They say lawyers aren't the type to take a leap of faith into entrepreneurship, but Sofia Lind speaks to four ex-lawyers who found success in going it alone

"Lawyers don't make natural entrepreneurs, with law firm training geared towards risk management and cautiousness." This sentiment from one former lawyer sums up the general feeling about lawyers as businessmen.

While a number of lawyers have successfully cashed in their chips to start afresh with their own businesses, it seems that many of the City's finest believe these ex-lawyer entrepreneurs to be the exception rather than the rule.

One of those to have made the daring step from legal partnership to business management is ex-Herbert Smith litigation partner Helene Kydd, who runs a coaching company. She started her business, Timelon, with a business partner two-and-a-half years ago and it now advises around nine City law firms on internal and external issues ranging from bullying to client communication.

The idea to move into training came to Kydd when she and her family spent three years in India, during which she took a sign language course and went on to teach children at a deaf school.

When she first left the top 10 City law firm in 2001 after eight years as a partner, it was partly for personal reasons. However, since then she has found that her experience in the sector has led to the natural focus of her business around law firms.

Kydd says: "I wanted to have autonomy and build up something of my own doing something worthwhile. I see opportunities in the legal sector because I understand the business and because I have noted that many lawyers manage to relate better to their clients than their teams."

Her best advice to other lawyers with entrepreneurial dreams is to keep at it and believe in yourself and your abilities. "You have to be brave and persistent. Sometimes lawyers underestimate the skills they have as lawyers which are actually transferable. Handling large pieces of litigation taught me project management, which helped me when I went on to do other things."

Taking a risk

Alastair Vere Nicoll (pictured) does not have a problem with risk taking, having come in and out of his position as a private equity lawyer at Freshfields Bruckhaus Deringer.

He first left the role as a two-year qualified associate in 2003 to go skiing across the Antarctic. He then lectured at BPP Law School and also began a writing career, publishing his novel, Riding the Ice Wind.

He rejoined the firm but left again in 2007 and has since set up his own emerging markets-focused renewable technology investment fund with three colleagues from other business backgrounds. The fund, which has yet to close, has so far managed to raise £100m despite the hardships faced by businesses during the financial downturn.

As to whether lawyers make natural entrepreneurs, he says: "Typically not, because of the risk aversion. But lawyers do have a rigour in process, they are executers. Lawyers make deals happen, but I don't think that naturally they enjoy the risk of entrepreneurship.

"When you launch a business you have to adjust your analysis of risk," he adds. "Lawyers advise on risk but never have to make the final decision. Here you have to weigh up the benefit of the risk. There is more real risk, which is for both good and bad."

He has been able to call quite extensively on his legal background, commenting: "A lot of what I do is quite heavily legal. That is how I add value to the partnership."

Rebecca Doyle (pictured) was also a two-year qualified private equity lawyer when she decided to leave her legal practice at magic circle giant Linklaters towards the end of 2005 in search of a better work/life balance.

Taking a rather different route to that of Vere Nicoll, long hours have prevailed in her life after her start-up business Chez Bec, which specialises in bridal jewellery, became a full-time award-winning business venture.

The business, run out of a studio in Kent, now has two jeweller employees but Doyle remains responsible for the design. Chez Bec supplies regularly to 15 bridal shops, with Doyle aiming for that number to grow to around 50 next year.

But success has not come without hard work and Doyle thinks her experience at Linklaters was of good value for this. "I think lawyers are hard-working and used to getting in at the deep end," she says.

She has plenty of advice for other lawyers with business ideas: "Use your lawyer skills to research your market thoroughly. Then make sure to market your business, both off and online." She adds: "Be prepared for long hours – although this was not such a shock coming from the magic circle."

The entrepreneurial Bar

Could it be that while solicitors are used to leaning on the security of their partnership that the self-employed barrister has a more natural make-up for entrepreneurship?

Tim Kevan is a barrister turned fiction author who also runs his own successful online webinar business. His first novel, Law and Disorder – Confessions of a Pupil Barrister (also known under working title BabyBarista and the Art of War), was derived from his acclaimed BabyBarista blog, while his second novel Law and Peace will be published by Bloomsbury in May 2011.

Kevan draws on his 10 years practising at 1 Temple Gardens in London. He specialised in credit hire, personal injury, civil fraud and sports law. Unlike many others who have left the law, he strongly intends to return to his practice, albeit in his new home of the West Country rather than the Big Smoke.

Kevan thinks the argument for barristers trumping solicitors as entrepreneurs is two-sided. On the one hand, barristers have the freedom to plan their own time and how much they work, but on the other, any day without work is a day without pay.

However, especially for his own writing career, he thinks being a barrister was helpful in developing his storytelling skills. He says: "Barristers are very much storytellers and communicators. You are constantly presenting the client's side of things in the best light possible." He thinks lawyers make good entrepreneurs: "Lawyers are bright, dynamic people so should translate quite easily into business people. As a barrister you are used to running your own business from day one."

And Kevan does have some advice that might suit the business-minded but risk-averse lawyer entrepreneur, whether they are a solicitor or not. "Go for it, if you want to. But the best advice is to start from the bottom up rather than the top down. Build up a base of customers first rather than just launching around a big idea. Then you are starting something that can grow organically."

• For more, see Career Clinic: Can lawyers make good entrepreneurs?