Shows / 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…
Episodes
Sidebar AdvisorsRasmeet 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…
Sidebar AdvisorsSteven 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…
Sidebar AdvisorsElena 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…
Sidebar AdvisorsSonia 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…
Sidebar AdvisorsJoe 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…
Sidebar AdvisorsElise 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…
Sidebar AdvisorsDennis 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…
Sidebar AdvisorsTara 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…
Sidebar AdvisorsSarah 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…
Sidebar AdvisorsThomas 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…
Sidebar AdvisorsNema 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…
Sidebar AdvisorsCody 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…
Sidebar AdvisorsMichael 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…
Sidebar AdvisorsPat 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…
Sidebar AdvisorsStacey 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…
Sidebar AdvisorsMarkus 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…
Sidebar AdvisorsQuinn 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…
Sidebar AdvisorsRyan 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…
Sidebar AdvisorsBrent Wible of White & Case: Success, Family, and the Doors You Choose to Walk Through
Send us Fan Mail What does a successful legal career actually look like over the long term? Brent Wible, partner at White & Case LLP and former senior official…
Sidebar AdvisorsVal Dahiya of Morrison Foerster: Building A Career Through Change and Challenge
Send us Fan Mail Not every career transition is driven by ambition. Sometimes it's driven by life. Valerie Dahiya, partner at Morrison Foerster and former SEC…
Sidebar AdvisorsRyan Fayhee of Akin Gump: DOJ to Private Practice - Risk & High-Stakes Decisions
Send us Fan Mail What does it look like to make legal decisions when the stakes extend far beyond the courtroom? Ryan Fayhee, partner at Akin Gump Strauss…
Sidebar AdvisorsCarolyn Daly of Cohen Seglias: Building, Growing, and Letting Go of a Law Firm
Send us Fan Mail What does it actually take to build, and eventually walk away from, a successful law practice? Carolyn N. Daly has experienced nearly every…
Sidebar AdvisorsJohn Hellerman of Hellerman Communications: Why Great Lawyers Still Need Marketing
Send us Fan Mail Most attorneys assume good work will eventually speak for itself. John Hellerman isn't so sure. John is the founder of Hellerman…
Sidebar AdvisorsShannon McClure Roberts of Blank Rome: Leadership, Growth, and High-Stakes Litigation
Send us Fan Mail Shannon McClure Roberts is a partner at Blank Rome, where she represents pharmaceutical and medical device companies in complex product…
Sidebar AdvisorsChuck Cotter of Morrison Foerster: Why Being Bad Early Doesn't Define Your Career
Send us Fan Mail What if being "bad early" doesn't disqualify you from long-term success? Chuck Cotter is a partner at Morrison Foerster and has built one of…
Sidebar AdvisorsBenjamin Softness of King & Spalding: Career Risk, Optionality, and Leaving a Dream Job
Send us Fan Mail For many attorneys, landing an in-house role at a company like Google feels like the destination. Benjamin Softness made the unusual decision…
Sidebar AdvisorsLaurin Johnson of MB Law Firm Consulting, LLC: What Lawyers Need to Know About Running a Firm
Send us Fan Mail Most attorneys spend years learning the law, but very little time learning how to run a business. In this episode of the SideBar Advisors…
Sidebar AdvisorsAbe Kwon of Lowenstein Sandler LLP: Career Risk, Success, and Building a Life That Actually Fits
Send us Fan Mail Success gets a lot more complicated once you actually start achieving it. Abe Kwon is a partner at Lowenstein Sandler LLP, where he advises…
