Sidebar Advisors

SideBar Advisors

Sidebar Advisors Attorney Podcast explores the career moves, risks, and decisions that shape a life in law.

Hosted by Niraj Chhabra, financial planner and founder of Sidebar Advisors, the show features candid conversations with attorneys, legal leaders, and professionals connected to the legal industry.

Guests share how they navigated firm changes, leadership, business growth, career pivots, and the moments that pushed them to bet on themselves.

Each episode offers a practical look at the professional, personal, and financial choices attorneys face as their careers evolve.

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36 episodes
Avg 54 min
English

Episodes 36

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#108
Thursday · 57 min
Alexandra Smyth of LexisNexis: How AI Is Rewriting the Economics of Legal Practice
Send us Fan Mail As AI becomes more integrated into legal practice, what happens to the traditional law firm business model? Alexandra Smyth, Executive Vice President and General Counsel at LexisNexis Legal & Professional, joins Niraj Chhabra to discuss how AI is changing the economics of law, from the future of the billable hour and shifting client expectations to the development of junior associates. Drawing on her experience leading in-house legal teams, working with outside counsel, and operating within a legal technology company, Alexandra explores what attorneys and firms may need to rethink as AI becomes part of everyday practice.
S2 · E107
Tuesday · 36 min
You Just Made Partner: What Changes Financially?
Send us Fan Mail Making partner can be a major career milestone, but it can also bring financial changes attorneys aren't fully prepared for. In the first installment of our new monthly series where we focus on financial planning topics for attorneys, Jared Correia of Red Cave Legal turns the tables on Sidebar Advisors Podcast host Niraj Chhabra to discuss unpredictable partner compensation, capital contributions, taxes, lifestyle creep, and the financial decisions that come with this transition.
#107
November 5 · 35 min
Rasmeet Chahil of Lowenstein Sandler: From 30 Failed Interviews to BigLaw Partner
Send us Fan Mail After 30 unsuccessful law firm interviews and a move across the country without an existing network, Rasmeet Chahil built an unexpected path to partnership at Lowenstein Sandler. She joins Niraj to discuss how she developed professional relationships from scratch, why demonstrating business development potential mattered more than an established client book, and what surprised her most about finally making partner.
#106
November 3 · 56 min
Steven Lerner of Law360: If AI Saves Lawyers Time, Who Gets the Money?
Send us Fan Mail AI is making certain legal tasks faster, but who's actually benefiting from the efficiency? Steven Lerner, senior reporter at Law360, joins Niraj to examine the growing divide between law firms and their clients over AI, what it means for the billable hour, and how technology could reshape law firm profitability, competition, and the development of future attorneys.
#105
October 28 · 48 min
Elena Deutsch of Women Interested in Leaving Law: Why Successful Attorneys Are Afraid to Walk Away
Send us Fan Mail How do you know if you're in the wrong legal career or simply going through a difficult stretch? Elena Deutsch, founder of Women Interested in Leaving Law, joins Niraj to discuss why attorneys feel trapped by money, prestige, and professional identity, how to recognize when something needs to change, and why finding a more fulfilling career doesn't always mean leaving the practice of law.
#104
October 20 · 1 hr 4 min
Sonia Lakhany of Formal Education: Building a Legal Career Around Freedom
Send us Fan Mail Sonia Lakhany never really wanted the traditional attorney lifestyle. Eventually, she stopped trying to make herself fit into it. After four jobs in her first four years of practice, Sonia left firm life and began building a trademark practice around something she valued from the beginning: autonomy. Today, she has built not only a successful trademark practice but Formal Education, where she teaches other attorneys how to develop trademark practices of their own. Sonia joins Niraj Chhabra to discuss how she built a career that allows her to work from virtually anywhere, why she deliberately chose not to keep scaling her law firm simply because she could, personal branding, networking, and how teaching other attorneys unexpectedly became a second business.
#103
October 15 · 1 hr 6 min
Joe Patrice of Above the Law: What the Next Decade of BigLaw Could Look Like
Send us Fan Mail BigLaw is making more money than ever, but the traditional career path inside it is becoming much less predictable. Joe Patrice, senior editor at Above the Law and co-host of Thinking Like a Lawyer, joins Niraj Chhabra to take a broader look at how the legal profession is changing and what those shifts could mean for attorneys building their careers today. They discuss the rise of non-equity partnership, an increasingly aggressive lateral market, changing relationships between firms and clients, and why developing a portable book of business has become more complicated. Joe also shares his perspective on AI, including why its biggest long-term impact may not simply be replacing work, but changing how the profession trains its next generation of lawyers.
#102
October 13 · 43 min
Elise Holtzman of The Lawyer’s Edge: Why Rainmaking Is a Skill, Not a Personality Trait
