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‘I don’t suffer fools gladly.’ The insurance tycoon who started over — twice

While City bankers are still stuck in something of a post-Covid torpor, one corner of the Square Mile is still making a killing. The Lloyd’s of London insurance market is in the pink — premiums are high, claims relatively low. That means huge paydays for the small group of top underwriters whose firms offer cover for the ships, aeroplanes and factories that would not be able to operate without them.
One such is Richard Brindle, a tough, hard-driving tycoon who’s amassed a personal fortune in the region of $500 million in a long career in the underwriting world.
Some former colleagues warn me before we meet that he’s “impossible”, “a control freak” — and worse. So it was with some trepidation that I sat on a low sofa by a coffee table as he towered over me in his chair in his 42nd floor office. A rowing machine was behind him by a window looking miles across London. He must feel like he’s flying when he’s on it.
If an icebreaker were needed, it is provided in the opening seconds when his larruping great labrador, Salvador, flies in. All legs, tongue and ears, he instantly shoves his big black snout deep into the milk jug by my cuppa.
“Haha, you didn’t want milk with that tea did you? Too bloody late if you did,” Brindle guffaws as Salvador gallops out to bring mayhem elsewhere.
Brindle — a fittingly canine surname — likes having his dogs in the office, and encourages staff to do the same. Non-dog lovers would be annoyed. But then, I’d imagine Brindle couldn’t give a damn.
Tall, bald, and no-nonsense, this is a man who has built or helped build no fewer than three insurance companies.
His latest is The Fidelis Partnership, which does what he has always done — sort insurance for organisations with big, risky problems. An example: for years, a rotting old oil tanker had been moored off the coast of war-torn Yemen with one million barrels of oil and toxic gas on board — a deadly mix that could have exploded at any moment. Then, last year, Fidelis led a consortium of insurers that allowed a United Nations-organised team to painstakingly decant the contents and make the vessel safe, ready for scrapping.
Much of Fidelis’s specialist cover is for war and political conflict, so these are busy times.
Insurers don’t comment much on their current clients, but a tale from Brindle’s youth gives you an idea of the type of work it is, and the type of man he is.
After reading classics at Oxford, he decided to get a job at Lloyd’s because he wanted to work in the City and, he says: “A college friend went there and said a lot of the people were post-colonial, arrogant and, frankly, lazy. Why be a wolf in a pack of wolves when you can be a wolf in a pack of sheep?”
He joined a firm of underwriters in 1984 as the Iran-Iraq war was raging. One Friday, his superiors disappeared to the pub, leaving him alone at the firm’s “box” at Lloyd’s — the place where insurers stand waiting for brokers to come and ask them to cover their clients. As the time ticked on, increasing numbers of oil tanker operators’ brokers were queuing up, looking to buy insurance for ships wanting to sail into the region the coming weekend.
As 2pm, 3pm, then 3.30pm went by and his colleagues remained at the boozer, he says: “It became clear to me they weren’t coming back. So, basically, I thought: f*** it, I’m just going to start doing this. I studied classics, I know more about geopolitics than any of these guys down the pub, so I made a market and started quoting some deals.”
On the Monday morning, his seniors tried to get him fired. But, far from bankrupting the firm, his judgment had been spot on; none of the ships was attacked and his trades made a fortune. The boss promoted him to be the firm’s war insurance underwriter at the age of just 22.
Brindle recounts such underwriting successes like a veteran footballer on his greatest goals. His biggest win? “First Gulf War, 1990. Huge demand for war insurance but the risk was soooo good.” He charged one oil tanker a $7.5 million premium when the risk of it being hit by a stray Iraqi jet was almost nil.
Lloyd’s bigshot, John Charman, wordily nicknamed “the king of the London insurance market” joined the syndicate and the pair turned it into the biggest in Lloyd’s, he says, renaming it Tarquin before selling it in 1998 for $500 million. Brindle doesn’t disclose his share of the spoils, but it sounds like he didn’t have to work again.
They got a big price partly because, following a disastrous year for catastrophes in 1992, with Hurricane Andrew and a California earthquake, the duo had decided to move into catastrophe insurance. With other insurers pulling out after suffering massive losses, Brindle explains: “Basically, I quadrupled the prices. The brokers had nowhere else to go.”
It was a trick he would pull repeatedly in the notoriously cyclical insurance market; wait until a disastrous run of claims forces your rivals out, then go in hard and charge high.
