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.

Access the updated BETA assessment launching in January: https://d8q79.share.hsforms.com/2B1LXFYArQl-q4_K8pGFVBA

In this episode of This Legal Life, Ben Chiriboga speaks with Liz Smith, former legal headhunter and now Head of Talent at Bamboo, about her powerful career transformation and how she’s challenging the traditional model of legal recruitment. After 20 years in the industry, Liz followed her inner voice and made a bold pivot—moving from transactional placements to helping lawyers reimagine their careers with purpose, flexibility, and entrepreneurial thinking.

Together, they explore how burnout, authenticity, and the search for meaning drove Liz to build a more human-centered approach to talent. From 4 a.m. reflections to guiding lawyers toward autonomy and alignment, this episode is a must-listen for anyone rethinking what success in law can really look like.

About our Guest:

Liz Smith is dedicated to attracting top legal talent and building meaningful connections across the legal community. Through strategic networking, headhunting, and coaching, she plays a vital role in connecting creative lawyers with opportunities that align with their ambitions. Known for her authenticity and trust-building approach, Lizzie is a passionate ambassador for her firm and an active voice within the industry. Her work gives her the autonomy to thrive—combining her natural strengths in relationship-building with her genuine enjoyment of meeting and working alongside inspiring legal professionals.

Connect with Liz on LinkedIn

In this episode of This Legal Life, Ben Chiriboga sits down with Sarah Cottrell — former BigLaw lawyer turned career coach and founder of The Former Lawyer Podcast.

Together, they explore the courage it takes to step away from prestige, perfectionism, and external validation to rediscover what truly matters. Sarah shares her journey through burnout, anxiety, and uncertainty — and why true clarity doesn’t come from overthinking, but from taking action.

About Our Guest

Sarah Cottrell is a career coach who helps unhappy lawyers ditch their soul-sucking jobs. She practiced law for ten years and specializes in helping lawyers identify alternative careers.

Sarah hosts The Former Lawyer Podcast, where she interviews lawyers who have left law for other fields and provides advice and strategies for those who want to do the same. She is an ICF-Certified Coach, a Certified Career Management Coach, and an Academies-Certified Strengths Coach.

🔗 Website: formerlawyer.com

In this deeply reflective episode, Ben Chiriboga sits down with Tony Albrecht, former insurance defense lawyer turned Co-Founder and Creative Director of CONTENDER, to explore how recovery, reinvention, and creativity can redefine success in law. From hitting rock bottom in Guam to helping mission-driven lawyers find their authentic voices on LinkedIn, Tony shares how embracing fear, storytelling, and self-awareness can turn even the hardest chapters into powerful new beginnings.

About Our Guest:

Tony Albrecht is the Co-Founder and Creative Director of CONTENDER. His path has been largely defined by recovery from two things: alcoholism and lawyering. He had his last drink in 2010, a year after graduating from law school.

In 2021, Tony walked away from the practice of law on the verge of making partner with an insurance defense firm in his hometown of St. Louis, Missouri. After leaving the practice, he gained traction as a creator on LinkedIn in 2022 and saw an opportunity to help others share their messages in ways that resonate.

Today, Tony is building CONTENDER, a personal branding and LinkedIn ghostwriting agency that creates magnetic online presences for mission-driven lawyers and leaders.

He now lives in Muskoka with his wife and their two kids. When he’s not hanging out online, Tony enjoys long runs and drinking too much coffee.

In this episode of This Legal Life, host Ben Chiriboga sits down with Patrick Patino—attorney, coach, and host of The Newfangled Lawyer Podcast—to discuss what it means to practice law on your own terms.

From a poet-turned-lawyer to a founder challenging conventional firm models, Patrick shares how authenticity, creativity, and presence shaped his journey. He reflects on failure, reinvention, and why lawyers should trust intuition over outdated playbooks.

This candid conversation is a roadmap for legal professionals ready to embrace change and build careers aligned with who they truly are.

About Our Guest:

Patrick brings a sensible, mindful, and creative approach to the practice of law. He is the host of The Newfangled Lawyer Podcast.

When not practicing law, he enjoys making pottery, reading chef memoirs, and going on outdoor adventures with his family.

Connect with Patrick

• LinkedIn
• The Newfangled Lawyer Podcast
• ALH Law Profile