Mid-Market Dealmaking Av Sinensky on Deal Strategy, Human Dynamics, and the Role of AI

Mid-Market Dealmaking Av Sinensky on Deal Strategy, Human Dynamics, and the Role of AI

In this episode of The Litigator’s Edge, host Aniket Sawant sits down with Av Sinensky, Partner at Falcon Rappaport & Berkman LLP, to explore the realities of modern middle-market M&A, deal psychology, and AI-powered legal workflows. Av shares his journey from New York BigLaw to advising founders, entrepreneurs, and private equity clients on high-stakes mid-market transactions ranging from $10M to over $100M across diverse industries. He explains why he gravitated toward transactional work over litigation and how collaborative dealmaking became the foundation of his practice. The conversation dives into the human side of M&A, understanding each client’s motivations, aligning co-sellers, managing emotions during negotiations, and why knowing the “why” behind a deal can determine whether it succeeds or falls apart. Av also breaks down common post-closing disputes, including working capital true-ups, and explains why buyers should never rely solely on representations, warranties, and indemnities instead of proper diligence. The episode further explores how AI tools are transforming contract drafting, diligence, markups, and legal research, while highlighting why efficiency and responsiveness are becoming critical competitive advantages for modern lawyers. In this episode: - Why understanding client motivations changes deal outcomes - The most common causes of post-closing M&A disputes - Working capital traps buyers and sellers overlook - Why diligence matters more than contractual protection - How AI is changing legal drafting and deal workflows - The “Anatomy of a Purchase Agreement” framework - Lessons junior lawyers should learn early in their careers - Negotiation insights inspired by Larry David If you’re interested in M&A, private equity, business law, negotiation strategy, or the future of AI in transactional practice, this conversation offers a practical and insightful look into how modern deal lawyers actually operate. #MergersAndAcquisitions #PrivateEquity #CorporateLaw #BusinessLaw #DealMaking #LegalInnovation #AIinLaw #LegalTech #Lawyers #LawFirm #FutureOfLaw #Negotiation #Entrepreneurship #TheLitigatorsEdge

Crossing the V: Ethan Goemann on Wage-and-Hour Litigation, Shadow Work & Plaintiff-Side Strategy

In this insightful episode of The Litigator’s Edge, host Aniket Sawant sits down with Ethan Goemann, partner at Sommers Schwartz and former defense-side labor and employment lawyer, to explore the evolving world of wage-and-hour litigation and why he ultimately transitioned to representing employees.Ethan shares his path from Duke Law and federal clerkship to defending employers at major firms like Womble Bond Dickinson and Seyfarth Shaw, where he specialized in wage-and-hour collective actions. He explains what led him to “cross the V” and how plaintiff-side work aligned more closely with his long-term values and career goals.The conversation dives into the mechanics of FLSA collective actions, common employer risks involving unpaid overtime, off-the-clock labor, and worker misclassification, and how modern litigation increasingly relies on digital evidence like login records, badge swipes, GPS data, and internal communications to uncover “shadow work.”Ethan also discusses proactive discovery strategy, differences between individual and collective employment claims, AI’s growing role in document analysis and damages modeling, and how changing workplace structures are creating new compliance risks for employers.In this episode:Why Ethan transitioned from defense to plaintiff-side litigationHow wage-and-hour collective actions workThe rise of “shadow work” and digital evidenceCommon overtime and pay-practice mistakes employers makeAI’s role in modern employment litigationCollective action strategy and discovery tacticsAdvice for workers, young lawyers, and in-house counselIf you’re interested in employment law, workplace litigation, labor compliance, or how technology is reshaping modern legal disputes, this episode offers a practical look inside one of the fastest-evolving areas of litigation.#EmploymentLaw #WageAndHour #FLSA #Litigation #LaborLaw #CollectiveActions #WorkplaceCompliance #Lawyers #LegalStrategy #LawPodcast #LitigatorsEdge

