In volatile industries where technology, media and advertising collide, stability is a myth and survival depends on how quickly you can pivot, Adrian Chung says. For lawyers, that reality is no longer an edge case; it is the operating environment.
Chung has experienced that volatility across insurance litigation, small-firm corporate work, entertainment, travel, automotive, and now as senior legal counsel at ad tech company Guideline. An openness to uncertainty, rather than a tidy linear story, now shapes how he thinks about disruption and legal careers.
He started in a conventional lane, articling at an insurance litigation firm, and “quickly realized it wasn’t for me,” he says. A move to a small Mississauga full-service firm let him learn “the meat and potatoes of corporate work, solicitor work, transactional law,” he says. Without Bay Street credentials, he relied on contract roles and document review to stay employed while he searched for something that felt less mechanical.
Entertainment became that target. Chung laughs that “entertainment lawyers are usually the lawyers that don’t want to be lawyers… they’re closet creatives.” He had no production background, just a long-standing habit of being “more of an active… audience or consumer of entertainment,” he says. A “law adjacent” contract manager role at Entertainment One became his entry point into a sector that had always looked out of reach. It was a seemingly short-lived pivot, as his contract at Entertainment One was not renewed due to a hiring freeze, and he soon found himself joining G Adventures as corporate counsel. This role combined his legal skills with his long-standing personal interest in travel.
During the height of the COVID-19 pandemic, he found himself stepping back on the entertainment-focused track, joining Meridian Artists, then moving to New Metric Media, and finally landing at Corus Entertainment. It was a few years of firming up an entertainment-focused profile and mastering “the nomenclature, the industry standards, the industry terminology [and] the types of agreements that you’re working with,” he says. The cost was a relentless grind. Each move felt “so hard won,” and he grew disillusioned with the entertainment market.
The work itself narrowed as the industry contracted. His days were often spent poring over “reams and reams of text,” negotiating similar contracts while budgets were shrinking. Inside Corus, he saw a pipeline where every project felt makeorbreak: “There was a sense that this needs to be greenlit… otherwise, we’re just not going to have enough money to … fund anything else further on our docket,” he says. With roles being cut and deals stalling, he stopped treating entertainment as a dream and started treating it as a shrinking, high-risk niche.
Leaving that niche then meant abandoning the idea of a perfectly curated resumé and being willing to move when the ground shifted. So he made a strategic shift to the automotive sector as senior legal counsel at Honda. “The company that I was at was no longer keeping afloat. People were being let go very actively, and so Honda seemed like the lifeline that was readily available for me,” he says. As senior legal counsel, he handled “bread and butter, corporate, commercial work” and supported financial services, but the parts that mattered most were work tied to the company’s online presence.
“I got a lot more experience with privacy, digital integration, marketing and advertising, tech, and even getting my feet wet with understanding AI and proprietary rights over AI,” he says. That exposure to data and technology issues became a bridge into something more aligned with where the market was moving.
This led to Guideline, a marketing strategy and ad tech company built around consumer data. Guideline operates an ad tech platform that uses consumer insights and data, aggregates and anonymizes it, and then sells that to brands either directly or through holding agencies in the advertising space, he says. For a lawyer who had stitched together experience in entertainment, marketing, privacy and tech, it was a logical next step.
Guideline wanted someone senior enough to operate alone but still “malleable” and “open to understanding an industry that was still actively changing and undergoing… some unpredictability,” he says. After its previous GC left, Chung stepped into the role as the only in-house lawyer, relying on external counsel selectively while owning the everyday calls on privacy, IP and commercial risk.
That structure forces him to move quickly without turning into a rubber stamp. He is expected to “be flexible to pivot from traditional ideas of how to review and negotiate contracts to understanding [that] you need to try on the business hat more often,” he says. In practice, that means knowing when to be flexible with contracts so a deal can advance, while using large RFPs with global advertising players “to create essentially super agreements” that can carry the company through future mandates.
For lawyers eyeing ad tech and data-driven marketing, Chung says curiosity and a tolerance for chaos are requirements. “There is no shortage of demand for information as it pertains to consumer intelligence, consumer insights, whatever data is out there,” he says. At the same time, advertising, media and entertainment have been “really battered by economic shifts…[and] the constant eating up of smaller companies by huge aggregate companies,” he says, which means there is work to do but little stability about where it sits.
“Understanding that there is no real stability, in terms of how traditional media used to be, is probably the best attitude to go into this space with, and just understanding that there’s always going to be work for you to do. It just might not look like what you thought it would,” he says.