PODCAST · business
Sidebar Advisors
by SideBar Advisors
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.
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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.
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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.
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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.
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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.
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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: [email protected]
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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.
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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.
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Stefani Schwartz & Kathryn Hatfield: From Colleagues to Co-Founders
Send us Fan MailIn this episode of the Sidebar Advisors Podcast, Niraj Chhabra sits down with Kathryn Hatfield and Stefani Schwartz, the founding partners of Hatfield Schwartz, a women-owned labor and employment law firm that has grown steadily since launching during the uncertainty of COVID.The two first met while practicing at a 60-lawyer firm and quickly realized they shared a similar vision for how a practice could operate — one grounded in partnership, autonomy, and strong client relationships.They talk through what was happening in their lives when they made the decision to leave, how they prepared financially and personally for the transition, and how they’ve navigated the dynamics of building and scaling a firm together.Along the way, Kathryn and Stefani discuss:• How they prepared for the financial realities of launching a firm• Why complementary strengths made their partnership work• What they’ve learned about hiring and mentoring younger attorneys• How they think about culture as their team continues to growTheir story offers a candid look at what it actually takes to step away from stability and build a practice with intention.
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Juliet Starrett: Movement, Career Pivots, and Building Control with Financial Readiness
Send us Fan MailIn this episode of the Sidebar Advisors Podcast, we sit down with Juliet Starrett -a former Big Law commercial litigator, world-champion whitewater paddler, and co-founder of The Ready State, a global platform focused on mobility, recovery, and longevity.Juliet’s career didn’t follow a straight line. Before law school, she spent years competing internationally as an elite athlete. After practicing at a major international firm, she and her husband co-founded one of San Francisco’s earliest CrossFit gyms—then built a second business that eventually became The Ready State, serving busy professionals who want to move better, sleep better, and stay sharp over the long term.In this conversation, Juliet shares:how her athletic background shaped her tolerance for risk and reinventionwhy she didn’t hate practicing law, but couldn’t see a long-term model she wanted to grow intothe financial groundwork she laid before leaving Big Lawwhat The Ready State iswhy movement isn’t optional for attorneys who want sustainable performanceIf you’re rethinking your health, your habits, or your long-term trajectory in the legal profession, this is an honest and tactical listen.
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Melissa Peters: What Really Drives Lateral Partner Hiring Today
Send us Fan MailLateral moves look straightforward from the outside. In reality, most fail for reasons attorneys don’t always see coming.In this episode of the Sidebar Advisors Podcast, Niraj Chhabra sits down with Melissa Peters, founder of MP Legal Search, to break down what’s actually happening in the lateral partner market — and how firms evaluate candidates behind closed doors.Melissa shares real-world insight into shifting compensation structures, how firms assess portability and fit, and the common mistakes that quietly derail otherwise strong candidates. The conversation cuts through the noise around lateral hiring and focuses on what matters now.They discuss: • What firms really look for when evaluating lateral partners • How compensation expectations are changing across the market • Why strong books still aren’t enough on their own • The most common pitfalls that derail lateral moves • How attorneys can make themselves more marketable before they explore a transitionA practical, candid conversation for partners and senior attorneys considering a move — or simply trying to understand how the market actually works.🎧 Listen to the full episode on the Sidebar Advisors Podcast.
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Hedieh Fakhriyazdi: What Growth Really Looks Like Inside a Big Law Firm
Send us Fan MailA lot of people in Big Law hear the phrase “professional development” — but don’t always know what it actually means in practice.In this episode of the Sidebar Advisors Podcast, Niraj Chhabra sits down with Hedieh Fakhriyazdi, Chief Engagement & Development Officer at White & Case, to talk about how growth really happens inside a global law firm — for associates, business services professionals, and everyone in between.Hedieh shares how White & Case thinks about development beyond titles and promotions, including how associates get real leadership experience early, why listening matters just as much as training, and how employee-led affinity groups shape culture from the ground up.They cover: • What “engagement” actually looks like day-to-day • How associates get a real seat at the table earlier than you’d expect • Why development can’t just be classroom training • How firms build trust by acting on feedback — not just collecting itIf you’ve ever wondered what a large firm can do better when it comes to growth, culture, and belonging, this conversation is worth your time.🎧 Listen to the full episode on the Sidebar Advisors Podcast.
