Sidebar Advisors

Hosted by SideBar Advisors

Business CareersInterviews guests

Website RSS feed

Episodes

Latest episode

Jun 2026

Language

EN-US

About the show

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.

Listen to episodes

60 recent

June 10, 2026Episode 811 hr 7 min

Laurin Johnson: What Lawyers Need to Know About Running a Firm

Send us Fan MailMost attorneys spend years learning the law, but very little time learning how to run a business.In this episode of the SideBar Advisors podcast, Laurin D. Johnson, Esq., LL.M., CEPA®, consultant with MB Law Firm Consulting, LLC®, joins Niraj to talk about the operational side of running a law firm — the part many lawyers are forced to figure out only after they become owners, partners, or firm leaders.Laurin works with law firms on operations, leadership structure, profitability, hiring, succession planning, and the systems needed to support sustainable growth. She explains why many firms struggle as they scale, how inconsistent processes quietly drain time and profitability, and why documenting and delegating work is essential if a firm wants to grow beyond its founders.This episode is a practical look at what it takes to build a stronger practice — not just a busier one.

June 3, 2026Episode 801 hr 5 min

Abe Kwon: Career Risk, Success, and Building a Life That Actually Fits

Send us Fan MailSuccess gets a lot more complicated once you actually start achieving it.Abe Kwon is a partner at Lowenstein Sandler LLP, where he advises founders, startups, and venture-backed companies.But this conversation was really about the decisions behind the resume — career pivots, risk, family, and figuring out what success actually means as priorities change over time.In this episode of the SideBar Advisors podcast, we talk about career pivots, taking risks when things are already going well, and how he found work that actually aligned with his personality and interests. Abe also shares candidly about balancing partnership, family life, nonprofit leadership, and the evolving relationship many professionals have with money, success, and time as their careers progress.A lot of legal careers look polished from the outside. This episode gets into what they actually feel like behind the scenes.

May 20, 2026Episode 7956 min

Dr. Anthony Mazzarelli: What Law Firms Can Learn From Healthcare Leadership

Send us Fan MailDr. Anthony Mazzarelli has built a career at the intersection of medicine, law, leadership, and public communication. A practicing physician, healthcare executive, bioethicist, and JD, he’s spent years leading in environments where decisions carry real human and institutional consequences. In this episode of the SideBar Advisors Podcast, we explore what law firm leaders and senior attorneys can learn from healthcare systems about:• Decision-making under pressure• Governance and accountability• Burnout as a leadership problem — not just a personal one• How incentives quietly shape culture• Why communication is now a core leadership skillWe also discuss how Anthony unexpectedly stepped into media, what being behind the microphone taught him about persuasion and clarity, and why credibility in high-stakes professions doesn’t require silence.Anthony is also the author of books focused on leadership, culture, and navigating complexity — work that reflects his belief that technical excellence alone is not enough to sustain modern institutions.If you’re a managing partner, senior attorney, or professional navigating leadership in a high-liability environment, this conversation will resonate.

May 13, 2026Episode 781 hr 1 min

Seth Rokosky: Career Decisions, Appellate Law, and Why Having a Plan Matters

Send us Fan MailSeth 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 dual legal career work, to carving out an appellate practice where few opportunities existed, Seth shares how long-term thinking, tradeoffs, and persistence shaped his path.In this episode, we talk about how he approached career decisions alongside his wife, what it really takes to build a niche practice from the ground up, and how his background in competitive chess influences the way he thinks about strategy, risk, and decision-making.A practical conversation on planning ahead, adapting when things don’t go as expected, and building a career that actually fits your life.

May 6, 2026Episode 7729 min

Elie Honig: From Prosecutor to CNN’s Senior Legal Analyst

Send us Fan MailElie Honig — former federal prosecutor and now CNN’s senior legal analyst — has built a career that doesn’t follow the traditional legal path.After more than a decade prosecuting major federal cases, Elie stepped into private practice and eventually into media, where he’s become a trusted voice translating complex legal issues for a national audience.In this episode, he shares what that transition actually looked like, including the risks, tradeoffs, and moments of uncertainty along the way. We discuss the differences between life as a prosecutor and in private practice, how credibility is built outside the courtroom, and what it takes to communicate legal ideas in a way people actually understand.It’s a candid conversation about career optionality, public-facing roles, and what lawyers can do with their skillset beyond the traditional path.

