Stephen Weisberg is a Detroit-based tax attorney who helps individuals and business owners resolve IRS controversies and tax-debt issues. In this episode, he shares how the 2008 recession launched him from corporate bankruptcy work into tax law, why most people wait too long to seek help, and what every lawyer (and taxpayer) should know before they get that letter from the IRS.
What You Can Do With a Law Degree
Stephen’s journey proves that a law degree is both a credential and a toolkit. His early work in bankruptcy law introduced him to financial systems and creditor negotiations, while his tax practice taught him how to translate that technical knowledge into advocacy for everyday people. Tax controversy work isn’t glamorous, but it’s vital—and it’s year-round.
“People think I’m busiest during tax season, but that’s when the IRS is focused on filing. My work happens the rest of the year," shares Stephen Weisberg on Episode 217 of You Are a Lawyer.He’s built a steady stream of clients through LinkedIn networking, attorney referrals, and partnerships with CPAs, CFOs, and financial planners. The relationships he’s developed prove that collaboration, not competition, sustains a modern law practice. Most of his cases are handled remotely by phone or Zoom, reflecting how legal work has evolved since the pandemic.
Did you know that children as young as 10 can be prosecuted as adults in Pennsylvania?
You Are A Lawyer has partnered with YSRP, the Youth Sentencing and Re-Entry Project, to bring awareness to their fight to keep young people out of adult prisons and to advocate for youth lifers.
Visit YSRP.org to support this cause. Thank you.
Sergio Gregorio is a lawyer, podcast host, and creative who’s redefining what it means to have a legal career. In this conversation, he shares how growing up in Brooklyn, studying journalism, and working in federal service shaped his storytelling instincts, and why today’s lawyers must balance visibility, authenticity, and creativity in the digital world.
LAWYER SIDE HUSTLES
Sergio’s podcast, Frolic & Detour, showcases the multifaceted lives of lawyers who have stepped outside conventional career paths. Through conversations that blend humour, culture, and creativity, he invites listeners to see law as a foundation, not a limitation. He’s also expanding his creative portfolio with food-review videos, blending his love of storytelling with his natural curiosity about everyday pleasures.
“People don’t really get to see the silly side,” Sergio Gregorio admits in Episode 216 of You Are a Lawyer, “The podcast can feel serious, but there’s more to me than that.”By bringing humanity into his work, Sergio embodies the podcast’s core philosophy: lawyers are people first. Thinkers, creators, and dreamers who deserve space to explore beyond the billable hour. His story is a reminder that embracing detours can lead to the most authentic destinations.
Did you know that children as young as 10 can be prosecuted as adults in Pennsylvania?
You Are A Lawyer has partnered with YSRP, the Youth Sentencing and Re-Entry Project, to bring awareness to their fight to keep young people out of adult prisons and to advocate for youth lifers.
Visit YSRP.org to support this cause. Thank you.
Laura Terrell is an executive coach, general counsel, and former special assistant to the president who has built a career across government, private practice, and nonprofit leadership. In this episode, she shares how coaching helps lawyers advocate for themselves, embrace career pivots, and find clarity in uncertain times.
LAWYER SIDE HUSTLES
Alongside her legal work, Laura built a thriving executive coaching practice. She now works with clients ranging from law firm associates to government lawyers, helping them prepare for promotions, navigate layoffs, or make strategic pivots.
“One of the interesting things about attorneys is we’re really good at advocating for clients. But sometimes attorneys are surprisingly reluctant to advocate for themselves,” shares Laura Terrell in Episode 103 of You Are a Lawyer.Her coaching practice fills that gap, giving lawyers the tools to ask better questions, push beyond comfort zones, and build sustainable, fulfilling careers.
Arivee Vargas is a first-generation Latina lawyer who went from Big Law litigation to in-house corporate leadership, all before pivoting to become an author, executive coach, and speaker. She shares the raw story of her identity crisis after having her first child and how that led her to develop the framework for her book, Your Time to Rise, focusing on aligning your career with your deepest values. This conversation is essential for any high-achieving lawyer ready to stop checking boxes and start building a life of true purpose.
