The £1bn entrepreneur who might be the world’s best boss

There was a time when Admiral – a company which today takes in £4bn a year – was just a tiny start-up company.

In those days there were just five men with a vision and a rather eccentric leader who would become known the world over as one of the best bosses you could have.

Henry Engelhardt – the founder and chief executive of UK insurance group Admiral up until 2016 – seems far too friendly and easy-going, maybe even too whimsical, to have guided a car insurance firm to global success.

The 63-year-old American has lost none of his enthusiasm and zest for life as he speaks from his Cardiff home and, despite having moved from Chicago three decades ago, he hasn’t lost that American twang either.

He might have stepped down as CEO of Admiral but that doesn’t mean he’s slowed down. In fact quite the opposite has happened as Henry has applied the same principles that guided his business career to a life in retirement.

Of course things are very different to the early 1990s when he was a fresh-faced 30-year-old with no idea he was about to change the face of insurance in the UK. Now, according to Forbes, he is ranked number 1,730 on the billionaires list with an estimated wealth of £1.15bn.

But back in the 1980s when he was still living in Chicago, with his French-born girlfriend Diane (who would become his wife) and desperately hating his job, things were a lot shakier, both in terms of his career and his family finances.

Henry Engelhardt with the putter he uses to play golf on the artificial putting green in his back garden
Henry Engelhardt with the putter he uses to play golf on the artificial putting green in his back garden
(Image: Richard Swingler)

After studying journalism at the University of Michigan Henry started out as a trader on the Chicago Mercantile Exchange. The first few years were fun but the dynamics and personalities of the firm suddenly changed and it was a less pleasant place to work, Henry said. It was a key moment and would come to shape his future management style at Admiral.

“I’ve had some bad bosses, my kids have had some terrible bosses, and the effect having a bad boss has on your life is amazing,” Henry says animatedly.

“It’s really hard to do something for eight or nine hours a day and just flick a switch and be a happy camper in the rest of your life.

“A bad working environment and a bad boss knocks your whole life for six. It’s not fair. We spend so much time at work that not being happy is not worth it. I swore that as long as I could help it I would not work where I wasn’t happy and I’ve tried to live by that.”

So Henry and Diane, who met as students, quit their jobs and travelled around Asia for six months before Henry enrolled on a Master of Business Administration (MBA) course in Paris. After a stint in London as a management consultant an ad for a job “which just said financial services” kept catching Henry’s eye and he decided it must almost be a sign telling him to apply.

“So I phoned and asked for more details… and it was for a job in car insurance. And I literally thought: ‘Oh no, how boring, what could be worse than car insurance?’.

“But I really didn’t want to be a management consultant any more so I applied, and I got the job, which was with Churchill. And I found out that car insurance was an incredible industry.”

Proving to have a natural flair for the car insurance game Henry spent two years at Churchill before he was headhunted by Lloyds of London to launch and lead a new company in the sector, which would go on to become Admiral.

From the outset Henry made something very clear to his team: he would not be working every hour under the sun to make this work.

“When there were just five of us working together, writing the business plan, I got the team together and I said: ‘I expect to have a good business career and I expect to have a very good family life and I don’t believe the two are mutually exclusive’,” he says.

“I managed to come to work after breakfast with my family and get home in time for dinner most mornings and evenings.

“It means I had to delegate. I couldn’t do it all myself. It eases my burden – they step up and feel valued and start doing other things and even better, I get off and do more interesting things more higher up the list in terms of the overall company.

“By delegating you are actually growing the people beneath you to do more and that’s very powerful.”

Henry and Diane, pictured here with Franklyn the dog, met as students and married in 1982
Henry and Diane, pictured here with Franklyn the dog, met as students and married in 1982
(Image: Richard Swingler)

As Henry recalls the early days every other sentence is about “the power of the team”. He reels off anecdotes and soundbites about using an “imaginary table” for meetings and keeping a “mood meter” next to his desk so people knew what kind of mood he was in every day. He’s even written down all his ‘Henry-isms’ in a book published in 2020 and targeted at teaching fellow Admiral managers how to be “great”. It offers an insight into his life and, to be quite frank, it all seems a bit too cliched.

But then Henry starts talking and it’s easy to see that this is a man who lives by his own rules because he genuinely cares. When he says he wants people to have fun at work he means it from the very bottom of his heart. His enthusiasm is infectious and it’s difficult to remain sceptical when Admiral has made the Sunday Times best companies to work for list every single year since the award began in 2001.

Less than 15 minutes in and he is already asking me about my long-term career goals and suddenly I feel like I’m the one being interviewed.

His challenge is simple: take a blank piece of paper and write ‘February 2031’ on the top and then write what you want your life to be like. Then ask yourself how you are going to get there.

“You’ve only got 10 years so how are you going to do that?” he says. “And if you take it out every year and ask if you’re 10 % of the way there, or 20% of the way, 10 years goes really fast.”

