Billionaire Tomorrow
"There was a real unfairness in the way the industry had been set up"
There can’t be that many highly-qualified lawyers on earth who work for nearly four years without a salary, or see their bank card declined. This was the first few years as an entrepreneur for lawyer Yvonne Wakefield who saw the good in working from home long before lockdown.
It shouldn’t happen to a lawyer and on that day that it did; in a smart restaurant too. It was a reminder that Yvonne Wakefield was a battling entrepreneur first and a legal eagle second.
Wakefield was at a shopping centre in South Africa having lunch with a big client who ran an investment fund. She approached the card machine with alacrity, but to no avail.
“I ran into a client, one of our earlier clients and he used us for a lot of deals. We had a lovely chat and we got to the till and were next door to each other and my card was declined with insufficient funds and he was standing next to me,” she says.
“I don’t know if he didn’t notice, or if he noticed and pretended to not notice, but he packed his things into the bag and said:’ goodbye’ and left. I was eternally grateful.”
I interviewed Wakefield on my all-time favourite TV show the Entrepreneurial Edge on CNBC Africa, in 2011, when she founded her company Caveat in Cape Town and began bootstrapping the business through lean times.
“We have grown astronomically, so now we have between 50 and 55 lawyers,” she says.
Ironically, it was the embarrassment of riches at the big legal firms of South Africa – where Wakefield cut her teeth – that gave her the idea for her own business.
For people just in from the moon, big legal companies in Johannesburg and most cities inthe world, for that matter, are buttered on both sides.
Even in the worst of times, to law outfits, large fees areas shiny and attractive as the massive, polished, wooden tables in their boardrooms paid for by the fruit of the labour of lawyers.
This opulence gave Wakefield her idea to cater for those small operations that couldn’t afford in-house lawyer nor the hefty bills of the big firms.
Chris Bishop and Yvonne Wakefield on a Zoom Call
“So, there was a real unfairness in the way the industry had been set up that I noticed. I also was unhappy about fee targets; they were kind of incentivized to bill as much as possible. That felt to me like there was a bit of a conflict because we should actually try to get a result for your client as quickly and as commercially viable as possible , rather than bill as much as possible,” recalls Wakefield.
“There were some parts of the profession that I thought were not optimally working in the interest of the market it was serving. Even back then I realized why are these guys working from this huge elaborate building.”

Wakefield’s business was virtual from day one, with lawyers working as and when needed, long before COVID-19 changed the way people worked. It was based on undercutting the opposition and doing this differently.
“I had these ideas brewing in my head. Then came across some examples of lawyers who were doing things differently – in the US predominantly. I saw an article in Forbes magazine about a lawyer who had found an entrepreneurial way of structuring a law firm in such a way that the overheads were stripped out. I thought it was interesting and slept on it a few nights and woke up in the morning and said:’ That is what I am going to do’. There is this huge gap in the market, totally unserved and I did a bit of market research just to check that my assumptions were well-founded and were actually reflected back to me from the market. Then went about designing it, what is so interesting about it, it is a completely simple model it is not that we use technology…is not technological innovation. The innovation is in the business model where you have a panel of lawyers The lawyers are not employees of the firm; call it a firm it is actually a private company. The lawyers are all contracted and then you have the client base. The company is sourcing work for the lawyers, putting lawyers together for clients. Making sure that the right matches are made,” says Wakefield.
She has completed a decade as an entrepreneur with the virtual online legal consultancy that started small and that has prospered through commercial and merger and acquisition work.
“ Our mark-up is 25%, which might sound high. The larger firms have a mark-up of 200 to 300 percent, so, to my mind, it is a no-brainer it means that the fees are…The lawyers choose which fees they want to charge because the panel is quite big and there is healthy competition within the panel of lawyers in the firm, the lawyers chose where they want to pitch their fees,” she says.
In many ways, Wakefield was destined to be a lawyer long before she studied the law.
“I liked to get my own way, that was the one reason and the other reason was that I had a deep sense of justice. I always found myself fighting for other people and wanting to help other people to be able to protect themselves.
I was one of three girls and if we had a grievance with the parents, I would be the one to voice the grievance and to take the push back and then have the argy-bargy on behalf of the siblings and then I would take the flak but eventually get some kind of progress for all of us.”
She went to university early and excelled and qualified as an advocate at the age of 22, but in the gritty courts of South Africa it was rough and tough.
“Going into working as an advocate at 22-years- old, very young, and a woman in a very male-dominated society, with a kind of taunting. It was bullying … but it was very carefully done in a way that you were not really sure. You feel intimidated all the time. There definitely was that and it was tough,” she says.
“I mean some of the things they would say and I only realize it now, were quite deliberate to unsettle you were things like: ‘I have had a look at your papers and I have never quite seen something like this before.’ They would say things like that and I would end up winning. Those types of comments, you hear that and would stress. It took a lot to keep myself grounded. Of course, I made mistakes, everybody makes mistakes. It was tough but it was still a very gratifying job.”
In recent years, Wakefield has batted away venture capitalists and is looking to new markets like cryptocurrency where they are getting an increasing amount of work.
“It is super interesting and obviously like the legal…the legislative and regulatory regimes are just so slow in catching up to the advancement . There are changes in the financial services regulations at the moment and soa lot of the exchangers and a lot of the investment platforms or crypto clients are looking ahead and needing advice around how best to formulate their strategies going forward, based on what the current regulatory landscape looks like and what the perceived future regulatory landscape is going to look like so they don’t have to make too many changes as the law changes,” she says.
It seems advocate Yvonne Wakefield – ten years on – has only just got started.