LAWYER SIDE HUSTLES
Arivee Vargas has successfully layered multiple non-traditional ventures alongside her demanding corporate career, demonstrating how a side hustle can evolve into a full-time business. While working full-time in high-level corporate roles, she became a certified coach and simultaneously cultivated her writing and speaking business. Her specific "hustle" involved writing her book, Your Time to Rise, which was written while she was still fully employed. She also established The Humble Rising podcast in 2021 as a platform to test and experiment with her ideas and voice before making the full-time jump.
“I started to realize, oh, I love coaching. I love, you know, doing this type of work,” Arivee Vargas shares in Episode 214 of You Are a Lawyer.Her current full-time business is built around executive coaching, speaking, and authoring, all centered on the theme of alignment, the process of ensuring what clients truly believe inside matches what they pursue on the outside. Arivee's focus with her clients is on "transformation from the inside out," working primarily with high-achieving lawyers and leaders who are looking for executive-level life coaching to navigate a career pivot and better align their professional achievements with their personal happiness.
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Partnership: Did you know that children as young as 10 can be prosecuted as adults in Pennsylvania?
You Are A Lawyer has partnered with YSRP, the Youth Sentencing and Re-Entry Project, to bring awareness to their fight to keep young people out of adult prisons and to advocate for youth lifers.
Visit YSRP.org to support this cause. Thank you.
Yladrea Drummond went from being “team no care about the law" to becoming a highly successful trial attorney and solo firm owner in Maryland and DC. She openly shares the grit required to get barred after a seven-year journey, how she transitioned her practice from family law to dominating criminal defense, and the non-negotiable value of complete autonomy that running her own firm provides. This conversation is a raw, honest look at the transition from legal disappointment to becoming a respected "big dog in court" who is truly building a legacy
LAWYER SIDE HUSTLES
While Yladrea is a self-proclaimed "workhorse" focused on the rapid expansion and day-to-day operations of her successful trial firm, she also acknowledges the importance of creative outlets that serve as a side interest and a form of therapy. Her personal hustle is in the realm of writing, specifically fiction, which is a powerful creative counterbalance to the high-stress demands of her criminal defense practice.
“I love to write,” Yladrea Drummond shares in Episode 213 of You Are a Lawyer.Although the fiction novel was ultimately shelved, Yladrea recognizes her love for writing remains strong. She notes that if she were to pursue a writing project now, after achieving success in her firm, she would aim to share her professional expertise in a non-traditional format.
LISTEN TO LEARN
WE ALSO DISCUSS
Partnership: Did you know that children as young as 10 can be prosecuted as adults in Pennsylvania?
You Are A Lawyer has partnered with YSRP, the Youth Sentencing and Re-Entry Project, to bring awareness to their fight to keep young people out of adult prisons and to advocate for youth lifers.
Visit YSRP.org to support this cause. Thank you.
Rob Levine is the founder of a multi-state law firm and an advocate for operational efficiency in legal practices. In this episode, he breaks down the vital role of case managers in improving law firm operations, building better client relationships, and increasing profitability. Whether you're a solo attorney or managing a growing team, this conversation will change how you think about delegation and workflow.
LAWYER SIDE HUSTLES
Rob’s “side hustle” is more like a second empire. In addition to his legal practice, he also runs businesses in medical records, call centers, and more. But everything he does is connected by a single goal: improving operational efficiency. His passion is not just practicing law, it’s optimizing it.
“I’m always looking at what we do and how we can do it better,” Rob Levine shares in Episode 212 of You Are a Lawyer.For lawyers who feel stuck or overwhelmed, Rob Levine’s story is a reminder that entrepreneurship doesn’t have to look like leaving law. You can innovate inside the legal industry by shifting your mindset and creating systems that support your bigger goals.
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Debra Whitson is a New York-based attorney, former prosecutor, family law mediator, and author of Divorce Like a Pro. In this conversation, she shares how mediation offers a healthier alternative to courtroom battles—and why divorce doesn’t have to destroy families. With decades of experience, Debra helps clients find clarity, peace, and dignity in even the most difficult transitions.
LAWYER SIDE HUSTLES
Debra’s side hustle became a calling: she wrote Divorce Like a Pro to provide an accessible, empowering guide for anyone going through separation or family breakdown. The book distills her real-world experience into practical advice and it’s a resource she wishes more people had earlier.
