This Legal Life: Lessons Learned from a Life in Legal

In this episode of This Legal Life, Jonathan Petts, CEO of Upsolve, shares his unconventional journey from being fired by two Wall Street law firms to building a nonprofit that has helped erase over $1 billion in debt for low-income Americans. Through moments of personal failure, unexpected mentorship, and bold experimentation, Jonathan reveals how rethinking bankruptcy as a tool for economic mobility—not moral failure—sparked a mission to scale access to justice. This conversation explores the realities of building in legal tech, the discipline of product focus, and how technology—especially AI—can unlock opportunity for millions who have historically gone unserved.

In this episode of This Legal Life, Ben Chiriboga speaks with employment lawyer Zack Anstett about how a life-altering medical diagnosis reshaped his perspective on success, ambition, and balance in private practice. Zack shares what it’s like to continue practicing law while navigating serious health challenges—and how that experience changed his relationship with billable hours, titles, and long-term career expectations. The conversation offers an honest look at resilience, flexibility, and the often-overlooked human realities behind legal careers.

About Our Guest: Zack Anstett defends Southeast-based employers when the workplace becomes a legal battlefield.

On the defense side, Zack has defended hundreds of employment cases in state and federal courts and before investigative agencies such as the EEOC and the Department of Labor. He understands how plaintiff attorneys build their cases because he has spent years strategically dismantling them.

On the prevention side, Zack’s litigation experience gives him a clear view of where companies tend to make mistakes that lead to lawsuits. He helps employers make difficult personnel decisions, develop practical HR policies, and draft employment agreements designed to reduce risk and keep disputes out of court.

Outside of work, Zack enjoys learning Farsi, cooking with his Persian mother-in-law, and losing at pickleball to his five-year-old daughter—while his three-year-old son and one-year-old daughter cheer from the sidelines with their mom.

🔗 Read Zack’s full bio: https://www.parkerpoe.com/attorneys/zack-s-anstett#tab/overview 🔗 Connect with Zack on LinkedIn: https://www.linkedin.com/in/zackanstett/

In this episode of This Legal Life, Ben Chiriboga speaks with Brian Scherer about the pivotal moments that led him from in-house fintech roles to founding Hey Counsel. Brian reflects on the frustrations of Big Law economics, the isolation of solo practice, and the perseverance required to build something entirely new in the legal ecosystem. The conversation explores how technology, community, and intentional reinvention are reshaping what it means to succeed as a modern lawyer.

About Our Guest: Brian Scherer is the co-founder of HeyCounsel and a fintech commercial and regulatory attorney. He has worked in-house at fast-growing startups including LendingClub, Opendoor, and Blend. Brian started HeyCounsel to help companies find strong boutique legal support at a lower cost than traditional Big Law. As it evolved, he recognized the bigger opportunity was supporting the lawyers themselves. Today, HeyCounsel is a community and platform where independent attorneys practice alongside one another, share expertise, and build thriving practices.

Links:

https://heycounsel.com

https://www.linkedin.com/in/brianscherer1/

In this episode of This Legal Life, Ben Chiriboga sits down with Joe Green, Chief Innovation Officer at Gunderson Dettmer, to explore how law firms are evolving — and what it takes to lead that change from the inside. Joe traces his journey from practicing corporate law through legal tech experimentation and his time at Practical Law at Thomson Reuters. He shares how stepping outside the traditional partner track allowed him to develop the skills and confidence needed to return to Gunderson and help shape a future-ready firm. The conversation offers timely insight for law firm leaders thinking seriously about innovation, talent, and long-term strategy.

About Our Guest:

Joe Green is the Chief Innovation Officer of Gunderson Dettmer. In this role, he leads Gunderson’s innovation strategy to transform the firm's service delivery platform and business model, with a focus on providing a more modern experience for clients, lawyers and business professionals. He was recognized by Lawdragon as one of the 100 leading AI and legaltech advisors.

Joe is a Lecturer in Law at Penn Carey Law, where he teaches a course on startups and venture capital. He has authored dozens of articles on startup-related issues, the business of law, legal technology and the future of the legal industry. He speaks regularly on these topics at industry and academic conferences, law firms and law schools, and his academic work has been cited by SEC commissioners and staff in public speeches and reports.

Joe was previously a senior associate at Gunderson and left to join Thomson Reuters as a Senior Legal Editor at Practical Law, the premier online legal know-how service for business lawyers. Joe began his legal career as a securities lawyer with Simpson Thacher in New York.