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Merle Vaughn: Making the Right Move in Law and Recruiting from the Inside
Send us Fan MailFew people have a clearer view into the legal talent market than Merle Vaughn, Partner and Law Firm Diversity Practice Leader at Major, Lindsey & Africa.In this episode of the Sidebar Advisors Podcast, Merle joins Niraj Chhabra to share her journey from practicing attorney to one of the most respected legal recruiters in the industry — and what she’s learned from advising firms and attorneys through some of their most pivotal career decisions.They discuss:• What law firms are actually looking for today — beyond résumés and credentials • How DEI efforts have evolved, and where firms still struggle to align intent with action • The shifting expectations between attorneys and employers in a competitive market • Why self-awareness is the most important starting point when considering a move • How relationship-building — especially with recruiters — shapes long-term outcomesMerle offers a behind-the-scenes look at legal recruiting and practical advice for attorneys and firms navigating change with clarity and confidence.🎧 Listen to the full episode on the Sidebar Advisors Podcast.
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Larry Pon: Tax Planning for Attorneys Entering 2026
Send us Fan MailAs the year closes and a new tax landscape takes shape, attorneys can’t afford to rely on outdated assumptions about withholdings, deductions, or firm structures.In this episode of The Sidebar Advisors Podcast, Niraj Chhabra sits down with Larry Pon, CPA/PFS, CFP®, a nationally recognized tax expert, to break down what the One Big Beautiful Bill Act (OBBBA) and recent tax changes actually mean for lawyers heading into 2026.Whether you’re an associate adjusting withholdings, a newly elevated partner navigating K-1 income and buy-ins, or a firm owner evaluating deductions and SALT limitations, Larry offers clear, practical guidance grounded in real-world scenarios.They discuss: • The common tax trap new partners fall into • Why tax planning, not tax prep, is essential for attorneys • Changes affecting pass-through entities, SALT limitations, and more • How high-earning attorneys should think about cash flow, estimated payments, and surprises • Law firm owners using student loan repayment contributions as a talent recruiting and retention toolThis is a timely, actionable conversation for any lawyer who wants to start 2026 with clarity instead of regret.🎧 Listen now on the Sidebar Advisors Podcast.
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Andrea Rivers: Building A Career In Big Law Lessons for First-Gen Lawyers Starting Out
Send us Fan MailSome career stories unfold neatly. Andrea N. Rivers story isn’t one of them, and that’s exactly why it resonates.This week on the SideBar Advisors Podcast, I sat down with Andrea, an associate in the Antitrust & Competition group at Baker McKenzie, whose path into law has been shaped by grit, community, and a whole lot of real-life juggling.In this episode we talk about: ⚖️ How she handled working full time through law school 🌱 The mentors who opened doors early on 💼 Navigating career moves between Akin Gump, Axinn, and now Baker McKenzie 🤝 Co-founding Black JD, Inc. to support first-gen and underrepresented pre-law students 👶 Balancing new motherhood with a demanding legal careerFor newer attorneys and JD candidates trying to find their footing, Andrea’s story is a candid look at the realities of starting out in Big Law.
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Neel Chatterjee: Leading With Authenticity in BigLaw & Building the Future of IP Litigation
Send us Fan MailIn this episode, we sit down with Neel Chatterjee, one of the nation’s leading IP litigators and a finalist for ALM’s Attorney of the Year award.We cover a wide-ranging conversation, including:His path into law and the mentors who shaped himThe bold decision to leave Goodwin for King & Spalding and his vision for building out an IP powerhouse in Silicon ValleyStrategies for managing landmark cases involving tech giants like Facebook, NVIDIA, and eBayThe founding of Law Firm Partners United and the coalition’s amicus brief defending the rule of lawWhy public interest and diversity remain central to his careerHow he brings authenticity and humor into BigLaw culture—from snacks in the office to his tongue-in-cheek business cards declaring him “the very handsom man”Neel also opens up about his heritage and upbringing, and how those experiences shaped his worldview, his advocacy, and his drive to lead with purpose.This is a thoughtful, funny, and inspiring conversation with one of the legal industry’s most authentic voices.
