What happens when a self-described introvert who went to law school to become a sports agent, spent years doing deportation defense and family law at a large firm that grew too fast, walks away mid-career with two partners and a grand total of one paralegal to see if they can do it better? In this episode of the Trustcast Show, Zane Myers speaks with Tim Sutton, co-founding partner of Win Roche Sutton in Maryland, about going from 30 clients to over 150 in under a year, why starting your own firm forces an introvert to become a networker whether they want to or not, and what it means to work backwards from the objective instead of getting buried in the emotion of a case. Tim explains why 99% of family law cases are really about control and money rather than the children, what makes appellate work feel like a box puzzle versus the open puzzle of a trial, and why he once deliberately set up an appeal he knew he was going to lose in order to come back later with an ineffective assistance of counsel argument that actually worked. They also discuss the difference between watching Paul Clement argue and watching Elizabeth Prelogar argue before the Supreme Court on cases she was losing, why immigration law is almost impossible to practice when the administrative rules change with every administration, how he used clips from My Cousin Vinny and To Kill a Mockingbird to teach younger attorneys courtroom technique, and his personal mission to visit every presidential gravesite and every major league baseball stadium in America — with Camden Yards already locked in as the answer to the stadium question. Tim Sutton is a co-founding partner of Win Roche Sutton in Maryland, admitted to practice before the U.S. Supreme Court and the Fourth Circuit. Connect with Tim Sutton: winrochesutton.com Maryland Chapters 00:00 Introduction to Tim Sutton 00:32 Visiting presidential gravesites — starting with John and John Quincy Adams by accident in Quincy 01:40 Growing up in Baltimore in the 80s when the Colts left and baseball was all there was 02:17 Leaving a large firm mid-career — when stable is not actually stable 03:54 How COVID shaped the team that eventually became Win Roche Sutton 04:34 What each partner brings — appellate, civil, family law, criminal, and business 06:04 How they keep overhead low with one paralegal and virtual everything else 08:16 Going to law school to become a sports agent and discovering he had the wrong temperament 09:43 Starting with the objective and working backwards to the strategy 11:05 Why family law is really about control and money rather than the children 13:18 The hardest part of family law — getting attached and watching clients ignore your advice 14:23 Representing immigrants facing deportation and the asylum win he's proudest of 15:20 Why immigration law became almost impossible between administrations 16:47 What makes appellate work different from a trial — the closed box versus the open box 18:25 How an appeal can turn on whether an issue was preserved — and what to do when it wasn't 20:11 Setting up an appeal to lose on purpose in order to come back with ineffective assistance 20:57 Being barred before the U.S. Supreme Court and the attorney gallery fast pass 22:00 What surprised him watching arguments in person — Paul Clement, Elizabeth Prelogar, and the justices' personalities 24:29 Rapid fire — 38 states, Wilson in the National Cathedral, Camden Yards, and My Cousin Vinny 26:17 Using My Cousin Vinny and To Kill a Mockingbird to teach younger attorneys 27:37 How the firm's diverse perspectives change outcomes for clients 30:00 Suing the governor on behalf of Her Resiliency Center for cutting funding to human trafficking victims 30:56 How to find Win Roche Sutton #TimSutton #WinRocheSutton #MarylandLawyer #FamilyLaw #AppellateLaw #TrustcastShow #LitigationStrategy #SupremeCourtBar #ImmigrationLaw #SmallFirmLaw
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