Or, as he puts it: “Write the most business when rates are highest and the least when rates are lowest. It sounds like a statement of the obvious, but nobody does it!”
After the Tarquin sale, and then in his mid-30s, he took time out to “have some fun”. He drifted into film production with a gritty arthouse flop called A Kind of Hush, starring Roy Hudd. He had a trendy London bar-restaurant and a nightclub called The End, which DJ magazine described as “seminal” to the capital’s rave scene.
But he eventually got restless: “I didn’t have a full-time job, I’d been fooling around with the bar industry and the restaurant but I didn’t have a real focus. I was,” he pauses, “a bit lost, I would say.”
Then, in 2005, came three hurricanes: Katrina, Rita and Wilma. Once again, the insurance market got utterly upended with megaclaims and premiums shot up, so, after a push from his wife, Katie, Brindle pounced, launching his own insurer, Lancashire Holdings, and floating it on the stock exchange to raise funds.
“Our timing was impeccable,” he says. “In our first year, we made an annualised return on equity of 45 per cent, or something crazy. We had a terrific run.”
Nine years later, according to the stock exchange announcement at the time, he “retired”. One of those there at the time claims that his bruising style had alienated his senior managers and he had been left with little choice. Brindle’s version runs thus: “There were three individuals I fell out with and I was given the option by the board of staying and firing them, or leaving. I chose to leave because, at that point, I just didn’t want to go through the aggro. I’d just had enough. I got very well looked after financially and left.” For “very well looked after” read: about £70 million.
Brindle is clearly not cut out for the role of a modern-day plc boss, with all the red tape that involves. Recalling his latter time at Lancashire, he says: “The walls gradually closed in. Running public companies can have a very perverse outcome on people like me. You spend less and less of your time on what you want to do and what you’re best at. You get sucked into so much corporate governance, compliance, investor relations.”
But that doesn’t explain the criticisms that he refuses to relinquish enough power to his staff and drives them too hard. “I can’t believe he’s got away with it for so long,” says one, even talking of “bullying”, a charge he vigorously refutes.
He looks shocked when I raise such allegations, declaring the Fidelis culture “fantastic”.
“I don’t know about ‘power hungry’. But I’m certainly hard-driving. Yeah, I don’t suffer fools gladly. I take the view that we are very lucky to live in a very developed country and make a lot of money, and we should work hard and take the opportunity; not always be going on about our entitlements and grievances.
“And I think it’s fair to say that within our industry there’s a lot of very entitled people who don’t really work very hard.”
It’s tough talk, from a man who admits his childhood has made him “perhaps too hard, sometimes.”
As a boy, he was very musical, and his mother, a talented pianist, dedicated her life to taking him to hours of lessons and concerts every week. But she died of cancer when he was 12 and he gave it up.
Then, his father got promoted to the top of the insurance company Sun Life of Canada and moved to Toronto, leaving him to fend for himself as a boarder at Winchester College, the public school, where he had won a music scholarship.
After that, he says: “I think, particularly in my early career, I found it hard to let people in. I felt it was me against the world, that sort of thing.”
Fidelis, which he launched in 2015, is moulded around the man he is today. He has arranged matters so that he can spend all his days underwriting, while sloughing off the boring plc management stuff to others. This is done by splitting the business in two; one, the underwriting arm, is private and run by him. The other is a New York stock exchange-listed entity based one floor up in the London base, which provides most of the financing. Brindle has a significant stake in both.
He clearly loves it: “If you’re an underwriter like me, you want to underwrite. And why would you have people like me spending time doing stuff they’re not very good at?”
So far, so lucrative. The firm is now underwriting $4.1 billion a year. It has just done a $2 billion debt refinancing led by the US investment giant Blackstone, which resulted in $850 million going back to its investors, including Brindle and his 400 or so other employee-shareholders.
He wants to create a £1 billion charity foundation, funding his global philanthropic interests, from microfinance in developing countries to animal rights.
“I don’t expect you to get the violins out here, but I don’t do this because I’m a greedy w**ker who wants to avoid tax and has 15 houses. I’m very idealistic about the world and I work this hard, yes because I enjoy it, but because I want to create an enormous foundation.”
Our interview ends with him rushing off to another meeting. Heading back to The Sunday Times, I pass The Lamb Tavern, an old City pub popular with Lloyd’s folks. It’s gone 2pm on a Thursday but the place is absolutely heaving. Brindle’s rivals, perhaps?

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