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Bree Herman: Bringing Financial Clarity to Growing Law Firms
Send us Fan MailBree Herman didn’t set out to specialize in legal accounting, but a childhood spent learning how to “find the missing penny” sparked a passion that eventually led her to launch Herman Ledger Services, a boutique firm supporting solo and small law practices with bookkeeping, trust accounting, Clio and QuickBooks integrations, and fractional CFO support.Today, Bree helps attorneys move from confusion to clarity by giving them the financial systems, compliance oversight, and strategic insight they need to run their firms with confidence.In this episode of the Sidebar Advisors Podcast, Bree joins Niraj Chhabra to discuss: 📊 Why so many attorneys struggle with bookkeeping and trust accounting ⚖️ The biggest blind spots lawyers face when starting their own firms 💼 How to scale from solo practice to multi-attorney firm without losing control of finances 🔗 The power of integrating Clio + QuickBooks — and how it saves 5–10 hours a month 💰 When it’s time to move from outsourced bookkeeping to fractional CFO guidance 🌾 How life on her New Hampshire farm unexpectedly shaped her approach to entrepreneurshipFrom compliance pitfalls to multi-state payroll issues to planning benefits for growing teams, Bree breaks down the financial side of running a law firm in a way that’s approachable, practical, and empowering.🎧 Listen to the full episode on the Sidebar Advisors Podcast.
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Emma Smizer: Leveling Up Law, How Video Games Shaped a Legal Career
Send us Fan MailWhen Emma Smizer started law school, her path was anything but traditional. From a rescinded Big Law offer to finding her niche in video game law, Emma carved out a career that blends creativity, advocacy, and authenticity.Now an associate at Frankfurt Kurnit Klein & Selz, Emma is part of the firm’s Interactive Entertainment Group, advising top developers and publishers on everything from in-game economies and licensing to regulatory compliance, consumer protection, and intellectual property.In this episode of the Sidebar Advisors Podcast, Emma joins Niraj to talk about how she built a thriving career in one of the most exciting corners of the legal world, and what it takes to stand out early in your career.They discuss: 🎮 How a rescinded Big Law offer turned into an unexpected career opportunity ⚖️ The rise of video game law and what makes it so complex and dynamic 💡 Building a client base early in your career through authenticity and visibility 👾 How gaming culture is shaping the next generation of lawyers 💼 The leadership lessons hidden inside virtual worldsEmma’s journey is a reminder that the most fulfilling careers aren’t always planned; they’re built through resilience, curiosity, and showing up with your authentic self.🎧 Listen to the full episode on the Sidebar Advisors Podcast.
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Courtney Schulnick: Bringing Mindfulness to the Modern Legal Mind
Send us Fan MailAfter two decades in litigation, Courtney Schulnick, Esq. stepped away from the courtroom to pursue something equally demanding, helping others manage the pressures of law with clarity and balance.Now a Mindfulness-Based Stress Reduction (MBSR) instructor, Courtney teaches attorneys and other professionals how to use mindfulness not as an escape from their work, but as a tool to perform at their highest level while protecting their well-being.In this episode of the Sidebar Advisors Podcast, Courtney joins Niraj to share how her career journey led her to mindfulness, what the practice actually entails, and why it’s a practical, evidence-based approach for thriving in high-pressure environments.We cover:⚖️ The science behind focus, clarity, and resilience at work🧘 How becoming a mother forced her to slow down and re-evaluate what fulfillment looks like 💼 Why mental well-being is a competitive advantage, not a distraction from success 🌱 How stepping away from law allowed her to teach others how to stay engaged and fulfilled within it🎧 Listen to the full episode now 🔗 Learn more about Courtney’s work: www.CourtneySchulnickMindfulness.com 📖 Download her free mindfulness workbook: https://mailchi.mp/97686ee6c88c/free-mindfulness-workbook 💻 Join Courtney’s free 15-minute drop-in mindfulness sessions every Tuesday at 12:30 PM ET via Jefferson’s: https://jefferson.zoom.us/j/95409363161#success
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John Quinn: Leading One of the World’s Top AmLaw Litigation Firms
Send us Fan MailJohn 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 Advisors Podcast, John shares the story behind Quinn Emanuel’s steady rise.We discuss:The early years of building Quinn Emanuel from the ground upHow the firm’s focus on excellence, autonomy, and results shaped its cultureThe importance for every lawyer to be a rainmakerLandmark cases that helped define the firm’s reputationThe balance between leadership, ambition, and longevity in lawJohn’s creative pursuits — from art and Michelin-star dining to hosting his own podcasr, Law, Disrupted🎧 Listen to this in-depth conversation about what it takes to build, lead, and sustain one of the top AmLaw firms.
