SideBar Advisors

Sidebar Advisors

Business EN ↓ 85 episodes

A podcast exploring the careers, choices and strategies shaping today’s legal landscape. Hosted by Niraj Chhabra, each episode explores the intersection of law, career growth, and financial decision-making. Through conversations on leadership, professional development and business building, we unpack the moments that define success. For those thinking about what’s next or looking to grow and feel more fulfilled in their current role, these conversations offer a thoughtful look at building a meaningful and successful career in and around the legal world.

Author

SideBar Advisors

Category

Business

Podcast website

sidebaradvisors.com

Latest episode

Jul 9, 2026

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Episodes

John Quinn: Leading One of the World’s Top AmLaw Litigation Firms 15.10.2025

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 Emanuel Urquhart & Sullivan , he has built the largest litigation-only law firm in the world, with over 1,300 attorneys across 34 offices , an 86% trial win rate , and a ranking of #19 on the AmLaw 100 . In this episode of the Sidebar A...

Candace Dellacona: Estate Planning, Caregiving, and the Sandwich Generation 24.09.2025

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 through the most personal and complex planning issues: from wills and guardianships to elder care, LGBTQ+ planning, and business succession. We cover: Why estate planning is about more than legal documents - it’s about family dynamics,...

Jacquette Timmons: The Human Side Of Money 17.09.2025

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 — financial behaviorist, speaker, author, and host of the More Than Money podcast — shares how decades of experience have shaped her mission to help professionals, especially attorneys, transform their relationship with money. Jacquette has see...

Erin Andersen: Recruiting in Law & Redefining Career Transitions 10.09.2025

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 attorneys through bold career pivots to introducing a flat-fee hiring model that challenges traditional recruiting, Erin brings fresh thinking to industries where culture and retention matter most. In this episode, Erin shares: How toxic workp...

James Wolff: A Conversation With The Tech-Obsessed Attorney 27.08.2025

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 college and chasing cutting-edge ideas long before they hit the headlines. In this episode, James shares how his lifelong passion for technology continues to shape the way he practices law, advises clients, and builds his reputation in the ind...

Gail Cummings: From Big Law to Therapist and Executive Coach 13.08.2025

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, with a thriving practice and two young children at home, she made the bold decision to pursue her long-standing dream of becoming a psychotherapist. In this episode, Gail shares her path from lawyer to licensed therapist and executive coach, th...

Andrea D’Ambra: Big Law, AI, and Raising a Family 30.07.2025

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 remarkable journey from leaving a major firm to pursue a true partnership track, to navigating Big Law while raising five kids and ultimately rising to leadership at one of the world’s largest law firms. We talk about her role co-chairing the...

Ian Murray: Student Loans, Lifestyle Design, and Planning Smarter 16.07.2025

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 role student loans play in financial planning - especially for attorneys earning at the higher end of the scale. They talk through how student loan strategy shifts across compensation tiers, how to balance repayment with long-term planning,...

Emily Logan Stedman: Finding Balance, Building a Brand, and Thriving in Big Law 02.07.2025

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 powerful personal brand she’s built along the way. Emily shares how she began her career as a teacher before making the leap to law, and how writing and blogging helped her find her voice in a demanding profession.   We dive into how her curre...

Derek Brainard: Navigating Student Loans + Supporting the Next Gen of Lawyers 18.06.2025

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 Institute—the nation’s largest nonprofit dedicated to supporting law students and legal education. We cover: The top resources AccessLex offers for law students and recent grads How practicing attorneys with student loans should approach repayment p...

Justin Savage: Purpose, Persistence, and Practicing Environmental Law at the Highest Level 04.06.2025

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. Justin shares his journey from the DOJ, where he helped try what was then the largest environmental settlement in U.S. history, to his current role advising major companies on high-stakes regulatory and litigation matters. But his story goes...

Stacy Phillips: High-Profile Cases, Advocacy, and Building a Legacy in Law 16.04.2025

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. With nearly four decades of experience, Stacy has represented some of the most high-profile names in entertainment, business, and beyond. From complex divorces to custody battles, she brings unmatched insight and grace to some of life’s t...

Davina Frederick: Building a Thriving Law Practice as a Woman Attorney 12.03.2025

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 lawyer, law firm growth strategist, and founder of Wealthy Woman Lawyer® , Davina has built a career helping women attorneys overcome business hurdles, set boundaries, and create sustainable success . In this episode, she shares how she went from...

Breeana Somers: From Teen Mom to Big Law Attorney, An Inspiring Journey 05.03.2025

Send us Fan Mail In this episode, we sit down with Breeana J. Somers, a litigation associate at Ballard Spahr, who shares her incredible story of resilience and success. From being a teen mom relying on government assistance to working multiple jobs while attending law school at night—Breeana defied the odds to break into Big Law. She opens up about hiding her motherhood from her firm, the challen...