“I wrote the book because I found myself saying the same things over and over again to clients… there are better ways.,” shares Debra Whitson in Episode 75 of You Are a Lawyer.When she’s not running her practice or writing, Debra is a global advocate for women’s rights through Zonta International. Her passion for service, travel, and equity informs her entire professional ethos, from her client relationships to her vision of justice.
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Elise Holtzman left Big Law to raise her children, without a clear roadmap for what came next. Now she’s a leadership coach and founder of The Lawyer’s Edge, helping lawyers build confidence, develop business skills, and grow professionally. In this episode, Elise shares the mindset shifts that led her from practicing law to coaching those still in the field.
LAWYER SIDE HUSTLES
What began as a curiosity became a calling. Elise explored executive coaching and soon realized she could use her background in law to serve other lawyers. That side interest eventually became The Lawyer’s Edge, which she now runs full-time, offering coaching programs, firm-wide trainings, and a popular podcast.
“I didn’t set out to start a business. I set out to help people,” Elise Holtzman shares in Episode 210 of You Are a Lawyer.Elise’s story shows how side projects can evolve into full-fledged careers. By paying attention to what energized her, and what drained her, she built a business that supports both her clients and her life. She encourages other lawyers to give themselves permission to try something new, even if it starts small.
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Lamia Rahman is a Forbes 30 Under 30 honoree, TEDx speaker, and co-founder of SEEKR, a tech startup creating wearable AI devices for the blind. In this inspiring episode, Lamia shares her journey from law school in Hong Kong to the front lines of legal tech, accessibility, and advocacy.
LAWYER SIDE HUSTLES
SEEKR began as a passion project and has since grown into a globally recognized AI startup. The company develops wearable devices that help blind and visually impaired users navigate the world more independently. Lamia co-founded SEEKR during her law degree, blending her passion for tech with her desire to serve.
“It was a small idea at first. Now we’re building something that’s used across countries. That’s wild,” Lamia Rahman shares in Episode 209 of You Are a LawyerMore than a “side hustle,” SEEKR is a mission-driven business, fueled by Lamia’s belief that tech should be inclusive and empathetic. In the episode, she shares what it’s like to build a team, pitch to investors, and develop AI that solves real-world problems, all while still figuring out what comes next in her legal career.LISTEN TO LEARN
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Daniel Rosenberg is a former prosecutor and defense attorney turned novelist who’s turning real-life courtroom experience into gripping legal thrillers. In this episode, he shares how his background in acting and law helped him build a successful writing career, why COVID was the creative catalyst he needed, and how his novels teach readers about the legal system, without getting lost in legalese.
LAWYER SIDE HUSTLES
Daniel’s side hustle as an author didn’t just stem from a love of books—it came from lived experience. Drawing from real cases he prosecuted and defended, he built compelling plots that read like fiction but are grounded in courtroom realism. He even test-ran his early manuscripts with a jury of trusted friends and lawyers for feedback.
“Write what you know… because I can spot right away someone who’s never been in a courtroom,” Daniel Rosenberg shares in Episode 208 of You Are a LawyerHe also manages his own publishing relationships and book marketing, blending legal savvy with entrepreneurial spirit. From book signings to readings to podcast interviews, Daniel shows that you can take a legal career and build something entirely new, without leaving your skills behind.
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Candace Spencer is a legal consultant, mediator, and food justice advocate based in Washington, D.C. With a unique blend of legal insight and a lifelong passion for food, Candace has built a career at the intersection of environmental mediation, sustainable agriculture, and racial equity. In this episode, she shares how she’s using her legal background to support Black farmers, empower dairy-free living, and reshape the food system from the inside out.
LAWYER SIDE HUSTLES
Candace’s side hustles are anything but side projects; they’re deeply aligned with her mission. Her YouTube series SSpilled Milk educates and uplifts the dairy-free community with humour and heart. She also creates downloadable legal guides for small food entrepreneurs, helping people start businesses with confidence.
Whether she’s consulting on food policy or baking allergen-friendly desserts, Candace is creating systems of care. Her legal and creative ventures work in harmony, bringing clarity, inclusivity, and joy to underserved communities.
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A.X. Foster is a former prosecutor and defense attorney turned novelist who’s turning real-life courtroom experience into gripping legal thrillers. In this episode, he shares how his background in acting and law helped him build a successful writing career, why COVID was the creative catalyst he needed, and how his novels teach readers about the legal system, without getting lost in legalese.
