Tech entrepreneur Jamie Wilson was making a splash.

Arm in arm with Boyzone singer and X-Factor judge Ronan Keating, the tuxedo-wearing former accountant grinned amid the spotlight of the Cancer Council fundraising ball.

“I am looking forward to being able to make the most of it, get people behind it,” Mr Wilson said that night. 

His Brisbane company was the headline sponsor and there to support the charity “for the long term”.

With an entertainer list including singer Dannii Minogue and techno-dance artist Redfoo, the 2014 fundraising Emerald and Ivy Ball in Sydney was a big night on the corporate social calendar.

And it was a successful coup for Mr Wilson.

The now 44-year-old founder of cyber-security outfit Cryptoloc has made roads into technology circles and the political sphere.

There’s more than $320,000 in political donations to both sides of politics in the past four years, accolades from state and local government politicians, while Mr Wilson this year was a finalist for the Brisbane Lord Mayor’s awards as a businessperson of the year.

And crowning it all is the Cryptoloc business just two months ago being announced as the contractor to deliver a new $15 million state government cybersecurity plan.

But behind the glamorous social profile, some problems lie with Mr Wilson’s business.

An ABC investigation has found delays with one company in paying staff wages and superannuation, and outstanding claims with the Australian Taxation Office (ATO). Mr Wilson has made admissions this year in affidavits filed in the Federal Circuit Court in Brisbane, revealed today by the ABC, about one company of which he is director, Your Digital File (Aust).

An executive had alleged wages were delayed in 2022 and Mr Wilson told the court: “It is true that on occasion, [the employee’s] salary was paid late due to cashflow issues.”

The executive, in a workplace dispute lawsuit, also alleged his superannuation had not been paid and the ATO had Mr Wilson “on their watch list” over such matters.

Mr Wilson denied the executive’s claims — initially insisting the ATO had agreed to pay the executive’s outstanding superannuation, due to a research and development tax credit the company had. But by March this year, things changed. Following an email from the ATO, Mr Wilson had the company cough up the $17,007 in unpaid superannuation.

Troubles worsened. Your Digital File was this week wound up following an ATO application for what the Federal Court heard was about a bill of almost $2 million.

The origin story

Mr Wilson’s story is not that of the generic IT garage geek. He grew up in Inala, a battler suburb on Brisbane’s west side, graduated from Queensland University of Technology and initially became an accountant.

His idea for a confidential online storage system came from tragedy. His father had terminal pancreatic cancer and the family had to gather his paperwork – think insurance, superannuation documents. 

He recounted the story on Cryptoloc’s promotional video, replete with footage of him dining with family or his mother flicking through the family album.

His invention, patented in 2014, was to create a centralised location to store information in a legally safe and hacker-proof environment.

His story takes a twist: Mr Wilson by his own admission wasn’t a computer coding guy – so he initially worked with fellow Brisbane local and cryptocurrency whiz Craig Wright, who later claimed to be Bitcoin founder Satoshi Nakamoto.

Accounts indicate the Cryptoloc technology, launched on market in 2020, had a stuttered start. 

Its head business was YDF Holdings, a publicly unlisted company whose subsidiaries include Your Digital File. 

COVID had impacted the business and it posted a loss of $716,000 off revenues of $3 million in 2021, the last time accounts were filed.

The entrepreneur machine

Yet good news emerged too: Forbes named Cryptoloc as one of the 20 best cybersecurity startups in 2020.

The company established offices in New York, South Africa and Japan, and Mr Wilson himself flaunted entrepreneurial trappings — he donned a black t-shirt (sometimes with a jacket) behind a brick-wall background and hosted video podcasts with pop-culture figures.

One this year was with US fitness influencer Jillian Michaels, who has 1.5 million Instagram followers, discussing business. 

Another video from seven months ago had Mr Wilson chatting with famed UFC announcer Bruce “It’s Time” Buffer about personal brands.

Another business relationship seemed more low profile.

For four years, another company of Mr Wilson’s had used LNP powerbroker Santo Santoro as a lobbyist, according to federal records. 

The use of the former Coalition senator for lobbying did not preclude Mr Wilson’s business developing ties with the ALP.

Another entity of which Mr Wilson was until last month a director, Cryptoloc Technology, spent almost $270,000 between July 2021 and August this year with the ALP and LNP, according to state and federal donation records. 

A large chunk went to Labor entities, including $33,000 this year on state ALP events.

Mr Wilson himself personally contributed almost $50,000 to both sides of state politics between 2020 and June 2022, and another $15,000 for an August ALP event this year.

Then there was the 2022 lunch with Cryptoloc at the well-heeled Brisbane Club with conservative party Lord Mayor Adrian Schrinner speaking.

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And in 2024, Queensland’s then ALP Premier Steven Miles also posted online about Cryptoloc being allowed to use its products with tech giant Microsoft. 

Just two months ago, Cryptoloc received even better news: the then ALP Small Business Minister Lance McCallum said the state would offer businesses free cybersecurity measures such as data encryption via a $15 million investment and Cryptoloc had been “chosen to roll out the solution”. 

Mr Wilson, quoted then as executive chairman, said it was an honour to work with the state.

That announcement came six days after the ATO filed a winding-up action against Your Digital File, and more than a year after the former executive’s lawsuit. A spokesman for Mr McCallum said he was unaware of the struggles or that entity itself, and the department had independently awarded the contract.

According to affidavits filed by the former executive, his wages were paid late on roughly eight occasions between June 2022 and November 2022, and he was made redundant due to operational delays two months later. 

Mr Wilson did not confirm the dates, but admitted pay was late due to cashflow issues. The remainder of the matter was settled in April.

On Wednesday morning, Mr Wilson, this time in a white-collared shirt, was back again in front of his office brick wall, as Your Digital File faced a winding-up application heard online. 

Mr Wilson told the court an R&D grant would offset some of the amount owed, and accountants were “doing those numbers”.

“This has been a matter with the ATO and I’ve tried several times to work with them, that’s been going on several years,” Mr Wilson said. He highlighted COVID and said that “unfortunately trying to grow has been a struggle”.

The grant of $1 million was only half of what the ATO had sought – Mr Wilson argued this included interest but conceded even if the grant came through tomorrow it would not “cover the whole lot”. The court ordered the company wind up.

Mr Wilson has not responded to multiple ABC requests for comment. His LinkedIn profile, home to inspirational business videos and messages, once quoted himself saying starting a business was like playing in a giant mud puddle: 

“Embrace the mess and make mud pies – success tastes sweeter when you’ve earned your dirt!”

His LinkedIn profile was deleted this week.