Connect with Joe:

LinkedIn: https://www.linkedin.com/in/joegreen1/

In this episode of This Legal Life, Ben Chiriboga sits down with Dana McKenna to unpack how a collapsing startup led her to rebuild her legal career from the ground up.

Dana openly discusses juggling uncertainty, discovering fractional GC work, and confronting internal barriers like imposter syndrome and people-pleasing. She highlights why today's companies need strategic legal partners who can manage risk, lead proactively, and simplify complexity. An inspiring conversation for lawyers designing a career that fits their strengths—and their life.

About Our Guest:

Dana McKenna is the Founder of Align General Counsel, a fractional GC practice built on one core belief: high-growth companies deserve legal leadership that operates in true alignment with how their business actually runs.

With more than 18 years of legal experience, Dana began her career in BigLaw litigation before moving in-house, where she spent over a decade advising Fortune 5 corporations, mid-sized businesses, and scaling startups. She has served as General Counsel, Chief Legal and People Officer, and trusted advisor to founders, boards, and executive teams—bringing a rare blend of legal strategy, operational insight, and business pragmatism.

Dana’s background spans tech, staffing, marketplaces, retail, and consumer brands. She specializes in employment law, California and multi-state compliance, commercial contracting, and litigation strategy. Over her career, she has led organizations through complex restructures, PAGA litigation, high-stakes internal investigations, M&A activity, and evolving regulatory environments.

Known for her practical and people-centered approach, Dana focuses on the intersection of legal, HR, and company culture. She partners closely with leadership to deliver guidance that is clear, candid, and designed to keep the business moving forward—without slowing growth or creating unnecessary friction.

Connect with Dana:

Website: https://www.aligngeneralcounsel.com/

LinkedIn: https://www.linkedin.com/in/danabethmckenna/

In this episode of This Legal Life, Ben Chiriboga sits down with Anusia Gillespie, legal tech executive and author of Soul Toll, to explore the inner work behind career reinvention. Anusia shares how meditation, misalignment, and seven roles in ten years shaped her understanding of the “soul toll” we pay in our professional lives. She explains why trusting yourself matters more than mentors when your path is still unpaved, and how her debut novel blends leadership lessons with fantasy storytelling. A thoughtful, powerful conversation for legal professionals navigating change, ambition, and authenticity.

About Our Guest:

Anusia Gillespie is a lawyer turned novelist and RYT 200 certified yoga instructor whose debut contemporary fantasy, Soul Toll, blends corporate ambition with personal awakening. Her writing is shaped by a career at global law firms, legal tech companies, and Harvard Law School Executive Education, offering a sharp, insider perspective on high performance culture and the personal cost of chasing success.

Well known in the legal industry for her insight on leadership and transformation, Anusia now channels those themes into fiction that invites readers to question the lives they have been told to want. In Soul Toll, a high achieving attorney’s search for clarity pulls her into a hidden world, and a battle for something far more meaningful than success.

Anusia holds a JD and MBA from Boston College and a BS in Management from Tulane University. She lives north of Boston with her husband, young son, and old dog.

https://www.amazon.com/Soul-Toll-Anusia Gillespie/dp/B0FN9PSS2N/ref=tmm_pap_swatch_0

www.anusiagillespie.com

https://www.instagram.com/anusiagillespie/

https://www.linkedin.com/in/anusiagillespie/

In this episode of This Legal Life, host Ben Chiriboga sits down with Tara Young, General Counsel of Spearmint Energy, as she walks us through her remarkable career from a 2008 layoff to navigating private equity pressures and ultimately finding her place as a strategic leader in the fast-changing energy sector.

Tara shares how mentors, executive coaching, and learning to be “comfortable being uncomfortable” shaped her path. Her story offers legal professionals a candid and practical look at what it takes to grow, adapt, and thrive in modern in-house leadership.

Meet Tara:

Ms. Young is a seasoned attorney with 20 years of experience including 15 as an in-house attorney and 10 in the energy industry. She is currently General Counsel, Corporate Secretary and Chief Compliance Officer of Spearmint Energy, a utility-scale battery storage developer. She has also held positions with Plus Power, NV Energy and Berkshire Hathaway Energy. Earlier in her career, Ms. Young worked at a variety of companies and law firms in Las Vegas where she resides. Ms. Young also serves as a probono attorney for children in foster care. Outside of work, Ms. Young is the mom of 5 children (ages 19 to 6) and runs marathons to maintain her sanity.