LAWYER SIDE HUSTLES
A.X.’s side hustle as an author didn’t just stem from a love of books—it came from lived experience. Drawing from real cases he prosecuted and defended, he built compelling plots that read like fiction but are grounded in courtroom realism. He even test-ran his early manuscripts with a jury of trusted friends and lawyers for feedback.
He also manages his own publishing relationships and book marketing, blending legal savvy with entrepreneurial spirit. From book signings to readings to podcast interviews, A.X. shows that you can take a legal career and build something entirely new, without leaving your skills behind.
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Gary Martoccio is an employment lawyer and solo practitioner who left a large firm after 12 years to build his own plaintiffs-side practice. In this episode, Gary shares what it’s like to advocate for employees, run your own firm, and earn multiple state licenses through bar exams and reciprocity. If you’re curious about employment law or considering going solo, this episode gives a real-world perspective you won’t find in law school.
WHAT YOU CAN DO WITH A LAW DEGREE
Gary’s journey shows how a law degree can provide both structure and flexibility. Even if your first idea doesn’t stick (or your clients don’t make it to the big leagues), your training equips you with skills to succeed in high-stakes environments.
Today, Gary practices employment law across multiple states thanks to a smart mix of bar exams and reciprocity. He reminds lawyers and law students that options expand when you take strategic risks early on and the earlier you pivot toward work that feels aligned, the better.
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Nick Troxel is a lawyer, entrepreneur, and co-founder of Troxel Fitch, LLC, a business-focused law firm in Denver. In this episode, he shares how he went from driving Lyft after law school to building a thriving firm with his law school roommate. If you've ever dreamed of starting your own legal business, or wondered if it's worth the ris, this conversation is for you.
LAWYER SIDE HUSTLES
Nick didn’t have a side hustle in the traditional sense—his firm was the hustle. He and his partner built it in real time, taking every contract and client they could, learning by doing, and stretching every dollar. The early months were full of late nights, part-time jobs, and small wins that added up to something bigger. Over time, that side hustle became a full-fledged, thriving firm.
In addition to running his practice, Nick also co-authored How to Be a Lawyer, a book that aims to demystify the transition from law school to practice. His passion for helping new lawyers build sustainable careers has become a core part of his identity. He proves that a non-traditional career doesn’t mean a lesser one. It often means a more fulfilling one, especially when it’s built with intention and courage.
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Rhonda Coleman Wandel is a commercial attorney, podcast host, and founder of RCW Strategies LLC, a legal consulting firm serving visionary companies and legal teams. In this episode, she shares her bold transition from education to law, her path through in-house legal roles, and why she recently stepped into entrepreneurship after years at companies like Accenture and Google. From Memphis to Chicago, single motherhood to legal leadership, Rhonda’s story is about clarity, courage, and walking your own path.
LAWYER SIDE HUSTLES
Rhonda is the host of the Rhonda Coleman Wandel Podcast, a platform she created to amplify women's career stories and celebrate nontraditional professional journeys. The podcast was born from her own pivot into law and a desire to show women that they can chart their own course—regardless of what the status quo says.
Through her show, Rhonda has interviewed remarkable women who’ve reinvented themselves, pivoted industries, and built lives of purpose and alignment. The podcast, like her legal career, is about service, voice, and visibility. It’s also an extension of her belief that success doesn’t look one way—and that storytelling can help us find freedom in our professional lives.
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Keith Shannon is a former lawyer, legal educator, and lifelong theater fan. Kara Shannon is his daughter and creative collaborator. In this episode, Kyla speaks with the father-daughter duo about their journey from legal careers and musical soundtracks to launching Fourth Row Center, a podcast celebrating Broadway and family bonds. Their story is a heartfelt reminder that success can look like connection, creativity, and choosing joy on your own terms.
LAWYER SIDE HUSTLES
Launching a podcast wasn’t just a fun hobby for Keith and Kara, it was a way to stay connected, be creative, and invite others into their world of Broadway fandom. What started as casual chats about shows turned into Fourth Row Center, a podcast that’s part review, part family banter, and part love letter to the stage.
“We started the podcast and love it together, so why not? And it gives us an excuse to chat a little bit,” Kara Shannon shares in Episode 202 of You Are a Lawyer.This father-daughter side hustle is a reminder that legal professionals can (and should) pursue joy. Whether you're behind a mic or in the audience, there's power in showing up fully—as a parent, partner, or creative collaborator.