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Candace Dellacona: Estate Planning, Caregiving, and the Sandwich Generation
Send us Fan MailIn 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, time, and mental health.The biggest challenges facing the sandwich generation, from caregiver burnout to family conflict.How women disproportionately carry caregiving roles - and what that means for long-term planning.Special considerations for LGBTQ+ families, professional athletes, and high-profile clients.Practical ways to approach sensitive conversations with parents and loved ones.Candace’s insights show why estate planning is less about wealth and more about protecting relationships and creating peace of mind.
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Jacquette Timmons: The Human Side Of Money
Send us Fan MailMoney 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 seen firsthand that wealth doesn’t erase fear or poor decisions — it only changes the scale. In this conversation, we explore:Why financial well-being starts with understanding the emotions behind money decisions.The risk-averse mindset attorneys bring from their work into their personal finances.How lifestyle creep, debt, and “herd bias” quietly derail attorneys’ financial health.Why financial intimacy—not just transparency—matters for lasting relationships and firm culture.This episode is a must listen for anyone who still experiences financial stress despite earning well.Jacquette’s insights remind us: you don’t manage money, you manage your choices around money.
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Erin Andersen: Recruiting in Law & Redefining Career Transitions
Send us Fan MailErin 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 workplace experiences inspired her to build a career around helping others navigate transitions.Why attorneys often struggle with identity and financial fears when leaving big law.The unique recruiting challenges law firms face — and how her flat-fee approach helps small firms scale strategically.The overlooked role of branding and visibility for attorneys, from LinkedIn presence to firm culture.Whether you’re an attorney rethinking your next step or a law firm leader looking to hire and retain top talent, Erin’s insights will shift how you view careers, culture, and growth.
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James Wolff: A Conversation With The Tech-Obsessed Attorney
Send us Fan MailBefore 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 industry. We explore the winding path that led him from engineering and entrepreneurship to law, and how his side projects —whether speaking on stage, writing books, or serving on forward-thinking boards— help position him as a thought leader in fast-evolving spaces. This one’s a little geeky, a little strategic, and packed with insight for anyone looking to future-proof their career.
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Gail Cummings: From Big Law to Therapist and Executive Coach
Send us Fan MailGail 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, the emotional and practical hurdles she faced, and why so many attorneys find themselves questioning the career they worked so hard to build. We also explore the mental health themes that come up repeatedly in her work with attorneys and the growing demand from law firms and bar associations for her expertise.Whether you're thinking of leaving the law or trying to make peace with staying, Gail offers compassionate, actionable guidance on how attorneys can build happier, more authentic careers.
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Andrea D’Ambra: Big Law, AI, and Raising a Family
Send us Fan MailIn 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 firm’s Women’s Initiative (WiN), her influential work with The Sedona Conference, where she helps shape best practices for the responsible use of AI in legal settings, and how she balances the intensity of law firm leadership with personal time ( including video games to decompress). This conversation is honest, inspiring, and packed with insights for attorneys navigating their own careers and values.
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Ian Murray: Student Loans, Lifestyle Design, and Planning Smarter
Send us Fan MailIn 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, and how lifestyle design and financial clarity go hand in hand.You’ll also hear thoughts on the latest student loan legislation and what income-based repayment means in today’s environment.Whether you're managing loans, thinking about career shifts, or building a more intentional financial plan—this one's packed with insight.
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Emily Logan Stedman: Finding Balance, Building a Brand, and Thriving in Big Law
Send us Fan MailIn 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 current firm has supported her passion for authenticity—whether that’s speaking openly about mental health, posting from the lake, or leveraging AI to streamline her work. Emily offers a candid look at how she balances high performance with well-being, and why the idea that Big Law and work-life balance can’t coexist is more myth than reality. We also discuss her journey to 21,000+ LinkedIn followers, her evolving approach to business development (with the help of a coach), and how she’s positioning herself for long-term leadership as she works toward equity partnership. Whether you're navigating a legal career or just curious about how to build a brand that aligns with your values, this conversation with Emily is one you won’t want to miss.