Angelica Cesario: Navigating The Intersection of Law, Education, and Inclusivity 26.02.2025

Send us Fan Mail In this episode of the SideBar Advisor podcast, we sit down with Angelica Cesario to discuss her career journey from practicing attorney to her current role in legal education. We dive deep into how diversity, equity, and inclusion (DEI) have evolved in the legal industry, the challenges firms are facing, and how they are responding to recent shifts in the DEI landscape. Angelica...

Gerry Williams: From Introvert to Co-US Managing Partner at DLA Piper 19.02.2025

Send us Fan Mail In this episode, we sit down with Gerry Williams , the newly appointed Co-US Managing Partner at DLA Piper . Gerry shares his inspiring journey to leadership, including how he overcame challenges being introverted by intentionally networking within his firm—an effort that ultimately propelled his career. He also discusses his vision for DLA Piper, his strategy for positioning the...

Judge Jose L. Linares: Leadership, Diversity, and Justice 29.01.2025

Send us Fan Mail In this episode, we sit down with Judge Jose L. Linares, a trailblazer in the legal field and the first Cuban-born Chief District Court Judge in the United States. Judge Linares shares his journey from immigrating to the U.S. as a young boy to navigating incredible challenges and ultimately rising to one of the most prestigious roles in the judiciary. He reflects on his leadership...

Michael Roybal: Building Nuooly and Balancing Legal Entrepreneurship 08.01.2025

Send us Fan Mail  In this episode, we sit down with Michael Roybal, founder of Nuooly and an accomplished attorney with a background in international trade law. Michael shares how he built his law practice from the ground up, starting with cold calls and business directories, and the challenges of growing a firm. We then explore his entrepreneurial journey, including how the idea for Nuooly emerge...

Anita Ventrelli: Navigating High-Stakes Family Law, Advocacy, Resilience, and Mentorship 18.12.2024

Send us Fan Mail In this episode, we sit down with Anita Ventrelli, Senior Partner at Schiller DuCanto & Fleck, who has dedicated her entire career to one of the nation’s premier family law firms. Anita shares how her first exposure to law came from helping her father navigate divorce paperwork, sparking a lifelong passion for advocacy. We explore the unique challenges of working with celebrit...

Mike Gold: Bridging Law and the Final Frontier, Space Policy, Innovation, and the Artemis Accords 11.12.2024

Send us Fan Mail In this episode, we speak with Michael Gold, Executive Vice President of Redwire Space and a trailblazer in space policy and law. Michael shares how he leveraged his legal expertise to pursue his passion for space, proving that you don’t need to excel at math to make a profound impact in STEM fields. He delves into his pivotal role in the Artemis Accords , a set of international a...

Vanessa Vasquez de Lara: From Immigrant to Trailblazer, Building a Thriving Law Practice and Empowering Working Mothers 27.11.2024

Send us Fan Mail In this episode, we chat with Vanessa Vasquez de Lara, an inspiring attorney who shares her journey from immigrating to the U.S. at age 10 from the Dominican Republic to growing a thriving legal practice. Vanessa started her firm in a 10x10 windowless office and, along with her husband, who left his engineering career to join her, grew the business from $1 million to $3.7 million...

Chaka Patterson: Leading with Purpose in Law, Justice, and Pro Bono Advocacy 20.11.2024

Send us Fan Mail On today’s podcast, we had the privilege of interviewing Chaka Patterson, a partner at Alston & Bird. Chaka has built an impressive career that spans both the public and private sectors, including serving as general counsel and trying cases for Fortune 500 companies. In addition to his legal expertise, Chaka is deeply committed to pro bono work, where he advocates for those wr...

Christine Amalfe: Championing Equality, Leadership, Wellness, and the Future of Law 14.11.2024

Send us Fan Mail In this episode, we sit down with Christine Amalfe, a trailblazing leader in labor and employment law. As chair of her firm’s labor & employment department, member of the executive committee, and human resources general counsel, Christine has been a champion for women’s equality. She shares her journey in founding her firm’s internationally recognized women’s initiative, her w...

Dylan Adams: Protecting Innovation, Patents, Shark Tank Success, and IP for Entrepreneurs 16.10.2024

Send us Fan Mail In this episode, we sit down with Dylan Adams, a patent attorney at Davis Wright & Tremaine LLP. Dylan shares his unconventional journey from dropping out of college to pursue a music career, to later finding his passion in law. Now a successful patent attorney at an AMLaw 100 firm, Dylan has appeared on CNBC's *The Profit*, worked with *Shark Tank* contestants, and autho...

William Barrett: From Big Law to Big Growth, Journey to Leading 100+ Attorneys 09.10.2024

Send us Fan Mail  In this episode, we sit down with William Barrett, CEO of a prominent law firm, to discuss his remarkable journey from Big Law to leading a firm of over 100 attorneys. William shares how he took a 50% pay cut early on to prioritize work-life balance and the strategic moves he made to build a specialized practice in dental and medical transitions. Tune in to hear how his leadershi...

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