In this episode of This Legal Life, host Ben Chiriboga welcomes Tom Martin, founder of LawDroid and co-founder of Vancouver Legal Hackers, for a thoughtful discussion about community and innovation in the legal industry. Tom shares his journey from East Los Angeles to becoming a builder of legal communities, reflecting on the moments that shaped his commitment to connection and collaboration.

Together, Ben and Tom explore what Tom describes as the “time between stories,” a period of transition where the legal profession is redefining how it works, connects, and creates value. They discuss the growing need for presence, authenticity, and human-centered leadership as technology accelerates rapid change.

Tune in for an insightful conversation about belonging, resilience, and the role of community in the future of legal work.

Meet Our Guest:

Tom Martin is CEO and founder of LawDroid, a generative AI legal technology company, and Principal of Deep Legal, a legal AI transformation consultancy. He is an Adjunct Professor at Suffolk Law School, where he teaches Generative AI, and author of Generative AI and the Delivery of Legal Services, a textbook adopted by law schools nationwide. An ABA Legal Rebel and Fastcase 50 honoree, Tom serves on the ABA Center for Innovation Governing Council and has launched Law Answers AI and Depositron to expand access to justice. He hosts the LawDroid Manifesto newsletter and podcast for 6,000+ subscribers, writes "The AI Law Professor" column for the Thomson Reuters Institute, and speaks at major legal technology conferences including ABA TechShow, LegalWeek, and ILTACON. A Yale University and UCLA School of Law graduate, Tom lives in Vancouver, Canada, with his wife and two daughters.

You can follow him and his podcast at: lawdroidmanifesto.com

In this episode of This Legal Life, host Ben Chiriboga sits down with Matthew Korn, Partner at Fisher Phillips and founder of Dad, Esq., to explore the real meaning of success in today’s legal world. From his first job at McDonald’s to navigating layoffs, in-house roles, and the partnership track, Matt shares an honest account of burnout, resilience, and rediscovering purpose as both a lawyer and a father.

What began as a search for connection has grown into a global community where lawyer dads support one another in navigating work, parenthood, and wellbeing. Through candid reflection and practical lessons, Matt shows that community is not just support; it is the foundation of sustainable growth in law and life.

For anyone balancing firm life with family or seeking a more human approach to leadership, this conversation is a reminder that you do not have to do law or fatherhood alone.

Meet Our Guest:

Matthew Korn is passionate about helping employers navigate complex employment law challenges with practical, business-focused solutions. His experience as in-house counsel for a multinational, publicly traded company gives him a unique perspective on the client side of employment law. He uses that insight to help clients align compliance with their broader business goals.

Matthew has extensive experience across industries including healthcare, hospitality, construction, mining, pharmaceuticals, and manufacturing. He also has a special focus on working with ABA providers to build compliant employment policies, minimize risk, and prevent litigation.

Beyond his legal work, Matthew is the founder of Dad, Esq., an online community for lawyer dads to connect, share stories, and support one another through the challenges of balancing law and fatherhood.

Links:

• Dad, Esq. Community: https://DadEsq.mn.co
• Website: https://DadEsq.com
• Linktree: https://linktr.ee/DadEsq

In this episode of This Legal Life, Ben Chiriboga speaks with Charlotte Smith, a UK lawyer turned legal tech founder and executive coach, about the courage it takes to start over. After moving from London to California, Charlotte faced an identity crisis that forced her to redefine success and rediscover her purpose. Through resilience, coaching, and curiosity, she rebuilt her confidence — proving that growth often begins with unlearning.

About our Guest:

Charlotte Smith is an Executive Coach and Management Consultant who blends deep legal expertise with a passion for guiding teams, leaders, and organizations to reach their full potential.

She began her career in the UK, becoming a partner at a top-tier firm by age 30, recognized for her forward-thinking approach—including launching a subscription-based employment law service for the travel and hospitality sector.

In 2014, she moved to Silicon Valley, pivoting from lawyer to entrepreneur and coach, combining her legal background with a commitment to innovation and human development.

Charlotte is also the author of How to Attract, Engage, and Retain Top Legal Talent (Globe Law and Business), a resource for teams that embrace change, leverage technology, and optimize human performance. Her consulting engagements have included a wide range of law firm organizations and in-house legal teams.

By integrating energy management, human performance, and mindset strategies, Charlotte empowers General Counsels, law firms, and in-house teams to tackle leadership dysfunction, align teams, and thrive in today’s rapidly evolving legal landscape. Balancing technology, AI, and emotional intelligence, she ensures leaders drive meaningful results without sacrificing well-being.

If you’re ready to transform how you lead, Charlotte is here to help.

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