Entrepreneurial lawyer Nathan O’Connor remembers the exact moment he decided to sell his Liverpool-based startup Online Legal.

The technology-led customer acquisition specialist for the legal sector was acquired in 2022 by competitor Blume for an undisclosed sum.

“There’s a right time for every founder to exit their business,” recalled O’Connor. “Mine was in 2021 about three weeks after our daughter Isabella was born.

“I remember it was about 3am or 4am and Meta had updated their algorithm and I had to work intensely through the night.

“Then Isabella started crying and I had to give her a bottle. I thought ‘this isn’t what I want to be doing at 3am-4am in the morning, I really just want to be feeding my daughter and giving my wife some more support.

“It was about looking at the priorities in life. It’s only when you look back afterwards that you realise how stressed you were and doing things liking eating takeaways at night.

“At this stage I had been approached by multiple parties about acquiring the business in the previous 6 months and my decision started to become much clearer – I was ready to exit.

“From when I first started Online Legal, I had always had a plan to exit the business within five years and move on to new projects.

“The five-year mark also coincided with the arrival or my daughter, and really helped to make my decision.

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“Online Legal was also at a stage where we needed to scale and make key appointments to drive the business forward.

“I could no longer be responsible for HR, finance, marketing and anything else you wanted to add to the mix! I felt that this could be achieved much quicker with the help of a bigger organisation and a wider support network.”

O’Connor first displayed his entrepreneurial flair when he was a student at the University of Liverpool.

“I used to run a laptop comparison site,’ he recalled. “It was a bit like a for laptops. Think of it like that.”

He was awarded the Young Entrepreneur of the Year in 2008 by the Steve Morgan Foundation, which was set up by Redrow founder Steve Morgan.

In 2011 he joined JMW Solicitors before becoming legal counsel for Shop Direct (now The Very Group).

It was during his legal career that he identified a gap in the market that became the inspiration for his eventual business Online Legal.

“I’d always had a big interest in digital marketing and online advertising,” he said. “Anything tech-related.

“The legal marketing industry was dominated by large advertising companies that were heavily reliant on TV and traditional radio advertising.

“They had an online presence but it wasn’t very good. They weren’t utilising some of the things I saw in Very, like personalisation.

“When I looked at their websites and their online activity I thought ‘I can do that better in the legal sector’.

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“The opportunity was in making your website relevant to your customer.”

Eventually he left his job at the age of 30 to set up Online Legal in 2016, initially focusing on medical malpractice.

“This was quite daunting in itself as I was leaving a well paid and secure white collar job, but ultimately I knew the opportunity was too good to miss,” he said.

“We introduced a personalisation chatbot. I refer to it as ‘total website relevance’. If the website isn’t totally relevant to what users are looking for, they’re going to look elsewhere.

“That’s where the law firms and advertising collectives were letting themselves down, I thought.”

Online Legal’s technology matched members of the public with the most appropriate law firm.

“We got paid by the law firm and would have a KPI to generate a set number of inquiries,” explained O’Connor.

He grew the business to £3m turnover and 10 staff but as the business grew, so did the pressure.

“It was great from a financial point of view as you see the business grow but the stress increases as you become bigger,” he said.

“You have to lend your hat to so many more things, be it a staff issue or somebody not paying an invoice.

“At the point that I sold the business we were probably spending £150k a month on socials and advertising.  It could all change at the drop of a hat. Google could suddenly change their algorithms on SEO. It was stressful.

“My main passion was digital marketing but I was doing less and less of it.”

Online Legal’s main competition came from Blume, who eventually bought the business.

“The deal process is pretty intense,” he said. “Both companies had a similar ethos and focus, which made us a perfect strategic fit.

The sale was subject to approval from the Financial Conduct Authority (FCA).

“As soon as the sale went through you have a feeling of ‘I’m not in charge now’ but the positive feelings overwhelm that very quickly.”

O’Connor agreed to stay for an initial 12 months and has recently agreed to say for another year.

“It was a strange feeling seeing other people make decisions, especially in the first couple of months,” he said. “But Isabella is now two and I have no regrets and new projects brewing in the pipeline.”