Sidebar AdvisorsDr. Anthony Mazzarelli: What Law Firms Can Learn From Healthcare Leadership
Send us Fan Mail Dr. Anthony Mazzarelli has built a career at the intersection of medicine, law, leadership, and public communication. A practicing physician…
Sidebar AdvisorsSeth Rokosky of Duane Morris LLP: Career Decisions, Appellate Law, and Why Having a Plan Matters
Send us Fan Mail Seth Rokosky, partner at Duane Morris LLP, didn’t build his career by following a straight line. From choosing New York over D.C. to make a…
Sidebar AdvisorsElie Honig: From Prosecutor to CNN’s Senior Legal Analyst
Send us Fan Mail Elie Honig — former federal prosecutor and now CNN’s senior legal analyst — has built a career that doesn’t follow the traditional legal path…
Sidebar AdvisorsKenneth Nunnenkamp of Blank Rome LLP: Career Risk, Recalibration, and Defining Success Over Time
Send us Fan Mail Kenneth Nunnenkamp, partner at Blank Rome LLP, has built a career that certainly didn’t follow a straight line. Early on, he made a high-risk…
Sidebar AdvisorsBruce MacEwen of Adam Smith, Esq., LLC: The Future of Law Firms Isn’t What You Think
Send us Fan Mail What actually separates durable law firms from those that won’t make it through the next decade? In this week's episode, Niraj Chhabra, CFP…
Sidebar AdvisorsJill Cruz: How Attorneys Can Advocate for Their Value More Effectively
Send us Fan Mail Negotiation, compensation, and advancement shape a lawyer’s career — but most attorneys are left to navigate those decisions without much…
Sidebar AdvisorsMichelle Calcote King: How Law Firms Actually Build Visibility, Credibility, and Demand
Send us Fan Mail Michelle Calcote King, Principal & President of Reputation Ink, joins the podcast to break down how professional services firms — especially…
Sidebar AdvisorsTrini Ross of Harter Secrest & Emery LLP: Leadership, Public Service, and the Weight of the Role
Send us Fan Mail Trini Ross spent over 30 years in federal service, ultimately serving as the United States Attorney for the Western District of New York —…
Sidebar AdvisorsStefani Schwartz & Kathryn Hatfield of Hatfield Schwartz: From Colleagues to Co-Founders
Send us Fan Mail In this episode of the Sidebar Advisors Podcast, Niraj Chhabra sits down with Kathryn Hatfield and Stefani Schwartz, the founding partners of…
Sidebar AdvisorsJuliet Starrett: Movement, Career Pivots, and Building Control with Financial Readiness
Send us Fan Mail In this episode of the Sidebar Advisors Podcast, we sit down with Juliet Starrett -a former Big Law commercial litigator, world-champion…
Sidebar AdvisorsMelissa Peters: What Really Drives Lateral Partner Hiring Today
Send us Fan Mail Lateral moves look straightforward from the outside. In reality, most fail for reasons attorneys don’t always see coming. In this episode of…
Sidebar AdvisorsHedieh Fakhriyazdi of White & Case: What Growth Really Looks Like Inside a Big Law Firm
Send us Fan Mail A lot of people in Big Law hear the phrase “professional development” — but don’t always know what it actually means in practice. In this…
Sidebar AdvisorsMerle Vaughn of Major, Lindsey & Africa: Making the Right Move in Law and Recruiting from the Inside
Send us Fan Mail Few people have a clearer view into the legal talent market than Merle Vaughn, Partner and Law Firm Diversity Practice Leader at Major…
Sidebar AdvisorsLarry Pon: Tax Planning for Attorneys Entering 2026
Send us Fan Mail As the year closes and a new tax landscape takes shape, attorneys can’t afford to rely on outdated assumptions about withholdings, deductions…
Sidebar AdvisorsAndrea Rivers of Baker McKenzie: Building A Career In Big Law Lessons for First-Gen Lawyers Starting Out
Send us Fan Mail Some career stories unfold neatly. Andrea N. Rivers story isn’t one of them, and that’s exactly why it resonates. This week on the SideBar…
Sidebar AdvisorsNeel Chatterjee of King & Spalding : Leading With Authenticity in BigLaw & Building the Future of IP Litigation
Send us Fan Mail In this episode, we sit down with Neel Chatterjee, one of the nation’s leading IP litigators and a finalist for ALM’s Attorney of the Year…