As someone who had an “amazing” free-range childhood growing up in Chicago Henry took a lot away from watching how his dad ran his own meat wholesale business and acted in his retirement. He is acutely aware of the relentless passing of time and the fear of wasting it is almost tangible as he talks.

“I saw my father have his first heart attack and bypass operation when he was 59 and he must’ve been 64 or 65 when he had the second one,” Henry says.

“He died when he was 94. He was basically in retirement for 30 years and I would say he didn’t really accomplish very much. He didn’t get closer to his kids or his wife, he bought a bunch of jumpers on sale, he traded cars, and I think it’s because he didn’t have a plan. He didn’t have a goal.

“For me I’m still in my early 60s, I’m physically in decent nick, I’ve got most of my brain, but in 10 years time, both of those things are going to diminish. It’s easy to waste those 10 years.”

So has he got a “road map” for the next 10 years? “I did mine a few years ago and I probably need to go back and do it again. But I know my bad days are because I didn’t do anything I felt was productive for today or my future. And I realised I don’t want these years to slip away, that I don’t want to turn around when I’m 73 and go: ‘Gosh, now I can’t do blah blah anymore’.”

Henry believes life's too short to do a job you hate for a living
Henry believes life’s too short to do a job you hate for a living
(Image: Richard Swingler)

Charting progress and success is something Henry applies not only to business but also to his lifestyle. He may hail from Chicago but his morning regime makes him sound more like a Californian fitness fanatic. Rising early, he heads down to the exercise room at his home in Lisvane, where he has several fitness machines. Most mornings start with a yoga or pilates routine led by Diane followed by fresh juice and a smoothie.

“I measure everything,” says Henry. “I’ve got charts like you wouldn’t believe it – all my exercise, my weight, things like this.” It’s not just a hangover from a life in business but part of the way Henry operates.

“A key is keeping your own charts and numbers because that’s really where you get the familiarity,” he says.

“Because running your own business, especially in the early days, I kept all my own numbers and I knew immediately when one of them was out of sync. And I was on the case. I’d think: ‘We’ve got a problem here’.

“Most businesses, the monthly report is three weeks after the month end and by the time you look at it it’s almost the end of that month. So at the end of February you’re looking at January’s numbers.

“That’s just not agile enough. Or fast enough in today’s world. You’ve got to know your numbers and watch it for a couple of days and, if nothing changes, you’re going to do something on day four.”

So that’s why each of his daily exercises is religiously recorded with a “little sticky star” that he sticks onto a yearly calendar. “Every time you do your workout put a little star for yourself,” he says.

“It’s amazing on the days you say: ‘Oh, I don’t feel like working out, but then think you won’t get your star, so you think: ‘Okay, I’ll do a little something and then I’ll give myself my star’.

“Then you can go back and measure it. So I can tell you in prior years to 2020 I worked out 67% of days and in 2020 my number was up to 77%.”

It’s a “great lesson learned”, he adds, and he is constantly thinking about how he can apply that in business.

Henry peppers his conversation with examples of how introducing ‘fun’ into the working environment can transform a business. If it all sounds too cringe-worthy and too good to be true then you only have to look at Admiral to see that, actually, it’s a damn good idea. The business has gone from scratch to a £4bn turnover and made £3bn profit in its first 26 years. That’s over £300,000 every single day for quarter of a century.

Henry's relaxed, down-to-earth management style is a world apart from other businesses belonging to the FTSE 100 index of the largest companies listed on the London Stock Exchange
Henry’s relaxed, down-to-earth management style is a world apart from other businesses belonging to the FTSE 100 index of the largest companies listed on the London Stock Exchange
(Image: Richard Swingler)

“To get managers to realise that you actually get a lot more from people if you do nice things for them and with them is important,” says Henry.

“You end up winning because the economic gains, as shown by Admiral success, are down to the kind of people who wake up and go: ‘Yeah, I’m kinda happy to go to work’, and who don’t wake up dreading work in the morning as so many people do.”

So is Admiral’s success purely down to having a good time at work or was it just being in the right place at the right time when it launched on January 2, 1993?

“It’s both,” says Henry.

“We got into car insurance at a really good moment in the UK. Car insurance, and insurance in general, had been suffering badly since Hurricane Andrew in the late 80s and the recession of the early 90s and the housing market collapsed and car insurance was no different. The premiums were sky-rocketing and in we walked.

“Other companies had to pay for bad results in the early 90s but we didn’t have to pay for that so while they had to top up their prices we were able to walk in and start writing virtually profitable business from day one. We did get lucky and there’s nothing wrong with luck – and then we ran with it.”

