Tristan Dollie, Partner at Brown Rudnick — On Special Situations, High Net Worth Clients and the Evolution of Modern Dealmaking

In this episode, Tristan Dollie, partner in Brown Rudnick’s special situations team, explains what “special situations” actually means in practice and why some of the most interesting deals in the market sit outside conventional legal structures.Tristan breaks down the three broad categories of special situations work and explains how his team combines legal expertise with investment banking and commercial advisory experience to help clients structure and execute unconventional transactions.The conversation explores the types of clients Brown Rudnick works with, including high net worth individuals, family offices, entrepreneurs and opportunistic investment funds, as well as how these relationships differ from working with traditional institutional clients.Tristan shares insights into how the firm sources work and develops client relationships, including travelling internationally to meet investors in places like Monaco and Dubai and why face-to-face interaction remains essential in a relationship-driven market.The episode dives into how special situations lawyers often go beyond purely legal work — sourcing opportunities, introducing equity partners, speaking to lenders and helping clients identify off-market assets and investment opportunities.Tristan explains how this approach differs from the traditional image of transactional law and why entrepreneurial thinking, commercial awareness and creativity are becoming increasingly valuable skills within modern legal practice.Tristan reflects on the unpredictability of deals in the special situations world, sharing examples of transactions that evolved completely differently from how they were originally structured and why adaptability is essential when operating in this environment.Tristan also discusses what makes a successful special situations lawyer, including curiosity, comfort with ambiguity and the ability to think creatively across multiple disciplines rather than simply applying standard precedents.The conversation then turns to broader market trends, including the growing investor interest in healthcare assets, care homes and alternative real estate investments, as well as the evolving future of offices, retail and mixed-use developments.Tristan shares insights into how shopping centres and retail assets are adapting post-COVID, including the increasing focus on entertainment, food and beverage offerings and experiential destinations rather than traditional retail alone.Finally, Tristan reflects on the changing nature of legal careers, why some of the most interesting opportunities exist outside traditional law firm structures and how young lawyers can differentiate themselves through commercial thinking and relationship building.00:00 Introduction  00:20 Meet Tristan Dollie & Brown Rudnick  01:00 What is a Special Situations Team?  02:00 Complex Transactions, Distress & Litigation-Linked Deals  03:00 Working with Difficult Jurisdictions & Sanctions Issues  04:00 How Clients Are Sourced  05:00 Monaco, Dubai & Relationship-Driven Business Development  06:00 High Net Worth Individuals vs Institutional Clients  08:00 Bringing Additional Value Beyond Legal Advice  10:00 Sourcing Deals, Assets & Financing Opportunities  12:00 Lawyers Acting Like Investment Bankers  13:00 Entrepreneurial Law Firms vs Traditional Models  14:00 Brown Rudnick’s Approach to Dealmaking  15:00 What Makes a Good Special Situations Lawyer?  17:00 Why Curiosity & Creativity Matter  18:00 Working with Ultra High Net Worth Clients  20:00 How Different These Transactions Really Are  21:00 A Real Deal That Completely Changed Structure  23:00 Flexibility, Negotiation & Commercial Thinking  24:00 Hiring Lawyers from Non-Traditional Backgrounds  25:00 Market Trends: Healthcare & Care Homes  26:00 Retail, Offices & Alternative Asset Classes  27:00 E-Gaming, Shopping Centres & Experiential Retail  28:00 Why Retail Isn’t Dead  29:00 Final Reflections & Career Advice