Businessman who grew up in a council house plots Sheffield Wednesday takeover - but how did he make his money? | OneFootball

Ryan Howsam is the latest name to be thrown into the mix in the contest to take control of the Owls

Sheffield Wednesday are the hottest topic in the EFL right now thanks to their takeover saga, with a number of interested parties going public.

The Owls have been in utter turmoil for much of 2025 thanks to previous owner Dejphon Chansiri, but after the Thai businessman finally relinquished control of the club in late October, paving the way for administrators Begbies Traynor to enter the club to try and salvage it.

Unusually for a group of people whose job is to get the best deal for a stricken club and to make money themselves, Begbies Traynor have been very popular at Hillsborough already, with lifelong Wednesday fan Kris Wigfield involved in the current setup, and it has seen fans flock back to home matches and buying plenty of merchandise to help pump up the coffers in the short-term, whilst they determine which consortium or individual is the best fit to take the South Yorkshire outfit forward.

The likes of Mike Ashley, John Textor and John McEvoy have been prominent when it comes to takeover talk, but a new name has emerged in the form of Ryan Howsam - and he has plenty of connection to the city of Sheffield.

How Ryan Howsam made his fortune as Sheffield Wednesday takeover eyed

As reported by This Is Money, one of the bidders involved in the Sheffield Wednesday purchase process is the aforementioned Howsam, a self-made businessman from Sheffield.

Howsam revealed in an interview with The Sun in 2024 that he grew up in a working class family in a council house as a child, but he developed his finances through business at a young age, and having not lived in England for 20 years, the 59-year-old now resides in Dubai.

Detailed on his own personal website, Howsam began working in double glazing and alarm sales as a teenager, before going on to become an entrepreneur at the age of 21.

Howsam's main money-maker has been founding Staysure, which is a travel cover website which specialises in providing care for over 50's, especially with pre-existing medical conditions.

His website claims that Staysure has an annual turnover of £150 million, and they have acquired numerous other companies over the years thanks to their success, including Avanti travel insurance and payingtoomuch, whilst also investing in other different businesses.

He is also a majority stakeholder in The Legends Tour, the official professional golf tour for players over the age of 50, with Staysure becoming the principal sponsor of the tour in 2017, and three years later, Howsam took a majority stake in the Tour to expand his business interests.

Staysure - Howsam's primary business venture - was heading towards a valuation of £1 billion, according to a report in November 2024, and whilst his net worth is not common knowledge, he certainly has the successful business acumen that could prove important at Hillsborough, should he win out in the battle to buy Wednesday.