April 29, 2026Episode 7656 min

Kenneth Nunnenkamp: Career Risk, Recalibration, and Defining Success Over Time

Send us Fan MailKenneth 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 move leaving big law for an in-house role at a startup, trading stability for equity and opportunity. When it didn’t play out as expected, he had to recalibrate — eventually finding his way back to private practice with a clearer perspective on risk, value, and what actually matters over the long term.In this conversation, Ken shares how those decisions shaped his career, from his time as a Marine Corps JAG officer to his work today in national security, cross-border matters, and anti–money laundering. He also reflects on how priorities shift over time, why not every opportunity is worth taking, and how success becomes less about titles and more about doing work that’s genuinely engaging.A grounded look at career decisions, trade-offs, and building something that lasts.

April 22, 2026Episode 751 hr 5 min

Bruce MacEwen: The Future of Law Firms Isn’t What You Think

Send us Fan MailWhat actually separates durable law firms from those that won’t make it through the next decade?In this week's episode, Niraj Chhabra, CFP, MBA, CLTC, CRPC sits down with Bruce MacEwen, founder of Adam Smith, Esq., LLC, to unpack how law firm economics and structures are being reshaped in real time. They discuss why the traditional business model is breaking down, how the industry is shifting toward a smaller group of elite firms, and what makes those firms fundamentally different.A major theme throughout the conversation is AI — not as a distant threat, but as something that could quickly challenge the billable hour and reduce the need for large associate classes. Bruce also shares: why many firms aren’t prepared for what’s coming how career paths for lawyers could change dramatically what happens when firms are forced to shrink and why the most valuable skill going forward may not be legal expertise It’s a candid, forward-looking conversation for anyone thinking about the future of the legal industry.

April 15, 2026Episode 7443 min

Jill Cruz: How Attorneys Can Advocate for Their Value More Effectively

Send us Fan MailNegotiation, compensation, and advancement shape a lawyer’s career — but most attorneys are left to navigate those decisions without much transparency.In this episode of the Sidebar Advisors Podcast, Niraj Chhabra sits down with Jill Cruz, executive coach, career strategist, and founder of JLC Consulting. Before launching her practice, Jill spent years in senior HR and talent leadership roles inside law firms, advising on hiring, promotion, and compensation decisions. Today, she helps attorneys better understand their value, navigate career inflection points, and advocate for themselves more effectively. They discuss what Jill learned from seeing these systems from the inside, why so many attorneys underestimate their leverage, how negotiation really starts long before an offer is made, and why mindset plays such a big role in whether people step into bigger opportunities.They also talk about the structural and cultural barriers that continue to affect women and attorneys of color, and how Jill’s research has shaped the way she coaches today. To learn more or connect with Jill:Website: www.jlc.consulting Email: jcruz@jlc.consulting

April 8, 2026Episode 7356 min

Michelle Calcote King: How Law Firms Actually Build Visibility, Credibility, and Demand

Send us Fan MailMichelle Calcote King, Principal & President of Reputation Ink, joins the podcast to break down how professional services firms — especially law firms — can turn their expertise into real visibility, credibility, and growth.At Reputation Ink, Michelle works with law and other B2B firms to help them become known authorities, earn meaningful media coverage, and build reputations that drive business development.In this episode, we talk about why marketing should look different depending on firm size, how owned, earned, and paid media actually work together, and what clients are paying attention to today.We also get into what separates firms that consistently generate opportunities from those that struggle to stand out — and how to build a strategy that creates long-term visibility, not just short-term activity.If you’re thinking about how your firm shows up in the market, or why it’s not translating into growth, this is a practical conversation worth listening to.

March 24, 2026Episode 7253 min

Trini Ross: Leadership, Public Service, and the Weight of the Role

Send us Fan MailTrini Ross spent over 30 years in federal service, ultimately serving as the United States Attorney for the Western District of New York — overseeing major cases involving violent crime, civil rights, and public corruption. In this conversation, she shares what that level of responsibility actually looks like day to day — from leading through high-profile, emotionally charged cases to managing a team under constant pressure and scrutiny.We talk about how she built her career in public service, the mindset required to make difficult decisions, and the moments that forced her to step back and reassess. She also reflects on leaving government, transitioning into private practice, and why she chose to build something new rather than follow a traditional path.This is a candid look at leadership, responsibility, and what it means to do the job well when the stakes are real.