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Aman Costigan was once a partner at a Canadian law firm, teaching yoga on the side and quietly craving more freedom and alignment in her life. In this powerful conversation, she shares how she found her voice, launched Beyond Yoga for Lawyers, and began to merge wellness with law in a meaningful way. The episode captures a moment in time when Aman was redefining what a legal career could look like — and today, her journey continues beyond the courtroom
Lawyer Side Hustles
Beyond Yoga for Lawyers began as a side project. Aman felt a pull to share what she had learned through yoga and mindfulness, especially with other lawyers who were struggling with burnout and disconnection. She started teaching classes, offering workshops, and building a community.
Over time, that side hustle grew into a brand and a business. Today, she offers coaching, yoga, and wellness content specifically designed for lawyers who want more than just billable hours and burnout. It’s a testament to what’s possible when you start small, stay consistent, and let your vision evolve.
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Austin Brittenham is a first-generation lawyer, legal tech founder, and the creator of 2nd Chair, an AI-powered tool designed to help solo and small firm lawyers work faster and smarter. In this episode, Austin and Kyla talk about space law, law school culture, and what it really means to use your legal education creatively. From debating in high school to launching two startups, Austin proves that you don’t have to follow the traditional legal path to make a meaningful impact.
Lawyer Side Hustles
Austin’s side hustle is now his full-time gig. He founded 2nd Chair while still in law school and used his background in AI and education startups to build something lawyers actually need. The tool creates litigation timelines, drafts legal materials, and helps lawyers save time and serve more clients. But it’s not just about software, it’s about increasing access to justice and making legal practice more sustainable.
“We can distribute more justice, we can serve more people—or just have more vacation,” expresses Austin Brittenham in Episode 200 of You Are a Lawyer.Austin’s story reminds us that entrepreneurship doesn’t have to mean abandoning the law. It can mean expanding it, reimagining it, and making it more human. 2nd Chair exists because Austin saw a gap in the system and took the risk to build something better.
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Dr. Rhonda Glover Reese is a certified career and leadership coach with 34 years of FBI experience under her belt. From counterintelligence to white collar crime, her federal career was vast and dynamic. In this powerful episode, Dr. Rhonda shares how her dream of working for the FBI led to a fulfilling career in public service and how her new chapter as a coach helps others step into their purpose with confidence.
Side Hustles
Dr. Rhonda’s “side hustle” is far from traditional. After retiring from the FBI, she launched a coaching business to help others find fulfillment in their careers. Her passion lies in career and leadership development, especially for those in law enforcement. She also offers training, speaks at events, and creates space for honest conversations about burnout, purpose, and growth.
“I'm great at mentoring and coaching, particularly in that law enforcement space. I'm good. I'm great,” expresses Dr. Rhonda Glover Reese in Episode 199 of You Are a Lawyer.Her journey from federal agent to entrepreneur was not accidental. It was built on prayer, reflection, and a growing awareness that people were turning to her for guidance. Today, she is intentional about the size and structure of her business to maintain the life she wants; one that includes faith, flexibility, and continued service
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Bill Mitchell is a veteran litigator, negotiation strategist, and the author of The Disruptive Lawyer’s Little Black Book of Litigation Management. With three decades of experience, Bill has a bold message for lawyers: less litigation, more resolution. In this episode, he shares how he became a top 1% dealmaker by helping clients resolve cases faster and cheaper, without sacrificing strategy or results.
Lawyer Side Hustles
Bill’s side hustle? Changing how lawyers think. He authored The Disruptive Lawyer’s Little Black Book of Litigation Management and teaches a course called “Masters in Negotiation” for attorneys, claims professionals, and in-house counsel. His mission is to equip lawyers with the tools they didn’t learn in law school, including how to close cases with confidence and clarity.
“I do an eight-part series on negotiation. If 92% of all cases settle, you need really good negotiators,” expresses Bill Mitchell in Episode 94 of You Are a Lawyer.His upcoming book, The Disruptive Lawyer’s Little Black Book of Negotiation, builds on that mission. Whether training junior associates or consulting with Fortune 500 legal departments, Bill is helping shift the mindset from litigation to resolution.
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