Send us Fan Mail What if rainmaking isn’t something attorneys are born knowing how to do? Elise Holtzman, founder and CEO of The Lawyer’s Edge, joins Niraj to discuss why business development is a learnable skill, how introverts can build business without changing who they are, and why law firms should teach attorneys about leadership, client development and firm economics much earlier in their careers.
#101
October 7 · 49 min
Dennis DM Meador of Legal Podcast Network: Why Trust Matters More Than Credentials
Send us Fan Mail Being a good attorney matters. But when prospective clients are comparing lawyers with similar credentials, experience, and services, what actually makes one stand out? Dennis DM Meador, founder of The Legal Podcast Network, joins Niraj Chhabra to discuss how the way people evaluate and choose attorneys has changed and why building trust before the first conversation has become increasingly important. They discuss why attorneys should think beyond individual marketing tactics and build a more consistent ecosystem, how personality and authenticity can differentiate attorneys in a crowded market, and why Dennis believes “your competitive advantage is your humanity.” Dennis also shares his perspective on social media, podcasting, creating content that actually sounds like you, and why consistency matters more than chasing the next marketing idea.
#100
September 30 · 56 min
Tara Raghavan of Benesch: Rethinking Success and Taking Control of Your Career
Send us Fan Mail What happens when the definition of a successful career starts to change? Tara Raghavan joins Niraj to talk about taking greater control of her career, learning business development, navigating change when it doesn’t come naturally, and how experiences outside of work reshaped what success means to her. A fitting conversation about growth, perspective, and what comes next for the 100th episode of the Sidebar Advisors Podcast.
#99
September 24 · 1 hr 6 min
Sarah Coyne of Ropes & Gray: The Judgement Behind A Successful Legal Career
Send us Fan Mail What does it take to make good decisions when the stakes are high? Sarah Coyne, Partner at Ropes & Gray and former federal prosecutor, joins Niraj to discuss the judgment she developed handling complex investigations and high-profile cases, what changed when she moved to private practice, and why her definition of a successful legal career looks very different today. The conversation also gets personal, including motherhood, financial security, her experience with breast cancer, and how her definition of success has evolved from pursuing the next achievement to building a career that leaves room for the other parts of life that matter.
#98
September 22 · 39 min
Thomas Chou of Morrison Foerster: Building A Career By Betting On Opportunity
Send us Fan Mail Thomas Chou’s career has rarely followed a predictable path. Now Managing Partner of Morrison Foerster’s Los Angeles office, Thomas spent nearly two decades practicing in Shanghai and Hong Kong, building a corporate practice across the U.S. and Asia before eventually returning to Los Angeles. In this episode, Thomas joins Niraj Chhabra to talk about the opportunities and unexpected circumstances that shaped that journey, from being trusted to run a major Yahoo transaction as a senior associate to moving overseas, building relationships during the dot-com crash, and taking on leadership roles he never originally planned to pursue. They also discuss why some of Thomas’s earliest relationships still generate business 25 years later, what practicing in China taught him about client relationships, how attorneys can develop business before they’re expected to have a book, and why becoming a senior lawyer sometimes means knowing which clients and opportunities to walk away from.
#97
September 17 · 52 min
Nema Milaninia of Freshfields: From Prosecuting War Crimes to Advising on Global Risk
Send us Fan Mail Nema Milaninia’s legal career has taken him from BigLaw to The Hague, inside one of the world’s largest technology companies, and ultimately back to private practice. Now a partner at Freshfields, Nema advises companies and senior executives navigating complex investigations, regulatory matters, and high-stakes legal and reputational risk. Earlier in his career, he spent eight years as an international prosecutor working on cases involving genocide, war crimes, and crimes against humanity before later moving in-house at Alphabet. In this episode, Nema joins Niraj Chhabra to discuss what those very different environments taught him about practicing law, making decisions under pressure, and viewing a problem from more than one perspective.
#96
September 15 · 1 hr 1 min
Cody Barbo of Trust & Will: How Technology Is Reshaping Estate Planning
Send us Fan Mail Cody Barbo has spent his career building technology companies, but his latest venture brought him into one of the legal profession’s most traditional practice areas. Cody is the co-founder and CEO of Trust & Will, a digital estate planning platform that has helped more than 1.3 million families create estate plans. In this episode, he joins Niraj Chhabra to share the entrepreneurial journey that led him there, including being fired from his previous startup and identifying the opportunity behind Trust & Will just weeks later. The conversation also looks at the broader evolution of legal tech, the rapid growth of AI-powered legal companies, which parts of the profession Cody believes are most susceptible to disruption, and what attorneys can do to remain valuable as technology becomes more integrated into legal work..
#95
September 10 · 50 min
Michael Gordon of Gordon, Fournaris & Mammarella, P.A.: How A Niche Trusts Practice Became A National Business
