Herbert was made a director at Graphic Print Solutions Ltd (GPS) on 14 April 2023, after appointing a voluntary liquidator at LA Digital Print & Mailing Ltd on 23 March.

He has joined fellow directors Alan Ratcliff and Tony Baily at GPS. The three had previously worked together at Print It 247 (Group) Ltd, which was wound up on 21 December 2022 under heavy debts.

Baily, appointed director at GPS on 20 December, was joined by Ratcliff in February, at which point the two bought a majority stake in the company from its formation agent, Jolyon Alexander.

GPS had been a dormant company called Fullstream until the summer of 2022. Becoming active, it was renamed Graphic Print Solutions in November 2022.

Herbert, informing LA Digital’s customers by email on 9 February that the company had been sold to GPS, said he would remain with the business, which would “shortly be adding additional exciting products and services” trading as Print It 24 Seven.

The full directorship of the now-defunct Print It 247 (Group), therefore, has now taken up charge of GPS, trading as Print It 24 Seven and using the old Print It 247 (Group) website.

LA Digital’s sale, however, was not directly to GPS. LA Digital’s old owners – who up until that point had still had a majority stake in the business – sold to Winterbourne Holdings on 8 February.

Winterbourne Holdings is Herbert’s holding company, which also held a one-third stake in Print It 247 (Group) Ltd.

Shortly afterwards, Herbert put LA Digital into liquidation with an estimated deficiency of £589,000. Print It 247 (Group) had been wound up with a deficiency of £425,000.

Statements of affairs from each company show each one owing the other: LA Digital Print & Mailing’s statement showed it as owing Print It 247 (Group) £26,000. Print It 247 (Group)'s statement, meanwhile, showed a debt of £70,000 to LA Digital Print & Mailing.

Both companies, likewise, owed money to printing companies run by Andrew Studley according to the creditors' lists: Print It 247 (Group) owed £88,000 to Promising Print, and LA Digital Print & Mailing owed £10,000 to CDP Digital.

Both of Studley’s companies’ accounts were overdue at the time of writing.

LA Digital Print & Mailing and Print It 247 (Group) were not Herbert’s first businesses to go bust.

Eight years prior, in 2015, Herbert was director, and co-owner through his company Peak Holdings, of Monster Media Management, a Hampshire-based print management firm.

Monster Media, a relatively small affair, then bought struggling family business James Byrne Printing, transferring both businesses to the same site in Poole.

The two businesses ran side-by-side, with Herbert bringing an experienced print hand on board in August 2016 with the appointment of Ian Shenton, of Bournemouth Colour Press (BCP) as director. Kimberley Ann Shenton co-owned Peak Holdings.

By April 2017 Herbert and Shenton were forced to wind up James Byrne Printing, with a final shortfall of £609,000.

At the time, Shenton said of JBP: “We strongly believed we could turn it around.”

Immediately following the liquidation, Shenton and Herbert offered to buy JBP’s plant and machinery, valued at £29,000 in-situ, for an initial offer of £2,500.

Eventually settling for £18,000, the machinery was sold to Shenton’s company, BCP.

After two payments, the money stopped coming – BCP had been served a winding-up petition by one of its suppliers.

BCP, which subsequently collapsed under the weight of its own debts, and had liquidators questioning potentially challengeable credit notes and transactions from the company bank account, was no longer fit to pay. After a default letter, one of the directors, unnamed, arranged to pay £10,000 for the equipment.

Liquidators at JBP likewise demanded one of the company’s director/shareholders to repay allegedly illegal dividends totalling £22,000 to the business. A sum of £5,000 was paid in settlement.

Shenton now runs BCP Media Group, which sprung up shortly before BCP’s insolvency in early 2018.

Monster Media was helmed by Herbert until July 2019, when it fell into the care of fellow director Aubrey Aviss. The company lasted until March 2020, at which point – still owned by Peak Holdings – it was placed into liquidation with an estimated deficiency of £202,000.

LA Digital, Winterbourne Holdings, and Monster Media Management’s accounts were all flagged as overdue at Companies House at the time of writing.

Herbert declined to comment. Baily, speaking to Printweek on behalf of the GPS directorate, also declined to comment while the liquidation of LA Digital Print & Mailing was ongoing, but offered to speak in "six months' time".