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Derek Brainard: Navigating Student Loans + Supporting the Next Gen of Lawyers
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 gradsHow practicing attorneys with student loans should approach repayment plans—especially with ongoing policy shiftsWhy it’s crucial to leave all your options open in an unpredictable loan environmentHow law school alumni can bring AccessLex’s tools and support back to their alma matersWhether you’re just a few years out of law school or advising the next generation, this episode is packed with practical insights on education, access, and long-term financial well-being.🎧 Referenced Resource: AccessConnex by AccessLex – a free financial coaching service for law students and attorneys. Learn more at https://www.accesslex.org/accessconnex
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Justin Savage: Purpose, Persistence, and Practicing Environmental Law at the Highest Level
Send us Fan MailFrom 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 way beyond the courtroom. A high school teacher inspired him to pursue college, a debate team flyer led him to his future wife, and together they navigated law school while raising a newborn — sometimes literally bringing the baby to class.It’s a story about grit, purpose, and building a meaningful career without losing sight of what matters most.
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Stacy Phillips: High-Profile Cases, Advocacy, and Building a Legacy in Law
Send us Fan MailIn 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 toughest transitions.We dive into her experiences working on cases involving public figures like Britney Spears and Bobbi Brown, her leadership in philanthropy, and her ongoing mission to create more space for women in law through mentorship and firm-wide initiatives like the Women’s Leadership Summit.This conversation is a must-listen for anyone curious about what it really takes to build a powerful, purpose-driven legal career.
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Davina Frederick: Building a Thriving Law Practice as a Woman Attorney
Send us Fan MailWomen 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 running her own practice to coaching women lawyers on business development, mindset shifts, and the systems that make firm growth possible.
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Breeana Somers: From Teen Mom to Big Law Attorney, An Inspiring Journey
Send us Fan MailIn 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 challenges of balancing it all, and how embracing her authenticity changed everything. Breeana also discusses her journey with ADHD, from a misdiagnosis to sharing her experience publicly—leading to women reaching out to her for support and even driving new business her way. Tune in for an inspiring conversation on perseverance, breaking barriers, and the power of owning your story.
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Angelica Cesario: Navigating The Intersection of Law, Education, and Inclusivity
Send us Fan MailIn 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 shares valuable insights on what’s working, what’s changing, and what the future of DEI in law might look like. Tune in for a thoughtful discussion on the intersection of law, education, and inclusivity.
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Gerry Williams: From Introvert to Co-US Managing Partner at DLA Piper
Send us Fan MailIn 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 firm as a leader across various practice areas, and his commitment to mentoring the next generation of legal professionals. Tune in for valuable insights on leadership, career growth, and the power of building meaningful professional relationships.
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Judge Jose L. Linares: Leadership, Diversity, and Justice
Send us Fan MailIn 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 philosophy, the importance of diversity in the legal profession, and how his personal experiences have informed his approach to resolving complex disputes. Tune in for this conversation on resilience, justice, and the transformative power of representation.
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Michael Roybal: Building Nuooly and Balancing Legal Entrepreneurship
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 emerged from a desire to fill a gap in the business community. Now spending most of his time on Nuooly, Michael explains how he’s surrounded himself with experts to drive the platform’s success. Nuooly is redefining how business professionals connect, and Michael’s insights offer a fascinating look at balancing legal practice with entrepreneurship.
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Anita Ventrelli: Navigating High-Stakes Family Law, Advocacy, Resilience, and Mentorship
Send us Fan MailIn 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 celebrity and high-profile cases, including the intense media scrutiny, emotional stakes, and even personal safety risks. Anita reflects on how she manages the stress of such cases and provides insights into handling contentious legal battles with grace.Beyond the courtroom, Anita discusses her deep involvement in community service, her commitment to mentoring the next generation of lawyers, and the lessons learned from a career built on resilience and excellence. This is an inspiring conversation for legal professionals and anyone interested in the human side of high-stakes law.