Send us Fan Mail Michael Gordon didn’t initially plan on becoming a trusts and estates attorney. Today, he leads a national estate planning practice at Gordon, Fournaris & Mammarella, P.A. In this episode, Michael joins Niraj Chhabra to share how he recognized an emerging opportunity around Delaware trusts early in his career and helped grow what began as a small, locally focused practice into a national estate planning group. Michael explains why Delaware has become an important jurisdiction for sophisticated trust and estate planning, the situations where attorneys outside the field should recognize potential planning opportunities for their clients, and what it takes to earn the trust of ultra-high-net-worth families.
#94
September 8 · 1 hr 3 min
Pat Murphy of King & Spalding: Why In House Isn't The Easier Path
Send us Fan Mail Pat Murphy has experienced the legal profession from almost every angle. Before returning to King & Spalding as a partner, Pat spent 26 years in-house, including senior litigation roles at GE Healthcare and Fresenius Medical Care. His career has also included time in the Marine Corps, FBI, Senate Judiciary Committee, and private practice. In this episode, Pat joins Niraj Chhabra to discuss what really changes when an attorney moves in-house, why corporate legal work can carry a very different kind of pressure, and what outside counsel often misunderstand about the executives they advise.
#93
September 2 · 1 hr
Stacey Brown Randall of Building A Referable Business: How Attorneys Can Build Referrals Without Asking
Send us Fan Mail Most attorneys know referrals matter. Far fewer have an actual system for generating them. Stacey Brown Randall, founder of Building A Referable Business and creator of the Referrals Without Asking methodology, joins the SideBar Advisors Podcast to challenge one of the most common pieces of business development advice: that you have to ask for referrals to receive them. Stacey explains why great work alone doesn’t create a consistent referral pipeline, how attorneys can identify and nurture the people most likely to refer them, and what it takes to stay top of mind without becoming overly promotional or transactional. We also discuss how referral strategies differ across practice areas, why authentic relationship-building matters more than gimmicks, and how one attorney went from receiving six referrals a year to more than 70 annually by building a repeatable system. For attorneys who want to grow through relationships without constantly asking for business, this episode offers a practical framework for doing it differently.
#92
August 26 · 1 hr 2 min
Markus Funk of White & Case: Inside Operation Family Secrets and a Career In Public Service
Send us Fan Mail Markus Funk has prosecuted mob murders, helped shape rule-of-law initiatives overseas, and built a career advising companies facing complex government scrutiny. In this episode of the Sidebar Advisors Podcast, Markus, a partner at White & Case and former federal prosecutor, takes us inside Operation Family Secrets, one of the most significant organized crime prosecutions in U.S. history. He shares how he unexpectedly landed on the case, what it was like prosecuting members of the Chicago mob, and the courtroom moment that resulted in a defendant threatening his life. Markus also reveals a remarkable detail about Casino: one of the real-life killers portrayed in the film actually appears on screen reenacting a murder he committed. Beyond the mob stories, we discuss Markus's work on rule-of-law initiatives in Kosovo, his transition from prosecutor to private practice, what he learned about business development in BigLaw, and why some of the biggest opportunities in his career came from taking risks without knowing exactly where they would lead.
#91
August 19 · 1 hr 10 min
Quinn Murphy of Gordon Rees: Building a Career by Playing the Long Game
Send us Fan Mail Quinn Murphy has built his legal career around a simple philosophy: play the long game. Now Managing Office Partner of Gordon Rees Scully Mansukhani’s Tampa office, Quinn joins the SideBar Advisors Podcast to share the career decisions that took him from a Division II basketball player and aspiring therapist to trial lawyer, business developer, and law firm leader. Quinn discusses why he began building his network years before he expected it to generate business, why he was willing to step backward in title to create better opportunities for his future, and what younger attorneys often misunderstand about the business of law. He also shares how athletics shaped his approach to criticism and delayed gratification, and how surviving stage four cancer changed his perspective on faith, family, and time.
#90
August 12 · 1 hr 1 min
Ryan Kimler of Financial Clarity: Hiring, Pricing, and Growing a Law Firm with Confidence
Send us Fan Mail Building a successful law firm requires more than great legal work. Ryan Kimler, founder of Financial Clarity and fractional CFO to professional service firms, joins the SideBar Advisors Podcast to discuss the financial decisions that shape a growing law practice. From hiring your first attorney to setting profitable rates and balancing personal income with business growth, Ryan shares practical advice for firm owners looking to scale with confidence. We also discuss why many attorneys wait too long to hire, the hidden costs of underpricing legal services, how to think about profitability beyond revenue, and why building the right financial team around your business can make all the difference.

Showing 1–20 of 36 episodes