“I got my ass handed to me during the last financial crash,” says Karl Deeter candidly.

Deeter, one of Ireland’s most recognised mortgage brokers and a vocal advocate for consumers, was not alone. Few sectors came through the crisis unscathed, but Deeter, working at the intersection of banking and property, was more exposed than most.

Deeter, however, dusted himself off and kept on going. Part of it was the necessity to earn a living, and part came from his personality. “I have always put in long hours. I have always worked hard, sometimes too hard,” he says.

As the mortgage and property market began to recover, so did Deeter’s broker business. But the more he looked at his sector, the more he determined it was ripe for disruption.

The way he saw it, the interface between brokers and banks was akin to a “slaughterhouse”. Brokers were using different systems. Some customers were going directly to banks, others were working through brokers. The system was disjointed, messy, and, according to Deeter, not giving the consumer the best possible outcome.

So, a little under five years ago, he launched a new business called OnlineApplication (OA). The company uses machine learning to get mortgages processed faster. The goal was to provide mortgage applications from your smartphone, with faster decisions and less paperwork.

Using OA, prospective homebuyers or loan switchers submit applications over their phones to a broker. Brokers then file these directly into the bank lending systems digitally.

The industry saw potential. Some 60 mortgage brokers and five lenders, as well as 200 life insurance intermediaries and two life companies, linked up with the platform.

Investors were also enthused. Hostelworld co-founder Tom Kennedy and Patrick Joy, founder of storage equipment specialist Suretank, backed the company. Deeter admits they were buying as much into his own track record as the product he was endeavouring to build. 

Enterprise Ireland also came on board.

Last week, it was announced that Deeter was selling the company behind the platform, Artificial Intelligence Finance (AIF), to London-listed Software Circle in a deal worth as much as €9 million.

Some €5 million of that is coming straight away, with 95 per cent of shares being initially sold.  An additional €4 million may be paid for the remaining 5 per cent stake if AIF meets specific performance targets in 2026 and 2027.

Deeter will be staying on site to help ensure those targets are achieved. He owned half of the business before its sale, so it represents quite a turnaround from when he was getting his “ass handed to him” during the crash.

“I learned from that. And one of the things I learned is that it is okay to take some chips off the table,” he told me last week after the deal was made public. “There is nothing wrong with taking cash off the table.”

Besides, the way Deeter viewed it, the company was always going to be sold at some point.

“If you are building in tech, you will always have people reaching out, looking to chat with you or looking to make introductions,” he says. “And we have had a lot of people reach out to us over the last few years.”

In fact, Deeter expected the business to be sold in 2023, before a deal eventually fell away.

“In mid-2023, there were a lot of people swarming around us. There were a lot of people courting us. It was a bit like Tinder for business, seeing who was going to swipe right. But we wanted it to be the right people, also. Some people kept on coming back looking for more and more information and trying to chip the price,” he says.

Instead of selling, he decided to buy. Last year, AIF acquired the insurance technology business Money Advice for an undisclosed sum. It was later rebranded as AO Life and CRM.

Eventually, the right suitor came around in the form of Software Circle. “Our investors have been great, and I wanted to make them whole. Software Circle were decent. They did not play around. They were straightforward to deal with,” he says.

Besides, being owned by a stock market-listed company will add further legitimacy to his business, Deeter argues. “It is a natural progression,” he says. 

I asked Deeter if he was apprehensive about selling a company he built from the ground up. “What else was I going to do? We are five years in now. Was I going to sit in it and keep working 12 hours a day without taking money off the table? I always work hard and I will continue to work hard, but there is nothing wrong with taking money off the table,” he says.

Deeter is less than enthused about the capital gains tax rate he is being hit with. “We talk a great game about being pro-entrepreneur, but sometimes it is hard to see it,” he says.

Still, he acknowledges that it is a conversation for another day. For now, he is happy that his vision has been validated. 

“Every so often, lightning strikes in your favour. I saw a problem in my industry, and I thought I had a solution. People believed in me to do it – investors, clients. They backed me when they probably did not need to,” he says. 

Now, with the ink dry on the deal and the future of AO secured within a larger group, Deeter finds himself at a new crossroads — one that feels less like an ending and more like a progression.

“I’m not done,” he says.

Elsewhere last week…

With IBI, Tom Godfrey has seen it all: market crashes, privatisations, and high-stakes mergers. What’s next for the man who’s helped shape Ireland Inc from the inside? I caught up with the dealmaker for an in-depth interview about his life and times. 

With private-equity backing and a pipeline of acquisitions, Dains Ireland is positioning itself as a major player in the Irish accountancy sector. Regional head Neal Morrison explained to Tom how culture, not just capital, is driving the firm’s next chapter.

Caitriona Ryan and Nicola Ralph, co-founders of the Institute of Dermatologists in Dublin, have been named IMAGE PwC Entrepreneur of the Year for their transformative work in skin health and dermatology in Ireland. They talked business models, inspiration, and the future with Fiona.

Last year, Keith O’Loughlin lost his best friend and business partner, Eddie Jordan. To celebrate the tycoon, he wrote a book and launched a foundation. But this is just one part of O’Loughlin’s story, which has seen him move from fixer to company builder.

As Europe’s energy crisis deepens, Germany’s rising reliance on imports reflects a broader EU retreat from energy independence. A new EU-US energy deal, framed as a solution, risks locking in long-term fossil fuel dependence, undermining climate goals and strategic autonomy. Constantin had expert analysis.

Midsal is being sued by Swiss real estate group Necron after it withdrew from a €14.25 million site sale, citing breach of contract on completion of the deal. The firm says it now intends to develop the hotel itself. Francesca had the story.