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Mike Gold: Bridging Law and the Final Frontier, Space Policy, Innovation, and the Artemis Accords
Send us Fan MailIn 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 agreements that establish cooperative principles for lunar exploration and the sustainable development of space resources.Michael also discusses his dynamic work in the private sector with Redwire Space, highlighting cutting-edge advancements such as cloning human meniscus tissue in microgravity, pioneering solar technology, and developing computer chips for use in space. He offers insights from his experiences testifying before Congress and collaborating with global leaders to ensure space exploration benefits humanity as a whole.For aspiring legal professionals, Michael provides invaluable advice on breaking into the growing field of space law, illustrating how creativity and adaptability can open doors to success in unexpected industries. Tune in for an inspiring conversation about blending law, innovation, and the final frontier.-Mike Gold is the Chief Growth Officer at Redwire. In this role, Mr. Gold leads Redwire’s civil, commercial, and national security business development; marketing and communications; and government relations activities. Prior to joining Redwire, Mr. Gold was NASA’s Associate Administrator for Space Policy and Partnerships, Acting Associate Administrator for the Office of International and Interagency Relations, and Senior Advisor to the Administrator for International and Legal Affairs. At NASA, Mr. Gold led the development and implementation of the Artemis Accords, which establish norms of behavior to ensure a peaceful and prosperous future in space for all of humanity. Mr. Gold also successfully led the negotiations to develop and execute the binding agreements for the lunar Gateway, the development and implementation of the first lunar resource purchase by NASA and updating planetary protection regulations. Due to this trailblazing policy work, Mr. Gold was awarded NASA’s Outstanding Leadership Medal in 2021. Before joining NASA, Mr. Gold was Vice President of Civil Space at Maxar Technologies and General Counsel for the company’s legacy Radiant Solutions business unit. Additionally, Mr. Gold spent thirteen years at Bigelow Aerospace, where he established the company’s Washington office, oversaw the launches of the Genesis 1 and 2 spacecraft, and was a recipient of a NASA Group Achievement award for the development and deployment of the Bigelow Expandable Activity Module onto the International Space Station. Mr. Gold is currently the Vice Chair of the Commercial Spaceflight Federation and has previously served as Treasurer. Mr. Gold is also a member of the Committee on Space Research’s (COSPAR) Planetary Protection Panel, representing the Committee on Industry Relations. Additionally, in 2022, Mr. Gold was appointed by the NASA Associate Administrator for the Science Mission Directorate to serve on the Agency’s Unidentified Anomalous Phenomena Independent Study Team which was subsequently given the NASA Silver Group Achievement Award for their collective efforts to advance the understanding of this phenomena. Moreover, Mr. Gold was appointed by the U.S. Secretary of Transportation to Chair the Commercial Space Transportation Advisory Committee from 2012 – 2019 and was appointed by the NASA Administrator to serve on the NASA Advisory Council and chair its Regulatory and Policy Committee in 2018. Mr. Gold has authored numerous law review articles and editorials addressing commercial space issues. He has also testified on several
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Vanessa Vasquez de Lara: From Immigrant to Trailblazer, Building a Thriving Law Practice and Empowering Working Mothers
Send us Fan MailIn 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 in revenue in under five years. Now leading a team of seven attorneys and staff, Vanessa has built a firm that offers working mothers flexibility, including subsidized office nannies and unique work arrangements. Tune in to hear her insights on entrepreneurship, growth, and work-life balance.
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Chaka Patterson: Leading with Purpose in Law, Justice, and Pro Bono Advocacy
Send us Fan MailOn 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 wrongfully convicted, helping them regain their freedom. His dedication to his community and legal service truly sets him apart as both a professional and a leader.
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Christine Amalfe: Championing Equality, Leadership, Wellness, and the Future of Law
Send us Fan MailIn 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 work on New Jersey’s Council on Gender Parity, where she helped institute paid family leave and equal pay for women, and her recent election as president-elect of the NJ State Bar Association. Christine also discusses her passion for promoting attorney mental wellness and supporting young lawyers. Tune in for an inspiring conversation on leadership, equality, and the future of the legal profession.
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Dylan Adams: Protecting Innovation, Patents, Shark Tank Success, and IP for Entrepreneurs
Send us Fan MailIn 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 authored the widely respected book *Patents Demystified*, which is used in top universities like Harvard, Stanford, and MIT, and serves as the official patent guide for the American Bar Association. Join us as we explore his remarkable path and insights into the world of patents.
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William Barrett: From Big Law to Big Growth, Journey to Leading 100+ Attorneys
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 leadership has grown the firm from 20 to 112 attorneys and the key lessons he learned along the way. This is a must-listen for anyone interested in career growth, work-life balance, and law firm leadership!
