[From this article]

Simon Yencken, lawyer entrepreneur, has always been one for trying something new. "My philosophy is quite simple," he says. "You can never discover new horizons unless you have the courage to lose sight of the shore."

Coming from an academic background of maths and law, Simon had not intended to pursue law as a career after leaving university in Melbourne. That changed following a chance meeting with Keith Skinner, then the second most senior partner with Moule, Hamilton & Derham (one of the Herbert Smith Freehills legacy firms) in 1977. Keith spotted something in Simon and offered him articles of clerkship. "I thought that might be interesting," Simon recalls, with characteristic understatement, "so I accepted. It was one of the best things I ever did."

After training and qualifying, Simon went on to become the youngest ever partner admitted in the Melbourne office and charged with developing the banking and finance practice. He had always hankered for a move to London, and that opportunity was to come in 1993 when he accepted the role to head the legal function of Reuters (now Thomson Reuters). At that time, the role of general counsel was not held in such high esteem as it is today, and there were certainly challenges.

As general counsel, Simon initiated a series of changes that were then considered radical but have since become commonplace. He created a panel of preferred law firms and he required all the company's outside counsel to enter into service-level agreements. He was among the first general counsel to call upon external legal services providers to demonstrate how they could add value to the relationship by, for example, providing secondees.

Simon certainly caused a stir in the UK legal market, which resulted in his being asked to speak at many conferences and seminars about his approach to instructing outside law firms: "Many of the changes I introduced were already happening in Australia. All I was doing was putting them into practice in the UK. Everyone got quite excited about how novel I was being, but there was really nothing novel about it," he says. He built up the Reuters' legal function, gave it cohesion and made sure that it operated to the highest professional standards. Simon was also made company secretary, to add to his responsibilities. However, increasingly he felt that he would like to be more engaged with the business.

That opportunity came in 1996 when Simon joined the board of directors of Tibco, a financial data software company that Reuters had acquired. Tibco was then split into two with Simon becoming chief executive officer of Tibco Finance. In order to fulfil this role, he was posted to Palo Alto in California.

One of Simon's legal colleagues asked him about the role as CEO at Tibco: "How do you have the guts to do that? I never would!" But this was yet another challenge which he felt he could take on. "I knew that I would have to learn quickly, but this was exactly the sort of mission I relished. I had a maths background, strong legal knowledge and an increasingly good understanding of how businesses operated. Why would I not give it a shot?"

Magic of tech

While the management aspects attracted him, what most excited Simon was the rise of the internet and its potential for business. He began to take an interest in other software companies looking to capitalise on online opportunities.

One of these was a company called Aconex, a collaboration platform for construction and engineering industries, which was introduced to Simon by his cousin. Simon invested in the company in the first round in 2000, joined the board of directors in 2008, and was chairman for three years (2011-2014). Aconex was also subsequently successfully listed on the ASX in Australia and has a current market capitalisation of A$948 million.

His next venture was in a company called NextSet Software, which provided specialist software products for banks. In 2003 NextSet was acquired by Razor Risk Technologies, an Australian public company, which was subsequently acquired by TMX (the Canadian stock exchange). That gave Simon and his wife an opportunity to return to Sydney. There they might have stayed but for a holiday to Palo Alto, where another opportunity came Simon's way. This was yet another start-up and, nine years later, is now Simon's principal focus.

The company is called Fanplayr, an online service based on the digital equivalent of shop assistants in bricks and mortar retail stores. As a visitor searches online for products or services, Fanplayr enables retailers to target particular segments of shoppers, based on a data analysis of where the consumer came from, what they are shopping for, prior purchases, and so on. This allows retailers to provide offers or other incentives to get shoppers to 'check out' or to increase their cart size, or to guide visitors to other potential purchases - all through the magic of algorithms and data crunching.

"What I like about start-ups is that you have to be prepared to do everything while starting from nothing," says Simon. "You get incredible highs and some desperate lows, but the feeling of satisfaction when it all comes together is very stimulating. In fact, it is almost an addiction!"

Simon continues: "I loved being a lawyer and law is one of my great passions, but equally I could have happily pursued a career in technology. I never really wanted to stay doing the same thing for too long. That prompted me to make shifts at different times in my life.

"I believe Herbert Smith Freehills is one of the world's most pre-eminent law firms," Simon reflects. "The firm's partners possess a unique ability to understand their clients' commercial objectives, and to provide a suitably tailored legal solution. I was pleased to see Aconex choose Herbert Smith Freehills for their IPO, and I am sure there will be many other opportunities to continue working with the firm."