinitely better by machines.

 

There’s something very pernicious about our relationship with mobiles. I love technology, and the whole history of human progress has been defined by our relationship with technology. But we need to recalibrate. When I was on holiday, I literally deleted the email app off my phone so I wouldn’t let temptation take over. I did it as an experiment at first. You discover you’re not that important, that life goes on. I was like: “Call me if you need me.” And no one calls you, because people are just getting on with it.

 

My idea for a four-day work week [being piloted by Simply Business] is rooted in John Maynard Keynes. In 1930, he predicted that technological innovations would reach the point where we’d be at a 15-hour week by 2030. So while the prediction economically was pretty accurate, the way he got there was wrong. We’ve seen productivity rise through technology. But productivity gains have gone to capital, not labour. If we can overlay technology into existing parts of a business to increase productivity, we can share that gain into a four-day week. On that fifth day, it’ll take pressure off the economy for people to look after their kids or retrain, or write poetry or whatever, which would help humanity flourish. At its best, it would create more civil harmony as productivity, capital and labour divide.

 

The leaders I admire understand the future is unknowable. This idea that the world is completely linear and understandable – it never was. It was an illusion. I worry about people who have great certainty about what they’re building for the future. Instead, their attitude should be: ‘I’m going to build an organisation that can adapt and respond to whatever comes up.’ Because the future is more complicated than it will ever be. Digital media and the amount of data we’re getting now is growing exponentially. So you’ve just got to keep moving.

 

Lysanne Currie is CEO and editor in chief of Meet the Leader and writes about business and luxury travel for magazines including Robb Report, Luxury Plus, I-M Magazine and Tempus.