Failure is an unsung hero. The well-trodden path of the Bar may not be seen as the most entrepreneurial by many, but for me, who was not an inevitable candidate for the Bar on paper, getting pupillage and developing a practice required: adaptability, persistence, a big glug of self-awareness and, critically, comfort with failure. The war cry of tech start-ups is ‘Fail Fast, Scale Smart.’ Meaning, test your ideas quickly, learn fast, adapt wisely and push forward when the timing is right. I could not agree more. I deploy that edict in my career at the Bar and the creation of Advocatr.

Inspiration favours the prepared mind. My favourite inspirational movie as a child was Working Girl, a ‘downtown’ girl trying to make it in the big city. One of the most memorable quotes from the movie for me was: ‘I read a lot of things. You never know where the big ideas could come from.’ The big idea for Advocatr came one sunny morning in Constantia, Cape Town, when we were enjoying our holiday before a friend’s wedding. I was doing what barristers apparently do on holiday: thinking about advocacy. Actually, I had been thinking about the advice that a Bencher from Gray’s Inn had given me and reflecting on the books I had been reading on communication, rapport and the art of persuasion. I’d also been thinking about how hard it was to get feedback on one’s advocacy outside the formal education setting. Specific, honest, detailed feedback on what you did, why it worked (or didn’t) and what to change next time. Then it hit me. What if there was an online advocacy training platform? One where you could record your performance and get bespoke feedback on your video from which you could develop. One where it did not matter if you were a primary caregiver and could not make the in-person CPD courses. Or if you did not live in a big city and you wanted to practise after your Bar course but before interviews. Or maybe negotiating public transport every time you wanted to participate in a moot was an additional mobility challenge.

What’s the worst that can happen? Many have noted my curiosity and willingness to experiment. I suppose curiosity is a reason why I decided to be a barrister, though the answer never made it into any of my pupillage interviews. On reflection, I am interested in people, in what happens in their cases, in how things work and in how to solve the problem… or persuade the court to solve the problem in my favour. Being curious only takes you so far without the willingness to experiment – ‘structured experimentation’. Testing whether a line of enquiry is necessary to pursue. Testing to determine whether an idea has any potential. That is how we approached creating our AI advocacy training platform, one that allows advocates to record their submissions and receive feedback on how to improve, enabling users to fail in the privacy of their homes, iterate and perform better each time. We had to test the limits of what we could do, what AI could do, and what they could do together. Some rabbit holes were more fruitful than others. The worst thing that can happen from structured experimentation is that you realise your idea did not work, and you occupied your time learning lessons that you can use again in future.

The harshest critic can be our greatest teacher. ‘It works!’ Heart-stopping when we realised that Advocatr could process the videos and give feedback. No longer a dream or a plan, but an actual functioning product that was… terribly rude. The first tests of functionality used non-advocacy video recordings of us and produced some savage responses: ‘The transcribed speech reveals an utter breakdown in coherent thought structure and legal content, rendering it completely ineffective as advocacy. This is not the standard expected of a barrister.’ Not the confidence builder we were working towards. We still laugh about it. But, underneath the rudeness, this was the moment I knew we had something real. It could hear you, see you, understand your facial expression and your manner. As it had when I was seeking pupillage, the harsh criticism spurred me on to adapt and improve. Myself. And the product.

Perfectionism is a poor co-founder. Throughout my career at the Bar, I have considered and debated what ‘good enough’ was. I even renamed the concept the ‘Gudenuff’, a giant, fluffy, multicoloured yet mysterious creature that everyone talks about as the goal while being unable to pinpoint it. At the Bar, done is not good enough; work is only good enough when it hits the high standards for your client and for the court. Developing and expanding a tech product calls for a different approach to the ‘good enough’. Viable is, apparently, good enough. That was an uncomfortable feeling when we shipped the minimum viable product at the end of September 2025, in an alpha phase: ‘What do you mean we have to give people the unfinished tool?’ However, whatever the guise, the lesson – no matter how elusive the Gudenuff is at the Bar – is that perfection does not serve you. The behavioural manifestations may be different, but the core tenets are the same: decide what is essential, be clear and honest about what you need to meet the essentials, and do that. Obsessing about the frills will not serve your long-term goals.

Push your limits. Delivering the essentials is not the same as playing it safe. Whether you are building a practice or building a business, you cannot be afraid to push your limits; it is only then you know how committed, and how strong, you really are. In the pupillage application process, I worked hard and saved ferociously to pay for a master’s or for living expenses during internships. In practice, I did the long hours and practised in areas I was not familiar with. Pushing yourself is pushing to learn and grow. We pushed out early with an AI-judged mooting competition, the world’s first so far as we could tell. That meant putting the model to work in a way that went beyond even our original idea. While the upload and download ended up being a frustrating hurdle (and thanks again to our fantastic participants who went on the journey with us), the whole experience rose to our expectations and beyond. The AI reports identified where each argument gained or lost force and which delivery habits were helping or undermining persuasion. Watching it work was the closest thing entrepreneurship offers to the buzz of a devastating cross-examination. It is absolutely right that ‘discomfort is the price you pay for a fulfilling life’.* Get uncomfortable.

If you are not afraid, it isn’t bravery. The initial idea grew into a mooting competition, debating practice and a mini-trial, and we are now building the functionality to simulate witness handling. Being vocal and backing your idea in front of your peers is extremely exposing. I have feared the judgement of colleagues, the mistakes (being a barrister is not the same as being a start-up founder), and that this will all come to an embarrassing end (it still may do). Yet, every modern innovation came from someone doing something that others thought was insane. To most, the idea of speaking in front of strangers, aloud, with no control over who may come into the courtroom, every single day is a mad one. Yet we do it. Taking a chance, being vulnerable, experimenting and accepting the risk of failure, and getting back up to try again is the hallmark of courage. Which is why we must look upon failure as our coach and our hero. 

 

* ‘Discomfort is the price you pay for a fulfilling life’, Shoes and Shots blog