Middleton's cake-making business, now defunct, was inspired by reading that a mother's baking is a highly evocative
childhood memory. Themed cakes were later provided for companies such as
Jigsaw,
3 and
Ralph Lauren. The business won
Smarta 100 and
Haines Watts Young Entrepreneur awards. In April 2011, he registered three businesses: Nice Cakes, Nice Wine, and Nice Group London and planned to expand the Cake Kit Company. In May 2020, Middleton launched Ella & Co, a mail order dog food company that offers freeze-dried, raw, organic dog food.
Boomf In 2013, Middleton and Andy Bell founded
boomf, a company that makes personalised marshmallows and greeting cards. Middleton had previously founded Nice Cakes, which specialised in personalised cakes. Bell had previously founded Mint Digital, Boomf launched in November 2013 without mentioning Middleton's involvement, to allow for a low profile launch. In January 2014, Boomf announced Middleton's involvement, believing that it would be impossible to keep it secret long-term. In 2014, Boomf raised over $1m and was backed by a number of angel investors, including
Nick Jenkins, founder of
Moonpig, Duncan Jennings and Matt Wheeler. In 2015, the company raised funds at a valuation of £10m. Boomf made a loss of £3 million between 2015 and 2018. In July 2015, Boomf launched a nationwide search for a new marshmallow designer. The winner was Bournemouth University student Izzy Burton. Middleton's brother-in-law, hedge fund manager
James Matthews paid Middleton €110,000 for 12,800 Boomf shares. In 2019, Middleton announced that the company had reached profitability with an income of £176,000 in the previous year - and an increase in sales of up to £4.4 million from £2.8 million in the previous year. The company moved into new offices in Reading with circa to warehouse space. Boomf raised $1m of funding in 2021, but by December 2021 the company had fallen into administration owing £800,000 to creditors, including £146,306 to
HM Revenue and Customs. Creditors voluntary liquidation commenced on 4 November 2022. ==Personal life==