Sidebar AdvisorsBree Herman: Bringing Financial Clarity to Growing Law Firms
Send us Fan Mail Bree Herman didn’t set out to specialize in legal accounting, but a childhood spent learning how to “find the missing penny” sparked a passion…
Sidebar AdvisorsEmma Smizer of Frankfurt Kurnit Klein & Selz: Leveling Up Law, How Video Games Shaped a Legal Career
Send us Fan Mail When Emma Smizer started law school, her path was anything but traditional. From a rescinded Big Law offer to finding her niche in video game…
Sidebar AdvisorsCourtney Schulnick: Bringing Mindfulness to the Modern Legal Mind
Send us Fan Mail After two decades in litigation, Courtney Schulnick, Esq. stepped away from the courtroom to pursue something equally demanding, helping…
Sidebar AdvisorsJohn Quinn of Quinn Emanuel Urquhart & Sullivan: Leading One of the World’s Top AmLaw Litigation Firms
Send us Fan Mail John Quinn is one of the most recognizable names in the legal world — and for good reason. As Founding Partner and Executive Chairman of Quinn…
Sidebar AdvisorsCandace Dellacona of Offit Kurman: Estate Planning, Caregiving, and the Sandwich Generation
Send us Fan Mail In this episode, Candace Dellacona, Principal and Shareholder in the Estates & Trusts practice at Offit Kurman, shares how she guides families…
Sidebar AdvisorsJacquette Timmons: The Human Side Of Money
Send us Fan Mail Money is never just about dollars and cents. It’s about choices, values, and emotions. In this Sidebar Advisors episode, Jacquette Timmons —…
Sidebar AdvisorsErin Andersen: Recruiting in Law & Redefining Career Transitions
Send us Fan Mail Erin Andersen, founder of Your Brand Networker, is on a mission to help professionals reclaim joy in their careers. From guiding burned-out…
Sidebar AdvisorsJames Wolff of Greenspoon Marder LLP: A Conversation With The Tech-Obsessed Attorney
Send us Fan Mail Before AI, commercial space exploration, or 3D printing became mainstream, James Wolff was already deep in the weeds - founding startups in…
Sidebar AdvisorsGail Cummings: From Big Law to Therapist and Executive Coach
Send us Fan Mail Gail Cummings began her legal career to meet expectations, but the deeper truth was harder to ignore. After more than a decade in Big Law…
Sidebar AdvisorsAndrea D’Ambra of Norton Rose Fulbright: Big Law, AI, and Raising a Family
Send us Fan Mail In this episode, we sit down with Andrea D’Ambra, Partner and Global Executive Committee Member at Norton Rose Fulbright. Andrea shares her…
Sidebar AdvisorsIan Murray: Student Loans, Lifestyle Design, and Planning Smarter
Send us Fan Mail In this episode, Niraj is joined by friend, colleague, and fellow advisor Ian Murray, CFP®, CSLP®. In this episode they discuss the real-life…
Sidebar AdvisorsEmily Logan Stedman of Husch Blackwell: Finding Balance, Building a Brand, and Thriving in Big Law
Send us Fan Mail In this episode, we sit down with Emily Logan Stedman, attorney at Husch Blackwell, to explore her unconventional path to Big Law and the…
Sidebar AdvisorsDerek Brainard: Navigating Student Loans + Supporting the Next Gen of Lawyers
Send us Fan Mail 🎙 On this episode of the SideBar Advisors Podcast, we’re joined by Derek Brainard, CFP®, Director of Financial Education at AccessLex…
Sidebar AdvisorsJustin Savage of Sidley Austin: Purpose, Persistence, and Practicing Environmental Law at the Highest Level
Send us Fan Mail From skateboarding teen to leading one of the top environmental law practices in the country — meet Justin Savage, partner at Sidley Austin…
Sidebar AdvisorsStacy Phillips of Blank Rome LLP: High-Profile Cases, Advocacy, and Building a Legacy in Law
Send us Fan Mail In this episode of the Sidebar Advisors Podcast, we're joined by Stacy Phillips—renowned family law attorney and partner at Blank Rome LLP…
Sidebar AdvisorsDavina Frederick: Building a Thriving Law Practice as a Woman Attorney
Send us Fan Mail Women attorneys face unique challenges when it comes to growing and scaling their firms—something Davina Frederick knows firsthand. As a…