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Zach Ratzman: Navigating Legal Innovation, Practical Law and Career Insights
Send us Fan MailOn our latest podcast, we interviewed Zach Ratzman, Director of Product Management at Thomson Reuters. Zach shared insights from his career journey, from his work with the Department of Homeland Security to his current role at Thomson Reuters. We dove deep into the Practical Law product, exploring its features, benefits, and how it stays up to date with the ever-evolving legal landscape. Don't miss this informative conversation!
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Sandra Radna: From Basement to Breakthrough, Building a Thriving Law Firm
Send us Fan MailThis week, we feature Sandra Radna, an attorney who grew her law firm from a small operation in her basement to a thriving practice with a team of 15. Specializing in family law and personal injury, Sandra's journey highlights perseverance and entrepreneurial spirit.In this episode, Sandra shares her transition from a nursing career to law, her grassroots approach to building her firm, and how networking and referrals fueled its growth. She also talks about balancing professional success with family life.Sandra has been featured on platforms like Court TV, discussing high-profile cases such as the Johnny Depp trial.
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Lisa Zeiderman: From Divorce to Triumph, Building a Law Firm and Advocating for Clients
Send us Fan MailTune in to our latest episode, where we sit down with the remarkable Lisa Zeiderman, founder of a thriving law firm that has grown to 50 employees in just 10 years. In this interview, Lisa shares the secrets behind her firm's rapid growth, emphasizing the importance of prioritizing client satisfaction above all else.Discover how Lisa and her partner effectively manage their business, including the dynamics of working alongside her husband. Delve into her strategic use of social media and her commitment to community involvement, both of which have played pivotal roles in her firm's success.But perhaps most inspiring is Lisa's personal journey into family law. After a challenging divorce experience, she was propelled to pursue her bachelor's degree and ultimately her JD and is now driven by a passion to advocate for others navigating similar challenges.
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Sheryl Axelrod: From Big Law to Solo Success
Send us Fan MailAttorney Sheryl Axelrod discusses how she successfully shifted from Big Law to a small ADR practice while continuing to handle cases worth hundreds of millions of dollars. She discusses her research on the ethical & financial advantages of diversity in the workplace and her efforts to promote a more inclusive legal industry.
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Dina Cataldo: Empowering Lawyers on Thriving in Law and Life
Send us Fan MailIn this episode of our podcast, we had the pleasure of interviewing Dina Cataldo, a certified coach who specializes in working with attorneys. Dina is the host of the Be a Better Lawyer Podcast and is dedicated to helping attorneys manage their time, overcome overwhelm, and find fulfillment in their careers. Her mission is to empower attorneys to achieve both professional success and personal fulfillment. Join us as Dina shares invaluable insights and practical strategies to help lawyers thrive in their demanding careers while maintaining a balanced and fulfilling life.Stay connected with Dina:The Busy Lawyer's Ultimate Time Management Guide: https://dinacataldo.com/busylawyerBe a Better Lawyer Podcast: https://dinacataldo.com/podcastLinkedIn: https://www.linkedin.com/in/dina-cataldo/Instagram: https://www.instagram.com/dina.cataldo/
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Michael Donahue III, Managing Partner at Stark & Stark: Leadership & Legal Excellence
Send us Fan MailJoin us in our latest podcast interview with Michael Donahue III, the seasoned managing shareholder of Stark & Stark. With three decades of dedication to his firm, Donahue shares invaluable insights on leadership, emphasizing the importance of fostering diversity even amidst shifting legal landscapes, such as recent Supreme Court rulings on Affirmative Action. Discover how Stark & Stark maintains its competitive edge through Donahue's approach of assertiveness without aggression, offering a blueprint for sustainable success in today's dynamic legal arena.
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Kristin Grant: Starting from Scratch
Send us Fan MailJoin us on the latest episode of the SideBar Advisors Podcast as we dive into the remarkable journey of Kristin Grant, Founder of Grant Attorneys at Law. From her early aspirations in pre-med to her dynamic transition into patent law, Kristin shares invaluable insights gleaned from her diverse experiences. Discover how her entrepreneurial spirit led her from running an online retail store to establishing and nurturing her own successful legal practice. In our conversation, Kristin reveals the art of balance as she deftly manages the demands of running a firm, carving out personal time, and engaging in meaningful civic endeavors. Tune in for an inspiring conversation with a trailblazer who embodies the essence of versatility and perseverance.
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ABOUT THIS 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.
HOSTED BY
SideBar Advisors
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