Despite being the CEO Henry never had a company car and had a normal desk on an open-plan floor
Despite being the CEO Henry never had a company car and had a normal desk on an open-plan floor
(Image: Matthew Horwood)

Today Admiral is practically part of the fabric of Wales – the shiny glass-fronted office blocks of the Admiral call centres dominate the skylines in Cardiff, Swansea, and Newport and the logo was plastered over Wales’ rugby shirts after a seven-year stint sponsoring the national team.

But it was also a little bit of luck which saw Admiral set up shop in Wales. The Welsh capital was chosen for its headquarters because after “sending off 10 letters to grant areas we heard from one place and that was Cardiff“.

“We didn’t hear from the other nine,” Henry recalls. “We were about to move into Brighton, we had property picked out, we were a few weeks away from moving, and then the Welsh Development Agency plumped for a £1m grant.

“We couldn’t turn it down. As a start-up that kind of money was amazing. So we loaded up the truck and moved down to Cardiff.

“I remember getting out the map with my wife and looking for Cardiff. Somebody said: ‘Just follow the M4 and it’s there somewhere’. And sure enough, if you followed it far enough, there was Cardiff.”

For their million quid Admiral has pumped around £2bn into the Welsh economy in 25 years, says Henry. Not a bad return.

Animated and entertaining: Henry at the official opening of the Newport Admiral building in 2014
Animated and entertaining: Henry at the official opening of the Newport Admiral building in 2014
(Image: Western Mail)

One thing that sets Admiral apart is that every member of staff gets shares in the business and that’s something Henry himself fought hard for in the early days.

“We want everybody to feel like this is their company and the best way to do that is to give them part of the company to own,” he explains.

“So we give out shares to everybody and everyone having a piece of the company made such a huge difference to how everyone acted in the business.”

In September 2004, after 11 years of trading, 1,400 members of staff split up nearly £60m. Today Admiral Group is valued at nearly £9bn. Thanks to Henry’s insistence 10% of that (£900m) goes into the hands of staff.

“That’s fantastic because the other shareholders will do better because of those staff having that shareholding,” he says gleefully. He is almost incredulous that more companies don’t follow suit.

Henry and Diane, who married in 1982, have four adult children, two who live in the UK and another two who have set up home in the US. What was it like for them growing up with a billionaire dad, I ask? It wasn’t always easy, Henry admits.

“Before Admiral I was working at Churchill as marketing and sales manager and we bought a property as the property market collapsed,” he says.

“My wife was out doing Avon door to door pushing a pram with two kids in it to do this because we were spending 70% of my take-home on mortgage.”

But having done “a bit better economically since” the couple have tried to have a balanced life for the sake of their children. Henry is not apologetic about his wealth but is also unwilling to let on too much about what he spends his money on.

“We live nicely, don’t get me wrong,” he says. “But also there’s no £220m yacht sitting outside the door. We’ve got to have our feet on the ground otherwise we’d probably go nuts. So we hope the kids too have their feet on the ground.

“Sometimes I pinch myself and ask: ‘Is this real, is it happening?’ Because it was so gradual and there were some difficult times. I think the whole thing is earned.”

They’ve been “stupid lucky” in terms of financial returns, Henry adds, which is why they feel they’ve got to give something back. That’s why Henry and Diane set up the Moondance Foundation, although Diane does all the “heavy lifting” in running it.

“It’s to give back to other people who don’t have opportunities that we’ve had and that’s really what it’s all about,” says Henry.

“We’ve got a special fund set up for Covid relief and in less than a year we’ve awarded 900 grants totalling not far from £10m, just for Covid.

“And every year we give Moondance more shares and it grows and grows and we’re hoping that will be a legacy. We want to pass this down and give our kids the same feeling of being able to help people and maybe their kids as well.”

These days he might not be at the helm of Admiral but Henry still keeps his oar in by mentoring people. His appetite for helping people and businesses grow is insatiable, it seems.

“I love mentoring,” he says. “I live vicariously, I don’t have sleepless nights, and I’m talking to amazing people every day who are capable of doing amazing things. I enjoy pushing them into different ways of thinking – helping people is really important to me.”

Henry knows what’s important to him and almost every morning he makes a note of the things he’s grateful for. Unsurprisingly his health and his family are at the top – something coronavirus brought into a much sharper focus than before.

He’s also enjoyed the slower pace of time brought about by the global pandemic.

“We used to travel and spend a huge amount of time booking flights, cars, and hotels and now we don’t,” he says.

“You learn to take the days carefully and slowly. They’re valuable – life is fragile if you didn’t know it already.”

So on a damp day in February in the midst of another lockdown in Wales, unable to play his beloved golf, where would Henry put his star on the mood meter he used to keep next to his desk? His ‘meter’ used to be a golf course and the closer to the flag the better his mood was.

“I’m on the green today,” he laughs. “I can’t go and play golf, I can’t see friends, and I can’t have a nice time at a restaurant so I’m not quite up by the flag. But it’s on the green – my wife and I have spent time together and we’re closer to our kids than ever before.”

WalesOnline – Swansea