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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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  • 26 episodes
  • weekly
  • Avg 56 min
  • English

Episodes 26

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  • #79
    May 20 · 56 min

    Dr. 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, 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 skill We 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.

  • #78
    May 13 · 1 hr 1 min

    Seth 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 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.

  • #77
    May 6 · 29 min

    Elie 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. 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.

  • #76
    April 29 · 56 min

    Kenneth 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 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.

  • #75
    April 22 · 1 hr 5 min

    Bruce 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, 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.

  • #74
    April 15 · 43 min

    Jill 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 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

Showing 21–26 of 26 episodes