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Raymond Sun is a tech lawyer, full-stack developer and content creator who loves to build AI programs. He also loves to dance hip-hop and play chess. Raymond describes it as “a weird mix of hobbies” and he admits that his path might not be your typical lawyer journey. He shares his story with LSJ in his own words.

It all started with chess

I was born and raised in Sydney. I went to primary school in the Georges River area. In year one, I picked up chess as a hobby after my friend gifted me a mini chess set for Christmas. I soon came to love the mix of strategy, problem-solving and creativity in chess. Chess became my first real hobby, and I got pretty good at it, winning local competitions. Looking back, I think chess helped to “wire” my brain to appreciate both spontaneous creativity and cold analytical thinking (two qualities often perceived as opposites).

From arcade to algorithms

I attended Sydney Technical High School. I enjoyed subjects that exercised critical thinking and analysis of evidence (e.g. history, legal studies, economics) because they gave me a similar stimulation of playing chess. So naturally, I developed an interest in doing law after high school. At the same time, I loved to play video/arcade games. My friends and I wanted to learn how to develop and sell our own games. That’s how I picked up coding (Java, Python, JavaScript, C) as another hobby and developed a general interest in all thing’s computers.

Hustling and hacking at uni

After completing my HSC, I attended law school at UTS. While I could’ve done a dual law and computer science degree, I chose to study a straight law degree as I wanted to finish my degree as early as possible. But I continued to code and build apps on the side.

Throughout uni, I found myself enjoying the more “commercial” subjects like contracts, IP and competition law. I also did electives that aligned with my tech interests like “Disruptive Tech and the Law” (which was a new subject back then) and programming subjects at the IT school (as part of my free electives). I felt my choice of subjects geared me towards a corporate/transactional lawyering career.

On the side, I picked up a few part-time jobs, including working as a chess coach for primary school kids, HSC tutoring, and an office clerk at a barrister’s chambers.

My most interesting gig was my internship at LawPath (a legal tech startup) where I wrote blogs on tech such as blockchain and privacy. Around that time, I represented UTS at the 2018 Global Legal Tech Hackathon. I was the developer in my team and designed a prototype interface that streamlined payments for barristers. When my boss at LawPath heard about my hackathon dev skills, I got moved into a “Legal Engineer” role to help build the company’s document automation platform. It was a very novel role at the time, and it gave me a taste of what a combined law and tech role could look like.

I also picked up new hobbies during uni. Inspired by K-pop and dance competition shows, I started to learn street dance (mainly Krump and Urban style) as a new form of cardio exercise, and I started attending dance classes regularly. I enjoy reading and formulating my opinions on areas with tech x law crossover, notably AI regulation.

Unexpected viral success

I was lucky enough to join the clerkship and graduate programs at Herbert Smith Freehills. But I started my grad program in 2020 at the peak of the COVID-19 lockdown. With so much time at home, I started posting vlogs of coding projects on YouTube in my spare time (under my pseudonym “techie_ray”). My most successful video was about my AI algorithm that could compare and grade similarity between my dance cover video and the original dance video. I applied my algorithm to grade K-POP dance performances and showcased those results in a video series, which went viral across social media (particularly in Asia). That’s how my content creation journey started, and I even got to collaborate with a Japanese entertainment company to repurpose my algorithm for a dance challenge as part of a popular variety show in Japan, “JO1-CTX” (which aired in September 2022). Since then, I have been experimenting with other creative applications of AI (e.g. music production and video editing), sharing my projects with a community of nearly 30,000 AI hobbyists, called the “techie_ray fam”. Indeed, the COVID-19 period was an ironic time for me – during the days of social distancing, I never felt more connected.

Tech lawyering

I am now a four year PQE lawyer who’s settled in Technology, Media and Telecommunications (TMT) practice at Herbert Smith Freehills. I fall more into the “Technology” bucket of TMT, advising clients (both small and large) on the regulatory and commercial contracting aspects in relation to AI, IT/software and data projects. Due to the cross-border nature of many tech projects, my work can get quite international, and I’ve done a fair bit of work sourced out of the UK, China and Singapore markets.

It’s hard for me to describe my day because I often work on a diverse range of matters so each day feels different. But typically, I start my day at 9.30am and finish somewhere between 8 and 10pm. My work can range from advising a local AI startup on their go-to market strategy, to doing due diligence on IT and privacy aspects of a multi-billion deal, to negotiating, to running workshops in China and Singapore on AI.

Night owl mode

After work, I like to do a quick dance workout before dinner. I like to relax by playing online chess or hacking away at my personal tech projects. To date, I have built and launched several apps, including a mobile app that uses AI to analyse dance (‘SyncTrainer’), a website that tracks AI regulation over the world (“Global AI Regulation Tracker”), and a news engine that curates tech news updates (“Global Tech Law News Hub”). I also spend some time before bed writing my newsletter (“Ctrl+AI+Reg”) and LinkedIn posts on my thoughts on the latest developments in AI. I typically go to bed around midnight.

Weekend downtime

When I’m not doing house chores or hanging out, I love to spend my weekends by either hacking away at my tech projects, creating videos about AI concepts or tools, joining an AI developers club meeting, or attending dance class. I tend to rotate through my hobbies each weekend, it’s not like I do everything at once!

Candle or bonfire?

That’s basically me in a nutshell! I’m still relatively early in my career and figuring out my path. As I continue on my own path, one mantra I like to follow is: “pace yourself”! Don’t feel the need to do or achieve everything at once. To use an analogy, I prefer to be a small candle that can last for a long time, then to be a big flashy bonfire that burns out quickly.