Tailwind Group targets Wales’ “missing middle” businesses

Tailwind Group, the consultancy founded by former law firm partner Matthew Tossell, is launching a new programme aimed at breaking the “missing middle” that has long hampered Welsh‑owned businesses.

Tossell, who now serves as co‑founder and chairman, warned that many founders reach a milestone – often around £1 million in turnover – and then convince themselves that “I have gone far enough”.

He argues that this psychological ceiling is as damaging as any commercial obstacle, because it curtails job creation and stifles role models for the next generation of entrepreneurs.

“I have done well,” he said, recalling the moment many founders feel they have achieved enough, only to see their companies stall before they can scale.

His own journey mirrors that narrative. Born to a painter‑and‑decorator and a dinner lady, Tossell left school for the steel industry before returning to study law.

After joining the firm then known as Hugh James Jones & Jenkins, he rose to partner and later managing partner, helping transform the regional practice into one of the UK’s top‑100 law firms.

Yet even at the pinnacle, he admits he “sometimes wonder[ed] whether I really belonged there”.

He confessed to a recurring dream in which a senior partner demanded proof of his A‑level results, a fear that lingered as his responsibilities grew.

“That sense stayed with me even as my responsibilities grew,” he said, underscoring how self‑doubt can persist despite external success.

According to Tossell, the same self‑imposed limits now surface among Welsh founders who have built thriving businesses but hesitate to push beyond the “good enough” point.

He warned that when indigenous firms stop growing, Wales loses not only jobs but also the inspirational examples that encourage aspiring entrepreneurs.

“When good businesses stop growing into the organisations they could become, Wales loses jobs, career opportunities and businesses of greater scale,” he explained.

He added that the loss extends to the broader economy, as fewer large‑scale Welsh enterprises mean fewer mentors for future founders.

Tossell’s critique extends to the support landscape. He noted that while Wales excels at nurturing start‑ups, there is a dearth of tailored assistance for established, owner‑managed firms.

“What I think is less well developed is highly‑tailored help for established owner‑managed businesses which have reached a point where the problems are more complicated,” he said.

He contrasted this with the incentives offered to inbound investors, who often receive assistance with premises and recruitment, leaving local firms at a disadvantage.

“Supporting inward investment and job creation can clearly have an economic purpose, but indigenous businesses should not find themselves at a disadvantage when they are trying to invest, grow and employ more people themselves,” he argued.

With a new Welsh Government now in place, Tossell hopes policy will shift to level the playing field for home‑grown companies.

Tailwind’s new service will work alongside owners, leadership teams and investors to pinpoint value loss, prioritise actions and deliver practical steps for growth.

“We could see founders who had already proven they could build successful businesses but were under enormous pressure and were not always sure how to move to the next stage,” he said.

The consultancy aims to create an environment that “unleashes ambition”, giving business leaders the confidence and tools to move beyond the plateau.

“No longer should business owners – or Wales itself – need to settle for ‘good enough’,” Tossell concluded.

Industry observers say the initiative could be a catalyst for reshaping Wales’s mid‑market sector, provided it receives adequate backing from both public and private stakeholders.

If successful, the programme may help bridge the gap between small‑scale start‑ups and large‑scale enterprises, fostering a more resilient and dynamic Welsh economy.