A New Chapter at SSW for Gabriel Olearnik

After years working across the litigation finance ecosystem, Gabriel Olearnik has joined SSW as a partner, where he will focus on identifying, underwriting, and executing both contentious and transactional opportunities. Gabriel brings a uniquely broad perspective to the role, having worked for funders and law firms, while continuing to serve as Chief Investment Officer at Burgundy Capital Management. In this Q&A, he discusses his new position, the advantages of experiencing litigation finance from multiple vantage points, advice for younger professionals entering the field, and his forthcoming book, Londoning: Tales of Canada.

1. You recently joined SSW as a partner. What attracted you to the firm, and what will your focus be in this new role?

What drew me to SSW was the combination of entrepreneurial energy, strategic seriousness, and breadth of opportunity. It is one of the leading Polish firms and routinely works with leading international clients on transactions and disputes in this region. 

Just as importantly, it is a firm with exceptional people, some of whom I have known for more than 20 years. There is a rare combination here: internationalism, ambition, and genuine depth.

At SSW, my focus will be on identifying, underwriting, and executing opportunities across both contentious and transactional matters. That includes evaluating claims and recoveries, structuring funding and risk-sharing solutions, and helping clients think creatively about how disputes and legal assets can be managed as part of a broader commercial strategy.

What particularly appeals to me is that the role is not confined to a narrow segment of the market or to a single jurisdiction. It allows me to bring together litigation finance, legal analysis, deal execution, and strategic advisory work within one practice.

2. You have worked on several sides of the litigation funding ecosystem. How has that experience shaped the way you evaluate and structure funding opportunities today?

The varied workplaces have made me look at cases in the round. It is never simply whether a case is legally strong. It is whether the opportunity works in the real world. That means looking at the claimant, the legal team, the documentary record, the economics, the jurisdiction, the enforcement pathway, the likely behaviour of the respondent, and the route to monetisation.

It also means being honest about human factors: whether the claimant is resilient, whether the lawyers are commercial, whether the information flow is reliable, and whether the matter can withstand pressure over time.

That broader experience also shapes how I think about structuring. Good structures align interests, leave room for sensible decision making, and anticipate points of friction before they arise. In many matters, the difference between a good and a poor investment lies not simply in case selection, but in whether the structure reflects how disputes actually unfold.

3. Litigation finance has evolved rapidly over the past decade. From your perspective, what are the most important trends shaping the industry right now?

A few things stand out.

First, the market is becoming more sophisticated. Litigation finance is no longer a niche concept; it is increasingly understood as part of mainstream legal and financial strategy. As a result, clients are asking more complex questions, and capital providers are under pressure to be more selective, more disciplined, and more imaginative.

Second, there is growing interest in portfolio and structured solutions rather than purely single-case funding. Clients increasingly want capital solutions that support a broader business objective, whether that is balance sheet management, risk transfer, or monetisation. That shift requires funders and advisers to think more like strategic partners and less like isolated case selectors.

Third, enforcement, asset intelligence, and active case management are becoming more central. A strong legal claim matters, but it is not enough on its own. The best outcomes often come from combining legal analysis with deep investigation, commercial leverage, and, where appropriate, communications strategy. In other words, value is created not merely by funding disputes, but by managing them actively.

Finally, the industry is maturing in a way that will reward credibility and long-term judgement. As the market grows, counterparties are increasingly differentiating between providers who merely deploy capital and those who genuinely understand disputes, law, recovery, and execution. I expect that distinction to become even more important in the years ahead.

4. Your career spans investment management, law, and litigation funding. What advice would you give to younger professionals interested in building a career in this field, and what paths are available to them?

My first advice would be to build real substance before worrying too much about labels. Litigation finance is inherently interdisciplinary. To be good at it, you need to understand law, risk, economics, negotiation, and people. The strongest early career foundation is therefore usually excellence in one demanding discipline, combined with curiosity about the others.

For some, that path will begin in private practice, especially in disputes, arbitration, or insolvency. For others, it may begin in investment analysis, special situations, or credit. There are also routes through insurance, asset recovery, investigations, or legal operations. The field is broader than many people assume.

The second point is to develop commercial judgement early. Younger professionals sometimes focus heavily on doctrine or process, but the real question in this industry is often: what is the asset, what are the risks, and how does this get resolved or realised in practice? People who can combine analytical rigour with commercial realism tend to distinguish themselves quickly.

The third is to learn how to write and think clearly. This industry rewards people who can absorb complexity and express a view with precision. Whether you are writing an investment paper, advising a client, or negotiating a structure, clarity matters enormously.

And finally, patience. It is a field in which pattern recognition counts for a great deal. Over time, if you remain rigorous, curious, and adaptable, there are many paths available, including some that do not yet exist.

5. In addition to your professional roles, you are also an author. Your new book, Londoning: Tales of Canada, will be published later this year. What inspired you to write it, and how does the creative process compare with your work in law and finance?

Londoning: Tales of Canada grew out of a long standing interest in memory, place, identity, and distance. Canada has always carried a particular imaginative charge for me: it is beautiful, melancholy, and morally textured.

It is also personal. My grandparents were supposed to emigrate there in the 1950s, but my grandmother developed what was then described as a “shadow on the lung”, which ultimately proved harmless, and they remained in England for health reasons. Had they gone, my parents would never have met. That story has always stayed with me as a lesson in contingency, and in how our own lives are, in some sense, improbable gifts.

The book tries to capture something of the Canadian landscape while also exploring deeper questions of humanity and inheritance. Canada is a place shaped by striking mixtures of English, American, Native, French, and other traditions. There is exile, longing, history, reinvention, and the strange emotional geographies people inhabit. I have also added some legends and a flicker of magic: there are werewolves, mermaids, nature gods - and a couple of wendigos.

In one sense, writing it was very different from my work in law and finance, because creative writing allows for greater freedom, ambiguity, and emotional resonance. You are trying to create something that speaks to the deepest things, the things that make us human.

At the same time, there are real similarities. Both require discipline, close attention, and a tolerance for revision. Both depend on precision. Perhaps most importantly, they both channel language to bridge gulfs, to create a commonwealth of understanding.