Kenwright began a career in retail at the age of seventeen, and there are reports in the news about his situation. He founded the retail clothing company Yes & Co six years later. Within six years, the company had 32 locations and eleven million pounds in annual turnover. After selling the company, he became involved in real estate and development. Working mostly in apartment buildings Kenwright declared bankruptcy in 2010 owing very large amounts of money. After the bankruptcy he began to rebuild his business.
Development
Kenwright repurchased the apartment buildings he lost in the crash within two years, refocusing on multi-bed apartments for large group rentals. During this period he cofounded the Titanic Hotel, a Titanic-themed hotel located in the building where the ship was first registered. Kenwright founded Signature Living in 2008, a developer that restores historic buildings. Many of his developments have become hotels, having four in the City of Liverpool. The company has about 250 million pounds in annual turnover. The company also provides some housing for those who have lost their homes. From late 2018, lenders and investors experienced difficulties in gaining their contracted returns. This resulted in extensive coverage in the media, such as the BBC and Liverpool Echo. By November 2019, Kenwright wrote to investors stating: "We cannot unlock your funds from these sites until they have been finished, but once they are finalized, we will either sell these hotels and re-finance them. In the short term we have put two of our hotels up for sale which have a combined value of £50 million with a retained equity of £22 million. We are actively progressing the sale and expect to complete the transaction in the first quarter of 2020." The transactions were not completed in the first quarter of 2020 as Kenwright stated they would be. All lenders and investors currently have not received their full returns and some have not received any funds whatsoever. Media coverage has reported this has led to significant financial hardships for many private lenders who have not been repaid their money. 12:28, 30 JUN 2020 - Signature Living, owner of 60 hotels, residential developments and other ventures, has collapsed into administration. The company runs hotels in Liverpool, Cardiff and Belfast. A new report published by the appointed administrators has laid bare the scale of the problems at the company, with creditors owed an estimated £113,331,594, the Liverpool Echo reports. Matthew Ingram and Michael Lennon, of Duff & Phelps, are joint administrators of the parent company and two other group companies - including the Shankly Hotel company, which is also in administration. They believe that a going concern sale of the company is now unlikely as there are "insufficient funds and assets available to enable the company to be rescued".
Television
Kenwright appeared on the episode "Building Hackney Kids" of the television series Undercover Angel, a National Geographic Channel program that covered his construction of a disabled children's playground for the non-profit organization Hackney Kids. At the end of the episode he donated twenty thousand pounds to the organization. Between Kenwright and his wife, they are, or have been, directors of over 100 companies over the last 9 years, 6 of which have been dissolved, 16 have had compulsory strike off action in the last year and 9 which have overdue accounts. In April 2020 Signature's Liverpool Shankly Hotel and the Signature group's parent company Signature Living Hotel Limited were put into administration.