Sidebar Advisors

Hosted by SideBar Advisors

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Episodes

107

Latest episode

Nov 2026

Language

EN-US

About the show

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.

Listen to episodes

60 recent

November 12, 2026Episode 10857 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.

November 10, 2026Episode 10736 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.

November 5, 2026Episode 10735 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.

November 3, 2026Episode 10656 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.

October 28, 2026Episode 10548 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.

October 20, 2026Episode 1041 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.

October 15, 2026Episode 1031 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.

October 13, 2026Episode 10243 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.

October 7, 2026Episode 10149 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.

September 30, 2026Episode 10056 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.