Jason Stockwood

Sophi Tranchell MBE, managing director, Divine Chocolate

Jason Stockwood, the vice chairman of Simply Business, thinks technology should give employers more freedom, believes we’ll one day look back on our “pernicious” relationship with our smart phones in the way we currently think about smoking – and, perhaps most headline-grabbingly, is in favour of a four-day working week. We talk to the self-described “accidental businessman” about philosophy, the importance of asking questions, and how tech should make us more fulfilled. “I love technology,” he stresses, “and the whole history of human progress has been defined by our relationship with technology. But we need to recalibrate.” 

“Remember, you die.” There can’t be too many authors’ lectures that always end with those three words, but then the writer of Reboot: A Blueprint for Happy, Human Business in the Digital Age does like to grasp his audience’s attention. “It’s the most depressing way to finish a presentation,” laughs Jason Stockwood. “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. 

Stockwood is a breath of fresh air – and an inspiration: hailing from tough, single-parent, council estate origins, the autodidact and philosophy graduate went on to manage the likes of lastminute.com, Match.com and the company he currently vice-chairs, Simply Business, the 2016 winner of The Sunday Times 100 Best Companies To Work For. 

“One of the perverse benefits of having the childhood I had was that there was no expectation to be successful,” he says of his impoverished, fatherless background (“I don’t know who my dad is to this day”). But, he says, he had a great childhood, three brothers he loves, “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”. Determined to get away and see the world, and following a scholarship to go to school in America, he lived on a kibbutz in Israel and worked at Disney World for a year – which is where he began to educate himself, reading beat poets like Jack Kerouac and Lawrence Ferlinghetti and discovering the common DNA between them all was philosophy.  

Taking advantage of the then free university and grants (and the first in his family to go to university), he applied as a mature student to study the subject properly. “Although I had lots of questions, I couldn’t frame them properly, which is why I went to study philosophy. It was about trying to find the right questions rather than the right answers.” Having a degree forced him to think more expansively, he says. “It informed my development as a leader, but I didn’t study philosophy with the end goal of becoming a leader.” To this day, he thinks asking questions is vital: “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.” 

He was never motivated by making money, he says. It was all about being around interesting people, and at lastminute.com he found his kind of people; a “hugely ambitious but very informal and relaxed” company – right up his street, during those optimistic, idealist 90s, led by “a version of socialism that was going to be more caring and inclusive”. Lastminute was “a weird balance of massive ambition and a desire to change the world… 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”. 

After management roles at lastminute.com, Travelocity and Match.com, he took on Simply Business, almost despite himself. Insurance was boring, he thought. “But 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 in he plunged, with the understanding he’d give himself two years with it. Back then, 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”. He rewrote the platform, changed some 50 percent of the staff, and had a “massive stroke of good fortune a couple of years in when fintech became a thing”. 

After some spectacular successes, he resigned as CEO last year – “the easiest rational decision, but the hardest emotionally” – due to wanting to spend more time with his family. “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”. 

Which is where his idea for a four-day work week (currently being piloted by Simply Business) comes in. If John Maynard Keynes predicted in the 1930s that technological innovations would free us up for a 15-hour week by 2030, it’s fair to say he got his prediction a bit muddled up. As Stockwood points out, “Productivity gains have gone to capital, not labour”. However, by overlaying technology into existing parts of a business to increase productivity, those gains might he shared 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.” 

Stockwood’s own philosophy is simple – but it’s been hard won. Once, when he was overwhelmed, spinning plates and saying ‘yes’ to everything, a coach gave him some “amazing” advice. Which was: “Rather than trying to find a way to say ‘no’ to stuff, instead, get people around you to support you so you can say ‘yes’ to more stuff, things that will fulfil your career and intellectual ambitions. Fill your life with activities and people you love and enjoy.”