Sidebar Advisors

SideBar Advisors
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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.

  1. 4 days ago

    Ryan Fayhee: 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 Hauer & Feld LLP and former senior official in the U.S. Department of Justice's National Security Division, joins the SideBar Advisors podcast to discuss his career investigating some of the government's most consequential sanctions and export control matters before transitioning into private practice. We explore how complex cross-border investigations unfold, what companies often misunderstand about regulatory risk, why strong leadership matters during a crisis, and how Ryan navigated leaving what he calls "the best job" he ever had to build a new career advising global organizations.

    Ryan Fayhee: DOJ to Private Practice - Risk & High-Stakes Decisions

  2. 15 Jul

    Carolyn Daly: 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 stage of a legal career: associate, partner, law firm owner, and now partner at Cohen Seglias.  In this episode of the SideBar Advisors podcast, she shares what she learned from building her own firm, why succession planning is often overlooked, and what ultimately led her to join a larger platform after more than a decade of running a successful practice. We also discuss business development, retirement planning for firm owners, burnout, authenticity in the legal profession, and how attorneys can make career decisions that align with both their professional and personal goals.

    Carolyn Daly: Building, Growing, and Letting Go of a Law Firm

  3. 9 Jul

    John Hellerman: 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 Communications, where he helps lawyers and professional service firms build credibility through thought leadership, media exposure, and strategic communications.  In this episode of the SideBar Advisors podcast, we discuss why reputation is what drives business development, how attorneys can become known for the work they want to do, and why the goal of marketing isn't simply getting noticed — it's creating trust before a client ever picks up the phone.   We also explore positioning, media strategy, career development, and practical ways lawyers at every stage can build authority in a competitive market.

    John Hellerman: Why Great Lawyers Still Need Marketing

  4. 6 Jul

    Shannon McClure Roberts: 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 liability and mass tort litigation. In this episode of the SideBar Advisors podcast, Shannon reflects on the decisions and experiences that shaped her career - from building a practice over nearly two decades at Reed Smith to making the move to Blank Rome, and how her perspective on leadership, business development, and long-term growth has evolved along the way. We discuss what it takes to lead in high-pressure environments, why authentic relationships matter in building a practice, how AI may reshape the legal profession, and why emotional intelligence will become an even more valuable skill for lawyers. The conversation also explores confidence, mentoring, career transitions, and creating opportunities for the next generation of women in law.

    Shannon McClure Roberts: Leadership, Growth, and High-Stakes Litigation

  5. 24 Jun

    Chuck Cotter: 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 the leading legal practices serving founders and consumer brands. His path there was anything but straightforward. In this episode of the SideBar Advisors podcast, Chuck shares how he went from struggling as a junior associate to building a niche practice that eventually brought him back to Big Law on his own terms. After relocating from New York to Colorado, he found himself starting over with no book of business, no established network, and growing pressure to prove himself. We discuss how he built a practice around industries he genuinely cared about, why authentic relationships matter more than traditional networking tactics, and how tactful translating of complex legal and financial issues became a key differentiator with founders and entrepreneurs. We also talk about leadership, business development, work-life balance, and why protecting time for family and health isn't separate from professional success—it's part of sustaining it.

    Chuck Cotter: Why Being Bad Early Doesn't Define Your Career

  6. 17 Jun

    Benjamin Softness: 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 to leave.  In this episode of the SideBar Advisors podcast, Benjamin, now a partner at King & Spalding, reflects on his path from private practice to Google and back again.  We discuss how in-house experience changes the way lawyers think, the tradeoffs between stability and long-term upside, and why career decisions become more complicated as family, ambition, and professional goals evolve. We also talk about AI governance, regulatory risk, dual-lawyer households, and what Benjamin calls the "cranking years" — a period when many professionals are simultaneously building careers, raising families, and investing heavily in their future.

    Benjamin Softness: Career Risk, Optionality, and Leaving a Dream Job

  7. 10 Jun

    Laurin Johnson: 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 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.

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

  8. 3 Jun

    Abe Kwon: 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 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.

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

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.

Information

  • Creator
    SideBar Advisors
  • Years Active
    2022 - 2026
  • Episodes
    87
  • Rating
    Clean
  • Copyright
    © 2026 Sidebar Advisors
  • Show Website
    Sidebar Advisors