Step Up to Stand Out: Melissa Jordon on Building a Successful Litigation Career

In this instructive episode of The Litigator’s Edge, host Aniket Sawant sits down with Melissa Jordon, partner at Hamilton Miller & Birthisel LLP and president of the Miami-Dade Bar Association, to discuss what it really takes to build a successful modern litigation career. Melissa shares her journey from overcoming childhood shyness and becoming the first attorney in her family, to working her way through complex commercial litigation and insurance defense, to becoming a law firm partner at a young age. She reflects on mentorship, professionalism, networking, and the experiences that shaped her growth as a litigator. The conversation explores her early career during Hurricane Irma litigation, her transition into broader insurance work, and lessons learned from a secondment with Canopius in London. Melissa also breaks down high-stakes cases involving COVID-19 business interruption claims and policy rescission disputes tied to material misrepresentation. Beyond litigation strategy, the episode dives into communication as a competitive advantage, remote deposition best practices, responsible AI use in legal practice, bar leadership, and navigating one’s internal impostor syndrome in a demanding profession. In this episode: Building confidence as a young litigator The role of mentorship and legal networks Lessons from London market insurance practice Winning high-stakes insurance litigation Communication as a litigation advantage AI’s role and risks in modern legal work Overcoming impostor syndrome and growing professionally If you're a lawyer, law student, or professional building a long-term career in high-performance environments, this episode offers practical insight into how strong legal careers are actually built. #Litigation #InsuranceDefense #LegalCareer #WomenInLaw #Lawyers #TrialLaw #LegalLeadership #AIinLaw #CommercialLitigation #LawPodcast #ProfessionalDevelopment #Mentorship #LitigatorsEdge

Inside High-Stakes Family Wealth Challenges: Lisa Cukier on Trusteeship, Mental Health & Divorce

In this enlightening episode of The Litigator’s Edge, host Aniket Sawant sits down with Lisa Cukier, partner and chair of fiduciary litigation at Rubin Rudman, to explore the complex intersection of family wealth, mental health, and high-stakes legal disputes. With a unique background in social work and law, Lisa brings a deeply human perspective to fiduciary litigation, representing high-net-worth families navigating crises involving incapacity, exploitation, and conflict. She explains how mental health challenges, ranging from cognitive decline to addiction and manic behavior, can put significant wealth at risk, and how legal structures are used to protect individuals and preserve family assets. The conversation also dives into the rise of “concierge trusteeship,” a high-touch approach to managing both financial and personal complexities, as well as her work as a private adjudicator, special master, and guardian ad litem. From romantic exploitation and undue influence to gray divorce and blended-family disputes, this episode reveals the often unseen legal battles behind wealth preservation and distribution. Lisa also shares her perspective on the evolving role of AI in legal practice, highlighting both efficiency gains and risks, and emphasizes the importance of seeking counsel early, before issues escalate into full-blown crises. In this episode: * The link between mental health and wealth preservation * What “concierge trusteeship” really means * Risks of exploitation, undue influence, and family conflict * The rise of gray divorce and its impact on wealth * How fiduciary litigation protects high-net-worth families * AI in legal research: benefits and risks * Why early legal intervention matters If you're a lawyer, advisor, or someone interested in how wealth, law, and human behavior intersect, this episode offers a rare, real-world perspective.

The Law Lifer: Ruth Kraft on Yale Law, Trailblazing, and Teaching

In this inspiring and anecdote-rich episode of The Litigator’s Edge, host Aniket Sawant sits down with Ruth Kraft, Yale Law graduate, former NYU professor, administrative law judge, and now founder of Kraft Employment Law Group. From deciding at just four and a half years old that she wanted to become a lawyer to building a distinguished decades-long career across academia, the bench, and private practice, Ruth's journey is an exemplar of trailblazing impact, commitment, and lifelong learning. She shares how she overcame early skepticism around gender, earned her place at elite institutions like Yale Law, and forged a career with mentorship, teaching, and service as its defining characteristics. The conversation explores her transition to the bench, her role as a “teaching judge,” and the deeply personal decision to step away from judicial service to care for family, before returning to build a successful employment law practice. Grounded in values shaped by her Holocaust-survivor parents, and sharing moving stories about their lives, Ruth reflects on ethics, reverence for the field, and advocacy for the rule of law. In this episode: - From preschool ambition to Yale Law - Overcoming bias and barriers in the legal profession - Life on the bench and becoming a teaching judge - Transitioning back to private practice - The role of ethics in legal decision-making - Mentorship, teaching, and lifelong growth If you're a lawyer, student, or professional thinking long-term about your career, this episode offers a powerful perspective on building a life in law. #Lawyers #LegalCareer #YaleLaw #WomenInLaw #LegalJourney #Judiciary #LegalEthics #EmploymentLaw #Mentorship #LawPodcast #LegalLeadership #CareerInLaw #LitigatorsEdge #LegalInspiration #LawStudents