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Hiscox slid to the significant loss from a 133 million dollar (£109 million) profit over the same period last year.
The business insurance specialist said the loss was partly driven by a sharp decline in the value of its investment portfolio over the period.
It recorded an investment loss of 214 million dollars (£175.7 million), having posted a profit over the same half-year in 2021.
Our big-ticket businesses have experienced positive market conditions and our well-balanced portfolio is generating attractive returns
Hiscox also told shareholders it faces losses from Ukraine and Russia of around 48 million dollars (£39.4 million), an increase from its previous forecast of 40 million dollars (£32.8 million) in May.
Nevertheless, group chief executive officer Aki Hussain said he was “pleased” with the firm’s performance over the half-year amid a 9.2% increase in premiums.
He added: “Whilst macro-economic and geopolitical concerns are affecting the global economic outlook, our strategy and diverse portfolio of businesses continues to create opportunity, and we are well positioned to generate high quality growth and earnings.
“Our big-ticket businesses have experienced positive market conditions and our well-balanced portfolio is generating attractive returns.
“In retail, ongoing investment in technology and brand is driving growth in 2022 and is expected to accelerate in 2023.”
Elsewhere in the insurance sector, More Than owner RSA saw a more positive reaction as its shares moved higher on the back of a £107 million pre-tax profit for the six months to June.
It compared with a £249 million loss over the same period last year.
RSA said it was boosted by an improvement in its underwriting business but still targets further growth in the division.